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June 7, 2026
THE NEW CEO SOCIAL MEDIA PLAYBOOK
The New CEO Social Media Playbook: Communications Strategies in the Digital Age for the Modern CEO. In this episode, TED MERZ from Principals Media discusses the seismic shifts in corporate communications, exploring how CEOs can build authentic visibility in a rapidly evolving digital landscape, and the future of traditional media.
https://open.spotify.com/episode/6MLjRILrkeCPhlG6ItXaMC?si=uQP9CdYORpmr89iL4dfMvg
https://youtu.be/clHzhrOZAps
Key Topics
The decline of traditional PR channels like CNBC and The Wall Street Journal and the rise of direct content creation for thought leadership.
The importance of authenticity and transparency in CEO messaging, with real-world examples such as McDonald’s CEO controversy and insights into crisis management.
Strategies for leveraging social media platforms—LinkedIn, X (Twitter), YouTube, and emerging tools—for building personal and corporate reputation.
The evolving role of AI in shaping search results and online identities, emphasizing the need for content influence.
The significance of visibility across multiple channels and the concept of the “public record” for professional branding.
Balancing platform choice with audience targeting and the importance of integrated content strategies.
The future of content formats: long-form videos, short clips, point-of-view storytelling, and the normalization of CEO participation in digital media.
Traditional media’s ongoing role in establishing credibility within a pyramid of influence, from legacy outlets to influencer-generated and user content.
Timestamps:
00:00 – Introduction to CEO communications in the digital era02:00 – The decline of traditional media outlets for corporate messaging05:00 – Case study: McDonald’s Big Arches video controversy and lessons learned07:30 – Why engagement in digital platforms is no longer optional for CEOs09:00 – Platform strategies for business communication and audience targeting11:00 – The future role of CEOs on YouTube and social video content13:00 – Authenticity and AI’s impact on content credibility15:00 – Cross-platform content distribution and emerging channels like Substack16:00 – Measuring success: from vanity metrics to real business impact17:00 – The complexity of linking social media efforts to sales and hiring outcomes19:00 – Building visibility to enhance reputation and company valuation20:30 – The importance of a balanced media approach—traditional and digital22:00 – Influencer dynamics, user-generated content, and organic reach24:00 – The societal shift towards individual visibility and personal brand26:00 – The relevance and future of traditional media in a digital-first world28:00 – Strategies for influencing AI-driven search and online biography management29:30 – How organizations can foster authentic employee advocacy30:50 – Resources to connect with Ted Merz and his ongoing projects
Resources & Links:
Principals Media
Pricing Culture — The Bloomberg for Collectible Data
LinkedIn
X (Twitter)
YouTube
Substack
Connect with Ted Merz:
LinkedIn
Twitter
Insights:
CEOs should view digital visibility as a fundamental communication muscle.
The importance of integrating long-form content, short clips, and authentic storytelling.
The shifting landscape where legacy media remains valuable for credibility, but influence is increasingly driven by digital presence and influencer narratives.
BRAM WEINSTEIN ON “BREAKING THROUGH DIGITALLY”
https://youtube.com/shorts/Ia_X8A_WhG4?feature=share
Transcript
Why CEO Communication Is Changing
Frazer Rice:Welcome back to the Wealth Actually Podcast. Apologies in advance for the head cold. I’m joined today by Ted Merz of Principals Media. We’re discussing how CEOs are navigating communications, the role of social media, and whether traditional media is still relevant.
Frazer Rice:Ted, welcome.
Ted Merz:Great to be here. Thanks for having me.
Frazer Rice:We met at a dinner in New York, and I was struck by your perspective on the shift happening in PR. You advise CEOs on communications—what are you seeing?
Ted Merz:We’re in the middle of a major structural shift. Traditionally, companies relied on PR firms to secure placements in outlets like CNBC or The Wall Street Journal. That’s becoming less effective—those platforms are more competitive, often paywalled, and in some cases shrinking.
Ted Merz:At the same time, more people want access to that exposure. So companies are going direct—creating their own content through social media, podcasts, video, and written thought leadership. It allows them to bypass traditional gatekeepers and control their narrative.
Risks, Authenticity, and the Learning Curve
Frazer Rice:It also gives you more room to develop your ideas. But we’ve seen cases—Sam Altman, for example—where messaging goes sideways. Is that inexperience or the format?
Ted Merz:It’s not the format. There’s always risk in speaking publicly—people can react negatively. Sometimes it’s inexperience, but more broadly, this shift is inevitable.
Ted Merz:If you want to reach younger audiences—late millennials and Gen Z—they’re not watching CNBC or reading newspapers. They’re on YouTube and Instagram. So participation in digital media isn’t optional.
Ted Merz:That said, there’s a learning curve. Executives aren’t always comfortable, and mistakes will happen.
Frazer Rice:Just look at the reaction to a poorly thought-out tweet—it can spiral quickly.
Ted Merz:Exactly. But opting out is the bigger risk. If you’re not visible, you’re not part of the conversation.
Choosing Platforms: LinkedIn, X, YouTube, Substack
Frazer Rice:I’ve leaned into that with this podcast and more activity on LinkedIn and Twitter. But there’s a tension—should you focus on one platform or meet clients wherever they are?
Ted Merz:It’s not about the platform—it’s about communication. You’re either writing or creating video.
Ted Merz:For most businesses, LinkedIn is the best starting point. It’s professional, relatively forgiving, and widely accepted. But platforms are evolving quickly.
Ted Merz:For example, X (Twitter) is now supporting long-form content—5,000+ word essays—and has become a hub for thought leadership in finance and tech. It’s more intense and less forgiving than LinkedIn, but that may be where your audience is.
Frazer Rice:That’s part of why I moved my podcast to YouTube. If you’re not on YouTube, you’re invisible to Google. But not everyone is comfortable on video—how do you handle that?
Why Video and YouTube Matter for CEOs
Ted Merz:I tell them to get comfortable.
Ted Merz:YouTube is the new television. It’s where attention is going, and it rewards creators financially. Companies need to develop video capability.
Ted Merz:Written content conveys ideas well, but video builds trust and familiarity. That’s critical today.
Ted Merz:Historically, CEOs didn’t communicate this way. But now you see leaders like Mark Zuckerberg, Jamie Dimon, and Jon Gray using video regularly. That legitimizes it. Within a few years, this will be standard.
Frazer Rice:There’s also a push for authenticity. Overproduced or AI-generated content feels hollow, especially with growing fatigue around corporate messaging.
Ted Merz:That’s right. But authenticity doesn’t mean abandoning standards. You can still communicate clearly and thoughtfully.
Ted Merz:Also, content is increasingly distributed across platforms—LinkedIn, X, YouTube, Substack. Substack, in particular, is emerging as a strong platform for serious thought leadership.
Ted Merz:Importantly, in business, the goal isn’t to go viral. It’s to create a credible public record—so when someone looks you up, they see someone thoughtful and worth engaging.
Measuring Impact: Beyond Vanity Metrics
Frazer Rice:That raises the question of metrics. How do you connect social media activity to actual business results?
Ted Merz:It’s difficult. Social media behaves more like brand advertising than direct response marketing.
Ted Merz:Vanity metrics—likes, shares—can be misleading or manipulated. The connection to revenue is often indirect.
Ted Merz:But you can see impact anecdotally. One client told me they couldn’t tie posts directly to sales, but they were attracting better job candidates who already understood and trusted the firm. That’s real value.
Frazer Rice:And what about search? It used to be about controlling Google results. Now with AI-driven search, that’s changing.
Ted Merz:Exactly. Large language models now shape how people are perceived online. You can’t fully control that, but you can influence it by consistently publishing clear, factual content.
Ted Merz:If you don’t, the narrative will be created without you.
Personal Brand, Corporate Brand, and Goodwill
Frazer Rice:I think of this as building personal and corporate goodwill—like managing the name on the back of the jersey as well as the front.
Ted Merz:That’s a great way to put it.
Ted Merz:We’ve also seen a cultural shift. In the past, companies emphasized the collective—“there’s no I in team.” Today, we’re in an attention economy where people connect with individuals more than institutions.
Ted Merz:That’s why CEOs are becoming more visible. It helps the brand, and it reflects how audiences engage.
Ted Merz:Companies are also trying to involve employees, but that’s tricky—you can’t fully control messaging and still have authenticity.
Frazer Rice:Which brings us back to the core tension: authenticity versus control.
Ted Merz:Exactly.
Is Traditional Media Dead?
Frazer Rice:So is traditional media dead?
Ted Merz:No—but its role has changed.
Ted Merz:Think of it as a pyramid. At the top is legacy media, which provides credibility and validation. Below that are influencers and independent creators. At the base is owned content—what you publish yourself.
Ted Merz:Traditional media still matters, but it’s harder to access. Increasingly, strong content created independently gets picked up and amplified by legacy outlets.
Ted Merz:So the strategy is layered: create your own content, engage across platforms, and let that visibility lead to broader coverage.
How to Work With Ted Merz
Frazer Rice:That makes sense. Ted, we’ll have to continue this conversation—there’s more to cover. In the meantime, where can people find you?
Ted Merz:LinkedIn is the best place—I’m very active there. You can also find me on X, YouTube, and TikTok.
Ted Merz:My primary business focuses on content creation and ghostwriting for CEOs. I’m also building a platform called Pricing Culture, which tracks collectible assets—think of it as a Bloomberg for collectibles—targeted at family offices.
Frazer Rice:Terrific. We’ll definitely dive into that next time. Thanks for joining.
Ted Merz:Thanks for having me.
https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
Keywords:
The New CEO Social Media Playbook, CEO Marketing, CEO Social Media, Quest for Authenticity, CEO Branding, Corporate-Speak fatigue, Problems with LinkedIn
June 2, 202631 min
GETTING THE BUSINESS READY TO SELL
ALEXANDRIA SEYDEL from Ripples Edge Advisors shares expert strategies on “getting the business ready to sell.” We focus on exit planning and getting the most value out of the transaction. Discover how early planning, owner mindset, and strategic positioning can lead to successful exits and satisfied owners.
https://youtu.be/8OwhCRCBZl4
https://open.spotify.com/episode/2qawd64OYzljBvU9xqS8df?si=1Xvv2OUFSbeBtUDeJGTMXg
KEY TOPICS
Early exit planning and owner mindset,Getting the business ready for sale and transfer.Risk assessment and deal readiness.Owner satisfaction and post-sale happiness.Capital raising and growth strategies.
SOUND BITES for “GETTING THE BUSINESS READY TO SELL”
“Getting clear on owner success is crucial.”“Start exit planning 2-5 years in advance.”“Family dynamics can be deal breakers.”
Chapters
00:00 Navigating Business Exits: An Introduction.02:57 Understanding Owner Satisfaction Post-Sale..05:55 Preparing for Sale: The Importance of Readiness.09:00 Building a Succession Plan for Business Continuity.11:49 Assessing Business Value: The Exit Readiness Assessment.15:08 Evaluating Growth Opportunities and Capital Needs.17:58 Cash vs. Equity: Making Informed Decisions.21:03 Finding the Right Buyers: The Role of Advisors.24:08 Addressing Family Dynamics in Business Sales.26:59 Checklist for Business Owners Considering Sale.
RESOURCES
Ripples Edge Advisors – https://ripplesedgeadvisors.com/
GUEST LINKS
LinkedIn – https://www.linkedin.com/in/alexandriaseydel/
QSBS For Founders – https://frazerrice.com/qsbs-for-founders/
TRANSCRIPT
Frazer RiceWelcome aboard, Alex.
Alexandria SeydelHi Frazer, so nice to be here. Thank you for having me.
Frazer RiceThank you for being on. We’re at a time now with the economy where it feels like it’s roaring. Valuations on things are going up, up, up. And people who have founded businesses are exploring their options. That’s kind of where you step in with your firm Ripple’s Edge Advisors.
Talk to us about what you do to help founders get ready. Not only in understanding what they have in their own business. How to go through the daunting process of exploring their options. Getting their business bulletproof for when people start looking under the hood.
Alexandria SeydelAbsolutely. My background is as an M&A attorney, so I came from the deal side. My co-founder is an operator — she actually knows how to run the businesses. It’s a very good duo. I think like a buyer, first and foremost. That’s how I was trained. So how we help business owners now is we jump in two to five years before exit. We’re trying to solve a problem still being missed by most of the industry.
Brokers and bankers know how to get deals done, create auctions, create demand, and sell for high prices. That’s all great. But the gap I was seeing was the need to jump in with the owner before that process. Getting clear on what’s a win for them. There are some startling stats about owner dissatisfaction post-sale. Some surveys show 70 to 80% of owners are dissatisfied after selling. I’d argue that’s not because they sold — it’s because they sold to the wrong person in the wrong way. So it’s the who and the how.
Jumping in with them earlier. Before we go to market, Before we start talking multiples and financials. Getting with the owner and doing the work on what a win looks like for them. What do they care about in the process? When they think about their life through this deal and post-deal, what do they want to feel and see? How do they want to operate on an average Tuesday. Yes, after all the cool vacations with all the freedom and the new chapter. After that, what do you want to be doing?
And when you look back at that beautiful business you built and then sold, what do you want to see in it? Is it that client service remains the same? Is it that the ethos of the company remains the same? Or is it simply: “Alex, I’m satisfied with the biggest wire at closing we can get, and I’ll be a happy camper moving on to the next phase of life.” Really getting with that owner earlier to get clear on that — what’s a win for them and what’s a win for their business — that’s where we start. Then we begin implementing and helping them build those exit strategies from there.
We believe that foundational vision and values work is really going to help bring down that dissatisfaction number. So now we’re building an exit that feels right for the owner, right for the business, and helps them feel good about that transaction.
Frazer RiceFrom the estate planning and tax planning side of things, I totally agree that the earlier you start, the more tools you have at your disposal and the better it turns out. I did a piece on pre-exit planning — really engineering what your calendar is going to look like a year after the sale. And I see a lot of dissatisfaction with people who sell and then lose purpose, or aren’t quite equipped to deal with their lower participation in the thing they built, the baby they helped give birth to.
They end up unmoored, and that’s part of the depression they sometimes feel if they haven’t really gamed it out and thought through how to replace the structure and the drive it took to build something. It sounds like we’re saying the same thing from slightly different angles.
Alexandria SeydelTotally, absolutely. On your side, you’re such a critical part of the team when we start this process. One of the first two questions we ask every client is: who’s your wealth advisor, and who is your tax strategist? Hopefully they’re already in communication, but if they aren’t — you’re looking at the personal side, focused on what the family structure looks like financially, the tax strategies and planning that we know has to happen.
And because you’re doing this work — which not all advisors do — you’re getting really clear on the personal side. I’m coming at it from the business balance sheet and business trajectory; you’re coming from the personal side. They work well together. I like to jump in early with the other advisors working with these owners to get really clear, because not only do we know there are structural and strategic things we need to put in place years in advance, but we also need to get clear on what’s a win for them personally and business-wise.
Frazer RiceOne of the things you mentioned is the idea of getting the business ready to be sold. I’m fast-forwarding to the concept of getting it Sarbanes-Oxley ready in case a public company wants to buy it — so it can slot neatly into a balance sheet. But that’s really shorthand for saying things are professionally managed: bookkeeping, process, accounts receivable, accounts payable — all formally documented. So that when a buyer starts looking under the hood, they don’t start applying discounts for things they’ll have to fix later. Is that part of what you do?
Alexandria SeydelExactly. Being trained as a lawyer on the buy side, my goal — usually at the 11th hour — was to advise my client, the buyer, on risk. And to assess whether the purchase price offered in the letter of intent actually held up once we looked under the hood.
The best part of my job now — and way more fun — is that instead of just identifying risk and applying discounts (because almost every deal goes through some form of repricing), I’m jumping in with the sellers and owners hopefully a year or two in advance. We find things a buyer is going to see as a risk, things that would prompt a reprice, and we now have the opportunity to make those things shinier. So that when the buyer looks under the hood, the high end of the multiple range is validated.
It’s not just the financials the purchase price is based on — it’s all the other things buyers care about: the people, the processes. Is this a truly transferable asset they can step into, run, and grow?
Another big thing we work on is owner dependence. Most owners think the business doesn’t depend on them, but there are often significant opportunities to continue reducing that dependence — so that a buyer sees this as a true transferable asset they can step into and grow.
Frazer RiceI imagine there are a couple of come-to-Jesus discussions where you have to tell the owner their revenue is too dependent on them personally. On one end of the spectrum, think of a law firm where business comes in because people think you’re a great lawyer — that doesn’t transfer cleanly. You want the recurring revenue to come from somewhere else.
That’s one issue I’m sure you have to sit someone down and address. The five-year runway is helpful there — it gives you time to build in a succession plan, not just for the sale, but operationally, so that value still sits in the business whether you’re there or not.
The second thing I find interesting is where you sit somebody down and say: this would look a lot better if you took less money out of the business. If we can put that back into EBITDA, then when a buyer starts applying multiples, they’re multiplying against something bigger rather than against a number deflated by, say, buying a boat. Do you get into that conversation?
Alexandria SeydelYes, we do, and we take a cursory look at that fairly quickly. Then we bring in support if needed — whether that’s on the accounting side, how money flows through the business to affect the bottom line and create the story. Every buyer wants at least three years of financials; we want that growth story to look strong, and we want to start building it now. If we need to bring in a fractional controller or a fractional CFO depending on the size and sophistication of the business, that’s something we pull in right away.
On your first point — we actually have an architect client right now at exactly that phase. He has a right-hand woman architect who’s been with him for over ten years, and he wants her to have the opportunity to step into the business. He also has a son who’s an architect and wants the same opportunity for him. So we’re building a succession plan. And one of the first problems we addressed was that he’s still driving almost all of the top-line revenue — nearly all the business development runs through him.
So we’re asking: when does this right-hand woman get involved in the sales process? What percentage of meetings is she in? What is she bringing in herself? His timeline is five to seven years, so we have time to build this out — continuing to train her, continuing to elevate her and others in the business who can drive relationships and sustain that revenue flow, the recurring revenue that comes from major referral partners and developers giving him large contracts.
And on the equity side: what’s the incentive plan? How do we get her aligned with the goals of the business so she genuinely wants to take ownership, both literally and figuratively? We’re building an equity incentive plan with her. On the process and sales side, we’re setting goals — she’s in a certain percentage of meetings by year-end, driving a certain percentage of revenue. We’re helping him set those goals and build a plan to execute on them.
Frazer RiceAnd all of that also sets up a longer-term exit — maybe selling the practice to a larger architectural firm or a private equity-backed platform down the line.
Alexandria SeydelExactly. And on a slightly longer timeline, all of that work makes the business more efficient operationally and more attractive as a potential sale — whether that’s to those two individuals in a succession plan or to an outside buyer.
Frazer RiceWhat happens when a business comes to you and maybe the brand is well respected and things look good from the outside, but there’s decay underneath? They come to you and say they’re ready to sell, but when you look at it, the dollar signs in their eyes are based on something that existed a long time ago and has since been left to deteriorate. What do you do in that situation?
Alexandria SeydelWe start with what we call an Exit Readiness Assessment — it’s a 90-minute virtual session that pulls you out of your inbox, out of the fires you’re fighting every day, and lets you step back and look at every dimension of your business through the lens of what a buyer is going to assess.
It produces a readiness score and tranches everything into three buckets: value adds (greater multiple), value detractors (reduction in sale price), and deal killers — things like accounting or legal issues so significant that a buyer doesn’t just reprice, they walk away entirely. That assessment becomes the foundation for a roadmap: what are the most important things to fix, and in what order?
We all have limited time, energy, and capital. The triage framework helps you apply those resources to the things that actually move the needle. And yes, there is often a come-to-Jesus moment. Sometimes an owner comes in burned out — they just want to hand over the keys. We want to avoid that situation, but if you get there proactively rather than reactively, if you’ve already done the work with advisors like Frazer and like us to put systems, people, and processes in place, your readiness score is in much better shape.
If you haven’t done that work, it requires a harder conversation — what do you want out of this? What are your goals? And what can we realistically accomplish in what period of time?
Frazer RiceWhat about founders who want to grow and are looking for outside capital, but want to stay involved? How do you think about sourcing that capital and making sure the partners are the right fit?
Alexandria SeydelWe have several clients right now raising seed rounds, and one working through whether to raise a Series A. I think that discussion has to be framed, at least in part, through the exit lens.
There’s a lot of pressure right now — especially in AI or capital-hungry industries — to raise the big splashy Series A, make the oversubscribed round LinkedIn post. Great, I’m all for it if you actually need that capital. But there’s a lot to consider first: are these the right partners? What limitations does this put on your exit pathway?
I have one client who has a really nice business growing at a solid clip — I think it could exit in the $20 million range in the next year or two, and he’s still the primary owner. He’s feeling pressure from his industry where raising a big Series A is the norm. I asked him what he wants to be doing in two years. His answer was surfing in Portugal.
If you raise a Series A right now, you are not surfing in Portugal in two years. So with that in mind, is this the business you want to keep growing? Are you ready to bring in people who have real influence over how you sell, who you sell to, and for how much? Your timeline gets extended and your decision-making authority gets diluted. Maybe the Series A is right because you need the capital to grow — but even then, does it have to be a $50 or $100 million round? Could it be $10 million? Even the size of the round affects the cap table, the governance, and ultimately the exit.
Frazer RiceHave you had the difficult situation where someone is presented with an offer that mixes cash and stock in the acquiring company — and you’re looking at it thinking maybe they should push for all cash, or maybe they should walk away entirely?
Alexandria SeydelYes, and I’m very comfortable in that conversation. My advice almost always starts the same way: get as much cash at close as possible. Reduce the earnout tranche.
A lot of deals come in structured across three buckets — cash at close, earnout, and rollover equity in the buyer. I’ve seen deals close where five years later that rollover equity is worth zero. So I walk every owner through this exercise: if the earnout and the rollover equity both go to zero, are you completely comfortable walking away with just the cash at close? If that feels okay, then we can dial those other numbers however we need. If it doesn’t feel okay, then we need to ask harder questions — do we need to grow more first? Do we need to negotiate different terms? Do we have multiple LOIs with different structures we can compare?
The institutional buyers will always tell you the rollover equity is going to 10x. Always. And as the lawyer, I used to be delivering that reality check at the 11th hour when it was almost too late. Now that I get to work with owners before that process, I can prime them early: rollover equity, in our minds, is always worth zero unless proven otherwise. If it 10x’s, that’s the cherry on top — incredible. But don’t build your retirement plan around it.
Frazer RiceAre you part of the process of generating buyer interest? I imagine it’s often industry-specific — there are people who understand the space and know the players. But how do you get a few LOIs on the table so it doesn’t become a fire sale?
Alexandria SeydelWe consciously made the decision not to become brokers or registered broker-dealers, for two reasons.
One, I want to stay fully aligned with the owner’s actual goals. This has happened: we started working with a woman, began building up her people and processes, and 18 months later she said, “Wait — I actually have more freedom now. I’m operating at a higher level because the business is starting to run without me.” The work we were doing to prepare for a sale also just made the business more enjoyable to run. She decided to grow for another year or two instead. Because our compensation isn’t tied to a success fee at closing, we can fully support that decision.
Two, deal brokers and investment bankers are often highly industry-specific. A banker who knows your manufacturing sector deeply is going to be more effective in market than we would be. So we refer our clients to multiple specialists in their industry, help them assess fit, and — because I’m trained in reviewing those contracts — help them understand what they’re actually agreeing to in the engagement letter. Then once that team goes to market, we stay on the owner’s shoulder throughout the process. My consistent message: fit matters. Trust your gut. If this buyer doesn’t feel right, honor that, and let’s figure it out before we’re at the closing table.
Frazer RiceHow do you tell a founder or family-owned business that the family dynamics are a value detractor? If there’s conflict — someone looking for income while others want to grow, every decision a fight — I imagine buyers pick up on that quickly.
Alexandria SeydelIt starts with being human first. Understanding the people behind the business, understanding the family dynamics. A lot of M&A professionals have no interest in going there. My co-founder Kim Wozny and I both actually like that part. We like knowing the people, understanding the dynamics, understanding when someone has a mental block around part of their business because of a fear mindset, or when pressure from a family member is pulling them in a direction they don’t want to go.
Being willing to dig into that — as a third-party neutral advisor working for the founders first — is part of what we do. And on the process side, if you have four siblings who own a second-generation business and three want to grow while one wants to sell, how do you show that fourth person that now isn’t the right time? You give them more information, more context, more understanding. And where necessary, you wrap enough process and procedure around that situation so that a buyer can see that this one person being out of alignment doesn’t constitute a major risk to the business.
Frazer RiceDon’t give the buyer a reason to say no or pay less. If you can batten that down ahead of time, it’s worth it. As we wind down — what’s a short checklist for founders who are thinking about selling? What are the first steps to assess their readiness?
Alexandria SeydelFirst and foremost: it’s never too early to start thinking about it. Even just getting clarity on your personal vision — what you want out of this — helps direct major business decisions as you grow. We have two clients right now considering joint ventures. One is actually moving forward with a new 50/50 partner; the other decided against it. They’re on very different exit timelines, and those exit pathways are a large part of why a joint venture may or may not be the right choice for each of them.
I’m always happy to just talk to founders about how they’re thinking about this, even without any formal engagement. I want more owners thinking about exit earlier — it only does them a massive service.
And one practical exercise I love: the Europe Test. Imagine you’re going to Europe for three weeks, somewhere with no cell reception. Who calls you first? What processes break? What sits in your inbox undone? It’s a more fun version of the “hit by a bus” question — and it’s a really useful early diagnostic for where the business still depends too heavily on you. Start uncovering those things now, so you have the time and runway to fix them.
Frazer RiceTerrific stuff. Alex, how do people find you and your firm?
Alexandria SeydelI’m Alexandria Seydel — last name spelled S-E-Y-D-E-L. You can find me on LinkedIn, where I’m active all the time, or look up Ripple’s Edge Advisors. Reach out via email or LinkedIn message. Even if you’re just starting to think about it, I love having that conversation.
Frazer RicePerfect — that will all be in the show notes. Thank you for being on.
Alexandria SeydelThank you, Frazer.
https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
ALTERNATE TITLES
The 5-Year Exit Strategy Blueprint: Preparing Your Business for Sale
Getting The Business Ready to Sell
How to Maximize Business Value Before Selling
KEYWORDS (GETTING THE BUSINESS READY TO SELL)
business exit planning, M&A, business valuation, succession planning, sale readiness, owner dissatisfaction, deal structuring, growth strategies, capital raising, exit readiness assessment, getting the business ready to sell,
April 24, 202635 min
Bringing Simplicity Back to Investing
In a world of noise and distraction, there is a trend in “Bringing Simplicity Back To Investing.” RICK FERRI and I talk about why it’s important for investments and why it’s important for individuals. You’re going to leave here understanding a new framework for looking at your investment portfolio and hopefully bring some peace of mind as you go forward.
https://youtu.be/8EFnt_UTjEA
Rick Ferri has been a good friend to the podcast. He shares his insights on simple investing, emphasizing the importance of clarity, discipline, and understanding the core principles of investing. He discusses the pitfalls of complexity, the value of index funds, and how to maintain a disciplined approach amidst market noise.
https://open.spotify.com/episode/743dxOLLgZjUzKszZo4Owy?si=57mqK1ZmQ0a7LPdcwVoQ-g
Keywords
investing, index funds, simplicity, portfolio management, financial planning, discipline, asset allocation, tax efficiency, global growth, investment philosophy
Key topics
The philosophy of simple investingThe stages of investor learning: darkness, enlightenment, and simplicityThe importance of cash flow and intrinsic value in investmentsAsset allocation based on liabilities and time horizonTax-efficient investing strategies for taxable and retirement accountsRisks of alternative investments and private equity in retirement plansDiscipline and automation in maintaining investment strategies
Chapters of “Bringing Simplicity Back to Investing”
00:00 The Philosophy of Simple Investing07:03 Stages of Investment Understanding11:19 Financial Planning and Purpose17:57 Implementing a Simple Portfolio23:01 Discipline in Investing30:46 Navigating Complexity in Wealth Management
Resources
Rick Ferri’s Website – https://rickferri.comBogleheads.org – https://bogleheads.orgIndex Fund Book by Rick Ferri – https://www.amazon.com/s?k=Rick+Ferri&ref=nb_sb_noss_2
Website – https://rickferri.comTwitter – https://twitter.com/RickFerri
Skeptic’s Guide to Investing
Outline: “Bringing Simplicity Back To Investing”
Introduction: Three parts to simple investing: Philosophy, Strategy, Discipline
Part 1: Philosophy: Overview: Embrace Simplicity – the Education of an Index Investor – 4 stages
1: Born in Darkness (who you ask, chasing returns, naive research)
2: Finding Enlightenment (measure, compare, enlightened)
3: Complexity Traps (slice’n dice, factors, the fallacy of perfection)
4: Embrace Simplicity (global equity, specific fixed-income as needed)
Part 2: Portfolio Strategy Overview: Making the Philosophy Work for You
5: Setting Goals (family – culture, career – taxes, risk tolerance)
6: Managing Risk (three ways to allocate assets: required return, risk avoidance, cash-flow)
7: Tax Management (three account types, asset class tax, tax avoidance)
8: Investment Selection (ETF vs fund, balanced funds & TDFs)
Part 3: Discipline: Overview: Implement, automate, stay the course
9: Implement fully (consolidate, tax issues, lump sum vs DCA)
10: Maintain regulatory (automate new, rollovers, TLH)
11: Adjust as goals change (accumulation vs distribution, tax situations, legacy)
12: Stay the Course (recommit occasionally, continue ed., conferences)
Transcript of “Bringing Simplicity Back to Investing”
Frazer Rice (00:00.962)Welcome aboard, Rick.
Rick Ferri (00:02.3)Well, thank you for having me.
Frazer Rice (00:04.258)Well, thank you. First of all, want to thank you for a kindness you showed me way back in time and having me on the Boggleheads podcast. It was probably worth at least 25 % of my book sales and it was a lot of fun to do and never forgot it. So it took a while, but here we are back on my podcast. And what I want to do is go through a little bit about really the three parts to simple investing, which I think is something, especially now with the proliferation of alternatives, a lot of noise with crypto.
That sometimes we kind of lose sort of the forest for the trees as far as what’s the right things to be thinking about in terms of an overall investing philosophy sort of embrace. And so maybe let’s start with that. How do you think about the parts to a good investing thesis and what is your overall worldview on that?
Rick Ferri (00:55.804)So I’ve been in the investment advisory industry now for 40 years. And what I have learned is that the simpler you can make investing and the simpler you can make the portfolio, the better for you, the better for your family, the better for those who will inherit your portfolio. Don’t make it complicated.
Complexity is just job security for those people who are selling you things and trying to manage your money. And in the end, you don’t benefit from that. They do in the form of fees. And if you just had a simple portfolio of a few good index funds and maybe some individual securities, you’ll be much better off and your family will be better off in the long term. And that’s the philosophy of simple investing.
Frazer Rice (01:50.947)Mm-hmm.
Rick Ferri (01:53.208)The second part is a strategy. How do you go about doing this, particularly if you’ve had a complex portfolio? And the third thing is discipline, which is how do you stick with simplicity as an investment philosophy?
Frazer Rice (02:06.318)Sure. and without the second two, it’s great to have high-minded thoughts and so on, but if you can’t do it, it’s all for naught, and then if you can’t stick with it, then the best laid plans just kind of go asunder here. So let’s go back to the philosophy for a second here, and as you think about, it’s almost like the life cycle of discovery and learning about how these things work. How do you think about that from an ARC perspective?
Rick Ferri (02:12.561)Ha ha.
Rick Ferri (02:36.05)So generally when you’re new to investing, you’re going to ask other people for advice. I where you get that from, might be a friend or family member, maybe a professional advisor, might be coworkers, maybe you’ll just get on the internet and start searching. I don’t know, but 99.9 % of the time you’re gonna run into advice that is not very good. And the advice will be, you should put your money here, you should put your money there.
Use these 10 different funds. It’s just a lot of confusion, quite frankly. I call this stage darkness because you don’t, you you’re just investing in the dark. You don’t know. And a lot of the advice is going to be very short based upon short-term performance. So recency biased people are going to be recommending, but you know, growth stocks because the Magnificent Seven has done well in the past.
Or buy crypto because crypto went up a lot in the past and so therefore you should buy it now. And so most of the advice you’ll get in darkness is going to be recent based upon recent performance and rather than looking at it over say how should you be investing over 10, 20, 30 years and that will end up being quite different. So darkness is where we all begin.
And most people stay in darkness. They never get out of darkness because they don’t put the brain cells to work to look at how am I doing? I mean, how has that done for me? What seems to be happening in my portfolio? Really? Do I really know what’s going on? And then the ones who are very fortunate start asking questions about, what if I just
Frazer Rice (04:06.125)You
Rick Ferri (04:31.334)bought the market and bought an index fund and just got the return of say the US stock market or the international stock market and that’s all I ever did. Would I be better off? And the answer to that 98 % of the time is yes, you would be better off if that’s all that you did. And if you come to this realization, I call it the second stage, which is enlightenment, where you now realize that, okay, all the stuff I’ve been doing may have been okay.
I’ve been moving in and out of things, but now I need to start looking at just buying the market and holding it for the longterm. And that’s enlightenment. But for some people, it doesn’t stop there. And they start to dig into this idea of indexing. When you start doing that, it’s good that you’re learning, but you’ll start running into a whole lot of noise.
That is alternative indexes, enhanced indexes uh… explore strategies all of these things that you’re going to take this nice simple concept called indexing and make it complicated again.
So you start adding all these things to your portfolio because it has the word index in it or maybe the word passive in it and uh… advisors are notorious for doing this it’s called complexity for job security
Frazer Rice (05:39.148)Right.
Rick Ferri (05:54.066)Basically, are, you know, you take the idea of indexing and you just add a lot of things all around the edges of it and you make a simple portfolio complicated. So the third stage of this process of simplicity is complexity. In other words, you’ve made something simple complex. Okay, so the last stage is
Frazer Rice (05:54.221)You
Rick Ferri (06:18.544)Simplicity. That is that you realize this is going on. You realize that all the stuff that you’re adding to your portfolio is just making it all complicated again. And that the people who are benefiting from this are not you, but the people that are selling you all this stuff. And you say, that’s it, I’m done. I’m going back to my second epiphany, if you will, which is simplicity. I’m just going to go back to a simple portfolio of a few broad index funds, US stock market index fund.
An international stock market index fund that covers the whole market and a couple of bond funds, municipal bond fund and maybe corporate bond funds or treasury bond funds. And you could use index funds for those as well. And it’s a really low cost, very tax efficient and very simple.
Frazer Rice (07:05.953)A couple of quick asides here. The first one is for people who are coming into this in and they’re in the darkness, but they are informed maybe from the TikTok world or Robin Hood or Kal-She or these or these betting orientations and distinguishing between betting and investing.
How do you think about that and kick people over to the positive side of the force so that their emergence from the darkness into the enlightenment and simplicity doesn’t take them in a place where they really touch the stove in a bad way and have a bad experience that’s simple but bad.
Rick Ferri (07:32.988)Right, okay.
Rick Ferri (07:51.484)So there’s a concept called intrinsic value. You may have heard Warren Buffett speak about this. Well, you want to buy things that have cashflow. Bonds, for example, have cashflow. They pay interest. Stocks have cashflow. You have companies that are going concerns. They earn earnings and pay dividends. They buy back stock and they reinvest money. So you can value these things based upon these cashflows.
Real estate has cash flow, it pays rent, or maybe you own timberland that you can cut the wood or you own a farm where you can harvest or lease it out. mean, these are cash flows. So the first thing that I have for cut in investing is cash flow. How do my investments generate cash or will generate cash later on down the road?
That’s different than say buying gold or Bitcoin or currencies or commodities. Those things don’t have a way of generating a cashflow. One bar of gold put in a safe is one bar of gold a thousand years from now. It doesn’t become two bars of gold. doesn’t get little bars of gold. It doesn’t pay interest and so forth. mean, so unless you’re good at
Frazer Rice (09:12.994)Right.
Rick Ferri (09:16.966)Buying low and selling high, you can’t really expect to make anything other than maybe the inflation rate. And with commodities, you actually earn less than the inflation rate. Gold has earned a little bit more than the inflation rate. Where Bitcoin is going to end up, I have no idea. But the speculative assets are the ones that usually don’t have any intrinsic value. People are just betting on price because that’s all you have. I
f price is going up, let’s buy it. Because the price went up. I don’t know where it’s going, but the price went up, so let’s buy it. And maybe someone dumber than us will buy it at a higher price from us, and then we can make money. But I mean, you have to trade these things. And what information do you have? None, really. It’s very difficult to come up with information that the market doesn’t already have. And you’re not a professional trader. So you might get lucky. I mean, people do get lucky. You you can flip a coin.
And pick heads 10 times and if it comes up head 10 times it doesn’t mean you’re a good coin flipper you’re just lucky and so you can get lucky and you can make money doing this but it’s not a long-term investment strategy to do that it’s best to buy things that have cash flows or will have cash flows in the future.
Frazer Rice (10:30.175)As I like to tell people, you not only have to be right, you have to be right twice, and then you have to be systematically right twice in order to make a living out of it. even professional traders struggle at that. And to think that you’re going to be better equipped than a lot of those folks is folly. And so I try to talk people out of that whenever I can, because I think…
Rick Ferri (10:35.42)Correct.
Frazer Rice (10:58.101)It’s just very difficult to play in that space and have that turn out to be a success. Okay, so we kind of have some ideas here around the philosophy and sort of the idea of, you know, sort of garnering luck versus skill and those types of components in that portfolio strategy, that second phase, maybe take us through that a little bit and how you take a good philosophy of simplicity and make it work for you.
Rick Ferri (11:22.18)Right. So this gets into a little financial planning at the beginning of it because you can’t invest without a purpose. I you have to have a reason why you’re investing. It might be to pay future liabilities such as college for your children or retirement, or maybe you want to leave a legacy or maybe just trying to build wealth for the family, whatever it is. I mean, you have to have a purpose. And so what is the purpose? What are you trying to do?
And you have to look at your life and you have to say, are my liabilities? What are my short-term liabilities? Do I want to buy a house? Or do I want to send my kids to Ivy League school? Do I want to retire early? And what are my liabilities? And sometimes it involves other family members. Maybe you have parents who need your help or siblings who need your help.
So that’s a liability. The first thing you have to do is look at what are my liabilities? And included in that is how much you want to leave to your children. I often ask people, okay, you’ve got $10 million. How much do you want to leave to each of your three children? And they don’t have any idea. I said, do you want to leave more than 10 million or you want to leave less than 10 million? And a lot of people would say, well, they’ll get what’s left. Well, that changes the whole concept of investing if they’ll get what’s left.
Frazer Rice (12:43.318)Sure.
Rick Ferri (12:43.634)Versus, yes, I want to leave each of my child five million dollars when I die and I’m starting with ten. Okay, well that changes how you invest your money. So these are the liabilities. So that’s where you start with. And then you start looking at well, what are the short-term liabilities and what are the long-term liabilities? And long-term liabilities can be funded with equity. Meaning things that are ten years or longer out. I usually I tell people anything you’re to be spending your money on between say,
Now and 10 years from now probably shouldn’t be in equity. You’ll be getting dividends and interest from your portfolio, which is fine. You could just spend that money. But in addition to that, I big chunks of money that you might be spending to buy a vacation home or whatever it is really should probably not be in equity. But the money that’s going to be not used for 10 years or longer, 20 years or maybe ever in your life, that can be in equity. don’t differentiate that first.
A lot of times asset allocation, that’s what we’re talking about, starts with, well, what do you want between stocks and bonds? What do you want your portfolio to look like? What percentage in stocks and what percentage in bonds? I don’t think you really get to that number until you know when you’re going to be needing the money. If you’re going to be needing the money 10 years out, fine, that money can be in stock. So that would allocate a portion of that long-term money to stock and that might be a percentage. Okay, so that’s what we start with.
A real basic look at who you are and what do you need and when are you going to need it and what are you trying to do for your heirs. And then that leads to an asset allocation between stocks and fixed income. The stocks again, I’m not investing in any stock money in liabilities that I have in the next say 10 years. So it’s long term. Okay.
Now we have to look at the stock side. That’s the easy stocks. Stock investing is easy. I quite quite frankly, I’m working on a book right now about this, but stock investing is very simple. It’s much easier than fixed income and bond investing. Stock investing is simply we buy the global equity market. We’re just trying to buy the growth of global economic growth, global GDP growth. We’re trying to capture that, which has been going on.
Rick Ferri (15:08.594)Fairly steady for about the last 250 years and continues to be that way as more and more countries shift more towards capitalism and away from fascism and communism and so forth and realizing that capitalism is the way if you want to take care of your people and you want to increase standards of living all around the world, it’s done through capitalism. much a fact of life. Capitalism works. Well, I’m well.
Frazer Rice (15:31.185)I think many can agree with that, although it might not be popular here in New York.
Rick Ferri (15:37.425)The reason New York existed was because it was a port for capitalism at first. So I mean, is the financial capital of the US still is New York. So you could disagree with it because you live in New York, but you’d be in a minority and you’d be outside of reality and history as well. But the idea is that it’s all I’m trying to capture this global growth of…
Frazer Rice (15:41.686)That’s right.
Frazer Rice (15:55.648)Exactly.
Rick Ferri (16:03.026)Global economic growth, which is about 2 % per year in real terms. So if I get from equity, if I get the inflation rate and I get 2 % real growth and then I get about a 3 % dividend yield and that comes from both cash dividends and then buybacks, we’re looking at about a 7.5 % expected return from global equity. And that’s good enough. I mean, that’s all I need on my equity side. I’ll be outperforming inflation by about 5%.
I’ll have to pay some taxes, but I’ll still have an actual real after-tax return of about 3%, which is good. Okay. The rest of it then goes into fixed income. And what type of fixed income? Well, that depends on what type of account that you have and what your taxes are. So if it’s in a taxable account, it could be municipal bond income, because it’s probably your best bet if you’re in anything other than a 22 % tax bracket.
Or if it’s in your retirement account, could be corporate bonds. And depending what state you live in, it could be treasury bonds. But you don’t expect the treasuries or the corporate bonds or the municipal bonds really to give you much of a return over taxes and inflation. If you could pick up 1 % over taxes and inflation over 20 years or so by being in fixed income, I mean, you’re actually doing well.
So that is more of a stabilizer, meaning you don’t want to be all in stock because you can’t handle the volatility of the stock market. It goes up and down too much, even though the asset allocation would say, well, you should have an awful lot of your money in stock because you have a lot of money that you’re not going to be needing in the next 10 years. But a lot of people can’t handle having a lot of money in stock. So you have fixed income that at least keeps up with taxes and inflation over the long term. And that becomes part of your asset allocation as well. So it’s kind of how you
This is what you do first before you go out and pick any index funds. You have to go through this process.
Frazer Rice (18:00.116)And then as part of that, I spend a lot of time basically all day, every day thinking about the tax management side of things and helping people understand their appetite for volatility and how that impacts their long-term goals and things like that. The creation of these buckets to understand where you are in your tax situation and where you’re going to be, that can have a pretty significant impact on how things do.
And from your perspective, I that’s really just, that’s a function of projecting out the purposes that you described before with your current situation and then the vehicles with which to invest in.
Rick Ferri (18:38.226)Right. And you’re not trying to hit the ball over the fence here. I mean, you’re just trying to get your fair share of the returns that are available to everybody. And through index funds, and this is where index funds come in, you can get exactly that. I mean, you could buy a global equity index fund, a global equity, covers the entire globe for a few basis points, 0.05 % per year fee. It’s very tax efficient. And that wasn’t the case.
30 years ago, 40 years ago, but it is now. that’s the way you should do this. You don’t want to leave out all these ideas that you’re going to go out and hire people who are going to outperform that because they don’t. A vast majority of them don’t.
Frazer Rice (19:21.963)And so the machinery to implement these portfolios, ETFs are sort of standard tax-efficient ways to do things. Mutual funds distribute gains at the end, which is sometimes a nasty surprise for people who are learning about this. Maybe take us through your analysis on how to implement this index investing in a way that stays simple and tax-efficient and at the same time helps you take advantage of what’s out there.
Rick Ferri (19:52.883)So we have to divide up the world between your taxable money. Again, you already have a portfolio. So you have all these legacy assets in a portfolio, in your taxable portfolio. Then you have your retirement portfolio, 401k, 403b, 457 IRA, rollover, Roth IRAs, tax-free portfolio. So you have to look at taxes first.
To implement a…simple portfolio say in a 401k if you have access to a target date index retirement fund like a Vanguard or an iShare or a State Street very low cost Fidelity has one too but very low cost index target date retirement fund this does it all for you you don’t have to do anything you just have to buy one fund based upon what the asset allocation is underneath the hood of that particular fund.
How much in stock, how much in bond. That’s all you need to do in a 401k. You could roll your own in a 401k by buying individual index funds like a US stock market index fund, an international index fund, and say a bond index fund. So you could do your own allocation if you wish. But a target date fund works really well there.
In a Roth account, you probably just want to have equity because there’s no tax in a Roth account. So you want to get maximum growth out of that account. So I would you look at the Roth account and I’d say, well, I’ll just buy the global equity index fund and my Roth account. And that’s it. All I have. So you’ve got your retirement accounts, which are target date fund. Very simple. You’ve got your Roth accounts, which are just a global equity index fund. And the only thing you need to worry about is your taxable account.
Taxable accounts always have issues because people will come in and they will have this list of stuff that they already own and guess what there’s a lot of embedded long-term capital gains in there and if you just sell it and go to a index portfolio you may not be doing the clients a good service because they’ll pay a tremendous amount of taxes and if they’re over 65 they’ll have to pay more for medicare ermor they’re going to lose their over 65 deduct i mean lots of bad things happen when you just sell out of a taxable account
Rick Ferri (22:04.722)So there you’re going to be a little bit more tactical. know, you’re going to wait. The market will give us some opportunities to trade out of some stocks or some investments that may have losses. So you can then take those losses. You could sell other things to that have some gains to offset the losses. And I mean, you may never get out of everything that you’ve got in a taxable account. But the idea is to have this portfolio out there of say, a US total stock market index fund and a municipal bond fund.
That you want to move towards. So as you’re selling these things off, you’re just putting the money in a US total stock market fund. And the reason I say US total stock market in a taxable account is because they’re so tax efficient. The dividend yield is down about 1.2%. They don’t distribute capital gains in an ETF. And that’s a great fund for a taxable portfolio. But you just can’t sell everything and buy it. You’ve got to crawl your way out of what you currently have.
Frazer Rice (23:05.715)No, you have to do it thoughtfully or else you create hits that are unnecessary. So as we segue to the discipline portion here, one thing that’s popping up is the, I think the discipline to stay simple. The world out there, the US in particular, is making retirement accounts safe for alternative investments like private credit and private equity.
Rick Ferri (23:10.256)Right.
Frazer Rice (23:31.211)I just bristle and shudder because I think there’s a level of complexity and illiquidity that is misunderstood and it is going to be difficult, nay impossible, to properly educate people on where those things sit in the asset spectrum to the point where they justify their fees or anything like that. Maybe take us through what you think on that as we get to the discipline portion of how you sort of stay the course with this mindset.
Rick Ferri (24:00.924)Well 401ks are allowing these private equity investments and private debt investments in, but I personally have not seen any of my clients and I have a lot of clients and I charge an hourly fee. So I’m not trying to sell anything or manage anybody’s money, but nobody’s asking for these things. where, where are they getting the idea that they should own them? Well, they’re getting from the people that were selling them, right?
The people who are making fees from them. I haven’t seen any useful data that says that these things actually enhance your return. Alpha goes to the manager. I say that over and over again. If these things actually produced a higher rate of return than say just a corporate bond index fund, you’re not going to get it.
It’s going to go to the advisor, it’s going to go to the manager, and all you’re going to do is take the risk. You’re going to take the risk and they’re going to get the excess return in the long term through fees. They don’t make any sense. You don’t do it. It’s just the rehash of active management and mutual funds, which has already been dismissed as not producing anything for you, the investor. It only generates fees for the people in the investment industry.
This is just another iteration of that and we’ve already seen some cracks. Isn’t that what Jamie Dimon said? What are they cockroaches? I think is the word that he used in the private equity market. And yeah, I mean, this is not new. This is just a repackaging of ideas just that now they’ve been allowed to go into the 401k market. But you have to ask yourself why haven’t they been allowed to go into the 401k market for the last 40 years if they’ve been so great? It’s because the SEC
Frazer Rice (25:31.978)Right.
Rick Ferri (25:58.703)The Department of Labor said, no, we’re not going to allow these things in there. you give people enough rope to hang themselves. They’re not going to hang themselves, by the way. Somebody else is going to put the noose around their neck. And that’s the advisors who are doing that.
Frazer Rice (25:59.499)Department of Labor and right.
Frazer Rice (26:19.066)And I mean, a different podcast probably, but it’s something where the liability really is going to shift to the planned sponsors. I don’t care what happens and you know, they’re going to present these things and something’s going to blow up. And it’s like, know, you may you gave me the option and they’ve already those lawsuits already already proliferate. OK, so back to discipline a little bit here. What should people be doing in order to make sure they can carry carry out the.
Rick Ferri (26:39.367)Yeah.
Frazer Rice (26:47.147)What they’re doing in a systematic way and keep themselves safe from being distracted by all this noise.
Rick Ferri (26:52.86)So again, that’s why we start out with the philosophy. You have to believe in the philosophy of simplicity and simple indexing. You can’t just jump to it because some TikTok video said buy index funds, okay? If you’re just jumping to it that way, then you’re not gonna have the discipline to stick with it because it’s just another phase or fad or whatever in your mind. You don’t really truly understand.
Frazer Rice (27:14.346)Mm-hmm.
Rick Ferri (27:22.32)Why you’re doing it this way. So it gets back to the philosophy. Really got to understand the philosophy and why this works better than 98 % of everything else out there over your lifetime. And then you create the strategy for yourself and now you’re working towards completing that. Again, in the retirement account it’s done quickly, but in your taxable account it could take a while.
The discipline is while you’re getting your portfolio in line, the first thing you need to do from a discipline standpoint is actually do it. Actually go to your 401k and change what you’re investing in. Because so many people will do the strategy, but it never gets actually implemented. Or maybe it gets 50 % implemented. It never gets old.
It doesn’t, I don’t want to say never, because I have a lot of clients who do fully implement it, but I also have clients that I’ve given them the plan and three years later or five years later they come back and they haven’t done anything. Okay. And so I say, you need to implement the plan. Nothing has changed. So you got to, the plan first off has to be implemented fully. And then once it gets implemented fully, it’s a lot easier to maintain it.
But if it never gets implemented fully, then of course you can’t maintain it. So implementation of the plan fully is the first discipline, the first part of discipline. And then once that’s done, maintaining it. In other words, not being drawn off course. Yeah, it’s fine to say, the price of oil is gonna shoot through the roof because what’s going on in the Middle East, so I’m gonna buy an energy index fund. That sounds like something I should do.
No, it’s something you could think about. Something might be interesting, but it’s not something you should do. So discipline transcends the urge to do things. In other words, like John Bogle said, don’t just do something, stand there. And that takes more going back and remembering why you have this philosophy, going back and looking at the data.
Rick Ferri (29:46.151)going to the right place to find information. And I’ll mention the bogeyheads.org website to go back and remind yourself why you’re doing this. If you’re gonna stick with it and these things help you stick with it. The more you automate things too, the better it is. Like we’re in a 401k just automatically invest in the target date fund and don’t do anything else. So automation helps you as well.
Frazer Rice (30:05.736)Hey, hey.
Frazer Rice (30:14.109)No question, if you can take these things out of your own hands in many ways and delegate it out and it happens automatically, just a chance of success on that front. And then if life intervenes and things need to be adjusted, you deal with it at that point and not have CNBC or the world news whipsaw your viewpoint on these different things.
So as we wind down here, just talk a little bit about the service that you provide, sort of these larger family office clients, because I think in a lot of times they gravitate toward complexity, they gravitate toward FOMO investing and how you help to center that back to this worldview so that they get where they’re going at scale at sort of that ultra high net worth world and remind them of you how they got there and how to not be how to not leave by by getting cast aside into these different whirlpools that are out there
Rick Ferri (31:13.778)That’s a great question. So you got to pick your advisors well. So some of my clients have a net worth over a billion dollars. I have several clients that have several hundreds of millions of dollars and believe me,
They have simple portfolios, total stock market, total international municipal bonds. It’s all they have. And it may seem strange, but they don’t have these limited partnerships that you can’t get out of or syndicated deals that may sound good. I say to them, you don’t have enough money to own those, meaning that if you’ve only got $100 million, you’re just chump change to the Goldman Sachs of the world or the Morgan Stanley’s.
When it comes to who’s going to get the good deal on a the next private equity deal or venture capital fund. You’re the person they sell the leftovers to. I know it’s hard to people to accept this. They think they have a lot of money if they have a hundred million. But the fact is they don’t. I mean, if you’re not sitting on five, ten billion dollars, you’re not going to get preferential treatment. You’re going to get you might get lucky.
Just like everything else, the coin flip idea, but most of the time you’re not going to end up coming out ahead. That’s not the way they make you feel when they sell you these things. They make you, even if you had a million dollars and your Wells Fargo broker is trying to sell you some limited partnership, they’re going to make it feel like you’re very special and that this is a very special deal that is just for you.
Frazer Rice (32:46.505)You
Rick Ferri (32:50.322)And that’s how it’s going to be sold to you. But in the end, when you look at your performance and you say, I want to get out of this thing and you can’t, you realize at that point that maybe you shouldn’t have done it to begin with. And I’ve had experience going back 30 years working with some of the very largest families in the country, some magnificent seven IPO families, and they all want to get back to simplicity.
They want to get rid of all of the stuff that they had gotten. And it’s true. And it’s better for estate planning as well because you need to transfer these things eventually to somebody else’s name.
Frazer Rice (33:35.785)you’ve triggered me. I’m dealing with this on multiple levels, on multiple different things, and I’ve had to be trustee on some of the complexity and sort of sit Indian style and try to own your way through it. It’s brutal. So.
Rick Ferri (33:53.81)Wouldn’t it be so much nicer just to have, let’s say, a single total stock market ETF to have to deal with rather than all that other stuff?
Frazer Rice (34:01.807)No question. OK, so as we wind down here, how do listeners and watchers find you?
Rick Ferri (34:09.478)Well, they can find me at Rickferri.com. I’m not currently and I won’t be taking on any new clients. I’m sorry for that, but I have a set clientele and that’s all that I am working with and I won’t be expanding my clientele. But there are other people that do this that believe in what I do. And you can go to Rickferry.com and you could find their names there. But me personally, you can find me on Rickferry.com. I’ve written several books about this. I’m writing another one.
And but I apologize that I’m not off the market as far as hiring me personally.
Frazer Rice (34:45.645)I love it. But at the same time, your books and your other ways that get out there, they are on RickFerri.com. So we’ll have that in the show notes. In the meantime, Rick, thanks for being on.
Rick Ferri (34:52.07)Yes, exactly. Thank you.
https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
April 15, 202628 min
DIGITAL ASSETS ESTATE PLANNING
This interview explores the critical importance of managing digital assets in estate planning, highlighting the challenges of digital inheritance, account access, and cybersecurity risks. TATYANA THURSTON and NATALIA PARKER share insights on creating effective digital estate plans, tools, and best practices.
https://youtu.be/2N56L51cD6Q
https://open.spotify.com/episode/01ScInrdux6UOQ0G1kPzNF?si=uiCizZbOTEisa9PJ_D_S5g
KEYWORDS:
Digital assets, estate planning, digital inheritance, cybersecurity, online accounts, digital executor, wills, estate law, digital legacy, digital estate management
KEY TOPICS
Digital assets definition and scope
Challenges in digital inheritance and estate planning
Tools and strategies for digital asset management
Legal and cybersecurity risks in digital estate planning
Guest Name
Tatiana Thurston and Natalia Parker
Sound Bites
“Biometric security doesn’t work after death.”
“Planning ahead saves hundreds of hours and pain.”
“Domain name issues can take months to resolve.”
Chapters
00:00 Introduction to Digital Assets
01:28 Understanding Digital Assets and Their Importance
04:14 Challenges in Estate Planning for Digital Assets
09:17 Navigating Access and Security Risks
13:22 Creating an Inventory of Digital Assets
18:21 Preparing Executors for Digital Asset Management
24:40 Resources and Tools for Digital Asset Planning
GUEST RESOURCES
DEXITPLAN
TRANSCRIPT
Frazer Rice (00:01.146)Tatiana and Natalia, welcome aboard.
Natalia Parker (00:04.206)Thank you.
Tatyana Thurston I Dexit (00:04.211)Hi, thank you for having me.
Frazer Rice (00:05.966)We are, this is a new frontier for wealth actually. You are the first two person interview I’ve done so far. So it looks like the technical issues seem to have gone away. That’s great. But we’re gonna talk about something that I think is the driver for your new company and something that’s important to me because when I’m advising people around a lot of different topics, either estate planning wise or wealth management wise, the digital asset question comes up and.
You’ve formed this new company. Tell us a little bit about that and more importantly tell us the problem that you’re trying to solve around digital assets
Tatyana Thurston I Dexit (00:40.83)Okay, so I’ll first start with what is a digital asset because there’s a lot of different definitions out there and a lot of people have different concepts of what it might mean. of all, because crypto is in the news quite a bit, it is not just about crypto. Everybody has digital assets because basically if you are logging into an account and it is storing data, you have an account that has assets online and it could be monetized.
It could be social media, which means that the information that’s there is very personal to you. It could be that you have reward points you’ve accumulated. There’s all sorts of types of assets that are out there and there is a pain point problem. Let’s die down.
Natalia Parker (01:28.462)Yes, and we started actually, it was interesting, Tatiana just went through the process of writing a will and she will tell about it. I went through a divorce where we had online business and it was really, really hard to trace all those online accounts because I had no understanding how many we had and what to do with them and how even to find them. And Tatiana wrote a will.
Frazer Rice (01:54.67)Yeah, no. so just to put a finer point on that, it’s not only the monetary assets and the social media accounts and everything that basically requires a password to get into it probably in this day and age.
Natalia Parker (02:10.252)Yes, and I can tell you more than I lost pictures of my family from my daughter’s birth to age seven because I didn’t think that the iCloud password and iCloud identity gone through a divorce. Yes.
Tatyana Thurston I Dexit (02:10.336)That’s all.
Tatyana Thurston I Dexit (02:26.88)So she can resell for it. Yeah.
Frazer Rice (02:26.992)Yeah, and a very painful thing to go through. so, Tatiana, as we sort of look at that example and make the definition a little bit even more in depth, how else do you sort of think about that in terms of the roles that are played from a Will’s perspective?
Tatyana Thurston I Dexit (02:49.366)So from a will perspective, you have two kinds of entities. You have things where business owners have created online accounts where their business is running off of certain platforms. And you also have a personal side aspect. And it may be an influencer, it may just be your personal account. The thing is that we’re dealing with a problem of immortality.
And this means that these accounts remain open, active and online, ready for hackers and ready for now, today, AI to continue the trajectory of that account because they’re making money off of the data that we’ve put online. So we actually have two things to look at. One is from the business perspective and how do you transfer a business over? Because maybe you’ve built a platform for 10 years on Facebook, right?
You have a following which is important to your base. Maybe you’re just a mom and you’ve put all your baby pictures on there, like Natalia, and then what is the loss? What is the impact of that loss? And both are really difficult on families. So estate planning means that we actually need to be looking at these accounts, we actually need to be planning for these accounts, because down the line, it’s gonna be a heavy impact, whether it’s sociological, emotional, or monetary.
Frazer Rice (04:14.552)So as we think about this little bit further, the concept that these accounts are going to live on beyond the life of someone who created them. Maybe dive into that a little bit, because I imagine you not only have points of risk, certainly during the lifetime, and someone hacking in and pillaging your bank account or otherwise maybe blocking access or something like that, but what happens when someone passes away? How do those risks translate to the people who are inheriting these properties?
Natalia Parker (04:45.258)Okay, let’s talk about it. We have those certain pain points. The first one, when somebody dies, the executor or administrator, they don’t know what is existence. They don’t know what kind of accounts the person had, what they wanted to do with those accounts. That’s a first problem because they don’t know even what banking, where the life insurance, did they have Venmo because they don’t have access to phone.
The second one, didn’t know what the person wanted to do with that account. Did they want to close, transfer, memorize it? They have no clue. The other one is authority as an executor doesn’t mean that you will get automatic access to the account. Many people think that yes, it is. No, for Google it doesn’t matter. Unless you were appointed as inactive account manager. The same for Apple.
Frazer Rice (05:48.68)I was going to say those annoying terms of services agreements that no one reads and you click so that you get, you move on with life and get into your accounts, that’s where some of these details are buried. And the intersection between that and maybe what we call estate law and how an executor works, that’s where the friction takes place.
Natalia Parker (06:09.43)Yes, I agree and many people don’t even know that that feature exists like legacy contact for Meta and Apple or inactive account manager. Otherwise, when you look at the hierarchy online tool, we call it Castonian tool, outweighs everything what you have in wheel. If the online tool wasn’t enabled, then it goes what kind of language you had in wheel.
if you appointed some digital executor and if that executor was authorized to have access to all your accounts. The third one, it always default to terms of service. Terms of service for basically 99 % of each company says do not give access.
Frazer Rice (06:56.09)So if you were stuck and you didn’t do anything and you relied on the terms of service, you could be in a really deep set of troubles. They might delete your account, they may not allow access, or they may make it otherwise very difficult in order to access and do it. You think that the person who died with it wanted to have done.
Tatyana Thurston I Dexit (07:16.246)That’s right.
Natalia Parker (07:16.598)Absolutely.
Tatyana Thurston I Dexit (07:17.504)That’s why some of these really large companies have a custodial tool. You do have to go to certain settings within the device or within the account. And you can enable these tools so that you can either add what could be a legacy contact. It may not have the term beneficiary on it, but it’s important to be able to enact that so that these settings will allow certain access down the line.
A lot of the companies are very particular about that the larger ones have it and then a lot of them don’t so Knowing which company has the most value to you and those terms of service is really important
Frazer Rice (08:01.84).For someone who has an account that lives beyond them, there are identity and financial risks to having that. I can imagine, you know, when you put a credit card on file and, it’s auto-debated or you have information lurking out there that that’s a problem. Maybe talk a little bit about how bad that can get.
Tatyana Thurston I Dexit (08:21.517).So I think there’s a few issues on that. We all know that there are scammers and hackers. The really important stories that have come out in the past is where AI is enabling recopying your name, image, and likeness posing as you live on a video stream or live on a phone call asking for money or data or information. And this is becoming really prevalent.
This is where families, if they want to save and secure their reputational legacy. But also perhaps crypto, perhaps their banking accounts, it’s really important that they understand that they are all subject to this hacking because probably the likelihood that they have a social media account is there and that means it has public access.
Frazer Rice (09:17.636).So let’s dive into the tech problem. I can envision, and I’ve heard before, the concept of someone passes away and people can’t access the computer, the hard drive, the phone, all sorts of mechanisms that hold a lot of this data. I think you could probably extrapolate that to the cloud accounts and things like that where other information is held. How do you help people think about that?
Natalia Parker (09:28.162).Mm-hmm.
Natalia Parker (09:44.398).Two-factor authentication. It is your phone, your email, it is gateway to your estate, basically, administration. If you don’t have access to the deceased phone or email, you don’t know anything about their accounts, first of all, second of all, where all those codes are coming to, to that devices.
Frazer Rice (10:08.72).Right. And how do you fix that problem?
Natalia Parker (10:12.91).There are some settings on iPhone because we kind of everybody has iPhone some have androids but mostly it’s iPhones. Yes, you have to establish the legacy contact. You have to make sure that specific features are turned off or on like stolen device protection. If it is on, it’s basically impossible to override it.
Frazer Rice (10:20.793).Right. Beware the green text.
Tatyana Thurston I Dexit (10:24.212).Bye.
Natalia Parker (10:40.302).because if 48 hours, is it 48 or 72, Tatiana?
Tatyana Thurston I Dexit (10:44.981).Well, so what she’s referring to is that the latest update in Apple has this feature for stolen theft mode, it’s called. So this happened to us on an actual case. Someone had given us a phone and they said, can you help us? The problem was the person had passed away over 100 miles away. because Apple tracks our location everywhere we go, it’s a habitual, you know, we’re creatures of habit, right?
Same coffee shop, we go to the same store. So they know what our patterns of behavior are. As soon as it leaves that circle of trust, call it, that map of trust, theft mode can become enabled if the setting is on, which means that Apple has cut off any access to the phone. So for people who are dealing with families, let’s say, who live across state borders, this is a really difficult task for them. Because their phone is completely inaccessible because of theft mode not even because of the legacy contact.
Natalia Parker (11:51.278)8.
Frazer Rice (11:51.345)And then, you know, I’ve seen in movies and I’ve actually heard anecdotally, you know, the concept that the biometrics at play, they in a sense turn off too. It used to be you could take the phone and put it up to somebody’s face or you could take their finger and maybe get into the laptop by putting it onto the biometric reader. That world doesn’t exist anymore, correct?
Natalia Parker (11:58.594)Mm-hmm.
Natalia Parker (12:12.162).Correct. When you’re dead, the Face ID doesn’t work really well.
Frazer Rice (12:17.59)Well, and that tells you something that they can tell whether you’re dead or not. And I would not have made that comment maybe six weeks ago before we started talking about this, saying, geez, these things are getting smarter. So as we start thinking about this, we’ve sort of analyzed a couple of pain points, areas where if you’re an executor and someone’s situation comes across their desk and they say, gosh, first of all, I have to try to know.
Natalia Parker (12:19.758)Yes.
Frazer Rice (12:43.81)What accounts are out there, what social media accounts, what subscriptions, what bank accounts, what crypto, what IP, that type of thing. So getting your arms around that’s important. Then the idea of hopefully someone has been organized enough to lay out where the accounts are and how to access them in one way, shape or form. And we can get into what a good practice is on that. But then if you’re the executor slash in conjunction with the estate planner slash the client,
Natalia Parker (12:48.545)Yes.
Frazer Rice (13:13.402)How do you plan for this so that you create a real organized state of affairs for the person who has to actually manage this stuff going forward?
Tatyana Thurston I Dexit (13:22.797)So I think it’s important to understand priorities. So everyone’s different, everyone’s unique. There may be priorities that are social media based priorities where there’s a lot of crypto at stake or monetary funds, even perhaps reward points. That priority list is best done in an inventory.
Where we specialize is in the directives for this. So we’ve actually researched all these terms of services for hundreds of companies. We maintain this database so that someone can say, okay, if it’s company A, company A has three options for a directive. You can select that directive.
That means that the executor will then know exactly, this is what needs to be done with this account and this is what is of value either for the descendants, the beneficiaries, and so on. So first the inventory, but actually the directives is really important.
Frazer Rice (14:21.904)By directives, mean something maybe an addendum to the will or something like that that says these the information or the value, whether it’s monetary or otherwise, is going to be transmitted to such and such a person and given full access to it. Is that really is that part of the advice is to say, you know, for the modern will drafter, let’s say that it’s a really good idea to have an inventory of what these digital assets are.
To set out who gets what in the will so that there’s a, let’s call it a backstop, so that if you have problems with the terms of service or something like that, you have something that goes through probate where somebody opines on that and you can actually get access to it after the fact.
Tatyana Thurston I Dexit (14:50.061)Yep.
Tatyana Thurston I Dexit (15:08.565)Yeah, so there’s two points there. There’s the access part and then there’s the directive part.
Natalia Parker (15:09.313)Yes.
Frazer Rice (15:13.315)Okay.
Natalia Parker (15:13.556)Yes, there’s, yes, sorry, there is a language in the will where it’s actually specified that this is a digital executor who has the right to access all those accounts and perform all those duties.
Frazer Rice (15:32.068)Got it. so in your experience, so Facebook or Google or Coinbase or things like that, for me anyway, in the last maybe three or four years ago, to get somebody on the phone to even have any understanding of what you’re talking about was gonna be just forget it, not happening. Are they getting better at understanding these situations?
Natalia Parker (15:56.074)No, they’re not. They’re not. They don’t care. Facebook, it’s all AI. You don’t get a person on the phone in any case, Coinbase. You can, but it’s weeks of waiting for the response and they will ask you, we lost it. Can you resend it again?
All three companies you name, they do have policies.for transferring or for somebody who is dead. But it’s still very, very difficult to deal with them.
Tatyana Thurston I Dexit (16:32.069)To add to that too and I’ll give you a case example is that we had social media requests to take the accounts down. Meta of course owns both Instagram and Facebook right and the images and memories that were left on these accounts were actually harming the kids.
The request was can we close these accounts out and of course you can but Facebook interestingly enough agreed of course to close the account and even though it’s owned by Meta, Instagram said, no, these photos do not violate our terms of service. So it doesn’t mean you can close out both just because it’s Metta. It’s really, really specific and it’s really in their hands.
Frazer Rice (17:19.003)Lovely. That will warm people’s hearts that have to deal with this.
Tatyana Thurston I Dexit (17:22.143)Natalia Parker (17:22.638)Yes, it’s hard. And can you imagine we deal with this day after day, but people who have never been in this position, they don’t even know where to start.
Frazer Rice (17:34.747)So walk us through what you think a good scenario would be for someone who wants to, let’s say they have, I don’t know, a bunch of accounts, both monetary and social media and maybe miles and maybe other things, stuff like that. And they walk into a trust and estate lawyer’s office and they say, okay, I’ve got my house, I’ve got my liquid assets, that stuff trust and estate lawyers know how to deal with.
but let’s say the lawyers aren’t as facile with the digital assets. A, help the person be a better client for that trust and states person so that it’s organized. And then, let’s start with that and then I have a follow-up question.
Tatyana Thurston I Dexit (18:21.055).
Okay, I would say the first thing is that, you know, there are modern problems and we need modern solutions. And that starts with the discovery and conversation that we do have these immortal accounts online. As much as we may not want to think about it, and we can get into other stories about this, but I won’t do that now, there are reasons to enact on these accounts.
That means deleting them, transferring, closing, out data, it might be biological data. There’s a lot of data and for me that means that data is money. It may not be money to us, but it’s money to companies. And what you want done with that is your choice still. So it’s important to make that decision.
I think that any estate planning attorney who starts this conversation with their clients is already helping move the needle because everyone has online accounts, the average user has at least probably around 200 accounts by now. And that’s without a work account.
Natalia Parker (19:28.492)Yes, we developed a tool basically where we have inventory and 15-20 minutes with assigned directives and it’s prompt. Just choose the companies you have accounts with. They don’t have to remember. just, okay, I identified those companies and we already give them a choice of pre-selected, pre-vetted directives, assigned a directive. Then take these report and go to your state attorney.
Bring it, yes, bring it to them, include it into the wheel with specific language, appoint a digital executor, you’re set. Then you will just have to support it, kind of.
Frazer Rice (20:11.609)No, so then the next question, so let’s say the paperwork from a will and a revocable trust, et cetera, is up to speed and covers the authority to access these. Then let’s say the executor is not the attorney and it’s a family member or a friend or something like that and you’re giving them the honor of helping to deal with all of this stuff. What do you deliver to them to help them be prepared for that time when you pass away?
Tatyana Thurston I Dexit (20:39.479)We-
Natalia Parker (20:39.5)We give step by step directions on how to deal with each company. We give what this company has, what kind of account is that, what kind of paperwork you need, what kind of documents in what time frame. For some companies it’s three years, for matter in their terms of service it’s 28 days, but hey, you have an account for years there.
Anyway, we give step by step directions. How to deal with this account to fulfill the directive. But if they can’t or they don’t want to, they can always hire and come to us.
Tatyana Thurston I Dexit (21:11.597)Go.
Frazer Rice (21:17.361)Sure. No, that’s the backstop too, is that you not only provide the tool, but also some support behind the tool and the experience of having dealt with some of those folks, maybe even the contacts to call it one or the other company to maybe get from A to Z a little bit faster.
Tatyana Thurston I Dexit (21:18.326)Well…
Natalia Parker (21:20.717)Yeah.
Tatyana Thurston I Dexit (21:21.26)you
Tatyana Thurston I Dexit (21:35.245)It can be very overwhelming, that is for sure, and I think tech is constantly changing and the terms of service is constantly changing. So we have lot of barriers to entry to enact professional executorship and do it as best we can and a lot of it is because of technical bottlenecks, if you like.
Natalia Parker (21:45.165)Mm-hmm.
Frazer Rice (22:00.101)So this is a bit of a catty question, which is how many times have you seen this properly set up? Because I can tell you right now, I feel like I’m pretty fashion forward as far as tech’s concerned. I see the issue. I know my estate plan. The poor person, in this case, my sister, who’s my executor, she’s gonna take one look at this and be like, thanks a lot, man.
Natalia Parker (22:08.651)None.
Tatyana Thurston I Dexit (22:25.901)What?
Frazer Rice (22:26.033)And so I’m guilty as charge number one, but is anybody doing this with any sort of specificity yet?
Natalia Parker (22:26.478)you
Tatyana Thurston I Dexit (22:34.785)Well, can I just… sorry.
Natalia Parker (22:35.112)No. I’ll start, Tatiana. Here’s the problem. We came across some people and they say that, I have spreadsheets where all my accounts and passwords are written down and my wife will deal with that at some point. First of all, there is no directives for those accounts. And second of all, it’s still illegal to log in under somebody else’s logins.
Frazer Rice (23:02.853)Right.
Tatyana Thurston I Dexit (23:04.567)And I was just gonna say the reason we started this company is exactly what you just described. My brother is my executor and I was like, man, there’s no way he’s gonna know how to start at all because I have my fingers in a lot of different businesses, my personal. And so, you know, that floor plan and sort of direction guide was sort of how we started this.
It became intense. I mean with Natalia. It became a really intense research project. We have a database that is constantly being updated. As executors become executors or as will writers are writing wills, we really want everybody to understand the importance of technology in this process. Because it’s moving really fast. Now that AI has come about we can even throw in the whole name image and likeness problem which a whole other sort of barrier of questions to ask.
Frazer Rice (24:11.501).No, I’m going to bring you all back on to tackle that one separately. I think it’s worth its own half hour sort of figuring that out. But in the meantime, tell us a little bit about how people can find you. One of the things that I think you have on your website and some of your materials is a digest.
Really almost like a questionnaire or a brief that allows people to think through where they may have digital assets. It’s not just social media accounts and your bank accounts. They’re like fruit and flower miles, things like that. I hadn’t thought of that, but yes, that’s a big one. Where can people find you and what kind of resources do you have that people can get familiar with the topic as they embark on this fun assignment?
Tatyana Thurston I Dexit (24:45.399)Thank you.
Tatyana Thurston I Dexit (24:59.809)So the first place is our website and it’s actually, even though our company name is Dexit, which stands for digital exit, it’s Dexitplan.com because where we are proud is the actual plan of action that we’ve been able to customize for any individual. And then yes, we do have a sort of discovery questionnaire so that they can understand exactly what impacts them the most, where they may want to look at these accounts and have a plan for them.
And yeah, contact us anytime, email, phone. We’re here, we’re not chat bots. We want to be sure that you are talking to a human. We know how this AI slop is turning out and we don’t want to be any part of that.
Frazer Rice (25:46.501)I was going to add on to that too. mean this is not just for the end clients, so for anybody who sort of understands that they have this issue, obviously check out your website and do all that. But I would argue that for the estate planners, the accountants, the wealth managers, etc. who are advising clients, it’s a good resource to kind of help you get your arms around it in terms of advising people who are looking for help on all these different things.
Tatyana Thurston I Dexit (25:55.041)Yeah.
Natalia Parker (25:55.575)Yes.
Tatyana Thurston I Dexit (26:04.68)See you
Natalia Parker (26:11.136)Yes, because you can have the most compliant language in the world. But the executor will still start with the zero on day one. They don’t know the inventory. They don’t have the directives. Finally, they don’t know how to deal with those accounts.
Frazer Rice (26:32.491).So give us the website one more time. Then take us out here with a funny story. One you’ve dealt with in putting this company up to getting it up and running.
Tatyana Thurston I Dexit (26:42.381)Okay, so that sounds great. So Dexit Plan. It’s D-E-X-I-T-P-L-A-N dot com. Dexit Plan dot com. And I guess I’ll leave you with a text story. We worked with a church here locally. They had their domain name purchased in 1997 and posted as in your own personal name. The person passed away over 20 years ago. Nothing was ever done with the titling of the church’s domain name.
But the church has been forever on this domain name. It’s been over 50 years so to remark it. Rebranding a dot org is not an easy task. Actually, no kidding it took us nine months to get the church back their domain name. That was finding people from 20 years ago reopening email accounts from a long time ago, getting signatures verified and processed.
It is actually doable, but it is definitely a task. So planning ahead of time would save hundreds of hours and a lot of pain. Absolutely.
Frazer Rice (27:52.241)No, good object lesson for companies too. That it’s a good idea to see who owns what. Your domain name, any other digital IP, we’ll call it that. If you don’t have that in place. You may have a real forensic accounting job in the tech world to get everything back.
Tatyana Thurston I Dexit (28:02.274)Yep.
Tatyana Thurston I Dexit (28:10.337)That’s right.
Natalia Parker (28:10.72)Yeah.
Frazer Rice (28:11.705)Natalia, Tatiana, thank you so much for being on and we’ll look forward to talking again soon.
Tatyana Thurston I Dexit (28:16.811)Thank you so much.
Natalia Parker (28:16.888)Thank you.
TRUSTEE RESOURCES
TRUSTEES AND DIGITAL ASSETS
NORTH CAROLINA ESTATE RESOURCES
Titles
Mastering Digital Estate Planning: Protecting Your Online Legacy
The Future of Wealth: Managing Digital Assets After Death
https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
April 7, 202629 min
QSBS ROLLOVERS
BRADY WELLER discusses the intricacies of QSBS rollovers, including eligibility, timing, and strategic planning for founders and investors. The goal is to help the listener maximize tax benefits and navigate the legal complexities of this powerful tool.
https://youtu.be/gvQ0ZskvWVI
QSBS, tax exemption, startup founders, rollover, legal structuring, investment strategy, tax planning, startup exit, C corporation,
Key Topics
QSBS eligibility and benefits
Challenges in executing rollovers
Legal and tax considerations for founders
Timing and risk management in rollovers
Strategic structuring for maximum benefit
“QSBS ROLLOVERS” Sound Bites
“60 days is a very short window for founders.”
“Rollover continues your holding period clock.”
“Partial rollovers are common for founders.”
Chapters
00:00 Understanding QSBS and Its Benefits
03:07 Challenges for Founders in QSBS Compliance
05:54 Advising Founders on QSBS Rollovers
08:57 Structuring New Ventures for QSBS Eligibility
12:00 Navigating QSBS for Tech and Non-Tech Founders
14:54 Investor Considerations in QSBS Transactions
17:46 State-Specific QSBS Regulations and Planning
20:57 Future of QSBS and Strategic Planning
Resources
Brady Weller on LinkedIn
qsbsrollover.com
qsbsreference.com
Frazer Rice and Michael Arlein discuss the nuts and bolts of 1202 QSBS Features for Founders
Guest links
LinkedIn
Transcript
Frazer Rice (00:01.314)Welcome aboard, Brady.
Brady Weller (QSBS Rollover) (00:03.043)Hey, Frazer, thanks for having me.
Frazer Rice (00:04.738)Well, you are the nice compliment to a piece I just did with Michael Arlene on QSBS. We covered some of the nuts and bolts around 1202. You come at it from a little bit different angle. It’s usually where people, founders especially, have issues sort of complying with things like the three and five year rule. And otherwise really maximizing the capability of the rollover and the tax significance for it. Tell us a little bit about who benefits and what you do here.
Brady Weller (QSBS Rollover) (00:35.107)Yeah, QSBS is.
by far the biggest tax exemption available to individual taxpayers in the U.S. So it’s been something that hasn’t been up. I should say there’s not a massive advisory network around it. So it’s not something that’s been taken advantage of, I think, to its full scope. Michael, who you had on recently, is a top trust and estate planner for founders of companies around QSBS.
The specific problem that QSBS rollover solve is for a shareholder of an early stage company. Most often founders or very early investors, say, maybe series A or earlier shareholders. It’s an incentive to basically hold your stock for a quote unquote long time. In this sense, that means, you know, now under some new rules, basically three to five plus years.
It’s a tax exemption available to folks who hold their stock for at least five years. Then they can exclude from federal income tax now up to $15 million of gains when they sell that stock. So you have to be a shareholder in an early stage C corporation, early stage company.
Frazer Rice (01:50.616).Those founders before three to five years are trying to figure out how to use this tool. What are the challenges in making sure they don’t blow up the transaction by transferring something poorly. Or having their company grow too large or have too much cash or those types of things? Maybe list out a little bit some of the challenges that are out there that that a founder needs to be aware of.
Brady Weller (QSBS Rollover) (02:22.509).Yeah. So we don’t have to constantly caveat. I’ll mainly talk as though we’re speaking about the pre July 5th, 2025 rules for QSPS. Anything, any stock issued after that date, middle of last year. is under a slightly different set of rules. They are more expanded rules, but I’ll speak to this sort of from those old rules. And so the old rules state that you have to hold your stock for at least five years. And if you do, you can exclude a large portion from federal income tax, usually $10 million for founders. But if you don’t hold the stock for five years, your only option is to take the cash from that sale. For example, say you sell stock at year three or year four,
and purchase new QSBS eligible stock with that cash within 60 days. So it’s sort of like the 1031 exchange. Folks maybe are more familiar with real estate property exchanges. Its sort of like a 1031 exchange for stock. So you take the cash and you purchase a like kind quote unquote asset with it. Now the challenge with that is 60 days is not a very long time. And when you’re a founder of a company who just went through liquidity. You just got your deal done and the whirlwind that that is.
Now you’re dealing maybe in a post liquidity world. You’re maybe running another team at the acquirer or you’re otherwise involved. 60 days is not a long time to be able to find and diligence a new opportunity. . It’s just not feasible. Especially for founders to use that cash to say buy stock in someone else’s company. It just doesn’t make sense. Like risk adjusted, I suppose.
Frazer Rice (04:05.579)No, it’s a miracle that your company did great. Now you have to go and find another miracle and make it work within 60 days. It’s crazy.
Brady Weller (QSBS Rollover) (04:10.143).That that’s the biggest that’s probably the biggest barrier to executing them. For the longest time there just weren’t a lot of people. They hadn’t come alongside founders to help advise them on structured ways that they could do these rollovers.
Yeah, the options are risky. It’s like take your money and invest it in Dave’s startup in San Francisco. He’s going to lose your money. So that may be what you want to do with that money. To keep your risk profile sort of moving. But that’s not tax planning in any way. Right.
To make that decision just to save on federal income tax might not be the best way to use your rollover. So we’ve seen it much more for angel investors, something that they might use. People who want to maybe have a lot of deal flow. A lot of investment opportunities in front of them. But they want to keep that risk profile moving. I’d say timing and risk are the two biggest challenges when you’re trying to execute a rollover.
Frazer Rice (05:13.805).As a detail on that, you’ve got your company. You’ve got $10 million coming to you. Hopefully tax free, similar to a 1031. You don’t have to go into one company, you could go into a basket of companies.
Brady Weller (QSBS Rollover) (05:28.579).Yeah, you could take the cash, say you make $10 million from a sale. You could pay taxes on $3 million of it, assuming you haven’t hit your five year requirement. Then, you could roll over the other seven in various other deals. You could put it all into one new company. What the rollover actually does is it continues your holding period clock from the last stock. So if you held for three years in your original company stock,
You sell. You’re able to reinvest those proceeds within 60 days. It continues your holding period. Once you’re beyond a combined five the next liquidity event in the second company. Now you have proper seasoning on your shares, for lack of a better word, and then you can sell them under the QSPS exemption.
Frazer Rice (06:17.143)So, this gets to what you do on a day-to-day basis. So a founder comes to you and says, all right, I’ve got this situation I think that’s coming. And I need some advice. You’re sort of letting them know what’s happening here. How do you advise them, in a sense, whether it’s through your company or even as a general matter? Do you have a suite of other founders and companies that are out there? And then…
Maybe also similar to a 1031, is there sort of an intermediary function that needs to happen in order for the asset or the cash to go into sort of a, for lack of word, like an escrow account to then be deployed correctly into the eligible next company so that you keep that period going.
Brady Weller (QSBS Rollover) (06:50.713)Boom.
Brady Weller (QSBS Rollover) (07:05.839)That’s a good question. It’s not as formalized as the, you know, in terms of the 1031 world where there’s sort of a designated intermediary and that’s sort of required step in the process. This is very much the wire goes into your checking account for the sale of company A stock.
Frazer Rice (07:11.703)Mm-hmm.
Brady Weller (QSBS Rollover) (07:22.281)You send a wire back out to purchase stock in company B. When someone comes to us and is looking for guidance on how to do a rollover, sometimes they’ve talked to tax or trust in state attorneys already, or maybe they’re CPA. And there are maybe 50 folks in the US who have, I’d say,
Frazer Rice (07:37.463)Sure.
Brady Weller (QSBS Rollover) (07:45.07)I call it advanced QSPS planning knowledge, which is they have the trust planning strategies, rollover knowledge, all of these things that sort of at their disposal that they can speak to, but it’s a very small network. so our firm is actually the only non-CPA non-law firm in the country that deals directly with founders on these. And so we ended up kind of playing quarterback, connecting them with the right attorneys, maybe the right CPA, if they don’t have one to make sure that the team is sort of assembled.
You know, because the risk profile of taking your money and investing in someone else’s company typically doesn’t align with most founders’ interests at that time, the service that we provide is helping them to roll that money into a new startup of their own.
We think these founder-led rollovers where the founder or the shareholder who sold their original stock can now direct the proceeds into a new entity that they own and control. It’s a really great way to execute this. It gives the shareholder, the founder the optimal amount of flexibility and control over the proceeds over time. So they can handle their own risk profile.
Frazer Rice (08:57.921)So for the founder who built their business originally, they sell it and you’re sort of with them along the way to roll it over into another founder led situation. Are there any mechanics that you help with to sort of ensure that that takes place correctly? There’s so many, it seems like so many tiger traps along the way that you can stick your foot in and you did every, your intent was there, but maybe you did something weird or incorrect.
Brady Weller (QSBS Rollover) (09:26.617)Yeah.
Frazer Rice (09:26.721)Maybe a better way to ask this question is what are the things in that receiving new QSBS rollover do you want to see or a founder should make sure they have in place before they go ahead and pull the trigger?
Brady Weller (QSBS Rollover) (09:41.904)We want to make sure it’s a C corporation. First of all, a lot of times when founders start their first companies, they just, you know, incorporate an LLC somewhere and start doing business. A lot of times there’s not even, maybe there’s, you know, two or $3,000 transferred to a checking account, you know, from their personal to their checking. That’s how you start most businesses. But when you’re, when you’re starting a rollover business, we have to see a couple other things. One is we want to make sure it’s a C corp from day one.
Frazer Rice (09:58.989)Right.
Brady Weller (QSBS Rollover) (10:09.123)You know, it’s okay if it’s a single owner C Corp where the founders, the, you know, only board member, only director. It’s, you know, it’s your entity. That’s fine. but we also want to see a purchase agreement, some kind of stock purchase agreement. So you can’t just transfer money from your chase savings account where the wire landed to the new business account and, know, go on about, about the business. we want to see a stock purchase agreement. And so some of those agreements, and the optimal way to do those for sort of the, the, the long run.
Sometimes, we would obviously we have our template docs in ways that we might advise to do it. But very often we refer that out to legal counsel and coordinate there to make sure that just all the purchase agreements and governance docs and those types of things are in a good place. You know, it’s really making sure we have the purchase agreements and that the money gets moved to the corporate bank account, the new business bank account within 60 days. It’s really not a long period of time. And we run into a lot of situations where
If someone’s not kind of quarterbacking the process, deadlines get away quickly and then administrative issues with a bank might push you beyond the 60 day window. We’ve seen that a few times and it can obviously cost you a lot of money.
Frazer Rice (11:24.468)The, when you get to a point where the next business that this is going into, often the qualifications of being a QSBS eligible business can be a little bit murky. I’m thinking healthcare for instance, where like a hospital or that type of thing would traditionally probably not be a QSBS situation, but a healthcare service provider or a biotech company or something like that is.
Brady Weller (QSBS Rollover) (11:46.937)Yeah.
Frazer Rice (11:51.029)Do you help founders think about that? in many ways, there’s sort of the which came first, the idea for the company or the company itself. How do you make sure people stay on all fours on that front?
Brady Weller (QSBS Rollover) (12:00.56)Yeah.
Yeah, I if you build a startup before, know that the ideas in the early stage sometimes are extremely malleable. And when you start testing things in the market, the business very often changes. You know, we majority work with tech founders and that’s not because, you know, QSBS is well suited for tech. I think a lot of people think that to be QSBS, to be a technology company. That’s not true. It’s just that we most often see QSBS.
We run into people who are knowledgeable about QSBS in the venture space. So venture backed start up, like traditional startup businesses, has 80 % plus of those companies are tech businesses.
And then the other 20 % is manufacturing, biotech, life science, e-commerce, those types of things. But majority of people that we do these transaction with are in tech. And so by virtue of that, their rollover business ends up being, most of the time, ideas that they have are tech adjacent. So that’s a great place to be.
I’d say some things to avoid. What we hear often people coming to us wanting to roll over into real estate in some way or another. And there are ways that the business that you start as part of a QSPS roll over can hold real estate assets long term, depending on the business type. But you have to be really careful there not to, in the eyes of the IRS, look like a real estate holding company or have too much of your assets tied up in sort of like passive real estate holdings. And so I’d say that’s the murkiest stuff that we run into.
Brady Weller (QSBS Rollover) (13:37.822).Most of the businesses that we are helping founders start and grow as part of a QSPS rollover are B2B or B2C tech. Either web applications or mobile applications, e-commerce stores. We have a few hardware sort of based companies or like very physical product based companies as well.
Frazer Rice (13:58.431)For a lot of tech founders, the idea of taking some money off the table is important. And I would think that maybe partial QSPS situations come up. This isn’t an all or nothing thing. You can take some money off the table and then allocate other parts, maybe half off and then the other half you can roll into the next company.
Brady Weller (QSBS Rollover) (14:14.137)Yeah.
Brady Weller (QSBS Rollover) (14:18.798)I’d say an extremely common situation that we see is maybe a founder.
in New York who is raising maybe a Series B, call it a 50 or $60 million Series B. We saw a lot of these size rounds with the AI kind of boom happening and might be an opportunity to take, you know, four to $6 million off the table as secondary at that stage in the company’s growth. so you have this founder who just got $5 million wired to their bank account, maybe their first money. They’ve been renting in a condo or apartment in the city and they’re still very much like in high growth stage with
company so they don’t have a lot of bandwidth to run a new business. And so they’ll really try and de-risk themselves. That is, maybe pay taxes on a million, a million and a half, give themselves a cushion right away, maybe buy a condo or you know whatever, stabilize their life just a bit and roll over the other four, three and a half million, you know, and manage a project on the side that way. That’s a really common situation we see.
Frazer Rice (15:19.624)For investors who are invested in a lot of different things and maybe you know, they’ve got six or seven companies that are QSBS eligible and they are sort of rolling the dice on that and sort of picking and choosing which one should go into which that type of thing What’s different about it from an investor standpoint than from an operator standpoint?
Brady Weller (QSBS Rollover) (15:43.758)Yeah, I think the biggest thing investors have to pay attention to is if you receive a distribution that isn’t QSPS eligible because of holding period, you cannot just take that money and invest it back into a venture fund.
and call that a rollover. The money can go into a venture fund, but that capital also has to be called and deployed into, an investment from that fund. Meaning you can’t just invest in the, in the partnership at the partnership level in a venture fund and it’s sit there undeployed and be eligible for QSBS. It actually has to be fully deployed into target, target opportunities within 60 days. So that’s something that I think that we’ve run into a couple of times with, with investors is they think,
I’ll just, know, Fund2 is open at, you know, XYZ firm. I’ll just roll the money over there. But it does have to be deployed still within that 60 day window. So that’s something that we hear a lot of. You know, if you’re an investor, I would keep, you know, you don’t always have the perfect deal ready at the right time. But keeping good relationships with the founders that…
you’re partnering with, you know, you never know when someone might be able to open up a tranche on the side or sell some secondary to you. if you’re trying to still get access to that deal sort of outside of a normal round.
Frazer Rice (17:07.445)So for the companies that are in your orbit, obviously you’re probably checking in saying, hey, you didn’t do anything to blow up your QSBS status. But for the companies that aren’t that way, and let’s say you’re a founder and you’ve got a nice situation where you’re able to take some money off the table and maybe put it into.
one of the things that your friends put together or something like that. How do you think about a checklist or what are the questions to ask to make sure that the recipient investor or recipient of the investment is QSBS eligible and will sort of stick to it?
Brady Weller (QSBS Rollover) (17:46.48)Yeah, you want to ensure first that the company is small enough. so under the old rules that I mentioned, the company would have to have less than $50 million of gross assets. A really great proxy for that is just how much has that company raised? You know, if you’re trying to invest in a company and they’ve raised $120 million, it’s very likely that they have at some point blown the asset test and they’re not issuing QSPS anymore. It’s very, it’s not always, but it’s very possible. A lot of people confuse that test for valuation.
which is a mistake, you could have a billion dollar company in terms of market value, you know, with only 20 or 25 million dollars worth of assets on the balance sheet. It is possible, especially in some of these high multiple high growth tech businesses. And so, yeah, not confusing valuation with gross assets is one thing to pay attention to.
the other is ensuring just that the company is a C corp, especially for early stage investors. I’m talking like first money in, maybe before, you know, pre seed or pre seed, would say, ensuring that the right structuring is in place such that, know, you’re getting stock issued directly from a C corporation at that time you’re investing. So I would say that’s something to worry about more if you’re, you know, an angel.
who does a lot of sort of direct sourcing of deals and you’re not going through a fund. Most of the time, if someone’s raised capital directly from a venture fund, all the paperwork and things that you’re going to look for as far as QSPS are going to be in place, because most VCs are pretty well acquainted at this point with, hey, let’s make sure this is eligible before we get in here.
Frazer Rice (19:27.913)Right. And just to distinguish, an LLC that elects to be taxed as a C Corp versus a C Corp, C Corp, is there any distinction there for our listeners?
Brady Weller (QSBS Rollover) (19:39.673)Yes.
Generally, we would say as long as the LLC has made that C-Corp election before issuing more at that stage, guess, membership units of stock, as long as they’ve made that C-Corp election prior to issuing the stock, then we feel generally good about it. But yeah, an LLC, it’s an entity structure whose default taxation is as a pass-through, but an LLC can also be taxed as a C-Corp and can issue quote unquote QSBS eligible shares.
or units as well, so it is possible.
Frazer Rice (20:12.683)I was gonna say, so for the listeners out there, C-Corp doesn’t just mean C-Corp, but the real operative language is that it’s taxed as a C-Corp component, and that should be part of your checklist as you go down the list of companies to potentially roll into. So for those people who aren’t exactly founders,
but maybe are investors or otherwise part of businesses that they’ve been included in, et cetera. Those non-venture-backed businesses, what are the opportunities there for QSBS and then the ability to roll it over into other things?
Brady Weller (QSBS Rollover) (20:48.708)Yeah, I would say it’s very rare that we see a non-venture-backed business in between the coasts, I’ll say, right? Like not one of these like kind of like call them coastal elite tech businesses. I’m talking about your like legacy family business in, you know, North Carolina.
Frazer Rice (20:59.488)I mean…
Brady Weller (QSBS Rollover) (21:11.856)Most of the time we’re going to see those as pass-throughs or partnerships, maybe like an S-Corp. You would see that type of structure and those businesses, while they could be amazing businesses, the interest in them isn’t QSPS eligible because it has to be issued from a C-Corporation. Most of the time, the planning opportunity we see with those types of businesses is around the time of maybe a generational transition or other type of transition planning where
Maybe the children take over from the parents and they establish a plan. Hey, we’re going to take it over, but we want to plan to sell maybe the next five to seven years. I hear this a lot. And opportunity. If you are in an industry in a sector where stock sales are common in the industry for exiting the businesses, changing, electing to
be treated as a C Corp or restructuring to a C Corporation from one of those pass through structures is an opportunity because you could sort of reorganize, reissue stock, now start your QSBS five year time clock. And, you know, hopefully the business keeps doing well and you can have that exit opportunity down the line. And at that point, take advantage of QSBS.
Again, the thing you want to pay attention to is that you actually be able to do a stock sale at that time because QSBS requires a sale of stock, not an asset sale. And so that’s a really important distinction. So make sure either that you’re in an industry where that’s common or you’re working with counsel who understands what you’re trying to accomplish before you make those decisions about how you’re setting your entity up at that stage.
Frazer Rice (22:41.353)Right.
Frazer Rice (22:56.758)I just have a comment for me with the passage of the new law that we sort of alluded to where previously you really didn’t start thinking about this until fully five years. The new law, people can start thinking about it within three. You get 50 % of the benefit of the exclusion at three years.
Brady Weller (QSBS Rollover) (23:08.282)Mm-hmm.
Frazer Rice (23:15.21)And I’ve run into people where three years suddenly seems like a short amount of time, whereas five years, I think everyone was sort of like, we’ll get there eventually. you know, they’re they’re they’re fighting for their survival anyway. And if that happens to work terrific in this case, I think that the law moving the timeline up a little bit has had an interesting impact on those conversion discussions, because I think people are now starting to say, hey, you know what? I can get to three years. And, you know, with the speed at the
and the rate at which things change at this point, it’s much more realistic than I think it might have been going back in time.
Brady Weller (QSBS Rollover) (23:50.896)And if you have a stable business where you feel comfortable making projections, say three years out, so to what that business could look like at that time, it’s really becoming more common now to do what you’re calling like choice of entity studies, right? So working with someone who can model out with the difference in taxation, both at the company level and at the point of.
Frazer Rice (24:05.482)Mm-hmm.
Brady Weller (QSBS Rollover) (24:15.276)selling stock, what the optimal structure may be depending on your time horizon tax it, your expectations for growth or lack thereof. So that’s something that some valuation firms, business advisories, some law firms or CPA tax advisories may be able to do. If you’re in that situation, you’re trying to figure out, hey, what’s the math look like based on my baseline assumptions of what this business will be and can help you sort of make those decisions about how to plan.
over the next three to seven years.
Frazer Rice (24:47.402)As part of that reorganization too, I’ve talked to a few people who are in, let’s call it personality-based businesses, whether they’re podcasters or influencers or other types of things that are a little bit adjacent to maybe typical software companies. And I’ve brought up the notion that you may be disqualified now, but you may have a future growth opportunity within your business to make it fall more in line with a QSBS-defined business.
And so, you if you’ve got the time and the ability and it makes a business sense, it may make sense to start thinking about either sectioning that off or developing that business line for something a little bit later on.
Brady Weller (QSBS Rollover) (25:27.95)Yeah, being strategic about where those adjacent businesses, how they’re structured and where they’re built. And I mean, where like in terms of a legal entity level sense, I’m thinking about, for instance, several golf YouTubers, make a lot of golf content online, but now they’re announcing partnerships to, you know, design clothing, you know, have their own clothing line, or maybe they’ve entered a, a joint venture with a golf club maker or maybe an emerging brand and they’re taking equity.
Frazer Rice (25:41.983)Mm-hmm.
Brady Weller (QSBS Rollover) (25:57.826)Those are really interesting options and I think that you still have the opportunity to leverage your personal brand to grow that business but separating them out so that you know your reliance on your personal brand doesn’t ruin QSBS. That’s actually getting to one of the rules around qualified small business stock which is that the companies can’t be based on the skill or reputation of a single person. And so that’s when we think about
Frazer Rice (26:24.938)Mm-hmm.
Brady Weller (QSBS Rollover) (26:27.632)Like entertainers, athletes, social media personalities. MrBeast, for instance, couldn’t sell MrBeast, the YouTube channel necessarily, as QSBS eligible interest because of that rule more than likely. And that’s obviously a broad brush, paying attention to where you hold your business interests is important for this if you’re in that space.
Frazer Rice (26:53.5)Any state thoughts? I know California QSBS is uncoupled from the federal QSBS and New York threatened it and apparently that got knocked down. New Jersey just coupled with the federal government so that people weren’t scared away from doing that. How does that figure into your analysis?
Brady Weller (QSBS Rollover) (27:04.304)you
Yeah.
Brady Weller (QSBS Rollover) (27:12.784)It’s sort of a battle of the coast. It’s like which coast of the United States is going to be most investor and founder friendly with relation to these things. Yeah, because California hasn’t followed it for a long time. Oregon and Washington state are close behind there. And then we have the sort of somewhat the opposite happening on the East Coast. So as an East Coast guy, I hope it becomes a hub. But yeah, there is some sort of.
Frazer Rice (27:19.528)Right.
Brady Weller (QSBS Rollover) (27:36.388)you know, state and local tax planning, strategic planning that you might be able to do if you have the foresight and, you know, the right data to determine where you might become a resident or taxpayer prior to an exit. You might talk with a.
assault attorney or assault advisor state and local tax is usually tax advisors CPAs or or tax attorneys who can help you think through Hey, does it make a difference whether or not I move from California to Texas? What does that look like for my family? What does that look like for my post-tax exit situation?
because where the company is headquartered, as long as it’s in the United States, doesn’t matter for QSPS, just has to be a domestic USC corporation. And so remembering that QSPS is fundamentally an individual taxpayer incentive means that regardless of where the shareholders are located, you’re gonna be beholden to that specific state of where you live and their roles around QSPS.
Frazer Rice (28:36.906)Terrific stuff. Brady, we’re winding down here. How do people find you and your company and any sort of parting thoughts?
Brady Weller (QSBS Rollover) (28:44.516)Yeah, I’m personally very active on LinkedIn. So you can find me there, Brady Weller and our website, qsbsrollover.com. We also have a sort of an open source QSBS advisory referral site called qsbsreference.com. And so you can find us at either of those places. We’d be happy to help you out and point you in the right direction.
Frazer Rice (29:05.13)Brady, thanks for being on.
Brady Weller (QSBS Rollover) (29:06.874)Thanks, Frazier, appreciate it.
Keywords
QSBS, tax exemption, startup founders, rollover, legal structuring, investment strategy, tax planning, startup exit, C corporation, legal advice
Titles
Mastering QSBS Rollovers: Strategies for Founders and Investors
The Ultimate Guide to QSBS Tax Exemptions and Rollovers
https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
March 25, 202623 min
Health as an Asset Class
https://youtu.be/FU5IvtBbtCY
JOHN SAMUELS from WELLWORTH ADVISORS discusses “HEALTH AS AN ASSET CLASS” and the nuances of personalized healthcare management for high-net-worth individuals. We contrast concierge medicine with comprehensive health advisory services. Learn about his book “WEALTHCARE” which lays out the frameworks of his practice. Finally, John goes into how expert navigation, team-based care, and strategic planning can significantly improve health outcomes and client relationships. Finally we hear a little bit about what his favorite medical shows are on TV!
Key Topics
Differences between concierge medicine and health advisory servicesTeam-based care and specialist involvementIntegrating healthcare with wealth managementDebunking myths about healthcare access and VIP treatmentStrategies for managing mental health and complex conditions
Key Frameworks of Health as an Asset Class
Team-based healthcare approachEvidence-based treatment decision-making
Action Items
Review your healthcare risk factors and create a plan.Organize your medical records and update legal documents.Engage a healthcare advisor to understand your coverage and treatment options.
Chapters in “Health as an Asset Class”
00:00 Understanding Concierge Medicine vs. Health Advisory02:11 The Importance of Team-Based Care03:49 Collaborating with Client Advisors06:23 Navigating Complex Healthcare Needs08:07 Addressing Client Misinformation09:40 Challenges in Mental Health Treatment12:24 The Purpose Behind the Book14:26 Debunking Myths in Healthcare16:31 Preparing for Healthcare Interactions20:56 Managing Healthcare Risks23:05 Finding Resources and Support
Resources
Wellworth Advisors – https://wellworthadvisors.comJohn Samuels’ Book on Healthcare Management – https://www.amazon.com/Healthcare-Management-Advisor-Guide/dp/B09XYZ1234
More From John on “Wealth Actually”: https://frazerrice.com/ep-126-john-samuels/
Guest links
Website – https://wellworthadvisors.comEmail – mailto:john@wellworthadvisors.com
https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
Keywords
healthcare, concierge medicine, health advisory, high-net-worth individuals, patient navigation, mental health, healthcare risk, medical research, healthcare myths, health insurance
Titles
Beyond Concierge: The Future of Personalized Healthcare for Wealthy ClientsHow Expert Care Navigation Transforms High-Net-Worth Healthcare
Sound Bites
“We map out the cost of treatment for clients.”“We focus on evidence-based treatment options.”“VIP care often doesn’t mean better care.”
March 13, 202644 min
THE FIGHT AGAINST GASLIGHTING IN THE WORKPLACE
“Breaking the Glass Ceiling: Julia Carreon’s Fight Against Corporate Gaslighting”
In this episode, Frazer Rice sits down with Julia Carreon to explore her recent high-profile litigation against a major financial institution and her powerful insights on women in leadership, corporate culture, and overcoming systemic barriers.
YOUTUBE
https://youtu.be/e05k7SVQ2xI
We discuss:
Julia’s experience with workplace gaslighting and her litigation journey with Wells Fargo
The importance of transparency, accountability, and protecting yourself in corporate environments
How societal and corporate cultures disadvantage women, especially around motherhood and leadership
The themes and motivations behind Julia’s book, Walking on Broken Glass
Practical strategies women can use to build political capital and safeguard their careers
The significance of external networks and understanding your personal strengths
The evolving landscape of equity, ownership, and governance in corporations
How to proactively prepare for and respond to systemic workplace challenges
SPOTIFY
https://open.spotify.com/episode/5c546gs6Qctx4bGOvalgXj?si=1dDyJxnwSyu4tnhXxpzVxg
Timestamps:
00:00 – Introduction: Julia’s litigation and book overview
02:03 – Gaslighting in corporate culture and early experiences
04:14 – Dealing with systemic backstage politics and fighting for justice
05:10 – Motivations for writing Walking on Broken Glass
08:08 – Diagnosing workplace culture and gender dynamics
09:33 – The weaponized HR department and accountability
11:38 – Protecting yourself: cultural awareness and bias
13:12 – Demographics, gender disparities, and moving forward
15:12 – Institutional misogyny and societal shifts
16:05 – Motherhood, work-life balance, and corporate support
18:28 – Questions of corporate culture change post-COVID
22:21 – The fear factor and change in workplace loyalty
27:12 – Tactical career strategies and building political capital
28:15 – Always Be Executing (ABE) and tracking success
30:53 – The ownership mentality and equity’s role in career resilience
34:45 – Building internal and external networks for support
36:49 – Understanding personal aptitudes through testing and reflection
40:12 – Leveraging political capital and seizing opportunities
43:31 – How to follow Julia and stay updated on her journey
Transcript
Frazer Rice (00:01.004)Welcome aboard, Julia.
Julia (00:03.32)Thanks for having me.
Frazer Rice (00:04.652)Well, as I said in the opening, the concept of gaslighting in the boardroom is something that certainly isn’t new, but it doesn’t make it any more comfortable for the people who deal with it on a day-to-day basis or as part of their career. And you’re in the midst of litigation right now with a major financial services company. Maybe talk a little bit about what’s going on there.
Julia (00:24.801)Yeah, so I am in a high profile lawsuit with my former employer. I would say this is not a path that anyone chooses on purpose. In my particular case, Frazer, I spent 20 years at Wells Fargo, 15 of which were pretty spectacular. I have come to realize almost maybe fairy tale like in terms of my experience.
I want to talk about some of the things later on that made it a fairy tale. So yeah, I wouldn’t have chosen this. I did not see the culture at my former employer coming for me. I was blindsided by it and it got ugly quickly. One of the things that I think I am doing here. Or at least trying to do is not be shy about it. Not hide from it. Try to show women a different way for how to deal with these situations. Because I have very strong feelings about the fact. With the rollback of DEI and the current administration’s point of view on women, that we’re going backwards. If women don’t start fighting for ourselves in a more public way and without fear, then I don’t know where we’re going to be in the next five to 10 years.
I am soldiering on and it’s not easy to your point. But it is what it is and it’s a fight that I believe is worthy.
Frazer Rice (02:03.608)So it’s a daunting task taking on a big bank. Big financial services firm, whether it’s in this situation or frankly any. It’s just these well-resourced big behemoths. What has been the experience been like so far? As far as gathering information? Of getting the walls built that you need to in order to live your life while you go through this conflict with this bank?
Julia (02:29.822)It’s hat that is the million dollar question. Right? I will say that in my case i got really fortunate and came across a quote. It’s going to sound really strange. But i came across a quote that said fear is fake and danger is real but fear is fake. I believe that the patriarchy wants women to be afraid.
So it tells us these bad things are going to happen if you take on a big firm like this. It is grueling. The days are long sometimes. But once I internalize the reality that it is all fake in terms of all of the bad things that you think could happen really can’t happen. Worst case scenario, there’s nothing
Like I’m not going to die. They’re not going to, you know, take away my family. Like all of these things, right? We tell ourselves that it could get really nasty. And in my case, I have to stay really grounded in the fact that what I’m doing is worthy. We tried my lawyer and I tried for 14 months to come to a different answer. And so in a way, not just telling myself fear is fake. But in another way, I kind of feel like it’s my destiny.
Because, I just want to say this real quick, I had 20 years at a place that was not toxic. And so I know what good looks like, and this is not good. So in that way, I really feel like it’s my destiny. And so that’s what you do, and you have to have a good support network. I have a great husband, so that really helps.
Frazer Rice (04:14.21)The, as I’ve told people, sometimes doing the right thing or going after something that upholds justice. It can be expensive and hard. I give you kudos for standing up. Not only for yourself, but others who are going through a difficult situation. Where you’ve had a significant wrong done to you.
You’ve written a book about this experience as well. We can take some time to think, to talk about what the book tries to do. First of all, writing one in tandem with the process here, I think is a bit unusual. Some people do it after the fact. To go through a catharsis after going through a difficult process. Talk about first the why of the book.thhen we’ll talk a little bit about what you talk about in it.
Julia (05:17.241)The book is called Walking on Broken Glass: Navigating the Aftermath of the Glass Ceiling.” It was co-written with a fabulous woman named Shannon Nutter. I hope people follow on LinkedIn. The book is not squarely about what happened to me the book came together.
With Shannon and I meeting on LinkedIn. Then discovering that we had a lot of the same shared experiences as we are Gen X. in hindsight. Our generation has had the opportunity to have the most benefit of the Gloria Steinem Women’s Movement.
Think about the fact that we got the advantage of the birth control and all of the DEI efforts that have been in the last 15, 20 years. And we really felt like there was still a long way to go. Then all of that is starting to go backwards. So last year when we met or the year before, we’re like, my God, the idea that we got the best of the best is shocking to us. And so what are we going to do about it?
We really wanted the book to speak to women of all ages in their career. But it was written from a lens of two then 53 year old women who had seen a lot. We wanted to give the book as a love letter or a gift to our 35 year old self. To say, this is what we should have or wish we had known 20 years ago. Because we would have done things differently if we had really faced kind of what the challenges were that women are facing at work. In a real way right not in a way that sugarcoats it or pretends to throw it under the rug.
And or always makes it the woman’s fault like the woman always has to be changing and evolving in order to adapt to the systems and i you know it’s exhausting right so the book was written for that reason and it does tap into a lot of the things that we both experienced.
Julia (07:35.17)But it isn’t a kind of a personal journal of what happened to me with my former employer.
Frazer Rice (07:39.82)Right, one of the things that I found useful about the book is you divided it into three sections. I think it brings us sort of clarity into what you’re trying to achieve here. The first one is just diagnosing the situation that you’re in. Maybe talk a little bit about that. Part one the understanding of your surroundings. What’s happening around you. The conditions that women are facing as they embark on these big situations in the workplace.
Julia (08:08.982)Yeah. So the first part of the book does give a primer on kind of the history of feminism and how did we get here and what are some of the big open questions that are still left to answer. We also want to set the stage that makes it very clear that women are accountable for our actions in the workplace.
Like this is not in any way a book that seeks to make someone who’s failing feel good about the fact that they’re failing, right?
Shannon and I both reached really high levels of corporate success at major global firm. There is a lot of work to do. So we really try to dimension how, what are some effective ways for you to approach that work? What are some of the pitfalls and how are some of the ways that you can handle that?
In a way that’s kind of clear-eyed, but never about putting the blame or the onus on the company. And if you don’t mind, I want to say something about that because it relates to my lawsuit. One of the things that I’ve heard criticisms about is that people on social media often I saw when I kind of scanned the landscape of it recently are, this woman is naive. She thinks.
HR is her friend because one of the things that I have sued my former employer for is a weaponized HR department and I want to get very clear. mean, Frazer, you don’t manage hundreds of people in 13 states like I did for a very long time successfully innovating, having great client experience team scores and having great employee team scores, right? If you believe HR is your friend.
So that’s not what i’m trying to say what i’m trying to say in my lawsuit is. HR shouldn’t be picking off people for political reasons either. We are saying all the way along there is shared accountability between the employer and the employee. That’s really important. I think that you know one of the backlash is going too far field here.
Julia (10:27.401)We went so far politically correct on some things that some employees do show up to work and think that they just need things handed to them. And I do think that that was part of the backlash, right? So I just am always striving for balance. I think we should all be always striving for balance.
Frazer Rice (10:45.13)One of the concepts too, I think in the book that I sort of grabbed onto and enjoyed was the idea of taking steps to protect yourself. You’re dealing with a lot of different asymmetries when you work for a big company. You’re dealing with information asymmetry, you’re dealing with political asymmetry, you’re dealing with resource asymmetry. Sometimes you’re even dealing with just…
Accountability asymmetry in terms of, you some people get free passes at other times people are judged on things or unfairly judged on different criteria that just don’t make a lot of sense.
If we step back for a second and for people who are trying to understand, I’ll put it in quotes, how the world works and how to how to be aware of one’s and to protect yourself, what would be the first couple of things that you would tell people to think about on that back?
Julia (11:38.471)The number one thing is I would be very aware of the kind of culture that you’re operating in. And it’s very easy to take for granted what a culture really is, what your own personal bias and history is, and then how is it that you are fitting. into that culture with your own shared history.
So I love to be candid, right? And provocative about my own situation. If I could do something different, I would be very aware of what my biases were going into Citi with 20 years of being at a place where
It was a really fair game, but probably because I had a lot of political capital and I grew up there. So I understood it. But I went into that place thinking that I was a fancy managing director, that obviously I was hired to be a change maker. I can do a lot of great things.
And I was, you know, doing my thing, not realizing that I was swimming in a different lake and that lake was filled. with a lot of different kinds of wildlife that I was unprepared for. So, I mean, that’s really important.
Frazer Rice (13:12.398)As we talk a little bit about some sort of bullet questions as far as how your experience has gone, the demographics of the workplace are different and changing. On one hand, college graduates are now majority women or higher in just about every college situation. Yet institutions like the CFP, the women make up…
Believe the number is somewhere in the 24 % range. So you have this weird dichotomy of more women entering the workplace, but not in the numbers necessarily that would indicate that they are in places to make as much change as they would like.
They are still in the vast minority in terms of boards of directors and executive positions at almost every Fortune 500 company that I can think of. As we chart a path forward where, let’s call it merit.
Julia (13:58.813)Mm-hmm.
Frazer Rice (14:04.494)presides over sort of misogyny and I guess I would call it sort of political gamesmanship. How do you think about that in terms of advice for people entering the workforce?
Julia (14:16.461)Yeah, look, so nobody gets to say that women aren’t in the pipeline, right? I mean, that just, doesn’t hold up, especially at the more junior levels, right, of entering the workforce after college. What starts to happen is that it starts to go downhill as you get higher and higher up into hierarchy.
And I believe that there is a mismatch between women who want to work and do the right thing. And we’re going to talk about this. Then what does it mean to also then become a mother and give birth and have to manage all of that?
And then coming up against institutional misogyny. Obviously my perspective in the last 18 months has changed about the degree to which institutional misogyny exists.
Because I had a fairy tale experience before I was able to be willfully blind about the realities. so a really direct way of answering your question is that our book is seeking to hit women in the face with the realities of this because I don’t think we’re gonna change it overnight, right? And it is so entrenched, it’s getting worse and it will get worse.
Before it gets better, but I do believe that it will get better eventually because the old system that’s, know, aging out, baby boomers are aging out. Like I think that there’s going to be cracks in that. And then there would be a tsunami of change. But right now the old guard is hanging on and, we are going backwards. And so we just have to be realistic about what it requires to go forward. And we talk about what that is.
Frazer Rice (16:05.58)One of the things, right, and so let’s touch back on the motherhood issue, is, that is biology. And so women who go that route and have kids. Which is frankly one of the big precepts in society. Unfortunately. n some ways takes you out of the normal trajectory of a corporate path, just from a time perspective.
Certainly, the balance of work that happens at the household level. Where that ends up alling usually, creates a stress that is not well understood or received at the corporate level.
What are your thoughts on that front? As far as charting a path that recognizes that reality and at the same time doesn’t put upon going the other direction necessarily in terms of favoring one outcome or the other.
Julia (17:02.019)I know a lot of women who did not have children because they felt like that it would, it would harm their career. And, um, certainly it’s a personal issue and there’s no judgment from me. I don’t think I would have had children if I hadn’t met my husband. He was willing to do 50 % of the workload and he has, and, always has probably does maybe more than 50.
It is a very deeply personal issue. What I have strong feelings about the fact that companies who lean in to, don’t expect the woman to lean in, but the company leans in to supporting pregnant women, have higher loyalty scores. They have better team member satisfaction. They get a lot from those women that they have supported.
This is a crazy story, Frazer. I was pregnant and or just coming back from maternity leave all three times I got major promotions at Wells. I mean, think about that. And I now, because I lived my life kind of in a vacuum for a long time, I didn’t realize that this wasn’t happening to other people, right? So look at me now. I am 25 years from when I got hired, still saying that Wells is a great company.
because of my own personal experience. And they got a lot out of me, but I gave a lot back. So to me, supporting women who are pregnant doesn’t have to be a zero sum game. Yet somehow that is the narrative. And I would love to ask you why that is. Like, I mean, what has happened to corporate culture that this is such a pervasive issue when
If you were to scan a lot of my Gen X friends, we did not have the same experience.
Frazer Rice (19:04.147)I mean, from my perspective, I don’t know. I think that I blame some of this a little bit on the COVID blip in the sense that managers of all types just have no idea where to go as far as how to treat people fairly, either from a work from home experience or how that reconciles with…
women in particular who are having careers and families in addition to what’s going on with other folks like the men in the world. My short answer is I don’t know. The longer answer is that I think between the shorter news cycle, social media, work from home, there are a lot of different change agents out there that have taken the focus off of.
maybe the issues that worth talking about right now. And as a managerial class, especially as millennials are taking up the mantle on that front, they’re either forgetting about this particular issue and understanding the importance that it has, or they are just so overwhelmed by change at this point and self-preservation that it’s just an area where they’re triaging the different issues that they can deal with.
Julia (20:22.492)Do you do you at all think that it is a problem of losing common sense and like letting rigid ideology take over from common sense. I certainly was benefited from working from home for most of my career, right? So it’s fascinating.
Frazer Rice (20:46.061)Common sense isn’t common. And depending on the institution that you’re dealing with, work from home is either an excellent tool or a cover to hide under if you’re a mediocre performer. If you’re a manager out of sight, out of mind is a difficult place to be.
I think that we’re I think everyone is reconciling to the relative absence of work and sort of acclimating to Zoom phone calls and things like that. And that gets you then away from taking care of the real issues, which is to make sure that the company’s doing right, the employees are doing right by the company, and at the same time that people are being treated fairly, because I think when people are so disparate, it just becomes a real management challenge.
What we’re talking about as far as making sure that women are treated fairly in the workplace,
Combine that with, I would say, message confusion that occurs in social media, where some loud voices may not be the right voices to be taking up this mantle, versus some of the quieter, stable people who are really the exemplars that we’d really like to point to. Sometimes that gets mixed. And I think the brew, if you stir it together, I think is created.
Maybe if we think that there was progress since the 70s on through the 80s, 90s, 2000s for fairness and women progressing within the corporate ladder nicely, I think this the COVID blip has been a bit of a toe stub on that front. That’s an opinion, extremely uninformed, but more of an observation.
Julia (22:35.713)No, no, but well, listen, I just I love it because I do want to unpack it just a little bit. It’s what’s fascinating to me is that I negotiated 15 years before covid to work remote and then my boss knowing that I had to be on the road three to four weeks a month regardless was like, I’d rather you be happy where you live because you’re to be on the road regardless. So
I got to work from home and then during COVID when they tried to bring everybody back, they’re like, well, you can’t be the only exception. And I’m like, okay, I have been an exception for 15 years. So that’s where I go back to, know, where is this right balance? did, I mean, COVID is as good a reason as any that it’s things are upside down. I mean, really it’s a great theory.
Frazer Rice (23:22.671)Well, it also bespeaks different corporations have different cultures and certainly some people are worried about other things than others. Muriel Siebert, who I think is an amazing example of someone who took a look at Wall Street and said, look, I refuse to be held back by anything here. She started her own company and to call it a company is to not give it the respect it’s due. She’s a major absolute force in Wall Street and one of the real legends.
To me, entrepreneurism is one way through this. to create the company that you want to work in is, in some ways, to me, one of the solutions for people who are having difficulty in a corporate environment that they’re in right now.
Whether they’re able to be the change agent within, which is often hard at a big, you know, bulky company that turns with the agility of a battleship as opposed to being nimble in doing things or going out and starting on their own, which involves its own risks.
That to me is one of the solutions. But again, not without risk, not easy by any stretch. Where did that fit into your mindset as you were thinking about this?
Julia (24:37.16)Well, so, so she is an icon, not just because of what she was able to accomplish, but she also did it, I think, without a college degree. And she did it. And this is important. She did it fearlessly. And what I would love to go back in time and have a conversation with her about where did she tap into that fearlessness? And you will start to see.
Frazer Rice (24:48.665)Mm-hmm.
Julia (25:06.77)On my own social media, am trying to tap into that whole mindset of women need to lose fear. I’ve already talked about it, but here’s what’s important to know, right? By 2030 in the US alone, women will control $34 trillion of investable assets. I believe that that is when you start seeing the game change.
Look at how Mackenzie Scott is giving without glory. I posted that in a remark that’s gone semi-viral on LinkedIn. Like she is giving without glory. She wants to give, she wants to be anonymous almost about it, and she’s giving without handcuffs. And what is she giving to? She’s giving to communities, she’s giving to schools, she’s giving to healthcare. I mean, it gives me goosebumps every single time. And so I feel like women
When we start to control more, we’ll start giving in, Alice Walton is the same way, giving in a different way to change society in a more meaningful way at scale.
And Muriel was a pioneer in that regard. And she is someone I think we need the next generation to know about. because she was so fearless and it’s an inspiration. But you and i both know that all kinds of things that women have accomplished are never spoken about in the same way that they are about man and about men.
I do think that that’s one of the great things about some of we can go into social media some of the social media change that we see happening with alpha female and all of these great accounts that are just starting to say, know what ladies, we don’t have to buy into the patriarchy.
We can do it our own way. And so I think we will finally see change, but I wanna be very clear, Frazer, it’s going to get worse before it gets better.
Frazer Rice (27:12.195)Got it. So for people who are in a corporate structure, corporate environment, aren’t ready to make the leap to starting their own business, which is obviously a difficult decision, but when you’re in there, what are the things tactically that one can do to prepare, not only prepare themselves, but protect themselves against these forces that are out there?
One of the thoughts I had is making sure that in the job description that you’re able to point to numerical or formulaic successes so that if a narrative is being built against you, you can point to dollars created or jobs saved or metrics that in the boardroom.
Not only just qualitative successes, but also quantitative ones that makes it difficult for people to ignore you from a pure dollar perspective. Things like that, what pops up in your mind? That you would tell people to think about in terms of art directing their career.
Julia (28:15.023)Yeah, well, the number one thing that I always say, and I’m kind of, it’s kind of a legend for it. So it’s ABE and it stands for Always Be Executing. And when I look back and see how successful I was in a corporate setting, of course, in my case, it was that I had a great boss and a great mentor and sponsor in him.
But actually, I was always focused on executing and doing it in a way that is collaborative so that you don’t have the knives coming for you from every direction. think a lot of people who the more successful that you get in your career, you think, I’m fabulous because I’m fabulous. No.
You need a mindset of I’m fabulous because I am creating a team around me, no matter who I am, even if I’m not the boss, to protect each other and help each other and lift each other up. if you are always executing and you hit on it, right, as a woman, you should always be keeping track of your metrics in a way that is tangible and defensible. But you also should
never take for granted the fact that no matter how senior you are, you need to be getting something done. And I do think that it is a big mistake for people to get high on their own supply and forget that. And then, and then the sharks will come for you. So always do something. And this is just a final thing, cause I have lots of people that I mentor. They’re like, just name one thing. I’m going to give you one thing. Send meeting notes.
If you go to a meeting, and everybody’s on a call, 15 people are on a call. If you’re the one who sends meeting notes and this is a hot button, right? For women, they’re like, well, I’m not the secretary. I don’t wanna take me. You know what? Put your ego, park it in a parking lot and send meeting notes. You would be shocked how much goodwill and how effective you’re perceived when those notes, like say a project is going downhill and somebody goes, but.
Julia (30:30.157)Such and so committed to this and you’re like, those meeting notes were written by Julia Carrion. Nobody has to do that. But corporations get unwieldy. lot of churn happens. A lot of stuff doesn’t get done in a day. If you can demonstrate that you are someone who is acting in good faith and doing small things to keep the needle moving, somebody in senior management is going to notice that, I promise.
Frazer Rice (30:53.763)The other thing I sort of, and this doesn’t just go for women, this is for people generally, is the ownership mentality and the move toward equity, and by equity I mean stock equity, where the mindset to me shifts when you move from sort of salary and bonus to equity in the firm.
And that subtle shift suddenly puts you in a different position in terms of sitting at the same table as someone who is, let’s call it quote unquote, making the decisions. When you’re there and your ownership of the firm, however small it is, is rendered unimportant.
First of all, that tells you to go. Second of all, I just feel like the people who exist on that plane bring up different things and then are thought of differently. Does that track with your experience?
Julia (31:48.819)It does, but I think that this goes to kind of how is the corporate world changing and then how does that impact employees? So, and where I’m going with this is when I was at Wells, my compensation was a third, a third, a third. So it was a third cash, a third cash bonus and a third in stock. Do you want to know what’s going on?
And I don’t know if you know what’s happened on Wall Street.
Every single major bank is moving to you only get a quarter in equity and the rest of it is cash. So I think that the onus to here is on corporations to be thinking about how they’re treating employees. And to your point, what, what does that mean when you show up and how vested are you in the option? Just real quick, I want to give a shout out to Maureen Clough.
I don’t know if you follow her, she just yesterday did an amazing six minute post on why companies are losing loyalty from employees. so like, again, this goes back to is everybody backsliding right now because these corporations have to realize that in order to keep good talent, you want them to have a stake in the game, but that’s winnowing, I think.
Frazer Rice (33:11.819)I know. I agree. Frankly you know to me at the larger institutions that aren’t willing to sort of play ball as far as involving people in the ownership that’s a signal and when it’s a signal then you know if you’re good at your job and you bring things to bear you know there are other there are other places out there.
I think those places that value you want you around and they want you to be able to participate and how the broader governance of the company works. It’s a lot like how Goldman Sachs was back when it was in the partnership days.
Everyone who was a partner there understood how everything else was working and ultimately that meant that, I don’t know, I feel like Goldman still does well now, but it’s a different climate, different firm where you’re completely involved in everything else and therefore the information is out there and… it’s something that you’re not blindsided as much by what’s happening in other divisions within your firm.
Julia (34:15.472)Yeah, totally agree.
Frazer Rice (34:16.911)One other thought that as we were sort of squiring through this was the idea that it’s important to have information sources or networks both within your company that are outside of your reporting line, but also information networks and support outside your company.
I call it sort of the kitchen cabinet of people who are similarly situated or in different spots so that you have context into which to sort of find out what your what you’re up against both inside the company and outside of it. Is that something that makes sense to you or is it something that was lacking in your current situation? How did you think about that?
Julia (34:57.906)Hmm. I love that because in 2017, I took stock of the fact that I had become too comfortable in my lane and I was seeing that my influence at Wells was waning for whatever reason.
And so I started blogging on LinkedIn in 2017. Because of a conversation with a Harvard sociologist that I write a lot about. Fscinating guy who predicted the current turmoil 10 years, almost 10 years ago. And so I started networking outside and I could not agree with you more that you need to be building your networks, not just inside. That goes without saying, right? Like I had a great career partly because I was a boss at gaining political capital at Wells all the time, right?
Giving goodwill and getting it back but outside is critical. during our book, what we found out is, that women are more likely to put that aside. Because we feel like we’ve got too many other things going on, work, know, kids, all of the pressures, trying not to, you know, have a nervous breakdown on any given day, trying to stay fit, dealing with menopause. Which of course is a whole other thing that is a whole other bag of tricks.
And so we don’t do it as much and it hurts us. So I absolutely think being deliberate about an external network is essential. When women ask me how to do that, I say to commit to a certain number of hours, half an hour to two hour, whatever you can give a week to doing it deliberately. I wish I had done that earlier in my career for sure. So it’s great advice.
Frazer Rice (36:49.865)Along that line, I’m a big believer in being aware of your surroundings. In a sense aware of yourself and what your skills. Things that you’re annoyed are at are and what you’re good at and what you’re not good at. Did you take any tests or anything to understand what your aptitudes were or what you were interested in or more importantly not interested in or how you interact with other people personality wise and
Is that something that resonates with you? sort of am a big sports fan. Dan Quinn, who’s the Washington commander coach. He got fired from the Falcons. He did a real deep soul searching and went in and got tested on a whole bunch of different things and where he came up short, where he was really good. And that allowed him to get hired again and to have at least some initial success with the team and hopefully going forward from my rooting perspective.
But where does that fit into your analysis for people?
Julia (37:50.351)Did somebody set that question up? That’s what I want to know. I am a huge believer in strength finders. Some people take discs, some do Myers-Briggs. The reason I asked if it was a setup is because strength finders saved my life. I was deemed top talent when I was like 34 years old at Wells and they gave me a career coach who by the way was Sarah Grady is her name. and she was Dick Kvasevich’s legend on Wall Street.
She was his leadership coach and she gave me strength finders and I very quickly was very clear my top five strengths and then my bottom five strengths are not a surprise. Like I am zero. I’m like negative zero at woo. I was like, it won’t even shock you for a minute.
Yes i do think that those kinds of valuations are critical and in fact i’m gonna talk to my twenty year old son about taking one i think you’ll end up taking disk but. One thousand percent if you if you do not know what you’re good at and why then try to find out because it can save your life i mean the awareness and the learnings that i got about myself.
From taking one test have stayed with me for 25 years. And I’m gonna be really blunt here. I forgot those lessons when I stepped into a new culture and it was painful. So I think you have to also be disciplined about…
Take it again, remind yourself, reread whatever book helps you stay grounded in who you are and how you’re showing up. And get some friends to give you feedback.
Frazer Rice (39:44.111)Well, mean, people get better or change or worse at certain things. And so you’re not the same person you were 20 years ago. And, you know, it merits revisiting every once in a while. As we wind down here, unfortunately, we probably could go on for about three hours, which I wish we could do.
But one of the things that I think is interesting, too, you talked about political capital and building it up, is that I think one piece of advice that I tend to give to people who are starting out and might be useful in the situation that we’re describing here is that when you have political capital, you’ve got to be willing to spend it occasionally.
Careers, in my experience, take quantum leaps in that you’ll be going around for a while and then something good will happen and then you’ve got to kind of take advantage of the advantage while you have the advantage of having the advantage and moving up and then reestablishing the plane.
And it’s a little bit like a ratchet where when the wrench turns, it doesn’t turn backward. You can kind of continue to elevate on that point. Is that something that you saw where, you know, as you were making the moves up the ladder that didn’t happen at the last situation that maybe might’ve been something that could’ve turned out differently?
Julia (41:01.791)Yes, and I think that being more aware of my surroundings would have helped. I don’t think it would have changed the outcome in the other example. But the political capital that I was able to gain is that I got promoted every single time Wells did a major merger when people were panicking about their jobs.
Frazer Rice (41:08.623)Mm-hmm.
Julia (41:31.061)And one of the things that I did that you and I could probably discuss for two days is I gave up control of trying to manage the outcome. In other words, I went to senior management with two major mergers and I said, you know what? I don’t care what I do for the time that the companies are trying to come together. You give me something hard to do and ugly and I will get it done the right way.
And then you decide whether I get rewarded or not. And when I crushed both of those tasks, I got major promotions. So I think it, I think a lot of people think, I’m going, I had a, had an employee who told me I should just get promoted because I’m sitting here and I’ve been sitting here for two years. mean, it really, life just really doesn’t work that way.
In my experience, you got to work your ass off for it. And, and you have to put your ego aside and you have to hope that the universe is gonna pay you back. And I believe that because the universe always has. I believe that even now with my current situation, like everything that has brought me here has made me a spokesperson for like a better way because of what happened to me, right? I had 20 years of goodness and then I had something really hard happen.
And I’m trying to make lemonade out of a very difficult situation because it is the only way, the only way out is through. So I just have to keep going through and I love the idea of yes, you’ve got to spend your political capital. can’t, know, George Bush said that you can’t just collect it. What are you collecting it for? If you’re not going to spend it.
Frazer Rice (43:17.817)Exactly. Okay, we have to disembark here, unfortunately. How should people keep track of your situation? How do they find the book? And how do people get in touch?
Julia (43:31.846)Yep. I have, um, I’m on LinkedIn. I have a website, juliacarrion.com. If you are looking for, I’m doing some consulting on a digital transformation always and org design or whatever. So you can find me there. And then, um, you know, today’s a big day. We are filing today or tomorrow, a response to my lawsuit.
So it would probably make the news. Thank you to you for being a great ally to women and having me on. The book is walking on broken glass.com. It’s such a great name. So you can order the book on the website from any of your favorite book resellers.
Frazer Rice (44:14.639)Super, well good luck with the legal proceedings. All of your information will have that in the show notes so people can find it easily. I think you’re coming off of a difficult situation. I think you’re gonna turn it into something far more transformative. Even you’re envisioning it right now. So I’m hoping for the best here.
Resources & Links:
Walking on Broken Glass: Navigating the Aftermath of the Glass Ceiling
StrengthsFinder Assessment
Julia Carrion on LinkedIn
Julia Carrion’s Website
Connect with Julia:
LinkedIn
Website
Stay tuned for updates on her legal case and ongoing advocacy efforts. Don’t miss her insights into transforming adversity into empowerment and systemic change.
https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
Keywords:
Gaslighting, Corporate Culture, Women in Leadership, Workplace Equity, Julia Carreon, Wells Fargo, Citi, Legal Battle, Glass Ceiling, Political Capital, StrengthsFinder, Work-Life Balance, Systemic Change, Weaponized HR
March 9, 202658 min
THE TRUSTEE CRISIS: Navigating the Challenges
There is a storm coming with the challenges of navigating the TRUSTEE CRISIS. It is one of the biggest blind spots in the “GREAT WEALTH TRANSFER” and will be the source of mountains of litigation for the unwary,
https://youtu.be/hwQev88A03M
Summary
In this conversation, Frazer Rice and Jennifer Zelvin McCloskey discuss the current crisis in trusteeship, highlighting the shortage of qualified trustees amidst a significant wealth transfer. They explore the importance of modern trust planning, the challenges faced by individual trustees, and the need for better education and training in the field. The discussion also covers the emotional and interpersonal aspects of trusteeship, the functions and responsibilities of trustees, and the necessity of managing risk effectively. They emphasize the importance of building a pipeline for future trustees and improving the perception of the profession, while also identifying opportunities within the trust industry.
https://open.spotify.com/episode/4qpkrVdaUa2AfDxgl7j3yN?si=XVgG3jE_Qpqq2JTqi8XLXQ
Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)
Takeaways
The coming crisis in trusteeship is already here.
There is a significant shortage of qualified trustees.
Trusteeship requires strong interpersonal skills and emotional intelligence.
Managing risk is a fundamental aspect of trusteeship.
Trustees critically need education and training.
The role of a trustee is evolving with increasing complexity.
Beneficiaries need to understand their rights and the trustee’s role.
Custodial responsibilities are essential for asset protection.
There are many opportunities for growth in the trust industry.
Trust law and investment management are distinct fields.
This Episode is for . . .
Anyone that has an estate plan with a trust in it and doesn’t know what a trustee does
Any advisor who works w/ multi-generational situations (that’s everybody in wealth management)
Any RIA looking to sell
Financial types worried about compliance world
Fiduciary litigators
Chapters of “THE TRUSTEE CRISIS: Navigating the Challenges”
00:00 The Coming Crisis in Trusteeship
02:06 Importance of Modern Trust Planning
04:11 Challenges with Individual Trustees
08:03 The Dwindling Pool of Qualified Trustees
10:06 Functions and Responsibilities of a Trustee
12:20 The Emotional and Interpersonal Aspects of Trusteeship
16:05 Managing Risk in Trusteeship
19:07 Building a Pipeline for Future Trustees
22:10 The Role of Education in Trusteeship
25:07 Improving the Perception of Trusteeship
28:19 The Need for Better Trust Education
30:39 Bifurcation of Trustee Functions
33:26 Distribution Functions and Beneficiary Relations
36:52 Custodial Responsibilities in Trusteeship
40:19 Consequences of Poor Asset Management
46:41 Curriculum for Trustee Education
52:13 Opportunities in the Trust Industry
Transcript of “THE TRUSTEE CRISIS: Navigating the Challenges”
Frazer Rice (00:01.068)Welcome aboard, Jennifer.
Jennifer Zelvin McCloskey (00:02.723)Thanks Frazer, how are you today?
Frazer Rice (00:04.782)I am doing great. We’re going to dive into a topic that is near and dear to both of our hearts. And that is what I’m describing as the coming crisis in trusteeship, but I think it’s already here. Which is the concept of qualified trustees being in short supply, right in the face of a gigantic wealth transfer. And first of all, before we get into that, just describe what you do on a day to day basis first.
Jennifer Zelvin McCloskey (00:33.445)Sure, I actually wear a bunch of hats. Day to day, right now, I’m a full-time practicing trust and estate attorney. I’m also an individual trustee for a variety of trusts that need either somebody here physically located in Delaware for a short period of time or even a successor trustee. But I’ve also spent many, many years building programs in trust management and trust administration.
Because there is this crisis of human capital that just does not exist. I built multiple programs. They’re housed out of the University of Delaware. So I act as a trust and estate attorney, do planning, administration, I teach in the area, I build programs in the area, and I serve as a trustee.
PEAK TRUST MANAGEMENT CERTIFICATE
Frazer Rice (01:23.182)A full plate to be sure. To me, I came out of Wilmington Trust and another trust company served an individual trustee too. I’ve seen all these different flavors of trusteeship. My general sort of bon mot around that is that the individual trustees. I’d say 95 % or higher don’t really have an appreciation of the risk and responsibility that they’re taking on. And then the corporates have their own issues, which we’ll get into in a little bit. If we pull back even further, modern trust planning in wealth management, why is this so important?
Jennifer Zelvin McCloskey (02:06.275)That’s massively important. It’s not just for the mass affluent or the ultra high net worth. It’s for everybody. We have all of these assets that we have this hyperfocus on building and increasing our wealth. Making sure that we have the ability to sustain ourselves throughout our entire lives.
But if we don’t do this type of planning, if we don’t have structures and implementation for when we die, then our assets that we’ve planned so diligently for will fall off of a cliff. We lose the ability to control ultimately what happens to those assets.
Layered on top of that, of course, is the tax component for ultra high net worth folks who are trying to really focus and direct their assets to make and create generational wealth transfers.
Without this type of functionality and wealth planning and estate planning long-term, people lose control of what they’ve spent so much time building.
Frazer Rice (03:13.338)One of the things I tell people as far as trusts are concerned is that, you know, we’re putting these structures together. They’re durable enough to withstand taxation or creditors or other asset protection features, create some guidelines around distributing the assets to the next generation or other constituencies. But also have some flexibility to be able to deal with the things we can’t look into the crystal ball and figure out over time.
And that those three things just putting a document together that tries to do all that is hard enough, but then to put it in the hands of somebody or something to administer and to exercise discretion around it. That’s where the real art and science kind of stitched together and create this issue.
You know, as we think about that too, the idea, the history of these types of scenarios kind of goes back to, you know, you’d put a structure in place and then you’d go hire a bank and they’d take care of everything.
How do you look at that and say, all right, we’ve gone well past banks to individuals and then to dedicated institutions. What is the problem there?
Jennifer Zelvin McCloskey (04:22.956)Now the problem, there’s two problems. In my opinion, what I see is that, you know, your individual trustee by and large is Uncle Joe, right? He’s the guy that everybody goes to in the family. The responsible one. He’s the smart one. The wealthy one who, great, doesn’t know what the fiduciary duties are. He doesn’t know that he has a duty of impartiality. He doesn’t know that…
Frazer Rice (04:32.419)Right.
Jennifer Zelvin McCloskey (04:48.475)He can’t self deal unless the instrument says so. Doesn’t understand how the instrument works. He doesn’t understand the nuance and the legalese written into the instrument. But he’s flying by the seat of his pants and everybody looks to him as the respected one in the family. No one knows that they have the ability to challenge him.
So with your individual run of the mill trustee named in the instrument, they just don’t have the expertise, they don’t have the technical knowledge. Don’t know what they don’t know. They can get into trouble in that way. The other problem that you have with professional individual trustees oftentimes is that they are not formally trained.
They may be an attorney who is working in that area, who’s doing plans for people who may or may not know what the full scope of being a trustee is. They may not realize, I have to get a special insurance policy because my malpractice insurance policy doesn’t actually cover this type of fiduciary engagement. There’s a lot of landmines that individuals can run into when they’re doing this type of work. On the corporate side, the problems that we run into is that there’s just a complete and utter lack.
Frazer Rice (05:50.061)Hmm.
Jennifer Zelvin McCloskey (06:12.059)Of available educational programs to teach people the proper way to be able to understand trusteeship. It has always been, and it just has developed over time through, you know, oh, we’ll give it to the bank, the bank will do it. This apprenticeship model, and that just does not scale well because if you learn improperly at the edge of a desk from somebody that learned improperly at the edge of the desk. Then the person that you’re teaching now at the edge of the desk is learning what you learned improperly.
So anecdotally, I did karate for a long, long time. And the man who taught me karate, I’m almost a secondary black belt to like, was serious in karate. And the man who taught me karate said, you practice, it makes permanent. Don’t practice wrong. Because when you’re practicing wrong, you’re making permanent wrong things.
And that’s what the apprenticeship model has the risk of lending itself to. It’s not that every trustee that learns at the edge of the desk learns wrong, but the risk is too high because the fiduciary responsibilities and the duties are too high to run that risk.
The other problem is that we have a dwindling pool of really qualified senior trust officers because of just the nature of the job. You’re a human being, you’re an individual, you age, you retire. And it’s not something that people go to school and say, when I grow up, I want to be a trustee. They fall into it sideways. And unless there are academic programs that are out there that people are aware of and that they can get some formal training, some formal education to enter into the field.
Frazer Rice (07:49.742)Yeah
Jennifer Zelvin McCloskey (08:03.82)Separate and distinct from, I’m in the field and now I want to get a CTFA. I want to earn my certification to really show that I have the chops in this area. We have this shrinking pool of expertise. We have a lack of knowledge, a lack of formal education, and an apprenticeship model that doesn’t scale. On top of, with the individual side and the corporate side, this massive wealth transfer and an explosion of trust complexity that’s all taking place at the same time.
Frazer Rice (08:31.918)One of the issues at the corporate level too is that as you say that the impregnance model is not necessarily the best way to do it. They’re cutting back on training programs. The business model around being a trustee or even a specific trustee does not make the big money.
And so the ability for those types of institutions to develop the people.who ultimately are now in a very sort of pro-employee environment where there’s such a demand for trustees that they can kind of switch around and get a 10 or 20 % bump each time they go because people are desperate to have them.
There’s a real cavern there to try to create the permanence that you’re looking for in a structure that really rewards consistency over time, especially as it relates to discretion and process of decision-making.
Jennifer Zelvin McCloskey (09:23.15)Yeah, that’s exactly right. And that leads to this revolving door in the industry, because people are just trying to make more money and they’re going and bouncing to different trust companies. And there isn’t that backfill.
Just because it’s a trust company and there’s policies and procedures, trusteeship is about relationships that you make with your beneficiaries, the relationships that you develop with multiple generations in a family. And when you have somebody that’s acting and serving in that and they move, they leave, they’re no longer acting and serving in that capacity, a new personality comes into the mix and it can really be disruptive. So having that consistency and minimizing the attrition is so valuable.
Frazer Rice (10:06.766)The other thing I try to bring up, especially to individual trustees, is that the thing that you’re signing up for is probably going to look a lot different in five or 10 or 15 years when people are aged on, they remarry, they have kids, etc. That the conditions are a lot different than what they were before. And it’s going to be difficult to take on a structure that has eight people when before there were two.
Jennifer Zelvin McCloskey (10:37.517)Yes, and that’s that complexity, that increased sophistication and complexity of trust structures that are available now to people. With the increase in the exemption, these trust structures, they’re not necessarily changed. For example, qualified personal residence trust, if people really need that anymore, but there’s a ton of them sitting around there. Are trustees properly administering it? Did you actually transfer the real estate into the trust at the time?
So there’s all kinds of sophisticated structures that the trustees may or may not have the right skills. But they’re saddled with having to do it.
Frazer Rice (11:19.47)Let’s take a step back and just talk about the functions of a trustee for a second. I break them down basically into three. Which is the first one. You have to administer the trust, meaning you have to dot the I’s, cross the T’s, make sure things get executed, tax returns are filed, statements get sent out to the extent that that happens, and that the administration of a structure like that occurs.
Then I talk about the concept that the investments have to be made monitored moved around decided and that they’re appropriate for all classes of beneficiary that are in there and then the distribution function which is The assets have to be distributed according to the law. First the trust then maybe the intent or the law if everything is silent and that those three things are very different components and that it’s tough to find somebody who’s great at all three housed within one brain.
Jennifer Zelvin McCloskey (12:20.217)Yeah, I agree with that 100%. It is a three legged stool. It’s the investments, the administration and the distributions. And in that administration umbrella in and of itself, there’s a tremendous amount of work that sort of goes unsung. know, it’s not the sexy stuff where you’re investing and making a bunch of money for your income beneficiaries and managing to preserve the corpus for your principal or your remainder beneficiaries.
And it’s certainly not the personal interaction that you’re doing with your beneficiary day to day. Making distributions, helping them, seeing the product of that help. It’s the making sure you file ax returns are properly. Understanding how to read that tax return. Even if you’re not preparing it, making a proper selection on the accountant that you’re using to prepare those tax returns if you’re not preparing it.
Make sure to set up statements properly, make sure that in this world of silent trust documents that you’re not sending a statement to somebody who’s not supposed to have it. Communicating with beneficiaries on an even keel. Making sure that you’re not inadvertently violating your duty of impartiality because it’s more than just a substantive duty, there’s a procedural duty as well.
That’s really, really challenging to find within one human being, let alone add on top of it somebody who’s financially savvy enough to understand investments and all of the different complex investment tools that are out there, as well as having the personality and the interpersonal skills to keep beneficiaries engaged and happy.
Frazer Rice (13:56.426)Just on top of that, the EQ, the bedside manner, and the ability to simplify the complex, et cetera. At the same time, that dedicated note taker that is able to document everything that happens within a decision. Whether distribution or investment or otherwise, that it’s just two different people most times. I find that something falls apart as time goes on. Ultimately if things aren’t laid out correctly, that’s when conflict starts to simmer. Then you know if there is something that’s wrong. That’s allowed to compound that’s where you get into a huge problem later on.
Jennifer Zelvin McCloskey (14:36.922)It’s all that feeling. People are behaving in ways that they may or may not be able to articulate their emotional proximity to. When you’re talking with beneficiaries. There’s something simmering under the surface that you inherited because you’re a trustee. You may not even be aware of it because the beneficiaries may not even be able to articulate it.
You have to have a certain sense. A gut check of feelings of rntuitively being able to read what’s going on under the surface. To pull it out of people in a very balanced and even keel way. It’s not an easy job by any stretch of the imagination. On top of financial literacy and personal liability and executive functioning skills, being detail oriented, making sure your documentation is not overly explicit. isn’t, you know, scarce. You’re now wondering how and why did you make those decisions?
People don’t think about the decisions that they make on a day to day basis. We don’t think in a way to articulate why I made this decision. Why I exercised this type of judgment. And that’s what we’re being asked to do as trustees is to document what is my decision making process? Why am I making the decision? What are my factors involved in making that decision in a way that’s defensible. If we ever need to defend it.
Frazer Rice (16:05.292)Well, in favoring one class of people over another is usually where the rubber hits the road on this. People who are used to seeing the income from a trust and don’t want that touched come hell or high water. Then future beneficiaries who’d like to see the trust go from X to 2X to 5X. So that they have something larger to enjoy.
You have a natural tension that you have to manage. It’s just not easy. If you don’t document the hows and whys of what you’re doing, you set yourself up for a problem. From one class or another looking at you saying, you you should have done it differently. To go back to that liability component. You’re the only one who sits in the chair of having made that decision. You’re the one with the bullseye on your back when it’s called to account.
Jennifer Zelvin McCloskey (16:53.093)That’s right, that is exactly right. And now add on top of it, you’re just named because you’re Uncle Joe and everybody goes to Uncle Joe. You have no technical background and you just don’t know the landmines that are there. You don’t know what you don’t know.
Wouldn’t it be wonderful if we were able to create a pipeline of really sophisticated entry level employees or folks that are, you know sophisticated in financial literacy that now want to take the job to become trustees, that we were able to give them this technical roadmap for what the job actually is and then have them get the ability to apprentice on all of those policies and procedures. What does this corporation do? How do we document things?
When you’re trying to learn it all at one time, it’s like drinking from a fire hose. Let’s give people the ability to really have a chance at doing it successfully.
Frazer Rice (17:53.048)So let’s dive into that pipeline issue for a second. We already diagnosed that the, let’s call it the trust companies or the banks are, they’re just not resourced enough. They can’t run people through an internal school to do it quote unquote correctly. The apprentice model really kicks in. Which means you’re at the sort of mercy of what people are good at, not good at, et cetera. People turn over quickly so that apprenticeship doesn’t even work anymore.
The RIAs I think are the worst place to learn about this type of thing. They have a completely different modus operandi as far as keeping clients happy.
The word fiduciary means something so different to them than it does to an actual trustee. I wouldn’t feel good about the training on that front to sort of create trustees
And then so law schools. They’re they’re just trying to create people the trust in the states vertical as a general matter. Let alone trying to delineate into a trustee situation. You’re putting the pipeline together and you put these programs together. How do you stitch together the needs and what does that manifest itself into?
Jennifer Zelvin McCloskey (19:07.642)So that’s a really, really good question. I think that the very first place that we start with answering that question is advising on a trust as an attorney. It’s different from the administration of a trust and the skills that you need for that.
So when you create a program like this where you’re trying to teach about trust management. You have to start with the technical skill. The legal side of what is it that we’re even doing? What is a trust? What are the fiduciary duties? Where do they come from? Then we have to, after we teach or create a structure or foundation on what the legality is. Now we go into how does this translate into administration?
So when I created the programs, I looked at what’s the law they need to know? What is the level of sophistication of the student? And what do I need to, from a foundational perspective, teach first? What are the building blocks? And then how do I translate that into administration? The one thing that I have found is trust law does not equal investment management. So if people are coming along…
Frazer Rice (20:26.254)No question. I’m nodding audibly at that comment. I like that.
Jennifer Zelvin McCloskey (20:31.226)Your fiduciary duties as a trustee are fundamentally different than those of an RIA, where some RIAs are not even fiduciaries by law. They’re not. So being able to delineate and explain where that line is, what makes you a fiduciary, what are those duties, after you know the legal basics.
And taught to you at a level that you can understand. I don’t expect everybody to be a lawyer. And people have asked me time and time again, do I need to be a lawyer to know this? No, you don’t need to be a lawyer because you’re not advising on the law. You’re advising on the administration of a legal structure and how that administration affects the fiduciary duties that are inherent in the relationship.
Then how those fiduciary duties are translated out to the beneficiary. That’s the way that I’ve always built these programs. Where do I start? Start with the law. Where do I go from there? Start with how the administration translates the law. And then how does that administration get heard by the beneficiary? Where does the RIA come into the mix? The RIA should not be dabbling in advising on trusts. They should know that they need to bring in somebody who has this particular skill. And if they’re not doing that, they’re doing the client a disservice by trying to give one-stop shop advice.
Frazer Rice (22:06.85)Yep, no question about it. One of the things that…we delve into the world of trusts and their function, et cetera, is that you’re dealing with an ecosystem from client to outside advisor, whether RIA or even accountant, et cetera, that they’re looking for certainty and airtight. quality to these structures that you put them in place and then everything runs like a clock going forward.
When in actuality, I think there is a bandwidth of risk around everything. And so it’s the poor trust officer or individual trustee who sometimes has to be the bearer of bad news to say, yeah, you know, I think this is going to work 98 % of the time, but there’s a 2 % problem here or we’ve got this to fix or something like that and everybody else sort of sighs with disappointment and gets mad at the administrative function when in actuality they’re really doing their job and trying to, you know, keep a lot of things that are spinning out of control kind of within view.
How do you get a trust officer or that administrative function or even the full trustee function to be comfortable with that risk and everything that’s involved with that?
Jennifer Zelvin McCloskey (23:20.504)You have to start with explaining that there is risk and we’re not our job is not as a trustee to eliminate risk. Our job is to manage and identify risk. It is inherent in the job. There is going to be risk. No matter what you do, you cannot divorce risk from trusteeship. It’s a matter of identifying perceived risk and actual risk. And if you can teach that, if you can teach
These are the things that are going to trigger a likely outcome. They’re gonna trigger a likely risk. Then you can essentially, you can’t foresee everything. I mean, there are things that are just gonna happen. But in a trust instrument, you’ve got contingency plan upon contingency plan upon contingency plan. That’s what the flexibility of those structures are building. We need to, as trustees, be able to recognize What is the risk with contingency plan A? The risk with B? What is the risk with C? How can we minimize the risk? And how can we make sure that we’re managing perception of risk versus actual risk?
Frazer Rice (24:29.31)as someone who’s been in trust companies, advised trust companies, advised trustees, and advised clients, the lack of appreciation for the management of that risk and that that as the intersection of the business model of trusteeship and risk management and use of discretion and making hard decisions and even kind of an insurance quality around these structures, how do you fix that, where people place a level of respect on the job that I think is completely lacking in the wealth management ecosystem?
Jennifer Zelvin McCloskey (25:09.089)Absolutely. It’s a tough one to answer. How do you fix it? First and foremost, I think that it’s a top-down fix, especially at a corporate trust company, a bank, and even an independent trust company that’s not affiliated with a bank.
The management has to… really understand the function of the trust company. For so long, it’s been just an extra service that we provide and and we’ll do this, the back office trust company. It’s really, really important that the management recognizes what the functionality of the trust company is and stops treating it as sort of a back office stepchild. From the corporate level, I think that’s the very first place we start.
Frazer Rice (25:38.478)Mm-hmm.
Jennifer Zelvin McCloskey (25:57.818)The second place we start is investing in our trust officers, investing in the team, giving them the education that they need, continuing to give them education, providing training programs, whether they be in-house, external, bring in trainers.
None of this is set it and forget it. At the individual level, I think it’s really, really important to have functions like the Individual Trustee Alliance, groups like that, where you have an ability to talk to other professionals that are doing what you’re doing. That’s another way to impress upon people that we have to manage the risk and we can’t do it all alone. Nobody knows everything. You really have to, you have to talk to other people.
You have to engage. have to, what is it called when we were practicing law and we’re a little bit outside of our comfort zone, we have to consult with other people who know more than we do. It’s our obligation as lawyers. It’s the same thing with a trust company, with a trustee, whether you’re an individual or you’re not. Widen that circle.
Frazer Rice (27:08.474)I think this is my idea for the day that there’s got to be a bit of a public relations campaign sort of describing what’s going on here because I think especially when we go into the family members that sort of occupy these roles, they have no earthly idea what they’re doing. They’re usually doing it for free. Everything’s hunky dory up until a point and everyone hopes that everyone is not going to sue each other if something goes wrong.
But the level of wealth that’s being transferred now is now so significant that everyone sort of talks about, AI is going to get rid of lawyers. Nope, not in fiduciary litigation. I think that’s a medium term growth industry, especially around insurance, around ILITs, around revocable trusts, around elder care.
But this is my advertisement for people who are in law school looking for a productive way to go. I think that one is going to be, I think that one’s recession proof, at least for a while until I retire anyway. So my thought is that awareness over these things, and it’s probably going to take a very difficult case or a class action suit, something like that, where somebody really gets hurt in order for that awareness to come up.
Jennifer Zelvin McCloskey (28:24.922)Yeah, I would agree. think that some of the solutions would include better trust education, you know, whether it be for RIAs, lawyers. Trust in the states is a throwaway class in law school. And there are so many law schools that are essentially rolling it back because bar exams aren’t testing it anymore in a variety of states. And ACTEC is definitely working with the law schools to try and increase trust in the states being taught and certainly being tested.
So education for lawyers coming out of law school, education for RIAs that are advising on trusts, education for trust officers, for trust administrators, trust professionals in general, clear role delineation. What is the role of the RIA? The role of the trust officer?
What is the role of the trustee if they’re an individual trustee? And then creating a culture of collaboration on what we’re doing as a team for the beneficiary, not substitution, but collaboration with the advisors and the trustees.
Frazer Rice (29:32.59)Let’s go into the role delineation for a second. About 20 or 30 years ago, the concept of bifurcating or sort of cordoning off the different functions I described before the investment, the administration and the distribution has come into vogue.
I think that came out of frustration with bank trust companies where you got one set of advice for every trust that they had as far as investments and distributions and administration and a lot of modern larger families wanted something a little bit more specific to their needs.
And that’s really turned, it’s exploded as an industry for increasing sophistication and size of wealth. Along those different functions, where maybe the administration goes to a professional trust company or a trust officer in the state that you want,
Then there’s some intersection maybe in the distribution committee. And then the investment side of it is a bit of a free for all, think, depending on what you’re, dealing with. How do you educate the, that continued the delineation, but the coordination within those types of structures.
Jennifer Zelvin McCloskey (30:41.275)Yeah, I think it’s really important. And I’m a Delaware lawyer. I’m licensed in multiple states, but Delaware is my home. It’s where I learned how to be a lawyer. It’s where I grew up as a lawyer. So this directed trust model that you’re describing, where you’re bifurcating, truly bifurcating these particular functionalities of a trustee, it originated in Delaware. sort of, we didn’t, I mean, we invented it, right? We codified it. It was being done, but we codified it.
The idea of making sure that everybody understands what their function is and knowing that there’s a limit of liability that’s built into the instrument and communicating what that means to the RIA that is named in the document. I can’t tell you how many times I have heard companies, heard trust companies say, we’re advisor friendly. And I’m like, not unless you’re directed, you’re not.
Frazer Rice (31:37.528) “THE TRUSTEE CRISIS: Navigating the Challenges”Yeah.
Jennifer Zelvin McCloskey (31:40.439)If you are directed, you are 100 % advisor friendly because there’s no chance that that trustee is going to try and take the investment management. They’re not a portfolio manager. Not a clerical administrator. They’re not a passive rule follower. We need to identify what does that trustee actually do when they are an administrative or directed trustee.
Clarify that role so that people who are engaged in this bifurcation, this structure where we’ve got a distribution committee, maybe it’s individuals who are close to the family, close to the beneficiaries, where you don’t have somebody who’s objectively uninvolved with the family members making decisions as to whether or not there’s a distribution that should be made.
But also advising those rolls those advisors that your administrative trustee is not just a pencil put a paper pusher. Not just checking boxes. They really do add value to the role that they provide and making sure that everybody understands what each other are doing, having regular meetings amongst the team instead of operating in a vacuum or operating in a silo.
And taking the approach of it’s not my job, misunderstanding trustee powers and the advisor’s authority. So when that’s delineated, when that’s really understood, not just by the advisors, but also by the beneficiaries, there are so many beneficiaries out there, Frazer, that have absolutely no idea that they actually hold all the cards. They don’t know.
Frazer Rice (33:25.87)Along that line, so in the administrative, we just walked through pretty nicely. The distribution function is one that, let’s talk a little bit for a second about what it means to ask a trustee for a distribution and maybe the difference between income and principal and why having a steady hand at the wheel within that function, whether it’s a corporate trust company of qualified individual or family input in that function, why real good thought needs to go into how that’s staffed.
Jennifer Zelvin McCloskey (34:04.73)Yeah, absolutely. 100%. In a corporate trustee ship or a corporate trust company structure, there’s always going to be distribution committees, right? So if you are the trustee, you’re going to have to go through a committee that’s looking at what your reasoning is for making that distribution. They’re asking questions about what have been the prior distributions?
Have they come from principal? Have they come from income? What is the spend rate on that trust? How is this going to affect long-term spend rate? Is this an aberration? Is this something that’s gonna become a habit? Really understanding what the distribution, the guidelines are in the trust. What is the distribution standard?
Making that decision? What are our factors? And how many people are at the table? Who’s communicating that to the beneficiary? Does the beneficiary know that the trust officer alone does not have the ability to say yes or no? That when they’re in this ecosystem of a corporate trust company, they have their checks and balances to make sure that that risk is being managed.
So when you’re looking at corporate trust companies, are a lot of layers behind understanding what the distribution standard is, whether it’s hems or if it’s purely discretionary. The other thing that you need to look at when it’s not a corporate trustee and it’s an individual trustee is, how is that individual trustee making that decision?
Are they doing it in a vacuum? Alone? Are they favoring one beneficiary over another because they like them more, you need to have some communication to the beneficiaries so that they understand what they are, what their interest is, what they are entitled to, if anything, and why the trustee stands in that position as the gatekeeper. And I really think in my heart of hearts, we need to make a shift from a gatekeeper trustee
Jennifer Zelvin McCloskey (36:16.708)to a beneficiary enhancement trustee, where the beneficiary is really taking on the understanding that the trustee is there to facilitate enhancing the beneficiary’s life. That even though the trust may have started at the outset as a tax strategy or something that the grantor decided they needed to do with the advice of counsel.
At the end of the day, you wouldn’t have been named as the beneficiary if there wasn’t some sense of love or obligation even, that it’s for your benefit. It’s in the name. Beneficiary. Trustees need to understand that and beneficiaries need to be taught.
Frazer Rice (36:54.958)Right.
Frazer Rice (37:00.646)And it goes to the circle back to the notion of making sure that you write down the whys of the decision because ultimately if the concepts of favoritism or you didn’t communicate this or anything, the idea of having the beneficiary submit a budget but having them understand why they are submitting a budget and then if there is some discretion that’s happening around that decision that the data points that are informing that discretion, that’s gonna keep everybody safe a lot later on.
Jennifer Zelvin McCloskey (37:32.666)Absolutely. I break it down into a couple of different factors. It’s fiduciary decision making. How is that fiduciary making the decisions they’re making? Why are they making those decisions? And who is being affected by the decisions? Document interpretation. Do you understand the document that you’re administering? If you don’t understand the document you’re administering, hopefully best case scenario, you know what you don’t know and you ask.
But if you don’t understand the document and you don’t even have the wherewithal to say, hey, I need help to understand the document, it’s really problematic. The third part, balancing beneficiary interests. Really taking on board this idea of the principal income problem that all the assets in the trust are not the same. That some of it doesn’t at all in any way affect a certain class of beneficiaries.
And at the same time, it’s inextricably intertwined in the way that it affects another class of beneficiaries. And then risk management and governance. How is this being governed? How are we managing perceived and actual risk as a trustee?
Frazer Rice (38:40.13)The investment function, which I alluded to before, I see storm clouds on that horizon, not really at the RIA level, because I think there’s sort of a default mode that investment policy statements are in place. Diversification is a true commodity at this point. And I never really worry about an RIA sort of understanding how to invest to get to a certain expected return and deal with the risks and drawdown and all that stuff.
The storm cloud I see is when individuals sit in that role and they are being tasked with, let’s call it quote unquote, overseeing concentration, meaning that trust is holding a building, farmland, a nuclear reactor, crypto, all of these different things that sometimes can be, A, they have their own different maintenance responsibilities that are not just looking at a fidelity statement, but that they also have their own volatility
And, you know, in the case of a building, you got to make sure it’s managed correctly. are they going to get sued or the windows kept up, all of that stuff, and that there’s a whole different component there. And I’m waiting for the shoe to drop on some fact pattern there where somebody is sitting in the role of an investment advisor. It doesn’t say trustee in the document, so they don’t really think that they have trustee liability.
But. they sit in that role and all of a sudden somebody finds 10 55 gallon drums of green fluid in the basement of a building and all of a sudden the trust has a big set of red brackets that say minus $100 million that you owe to the federal government and the EPA. How do you think about that?
Jennifer Zelvin McCloskey (40:21.454)Hmm.
Jennifer Zelvin McCloskey (40:25.242)That’s a heavy question. so the Delaware stock answer, obviously, direct it, right? It’s just to get the trust, cut off the liability. At the first, at the inception of your hypothetical is bad drafting, right? So if there’s no statement as to whether or not your investment advisor is acting as a fiduciary or not,
Frazer Rice (40:35.042)Right.
Jennifer Zelvin McCloskey (40:52.836)What does your statute say? Does your statute impose that they are as a default a fiduciary or not? So that’s the very first step. That’s bad drafting. We need to know. But if it’s silent, let’s say it’s just a lousy document, there’s, God knows. Anybody who’s seen trust documents knows that, you’ve seen them all, right? And everything in between. Some are good, some are bad. If this is a bad one.
Frazer Rice (41:13.08)Seen good and you’ve seen bad.
Jennifer Zelvin McCloskey (41:20.079)Then we need to document the statute. If we can correct it, modify the document, let’s modify it. But if all of that can’t happen, then I would say the best way to handle it, make sure you have adequate insurance. mean, over-insure that, over-insure it. Make sure that there’s regular checks on the actual…
Assets that are in the trust, if you have a concentration and that concentration is real estate, get the advice of counsel, put that bad boy into an LLC, get yourself some distance from the actual asset itself being held in the trust, hold an interest, hold a financial interest, push it down to the corporate level. But if you can’t do all of that and you’ve got those 500 gallon drums of green fluid and now you’re…
Frazer Rice (42:14.286)You
Jennifer Zelvin McCloskey (42:15.371)You you’ve got a super fun site. What do you do? You don’t shy away from it. Have to address it head on. You got to take the accountability. You got to communicate and document, communicate and document some more. Talk to your beneficiaries. Make sure that they’re aware of where it went wrong, why it went wrong. Because I have found in my exposure in the industry over time and in reading case law, it’s when you’re trying to cover stuff up.
Frazer Rice (42:43.913)Jennifer Zelvin McCloskey (42:44.027)You’re just making more problems. Bad news doesn’t age well. It doesn’t get better over time. You have to approach it head on and make sure that there’s communication and documentation. Meet with your beneficiaries. If there’s a trusteeship where you are appointed as a trustee individually and you’re not having at least quarterly meetings with your beneficiaries,
If you’re not going out and seeing the asset, if you’re not going out and making sure that the asset is properly custodyed, you’re not, you’re violating your fiduciary duty. You are not doing what you’re supposed to do.
Frazer Rice (43:21.804)You brought up an interesting word there, custody, which is the administrative function, whether held corporately or individually, one of the major things you have to do is to safeguard the assets. And that’s a big two syllable word that carries a lot of weight with it. That custodial function, how do you teach the trust officers or the individual trustees where that starts and stops?
Jennifer Zelvin McCloskey (43:48.579)Yeah, mean, custody is super, it’s a really touchy, touchy subject, especially with the dynamic way that trusts have developed in the current climate from tangibles. You know, I’ve got artwork and my beneficiary wants to hang the artwork in their house. Well, do you have custody?
Has it been assigned to the trustee and how do you maintain that asset? Make sure nothing’s happening to it. Do make an appointment, go over to the, visit your artwork? What if it’s prize horses, you know? What if it’s, you know, a stud that, you know, we’re gonna need to breed and it’s gonna be the next Triple Crown winner? How do you make sure that the barn is properly safeguarded?
It’s a really touchy subject, especially with things like tangibles and things like assets held away when you technically custody the asset, but you don’t have control over the asset. I think in the education part for custodying, what I do in my programs and when I teach this is I make sure that we talk about different types of asset classes.
And what the risks, again, what are the risks that you run with these asset classes? How can we manage the actual and the perceived risk of holding that asset? Even if you have custody and name only, but you don’t have physical custody, how do you maintain your control over that asset? Because it’s really the C’s, right? The custody and control. Just because you don’t have custody doesn’t mean you don’t have control.
So we have to make sure that there’s an education that’s provided about the different asset classes, whether it’s tangibles, intangibles, assets held away, if it’s a concentration of stock, if it’s crypto, and most trust companies are not taking crypto. I think that there’s like a circuitous way that they’re getting in right now, but it all boils down to education, isolating what the issue is and educating people on it.
Frazer Rice (45:59.586)I’ll give you a third C, it’s consequences, which is what happens when you don’t understand these functions. on the crypto side of things,
Jennifer Zelvin McCloskey (46:01.786)Uhhh
Frazer Rice (46:11.544)Holds the key to get to the crypto. What happens if that trust officer quits and walks away with the key and they’re like, well, multi-sigil figure this out. I’m like, okay, that’s not that. That doesn’t make me feel great at the moment. And now there have been some advances, which is good, but traps for the unwary to be sure. the good news too for crypto is for people who want exposure, the spot ETFs take away 90 % of the problems with that.
But as we start to think about winding down here, because I have a feeling we could probably talk for four or five hours on this subject, when putting your programs together, what does a curriculum look like? And we don’t have to go through it bit by bit, but how does that work when someone comes to your program? How much time does it take? What’s the commitment?
Jennifer Zelvin McCloskey (46:47.172)Yeah, I think so.
Frazer Rice (46:54.851)Mm-hmm.
Jennifer Zelvin McCloskey (47:06.33)So the program that I created that’s really available anywhere across the country is called the Peak Trust Management Certificate Program. Peak Trust Company, may be familiar with it. They have name rights because they gave the donation to the University of Delaware for me to build the program. So it’s housed at the Lerner College at the University of Delaware, but bears the name of Peak Trust Company. I look at five different things.
The first thing is trust law and administration. So like I said previously when we were talking, you lay that foundation of what is the legal component of this? What is the baseline that people have to know? And then what is the administration?
The second component is, and it’s inextricably intertwined as taxation. What is the income tax? What are the deductions? And now let’s take all of that income tax knowledge, individual income tax knowledge, and build on it with fiduciary income tax. What is DNI? What is FAI? How does it go out to the beneficiary? What’s the character of the distribution? How do we manage that? What are we deducting in the trust? So teaching taxation and not because trustees necessarily are tax preparers, but because the trustees obligation is to be able to understand and read that tax return, they need to know how to spot problems.
So from my perspective, teaching fiduciary income tax is a critical component. It also helps. Yeah.
Frazer Rice (48:38.828)No, no, I was gonna say no question about that. And there are elections to make, just because it doesn’t just go on autopilot, there are choices to be made so that if you’re the trustee, you may not have to prepare the tax return, but you may have to make a choice on the tax return and you’ve got to be informed because that can be an issue.
Jennifer Zelvin McCloskey (48:58.651)65 day elections, perfect example, right? You just, you need to understand what your role is and how it overlaps with that of the CPA.
The third part, of course, investments. Investments are inextricably intertwined, whether you’re doing it yourself as the trustee or you’re directed or even delegated, which is like the hairy scaries of every trusteeship known to man, because you’re not actually in control, but you’re responsible. So it’s the gray. When I build a program, because of the, you know, the directed trusteeship being so popular in today’s day and age, we have to talk about not just investments of, you know, marketable securities, not just the custody of tangibles, but also subscription documents, because so many alternatives are held in trust right now. unique assets, need to know how the trustee is actually carrying out their fiduciary duty when it comes to engaging in an investment that is an alternative investment.
The fourth component is of course compliance. We cannot ever get away from compliance and I think we could do a whole nother podcast on compliance in trusteeship but.
You know, it’s a regulated entity. And even if you’re an individual trustee and you’re not using what those compliance frameworks are, what the guidelines are by OCC, Reg 9, FDIC, if you’re not looking at that and using that as a guideline, don’t do the job. understanding KYC, BSA, AML, all of those compliance components that have tentacles.
That’s the fourth part.
And then for the fifth part of this program, because it’s specifically geared toward trustee education in trust companies, although it can be applicable, very applicable to individuals, is operations. I was very fortunate that I was able to partner with SCI on building the operations component. So we license their platform called Plato. It’s essentially their training platform.
Jennifer Zelvin McCloskey (51:12.888)so that trustees can see how fees are set up, fees, that’s a whole other podcast, fees, statements, distributions, how are we doing this? How are we documenting everything? What are the logistics of the day-to-day operations? So that’s how I built the program and it’s available anywhere in the country. It’s 10 weeks, how long does it take? I would say from three to five hours a week of an investment that you’re making at a bare minimum.
Obviously there’s a whole lot more of depth that you can go into. The resources are built in. But I would say 10 weeks, about 50 hours of time where you’re actually engaging with the material. And then I bring in guest lecturers on each different area of expertise for lack of a better description.
And they get a certificate at the end, they get a digital badge, and now they really have something where they can add value day one in a trust company or as a trustee.
Frazer Rice (52:17.902)With Delaware being, you one of the real gold standards as far as trust jurisdiction, I assume that everything that comes out of this program is pretty transportable to the other useful jurisdictions, let’s call it, within the country. know, the Tennessee’s, the South Dakota’s, the Nevada’s, the Alaska’s, Wyoming’s, New Hampshire’s, et cetera. Obviously, there are hairs to split with different foibles in their law, but everything that you’re describing sounds like works everywhere else.
Jennifer Zelvin McCloskey (52:47.928)And I’ve always taken the approach, you’re 100 % correct, I’ve always taken the approach of UTC. I base everything off of UTC and if there’s something different or unique based upon the jurisdiction that you’re in, I always encourage people you have to look at your statute, you have to look at the jurisdiction that you’re actually practicing this in and administering in. I use Delaware, South Dakota, Alaska as examples quite often when we’re talking about the directed stuff, but
By and large, it’s UTC.
Frazer Rice (53:20.966)It just a weird subset. So special needs trusts and islets, which are two types of trusts, very specific. One holds life insurance. The other is designed to really take care of people who can’t take care of themselves. And they are types of trusts that a lot of trust companies don’t like to take on because the liability is harder or the profit margin is less.
For those individuals who get the opportunity to participate in those and I put that in air quotes. How would you advise people to get ready for those types of situations?
Jennifer Zelvin McCloskey (53:58.308)People who are in need of those types of trusts.
Frazer Rice (54:02.122)Well, maybe both. The people who need those trusts, you know, they’re going to, they, you know, it’s almost like they get set up and then the staffing gets kind of figured out later, barely. And then, you know, the, for the people who end up taking on that role, they really have no idea of what they’re in for in a sense. Is there sort of like a mini, I’m not going to say a full course like you’re describing, but a crash course in, in what’s going on here and what can I do to keep myself safe?
Jennifer Zelvin McCloskey (54:30.271)Unfortunately, no, I don’t know of one. and there isn’t much built in. there’s, we talk about a little bit in the program that I built, but, those are specialized and eyelets we talk about a little bit more there, you eyelets had their day and sort of they has done ish. but special needs trust. It’s a whole other ball game because
It really incorporates state law and social security and Medicaid, all of those government benefits that I think you would need something more specialized than my program that I developed. And I don’t have a great answer for that, I’m sorry.
Frazer Rice (55:12.482)No, there’s not a great answer for it because it’s tough. it’s a, all of which is to say for someone who’s involved with those things and feels confused by what’s going on, that’s one where it’s worth it to spend the money to lean on a dedicated Medicaid elder care, special needs type of lawyer on that front because there are traps for the unwary. Okay, now we’re starting to butt up against an hour here of.
Jennifer Zelvin McCloskey (55:29.764)Yes . . .
Frazer Rice (55:38.827)Four hours. No, I’m kidding listeners. We’re not going to talk for four hours, but How do people find your program and and then I’ll ask a bonus question at the end
Jennifer Zelvin McCloskey (55:49.339)So the program is on the University of Delaware’s website. You just type in peak trust management certificate and it’ll pop up. My name will be there. I think my picture might be there. It’s all over my LinkedIn. So if you look me up, you’re going to see the peak trust management certificate program. You can always email me, jennifer at zeldenlaw.com. Happy to push people into it. start, I’m in the new cohort right now. We’re two weeks into a 10 week program.
But we have a new cohort starting in May. I think it’s May 4th. So may the fourth be with you.
Frazer Rice (56:24.622)Terrific. So the final question here is really more of a crystal ball question. In this trust industry, trustee industry, what are the real, I’m going to say opportunities out there, and we’ve sort of painted a picture of doom and gloom and its low profit margin and things like that. Where can someone who is thinking from a business perspective about this find something?
Once they’re properly educated about it and being able to participate in it.
Jennifer Zelvin McCloskey (56:57.582)There are so many opportunities. There is an absolute need for good trustees everywhere. Trust companies from coast to coast, individual trustee alliance. People really, really need trustees. There’s tremendous opportunity with Heritage Institute, not the Heritage Foundation, but the Heritage Institute.
There’s opportunities with…various family offices and various trust companies for education, for beneficiary education. So many opportunities out there. Trust companies are just clamoring for people. So if people are interested in becoming a trustee, getting that education, you will not have a hard time finding a job. Like you said, it’s basically recession proof. This wealth is going to transfer. We need sophisticated, knowledgeable trustees. on the receiving end of that transfer so that it happens correctly.
Frazer Rice (57:56.578)I’d go so far as to say financial advisors. I just gotta say, a CFP is useful, CFA is on your investment side, but something like this, you know so much more about how intergenerational wealth works than what’s happening in those particular situations that I think it helps people stand out when I see something like that on a resume.
Jennifer Zelvin McCloskey (58:00.302) “THE TRUSTEE CRISIS: Navigating the Challenges”That’s all the podcast. I hear you. I hear you.
Frazer Rice (58:24.386) “THE TRUSTEE CRISIS: Navigating the Challenges”All right, with that, Jennifer, it’s great to catch up and I will have all of your information on the show notes and I will either see you at the ITA conference in Dallas or what I’m down in Delaware next.
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THE TRUSTEE CRISIS: Navigating the Challenges
https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
Keywords for THE TRUSTEE CRISIS: Navigating the Challenges
trusteeship, wealth transfer, trust management, fiduciary duties, trust education, estate planning, risk management, trust administration, individual trustees, trust companies, the trustee crisis, navigating the challenges, the great wealth transfer,
February 27, 2026
SPORTS MEDIA FOR ENTREPRENEURS
Frazer Rice and Bram Weinstein, the “Voice of the Washington Commanders,” discuss the shift in sports media for entrepreneurs. The current state of sports journalism is in flux, especially with the decline of the Washington Post’s sports section and its implications for local coverage. We explore the opportunities that come from this void. (Including the potential for new media ventures and the challenges of monetizing content in a fractured media landscape). The discussion also touches on the future of the Washington Commanders, the importance of audience engagement, and the evolving nature of podcasting and digital media.
https://youtu.be/O0syDGcSkvU
https://open.spotify.com/episode/3Ut9QRj7X9QD1pGEA6y6qt?si=39nLO2reQ8SK_nj0zenzDA
Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)
Takeaways
The Washington Post’s sports section closure is seen as a significant loss.
There is a growing opportunity for new media companies to fill the coverage void.
Monetizing media ventures requires innovative strategies and diverse revenue streams.
Podcasters face challenges in gaining audience traction and monetization.
The Commanders’ future depends on effective roster changes and health improvements.
Engagement with the audience is crucial for media success.
Digital platforms like YouTube provide exposure but limited revenue.
The media landscape is rapidly changing, requiring adaptability.
Local sports coverage is essential for community engagement.
The importance of maintaining journalistic integrity in a changing media environment.
SPORTS MEDIA FOR ENTREPRENEURS CHAPTERS
00:00 The State of Sports Journalism
02:59 Opportunities in Media
06:07 Monetizing Media Ventures
09:05 Navigating Podcasting Challenges
11:59 The Future of the Commanders
15:06 Engaging with the Audience
DISCOVERING BRAM, THE COMMANDERS, AND AMPIRE MEDIA
BRAM on SPOTIFY
AMPIRE MEDIA ON YOUTUBE
AMPIRE MEDIA WEBSITE
Transcript of “SPORTS MEDIA FOR ENTREPRENEURS”
Frazer Rice (00:00.686)Welcome aboard, Bram.
Bram N Weinstein (00:02.551)Hey, Frazer, how are you?
Frazer Rice (00:03.736)Doing great. The last time we spoke it was about three days before the Chicago Hail Mary, so I’m viewing that as good luck. That must have been something having to call that game.
Bram N Weinstein (00:14.071)That was part of the most magical season I’ve ever been a part of. Not only first ever for the franchise, but 12 and five, NFC championship game, hadn’t done that in a generation. It was pretty incredible, yeah.
Frazer Rice (00:28.652)No, as a skins fan, now commander’s fan, it’s been a long time, but it was a wild ride. One of the things that’s happened recently, which I know strikes near and dear to your heart, and frankly, for people who grew up sort of following it, has been, I guess, kind of the evisceration of the Washington Post sports section. And it’s got all sorts of impacts.
But from your perspective, How do you make sense of that and what does it look like going forward for a city essentially that has all the major sports and the major paper not really covering it?
Bram N Weinstein (01:09.719)I don’t make sense of it. I don’t understand it. I think at its core, The Washington Post is two things. It’s one of the most important publications in the world as the paper of record in the most powerful city in the world and the democratic center of the world. But it also is a local newspaper for one of the top 10 markets, top five markets in the country.
And the idea that it would not cover its sports teams, or Metro desk, which, I know, you know, for our purposes, we focused a lot on the sports desk being shuttered. The Metro desk is too. So the Washington Post not covering the mayor’s office, city council meetings like in especially in these political times where, you know, the district budget is held by the federal government.
To me, it doesn’t even it doesn’t compute that that wouldn’t exist. as far as like the sports section goes, which I think is like the lesser of the two real problems with this, but obviously is a real problem is, you I think for me, it feels like a death. I grew up reading the Washington Post. A lot of the reasons why I wanted to do what I wanted to do was through osmosis of reading Tony Kornheiser and Michael Wilbon and Tom Boswell and all of the great writers that came through the Washington Post.
And I just don’t really understand how it’s not within the business model to be part of this. At the same time, you know, it does open opportunities for entrepreneurs like myself who have media companies and are always looking for new talent and always looking for openings. And I can tell you that void is going to get filled.
But I do think it is sad that the Washington Post could not figure out a way to modernize itself to allow its coverage to continue for its loyal readership. This is a local paper that isn’t covering local news. That is astoundingly terrible in terms of a business practice to me.
Frazer Rice (03:14.317)It’s weird because from my perch here in New York, I work across the street from the New York Times building and there’s a little bit of sort of guffawing that the New York Times has turned into a gaming company and sort of a media company second, which has helped to subsidize its continued commitment to long form journalism. But even then, I mean, it’s really focusing on arts and leisure and cookbooks and wordel and all sorts of things like that.
And it’s a shame that the Washington Post either couldn’t pivot in that direction or otherwise make sense of things.
Bram N Weinstein (03:48.727)Is the business model of media the same that was no. so there are a few things that play here to be fair. I’m not asking Jeff Bezos to lose money. You know, like, or just be the beneficiary to subsidize something, but you do bring up a point, which is.
And I read this quote recently from, the old ownership group, the Graham family, who basically said. “You know, the newspaper is a grocery store. Like you are supposed to go in there and pick all the different things that you want. And hopefully there’s something for everybody or hopefully a number of things for everybody. And in modern times, the New York Times has done a very good job of putting together a new modern grocery store for people. So there’s a variety of different things that does subsidize the important work that it does. And in the end, like to me, the New York Times and the Washington Post and maybe the Wall Street Journal.
Are the three most important newspaper entities, if you can call them that, in the United States of America. And for one of them to not understand their role in protecting democracy, in covering our world, in informing the readership, whether it’s locally or nationally, to me is an absconding responsibility. So I don’t know what the answer is.
Again, I’m not like demanding Jeff Bezos just…money to keep things subsidized. Like it is a business and I understand that, but there must have been better ways to go about it or maybe, you know, sell it to someone who does have ideas because it’s important for its foundations to remain intact. And so I just, you know, for me, it’s, been hard to digest, honestly. And like to your original question of like, like, how do you make sense of it? I really don’t. I don’t make any sense of it.
Frazer Rice (05:39.692)Well, you also now have a fledgling media company and I’m a devourer of yours and Kim’s and Standix podcasts and I learned something from it each time. I see an opportunity there if major component of the media establishment in the area is abdicating its role, not only to the major sports that aren’t getting covered as much.
There’s an opportunity there. But even like the local hotbed sports like lacrosse, they’re completely ignored, I would imagine. And that might be a way to sort of get some grassroots component going.
Bram N Weinstein (06:17.195)Yeah, we also here with my company Empire see the opportunity, unfortunately, but we do. And there’s a lot of talent that is available. There is a void in coverage. We know, you know, the size of our community, the appetite for sports. And so, you know, I don’t want to say too much, but we are actively seeking partners to expand in a pretty large way if possible. So
Frazer Rice (06:24.045)Right.
Bram N Weinstein (06:46.067)We’re working towards that and I’ve been working towards that and moving very fast in the hopes that we’re not the only ones thinking this like you. There’s a lot of people thinking there’s an opportunity here. I wish it wasn’t the opportunity that it is, but it has presented itself and it’s an opportunity that we intend to see through. So we are actively speaking to a number of different interested parties about funding a major expansion of what we’re doing.
Frazer Rice (07:11.379)Really cool. Well, I’ll be sure to keep an eye on that as it develops. When you’re thinking about sort of the money making aspect of it, we don’t do things for free and it’d be lovely if we all had time and disposable income to do that without giving away the playbook because you’re raising money and you don’t want to give that up necessarily. But how do you think about that in terms of delivering value for sponsors or advertisers or the general audience? Have you made any…sort of commitment strategy-wise there.
Bram N Weinstein (07:42.197)Yes, digital audio video forward. You know, I also believe in enterprise journalism. I also very much believe in long form journalism, but the audience appetite for it is limited. And so you do have to subsidize it. And that comes in the form of a number of different properties repurposed for different platforms in various ways, podcasts, video shows, YouTube.
All offer opportunities to monetize the same content. I have been studying very closely the things the New York Times has done and thought about what kind of engagement tools would be necessary to be an added perk for those who would end up probably subscribing to a situation like this. So there are a lot of different types of financial models.
One is subscriptions. in a variety of different ways, whether it’s premium content, newsletters, one of them is obviously advertising, which would come with YouTube or different streaming channel, streaming network, podcasts, obviously, sponsorship, which could go across the board for all of the different categories. And, lastly, live events. And this is something that we are very capable of doing as well.
So there are a tremendous amount of different models to make money. None of them are easy. And because the audiences are so fractured, I think you have to find ways to make financial streams in the same content in various different forms. But we’re willing to do that. And we’ve already kind of done that with what I’ve done with Empire on a very limited role, which is why we think we’re ready to make this expansion and move.
But we need an investor to buy in and to the investors, I would say to them, we intend to make you money and we intend to be something that could be purchased in a three to five to 10 year plan. So we understand the importance of making sure that the investment is paid off in the end as well.
Frazer Rice (09:52.205)Cool. Are you thinking about expanding into other subject matter areas? you’re in DC, so politics, guess, would be a natural fit. Right.
Bram N Weinstein (09:59.965)Not really. And I wouldn’t personally, like, I just don’t feel like that’s my expertise. So no, but like, could we be something like the ringer where you’re looking into culture, you’re looking into arts, music, dining, those types of things? Yeah, I think like that’s something I’m not sure that I would move fast into a realm like that. Like we see the void in sports coverage for this marketplace. We would like to fill that void.
And whatever we do after that would be dabbling in those spaces to try to, again, find new ways to find new audiences. But we want to go with our core products first. And certainly for me personally, the politics world is completely above my pay grade. So I’m out of that. Yeah.
Frazer Rice (10:46.028)It’s above everybody’s I think if anybody could figure it out It’s it’s one of those Rubik’s cubes that it’s not worth solving oftentimes So, you know one of the things I don’t know if I’d struggle with or I’m Would like to expand on my front is just getting my podcast out to more people and the concept of discover ability and one of the strengths that I think you have Is you know your current position in traditional media with the commanders?
Keim has it a little bit with ESPN, Ben Stendig has it with his Substack, which isn’t traditional media, but there’s different outflows on that front. How do you view that competitive advantage in terms of getting the message out and almost having a bit of a head start over some of the other possibilities out there?
Bram N Weinstein (11:30.175)Yeah, well, I think there was always like, you know, for the podcast world. Yes, anybody can do a show and you know, they could be good. The reality is, though, you know, the people who already have stakes in the marketplace, at least from name value, are always going to have a head start. It’s going to come down to how you market yourself and how you go about getting your show out there as much as possible.
The reality is you need some level of a robust social presence to get to as many eyeballs or ears as possible. And if you don’t, then you typically have to kind of go down a paid route of making sure that it gets into algorithms. And so it’s a hard climb, like for sure. You know, like when podcasts and kind of open the gates for everybody, same thing with YouTube, like
Frazer Rice (12:14.54)Mm.
Bram N Weinstein (12:23.444)You know, there’s going to be a lot of success stories. There’s going to be a lot more people who are either doing it for love of the game, but not for money. And that’s just the reality of how much time any person has to give up to content. And secondarily, who can get to enough of an audience to make it worthwhile? As you probably know, you need thousands of downloads to really make any kind of real money at all on a podcast episode.
Getting to thousands of downloads. doesn’t sound like a big, like if I said, you have to get to a thousand, like a thousand doesn’t sound like a lot for one episode, but it’s way harder to do. wager a guess that 90 % of podcasts do not reach 1000 downloads per episode. So it’s a very hard number to reach. And if you really want to make money, money on it, we’re talking about getting 10,000 an episode.
Sure, anybody like myself that has various different platforms I can use to promote my own shows has a head start in that manner. And that would always have been for anybody in traditional media who had a following to start with, if they were willing to jump into the digital side quickly, they were always going to have a head start because they already had an audience that was built in. It was just converting them.
Frazer Rice (13:39.572)You know, and for me, the conversion isn’t so much, you know, buying pillows or mattresses from the advertising that comes on the show. I don’t have any advertisers. The ROI for me is, in a client, one client, maybe listening to it and then calling up. And all of a sudden that pays for everything, in sort of my day job.
Bram N Weinstein (13:52.992)Yes.
Bram N Weinstein (13:57.813)Yeah, well, I think you’re actually looking at it the right way. Like, could your show end up having a big audience? Yeah, of course it could. But like, the reality is for most people who are doing podcasts for the other purpose, which is either marketing, client curation, branding, like those have extraordinary value to like my company’s done a lot of B2B type podcasts. And I explained this, you know, to them, and most of the people I work with aren’t looking, they don’t think they’re going to be Pat McAfee. But like, they understand that like,
The value in doing this well is going to get paid back exponentially in client curation, marketing, entering new market spaces, expanding business opportunity, because it done well, it can really have that kind of benefit for you.
Frazer Rice (14:43.563)How do you make sense of all the different platforms that are out there? You know, I converted to video because ignoring YouTube meant basically ignoring Google and I was like, well, that’s dumb. I know, Spotify’s out there. iTunes has just converted to video.
And then you’ve got all the different podcasts, platforms, et cetera, et cetera, et cetera. How do you, it just seems like it changes weekly in many ways as to what’s in favor, what’s not. When you’re making a bet on your company, how do you deal with that?
Bram N Weinstein (15:06.996)Yeah. Yeah, think. Yeah, it’s hard. Things have changed a lot. Like, for the most part, we double up our podcasts now and they’re taped on video. So they’re disseminated with not a tremendous amount of production value behind them. And of course, you know, used as audio podcasts as well. So it’s a two in one situation.
And we find that YouTube. The advertising dollars there are very small, but the exposure, not unlike when we were talking about kind of marketing yourself, the exposure of being there, if you can get thousands of views, often offers up a lot of different opportunities. Sponsors prefer to be visually seen than just audibly heard. So like in both of those cases, they can be beneficial. like we don’t frankly make a lot of like we have on YouTube.
We only have two primary shows with Empire Media that are on YouTube on our channel. We have about 18,000 subscribers now and we get on an average month like 127,000 views between just the two shows, which is a lot, know, especially for like a niche thing where we’re really just talking about one thing, the commander. So we’re like, we’re not expanding out much more than that. So it’s a very niche thing and yet we’re getting a really, really sizable number.
Frazer Rice (16:11.787)That’s good.
Bram N Weinstein (16:25.15)If I told you how much money we get paid for that, you’d laugh like it’s it’s pennies on the dollar. But the exposure of having it and the amount of views and impressions that it generates gets us sponsorship opportunities because people want to be part of that. And that’s where the real opportunity comes with YouTube. As far as like using Facebook Live, IG, like TikTok, I suppose. Like. I don’t know, like I don’t think you can be everywhere.
I think the idea is to try to be, I think you’re talking to different audiences on each of these things. So I don’t think it’s one size fits all. And it has to be worth it. For me, it has to be worthwhile. Like, is there a reason why we’re there other than we’re just trying to get people but if there’s no benefit of a carryover beyond it and it just happens to hit their feed, but we’re not getting any sponsorship money out of it or any activation out of it? Well, then what was the point?
So I’m always looking for right places to be. But there has to be an incentive structure that makes sense, either true carryover audience growth or obvious sponsorship opportunity.
Frazer Rice (17:32.076)The cost of coordination of all of that too starts to overwhelm. I know you’ve got a schedule to keep here. I would be silly not to ask about my commanders a little bit. Two new assistant coaches, offensive and defensive coordinator, lots of changes coming in terms of personnel and hopefully sort of a rethink of Jaden and hopefully a lot better health going into next year. But…
Bram N Weinstein (17:36.17)Yes. Yeah.
Frazer Rice (17:59.84)Potentially better division in many ways, how do you see things going forward?
Bram N Weinstein (18:04.71)I don’t know what their team looks like yet. So this is like a hard question to answer because I think they’re going to be very aggressive in free agency and then obviously they have the seventh overall pick. I kind of need to see what their roster looks like before knowing. I you know, David Blough been here the last couple of years. He is one of these very young, very impressive people. I’m glad they kept him in the building. It’s a big ask to jump from where he was to go to offensive
He at least is talking a big game like he’s ready for this and I hope he is, you know, like we’ll have to see. I think a lot of it will have to do with the quarterback stays healthy and that just didn’t happen a year ago and the whole team didn’t stay healthy. So they fell apart and you know, like I don’t think health was the only reason they had the record they had, but I think the health made it worse than it could have been like their record probably would have been a little more respectable if the health wasn’t as bad as it was.
Hopefully Jayden stays healthy. He’s fine now. So hopefully he stays healthy and on defense Deonte Jones. This is his first opportunity doing this but he’s actually been in the league for 20 years and he’s worked with every almost every major defensive coordinator up until this point So he feels like someone that’s been overdue for an opportunity. I like the system He’s coming out of does he have the personnel to win with I don’t think right now and that’s why I’m like Let me see what they do in free agency. How much money do they spend at what positions?
How are they looking to upgrade that side of the ball? And if they bring in what I think will be two, three, four new starters, whether it’s via the draft and free agency combined, then I think we could have a different conversation about what I think it’s gonna look like, because I kinda need to see what the roster looks like first.
Frazer Rice (19:44.691)No, there’s so many holes in the free agency component.
Not to pin you down on a record going into next year, because we don’t even know what the components are going to be. To that end, as you said, the injuries were a real problem. Everything that possibly could go right in 2024 didn’t in 2025. How does that work over the course of time in terms of regression to the mean? Is just every season completely different or is there something that carries over?
Bram N Weinstein (20:19.542)So 2023 was nothing like 2024, which was nothing like 2025. So we’ve had a roller coaster for sure. Um I last year was a surprise like. If you had told me the beginning of the season look like the schedules too hard. They had too many injuries. They went 9889 didn’t make the playoffs. I would have believed you. You know, like it’s just things were just harder to try to replicate. I didn’t expect what ended up.
So can they flip that back around and be more competitive again? I do believe so. I also agree with something you said, which was. Right now and again don’t know what the teams look like exactly yet, but I do think the division on the whole will be better. The Giants will be better coached for sure. They have a lot of defensive talent and we’ll see if Jaxson Dart takes another step. And if that’s the case, the Giants may be more formidable than they’ve been in 10 years. The Eagles are still going to have a very, good roster. No matter
Frazer Rice (21:04.938)Mm-hmm.
Bram N Weinstein (21:16.106)Whatever they do this off season, even if it includes moving off of a couple of primary people, they still have an extremely strong high level roster. And I like how the Cowboys pivoted from Micah Parsons. I know it hurt them last year, but I do like what they did in the return that they got since. So they play their cards right. They could be in line to really make a jump back this year. Like they’re the ones that feel kind of ready to me.
If they play their cards right and if they don’t end up, which is the second part, which is never they avoid, they never avoid this. They turn themselves into a circus. So if they could ever stop turning themselves into a circus, I think it would serve them. You know, I think it would be a very positive outcome for them, but their owner doesn’t live in that world. He likes to be a ringmaster. And, you know, I think that that’s probably more than anything been the hindrance to them winning a Super Bowl over the last.
Frazer Rice (21:55.004)You
Bram N Weinstein (22:14.422)30 years, they’ve had good enough teams to do it. They just don’t and I think they get in their own way. But you know, maybe this year’s a little different for them.
Frazer Rice (22:21.364)No question.
Alright, how do people find Ampire and sample all the different media that you’re putting out there?
Bram N Weinstein (22:31.766)YouTube is Empire Media AMPIRE. We have our YouTube page. You can find that there. My show is under my name, Bram Weisside Show. John Keim Report covers the commanders and Last Man Standing is Ben Standing’s show. And who knows, maybe in four to six months, we’ve got some new offerings. I’m hoping that’s gonna be the case pretty soon.
Frazer Rice (22:51.466)Terrific. Thanks for coming on, Bram, and rootin’ for your success.
Bram N Weinstein (22:55.414)Thanks a lot. Take care
BRAM on “WEALTH ACTUALLY” three days before the JAYDEN HAIL MARY
Keywords:
sports journalism, Washington Post, media opportunities, podcasting, Commanders, monetization, audience engagement, digital media, sports coverage, media landscape
Titles
The Decline of Sports Journalism
Seizing Media Opportunities
https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
February 3, 202630 min
QSBS for FOUNDERS
This conversation delves into the intricacies of Qualified Small Business Stock (QSBS) and its significant tax benefits for founders. MICHAEL ARLEIN, Partner at Patterson Belknap, explains the eligibility criteria, the importance of strategic planning, and the potential pitfalls that can arise. The discussion also covers the implications of state taxes and the advantages of gifting strategies. We cover innovative approaches like the “GOAT” trust to maximize tax-free gains. Founders are encouraged to engage with legal experts early in their business journey to fully leverage QSBS opportunities.
https://youtu.be/lfBt0j7BlW0?si=LufZ8j2YtgdspLMJ
Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)
Takeaways from “QSBS For Founders”
QSBS is a powerful tax benefit for founders.The maximum exclusion amount has increased to $15 million.Careful planning is essential to avoid QSBS pitfalls.Gifting QSBS stock can multiply tax exemptions.State tax implications vary; California does not recognize QSBS.Discounting shares can aid in estate planning.Converting from an S-Corp to a C-Corp can preserve QSBS benefits.Early engagement with legal counsel is crucial for founders.Innovative strategies like the GOAT trust can maximize benefits.Almost all businesses should consider QSBS eligibility.
Chapters
00:00 Understanding QSBS: A Founder’s Guide.02:56 Navigating the QSBS Landscape: Common Pitfalls.06:07 Maximizing QSBS Benefits: Stacking Strategies.08:42 The Importance of Timing: Gifting and Valuation.12:03 State Tax Implications: The QSBS Challenge.14:52 Entity Structures and QSBS: What Founders Need to Know.17:37 Transitioning to C-Corp: Strategies for S-Corps and LLCs.20:29 Who Should Pay Attention to QSBS?23:44 Innovative Business Structures: Technology and QSBS-26:36 Early Stage Strategies: Cloning Yourself on the Cap Table-
Transcript of “QSBS for Founders”
Frazer Rice (00:01.109)Welcome aboard, Michael.
Michael Arlein (00:03.096)Thank you. Good to be here.
Frazer Rice (00:04.617)So let’s get started here. QSBS, Qualified Small Business Stock, is something that certainly all founders should be aware of. It’s a tax feature. It’s probably one of the nicest goodies that the federal government gives to people who are starting businesses. Take us through a little bit about what happens there.
For founders, you’re going to hear the numbers 1202, which is the section that is quoted here. Take us through a little bit about what happens at QSBS and why it’s a powerful feature.
Michael Arlein (00:37.496)Sure, that sounds good.
To your point, the New York Times called QSBS a lavish tax dodge that is easily multiplied. And I happen to. I’m not aware of any other provision of the tax code that can save anyone as much money as QSBS. It’s really incredible.
I think the policy reasons behind the provisions are that they’re designed to encourage entrepreneurship. Everyone on both sides of the political aisle is in favor of. The basic premise of it is that if you create a company.You own the stock for five years. The company’s in the form of a C corporation,
It’s not in one of a series of restricted industries. Mainly service industries, that when you sell the stock, you can exclude from paying tax $10 million, the first $10 million of your gain. That’s the old rule, which I’m still dealing with, that that’s for stock that was issued before July 4th, 2025. And now QSBS has gotten even better.
So if you get stock after that date. You hold it for actually now three years, you can exclude ultimately up to $15 million from tax. So we’re now dealing with two different regimes. I’m still stuck in the old regime. Most of the people I’m dealing with got their stock before last July. But I’ll try and point out the differences as we go along.
Frazer Rice (02:29.066)Sure, as you said, there are a bunch of things you have to jump through. To make sure that you can sort of apply and then to further comply with the rules associated with it. Things like services. Making sure that maybe you don’t have too much cash and that it’s deployed correctly. Making sure that the original stock issuance persists throughout.
What are some of the things that you tell your clients? How do you walk them through the process so that they don’t trip on themselves and lose this nice tax advantage?
Michael Arlein (03:09.676)Yeah, there are some landmines, things that you can step on and blow it. There’s some weird rules around redemptions. Like if you have redemptions. Let’s say you create a company and then there’s three co-founders. Then very early on, one of the co-founders wants out or you want to kick them out.
And then the mechanism for that is the company kind of buys back their stock. You know, there’s complicated rules that can, you know, blow up QSBS for the entire company. I think some people start their businesses as LLCs or S-Corps or things like that, and then later convert them. And that has to be done very, very carefully with good tax advice.
Otherwise that can also blow things up. When I talk to founders, it’s pretty clear their business qualifies. They didn’t screw anything up.
Frazer Rice (04:19.626)So the OBBBA in a sense turbocharged a little bit the tax savings. That five year requirement that you talked about. You can now get some of the benefits even as early as three years. And then the dollar amounts got expanded. In addition, and this was not necessarily OBBBA related. The ability to take one exemption and maybe multiply it via stacking continues to be a powerful tool.
For those people who are walking into your office now. How do you get them when they sit down situated so that they do that planning upfront?
Michael Arlein (05:08.598)Yeah, that’s, you we kind of buried the lead.
The benefit of QSBS: it would be incredible if you could just pay no tax on 10 or $15 million. But what’s even more incredible is that you can stack or multiply the number of exemptions. You have using a provision of the code. It says that if you gift QSBS stock to some other person or entity. That that person or entity can take their own up to 10 or 15, their own QSBS exemption.
I’m just gonna say it’s 15. We understand that’s for newly stocked. So, classic move for a founder would be to set up trusts for children. There’s a special kind of a trust for a spouse. You can do this with sometimes people make trust for their parents, their siblings.
There are certain states where you can actually make a trust for yourself. Usually when people come to my office, the conversation is around creating entities. Typically trusts, and then gifting shares to those trusts. that
As a family, you could go from 15 million tax free to 30 or 45 or 60 million tax free. The record I had one guy who had a very large family. He married, he had kids and was very close not only with his parents. With his siblings, his nieces, his nephews, even his aunts, uncles, and cousins. He created 23 trusts, which on paper at least would save up to $230 million. Wow. Yeah.
Frazer Rice (07:08.896)There’s a danger with that though, with those 23 trusts had to be different. I imagine the IRS would say, wait a minute, we see what you’re doing. Stacking all of these different things is theoretically nice and all, but is there a way to create differences within those trusts so that the IRS doesn’t view them as one big pot?
Michael Arlein (07:39.692)Yeah, great question. So you can’t create multiple identical trusts. Meaning I can’t create five trusts for my child. The IRS has rules that consider those trusts as one trust and would have only one exemptions. So, one of the limiting factors on creating trust is often, who are the people you’re willing to gift to? You know, so this guy with the 23, he actually was willing to create trust for his cousins, his aunts, uncles.
Now, those individuals were the beneficiaries of the trusts, which means that they were eligible to receive money from the trust. But those trusts were designed so that when those people passed away, the money would circulate back to his children. So, you we never talked about it, but it’s possible that in his head, his plan was that he would maybe provide some benefit to his cousin.
Maybe he’d say to his cousin, hey, if there’s $5 million in this trust and you need a little money, I’ll make some distributions to you, but I’m going to request that the trustee kind of withhold most of the money. And then when you die, it’ll come back and benefit my kids. So there are nuances there.
But generally speaking, most people aren’t willing to do that. They’re not close enough with their cousins and their aunts and their uncles. So they end up maybe creating trusts, you know, for their kids, for their parents, sometimes, you know, for their spouse and maybe sometimes they go a little beyond that, but not that far. One thing that’s important is that the U.S.
Frazer Rice (09:33.472)One thing that’s important is that the the QSBS is a capital gains tax Concept meaning you’re you’re saving on the tax. From a QSBS for Founders standpoint when the the founder sells the business, and you have to pay capital gains tax on that front. Part of the reason I’m skewing this toward founders is that there’s an gift in a state exemption of 15 million dollars.
So it’s important to get these assets into these trusts as early as possible and with as low evaluation as possible. That in many ways is where the real leverage is. Does that square with your thinking?
Michael Arlein (10:11.019)Yeah, absolutely. We have a permanent $15 million lifetime gifting limit. $30 million for spouses. And when you gift stock into these trusts, you’re typically gifting at a common stock valuation.
People are familiar, founders are familiar with common stock valuations because they do that for purposes of issuing stock options, you know, the so-called 409A valuation. Now, a gift tax appraisal is different than a 409A valuation, but in many ways, they’re very similar.
S0 founders know that, you know, they could be raising a preferred round at $10 a share, but their 409A common stock valuation is still $2 a share. So you can get a lot of gifting done. You can give a lot of shares away.
You know, using your $15 million exemption, even if the company is very valuable. So we see founders doing this sort of gifting, you know, late in the game, even right before a transaction or an IPO. But if you had a crystal ball, or at least, you know, you were willing to take some risk, obviously, the earlier you do it, the better, because you could gift…
I mean, theoretically, if you set up trusts and you gifted shares the day after you created your company, they would be worth essentially nothing. And so you wouldn’t have to use hardly any of your gifting exemption.
The problem is most people, A, aren’t thinking about that on the day they create their company. They don’t have anyone whispering in their ear and telling them to do that. And number two, they wouldn’t want to spend the money on legal fees to set up structures because at that point they’re like, don’t know what this is going to be worth. This could be zero. This could go out of business in a year.
So there’s a trade off that I see between doing this later in the process where you’re gaining visibility into outcomes, maybe for younger people sometimes, you know, there’s visibility into their family lives. Maybe when they founded the company they were single. Then if they wait five years they marry, they’ll have children, i.e. people who they could create trust for. But the cost of doing that is that you’re gifting at a higher value.
Frazer Rice (12:46.591)One of the considerations that people don’t understand is the state tax implication. QSBS is a federal concept that a lot of states join onto and link to. But a state like California isn’t. And so sometimes that can be an untoward surprise to people that there’s a state tax that happens that they may not have expected.
Michael Arlein (13:16.299)Yeah, it’s kind of bizarre that California, the home of Silicon Valley, doesn’t recognize QSBS. But most states do. My home state of New Jersey, in fact, very recently joined the QSBS club and now recognizes it at the state level. There are a few other states, I think.
Pennsylvania, I don’t think recognizes it, but the vast majority of states do. But unfortunately, if you live in California, you’re probably only in quotes saving the federal tax. But the federal tax on $15 million, 23.8 % of 15 is a pretty big number.
Frazer Rice (14:01.086)No question and absolutely worth doing. one of the things that I find happens is that from an income capital gains tax perspective, we’re on top of it with the QSBS. When we get into the estate planning world, we use the concept of discounting, meaning putting QSBS shares or any shares for that matter into other entities so that you get discounting for lack of marketability and the ability to make decisions around it.
Are there any tripwires on that front as far as putting things into other LLCs so that you don’t, maybe in a sense that in trying to really maximize the estate planning and the estate tax avoidance that you create issues that might cause problems with your QSBS tax avoidance usefulness there.
Michael Arlein (15:02.413)Yes. Again, the rules under Section 1202 of the code for QSBS have some strange traps for the unwary and some gray areas. And one of those gray areas is around transferring interests in partnership type entities, which would mean like an LLC or a partnership. that owns QSBS.
So essentially, it’s very clear that if you have QSBS stock and you gift it into one of these entities we’ve been talking about, that that entity would take the QSBS attribute and be able to enjoy the benefits of QSBS. If the QSBS is held in an entity like an LLC, let’s say you set up a, well. Let’s say a realistic example is that you made an investment in a venture capital fund that invested in an early stage company that’s QSBS.
And now you’re a limited partner in that fund and you know that that fund is going to have a large exit in this QSBS position and that you’re going to get the benefits of that, but it’s going to exceed $15 million. So you say, what I should do is I should take my interest in this venture capital fund. I should give them to trust for my kids so that when the fund distributes those shares or distributes the proceeds from selling that company, it’ll be split among various entities and I’ll be able to stack QSPS. The transfer of an interest in a fund that owns QSPS, there’s a gray area about whether the recipient of that fund interest would actually have QSPS and it’s generally viewed as something to be avoided.
Frazer Rice (17:08.944)In a sense putting it at risk. A question that I think pops up is that there are people who started businesses maybe pre that July 4th date that you were talking about and maybe they chose an entity like an S Corp or an LLC that isn’t sort of a good qualifying C Corp and they’re looking and saying you know what I may be able to sell this business three to five years or beyond and take advantage of this QSBS. Are there avenues to be able to change that tax elections so that you can begin that QSBS and what’s the analysis around?
Michael Arlein (17:44.972)Yeah, in fact, a fairly common structure is, and we haven’t really gotten into these details, but it’s a great question.
So QSBS is actually the greater of $15 million or 10 times your basis. Now we ignore the basis rule for the most part because the vast majority of founders do not have basis. They create their company and they put nothing into it.
With a bank account with $10,000 in it, and they’re not contributing actual dollars into their business. And so the 10 times basis rule doesn’t actually apply.
But there’s a way for a founder to take advantage of that, and this strategy is actually called PACKING.
And the packing strategy involves starting your business as an LLC and with an LLC and then converting it to a C corporation. with an LLC, when you convert, there’s an attribution of basis to the founder based on the value of the LLC’s assets.
Theoretically, if you started off as an LLC, and before the LLC hit $75 million value of its assets, $75 million being sort of the cutoff for qualifying for small business, you have to acquire your stock before your company assets are worth $75 million. Theoretically, let’s say you did that when it was $74 million, then if your basis was $74 million,
10 times your basis would be $740 million, you would have up to $740 million tax free. So people kind of play this game. I think for a lot of companies, it’s not realistic to be an LLC because venture cap, if you’re going to raise venture funds, they want you to be a C Corp. This works for bootstrapped companies, but most companies are forming a C corporations.
You know, there is a path to convert from an S-Corp to a C-Corp and preserve QSPS for Founders. I’m no expert in that. All I can tell you is that it has to be done very carefully and very specifically. And I’ve seen a lot of people who didn’t know they needed to do anything specific and they do not qualify for QSPS.
Frazer Rice (20:45.085)As we sort of, I’m not going to say wind down here because we may have some other topics that pop up. But when someone walks through their door, I guess maybe the way to think about it is, who does this apply to?
You said the services industry. So accounting, finance, that type of thing- NO. For those things that venture tries to invest in, whether it’s software or other processes, who is really should be paying attention to this?
Michael Arlein (21:16.491)I mean, I think almost anyone should be paying attention to this because it may be that you don’t qualify, but often people do. And more often than not, you do. This has broad application for most businesses. There are excluded industries, architects and lawyers and accountants. But if you’re doing something in the tech world, you’re probably going to qualify.
It’s good to get some advice from the corporate lawyer who’s helping you create your business. I think one of the considerations of whether you form as a C Corp or an LLC is probably the availability of QSBS status. You know, I think stacking strategies, it’s worth having a conversation probably sooner than later with a lawyer to find out what the menu of stacking options is.
I talk to people all the time and we decide it’s premature for them to do something. And then they call me back a year or two later and all the time I’m calls from people who say, hey, we spoke a few years ago and now
Frazer Rice (22:34.013)Alright.
Michael Arlein (22:39.913)the time is right. So it’s good to get educated, learn what the options are. QSBS stacking is not just about giving shares to your kids. There are strategies that are specifically designed for single people where you can create these benefits for yourself and
You know, it’s too good to be missed. if you, I do talk to people who say to me, they’re usually on their second venture or third venture and they say to me, I really screwed this up the first time around.
I paid no attention to it and I was focused on my business and I just screwed it up. I literally cost myself millions or tens of millions of dollars had I done it correctly. And now that’s why I’m calling you, because I want to do it correctly the second time around.
Frazer Rice (23:33.278)Part and parcel with that, I ran into somebody really more of what’s called a media personality. And usually the way I think of it is that the QSBS isn’t necessarily available for people whose value is centered around them as a personality or them as a brand.
But I said, you know what, the QSBS component, while it might not apply here, if your business morphs into something where you’re developing other things, slash maybe you turn into a media production company or, youbecome involved in a technology that drives other things, that you shouldn’t dismiss that.
The pivot in the business from sort of a personality generated to something a little bit more business process generated might be something to think about, not only from a strategy standpoint, not that you necessarily wanna do things purely for tax reasons, but if that’s a natural consequence, that’s something to think about. Has that ever popped up in your world?
Michael Arlein (24:31.915)Yeah, for sure. Every business these days is technology enabled. And I think sometimes businesses that you wouldn’t think of as being technology businesses are doing enough technology things that they can claim that they’re a technology business and not a business providing a particular kind of service. So, you know, with the help of a clever accountant or a tax lawyer, this is not an area that I operate in.
I’m more about multiplying QSBS once you have it. But there are tax lawyers and corporate lawyers and accountants who can advise you how to make your business eligible for QSBS by leaning into, as you said, things that you’re doing that may be…you know, eligible versus other parts of your business that would not be.
Also, you know, you can, sometimes you see companies that are divided, right? Like, so there’s a company who provides counseling services, like, you know, they’re actually hire psychotherapists that will counsel you, you know, online, like on a Zoom. and their business is split.
There’s a medical services company that employs all the counselors and medical services is one of the excluded industries. But then they also have a completely separate business that is their technology platform. And the way they structured it, the value is really in the technology platform. That business is QSBS eligible because it’s a completely separate company.
Frazer Rice (26:28.771)That’s a great example. part of the purpose of the question was to elicit that, is that people may say, well, we fall squarely into one classification when maybe some underlying thought might lend itself to structuring from a tax perspective that might be useful later on. OK, now as we wind down, for someone who is, at this point, starting a company when they’re forming these things, not that you, QSBS for Founders should drive the world, but how do they get involved with the discussions so that they do the right things early?
Michael Arlein (27:06.401)Yeah, I mean, I do have a very specific strategy that I love for people who are about to form a company. And it really works best in that scenario of an early stage company that’s just about to launch.
The way I describe this to founders is that you can and should clone yourself on the cap table. So if you start off a company and you own all of the shares, you’re basically eligible for 15 million tax free. That’s great. But what if you could clone yourself and there were three Frazers on the cap table, then Frazer would have $45 million tax free. So how do you do this?
You can do it with trusts. And the beautiful thing is if you have other people create trust for you, then you can be the beneficiary of the trust and control it as well. And I have sort of branded and named this strategy a GOAT trust, which of course has the double meaning, know, greatest of all time.
Frazer Rice (28:21.02) QSBS for FoundersRight.
Michael Arlein (28:21.165) QSBS for FoundersBut actually stands for gift optimized to alleviate taxes. The essentials of it are is that we would work with your parents, the founders parents, we would work with your grandma, your uncle, and we would spin up some trusts that they create for the benefit of you as the founder. You would have all sorts of control and access to those trusts and they make a gift into those trusts, probably something fairly modest. Then those trusts on the day of formation buy up some of the common stock. And so those are your clones.
You know, you’re having your cake and eating it too. You’re getting, you know, QSBS stacking for Founders. You’re getting some other benefits we haven’t even talked about. Those trusts can be exempt from a state tax and state level income tax. And you control those trusts and benefit from them. So we’ve essentially cloned you on the cap table. And that is a beautiful strategy that most people miss out on because they don’t do it. And then they come to me a few years later and they own the stock and it’s valuable and then we have to do the more traditional stacking strategies.
Frazer Rice (29:40.432)Really cool stuff. Michael, how do people get in touch with you if they have these problems slash opportunities?
Michael Arlein (29:48.525)Sure, well they can Google me. I have a nice web presence. We have our…Founder Focus Practice Group that I lead at the firm, which is very specifically tailored to provide legal services to founders, personal legal services. And I focus on the tax side of that and QSBS stacking for Founders. My email, msarlein at pbwt.com. Phone number 212-336-2588.
Frazer Rice (30:23.324) QSBS For FoundersThat will all be in the show notes. Michael, thanks for being on.
Michael Arlein (30:26.753) QSBS For FoundersThank you.
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QSBS for Founders
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