The Weekly Wealth Podcast

Hosted by David Chudyk

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Aug 2026

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Exploring the Mindsets, Tactics, and Strategies to help you to build and maintain wealth.

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September 11, 202614 min

Ep 280: REBA can be your best benefit!

The Bonus Your Best Employee Doesn't Know They're Getting Every business owner has that one person. Not a partner, not family — just an employee who makes the whole place run. And every business owner has, at some point, faced the moment when that person gets a call from a recruiter. The instinct is to counter with a bigger number. The problem? A raise is just a number, and someone can always beat a number. What actually keeps a key employee in place is a reason to stay that a bigger paycheck somewhere else can't undo. In this episode, David Chudyk, CFP®, CLTC breaks down one of the most underused retention tools available to business owners: the executive bonus plan. He walks through why it beats the alternatives, what it actually costs once taxes are factored in, and — most importantly — the difference between a version that barely works and a version that actually has teeth. Why Qualified Plans Don't Solve This A 401(k) or profit-sharing plan sounds like the obvious retention tool, but it's built for retaining everyone , not one or two irreplaceable people. Qualified plans have to pass IRS nondiscrimination testing, which means you generally can't do something generous for your top performer without doing something for the whole team. That makes qualified plans expensive, slow to build meaningful value, and — frankly — impersonal. Small business owners with one or two key people are often stuck choosing between "give everyone the perk" or "give no one the perk." An executive bonus plan is the middle option nobody talks about. What an Executive Bonus Plan Actually Is Sometimes called a Section 162 bonus plan, the mechanics are simple: the company pays a bonus to a key employee, and that employee uses it to purchase a permanent life insurance policy on their own life. The employee owns the policy outright. Cash value builds inside it over time, and a death benefit protects their family. There's no IRS approval process, no plan document filing, and no nondiscrimination testing required. It can be set up for one employee and no one else — because legally, it's just a bonus. What the employee chooses to do with it is what makes it an executive bonus plan. Why It Beats the Alternatives Deferred compensation: the promised money still technically belongs to the company, leaving the employee as an unsecured creditor if the business runs into trouble. Qualified plans: broad-based by law, slow to build value for any one person. A straight cash bonus: gets spent, builds nothing, and gives the employee no reason to think twice about the next recruiter call. An executive bonus plan: deductible to the company, fully selective, and builds real value over time. The Numbers, Honestly Here's the detail that trips up a lot of owners: a bonus is taxable income to the employee. Hand someone $10,000 and they may only net around $7,000 after taxes — which means the policy doesn't get funded the way you intended. The fix is a "double bonus," or gross-up: bonusing enough extra to cover the employee's tax liability so the full intended amount actually lands in the policy. As a rough rule of thumb, funding $10,000 into the policy often means bonusing closer to $13,000–$14,000, depending on the employee's tax bracket. It's a five-minute conversation with the right advisor — and one worth having before the first check goes out, not after. The Naked Bonus Plan (And Why It Doesn't Really Work) There's a simpler version of this plan that a lot of owners stumble into first: pay the bonus, and simply suggest the employee use it to buy a policy. No plan document, no contract, nothing tying the bonus to the insurance at all. This is sometimes called a "naked" bonus plan. It's appealing because it's free to set up and takes one conversation. But it has a serious flaw: there's nothing stopping the employee from spending the bonus on something else entirely, or from buying the policy and then cashing it out the same day they resign. The tax treatment is identical to a formal plan — but the retention benefit is close to zero. As David puts it on the show: trust isn't a plan . The Fix: A Restrictive Endorsement Bonus Arrangement (REBA) A REBA solves the naked bonus plan's biggest weakness. The company still pays the bonus and the employee still owns the policy — but the company places a restrictive endorsement on it that limits the employee's access to the cash value for a set number of years. If the employee leaves before that restriction lifts, the retention teeth stay in place. Because the employee still technically owns the policy throughout, the arrangement avoids the rules and testing that come with qualified plans — while giving the business an actual reason for a key employee to stay, not just a handshake. Who This Is Actually For This isn't a broad-based benefits strategy. It's built for the one or two people a business genuinely can't afford to lose — especially when there's no appetite for a qualified plan, or when an owner wants something more targeted for the people who matter most. Structuring it correctly means getting the comp strategy, the tax treatment, and the insurance design all right at the same time, which is exactly the kind of decision worth bringing in the right people for rather than tackling alone. Frequently Asked Questions What is an executive bonus plan? It's an arrangement where a company bonuses a key employee, who then uses that money to buy a life insurance policy they own personally. It's deductible to the company, fully selective, and requires no IRS approval or plan filings. What's a "double bonus" or gross-up? Because a bonus is taxable income to the employee, a gross-up bonuses extra money to cover that tax liability — so the full intended amount actually reaches the policy instead of being reduced by taxes first. What is a naked bonus plan? It's an informal version of an executive bonus plan where the company simply pays a bonus and suggests the employee buy life insurance with it, without any contract or restriction. It carries no real retention protection, since the employee can spend the money elsewhere or cash out the policy immediately upon leaving. What is a Restrictive Endorsement Bonus Arrangement (REBA)? A REBA is the formal version of an executive bonus plan. The company places a restriction on the policy's cash value for a set number of years, so a key employee who leaves early forfeits access to those funds — giving the plan actual retention power. Is this the same as a buy-sell agreement? No. A buy-sell agreement funds the transfer of a business owner's stake if they die or exit. An executive bonus plan is about retaining a key employee, not transferring ownership. Ready to Talk Through Your Business? If your business depends heavily on one or two people, that's not just a staffing question — it's a valuation risk. Get a free Sellability Score assessment at weeklywealthpodcast.com/sellabilityscore . Want to talk through whether an executive bonus plan makes sense for your business? Book a free 20-minute Vision Call at weeklywealthpodcast.com/vision .

September 4, 202624 min

Ep 279: LIAM 2026 is here!

Every September, the insurance industry runs Life Insurance Awareness Month — and most of the advice sounds the same: buy term, protect your family, don't wait. That advice is correct. It's also, at best, half the story. Life insurance has two entirely different jobs depending on where you are in life. For a young parent with a mortgage and a new baby, it's the thing standing between "we'll be okay" and financial free-fall. For a business owner who's spent decades building something real, it's a liquidity and legacy tool that has almost nothing to do with dying too soon and everything to do with protecting what's already been built. Most people only ever hear about the first version. This episode covers both — plus a living-benefit feature almost nobody explains correctly, and the reason you should be skeptical the moment someone tells you they've "properly structured" your policy. By the numbers: Roughly 100 million American adults are uninsured or believe they need more life insurance coverage (LIMRA & Life Happens, 2025–2026 Insurance Barometer Study). Healthy young adults overestimate the true cost of term coverage by 10–12 times. Estate taxes are typically due within 9 months of death — often with little cash on hand to pay them. The average life insurance coverage gap is approximately $200,000 per U.S. household. The Foundation: What Term Life Actually Solves (~1:30) For young families, term life insurance isn't complicated and it isn't expensive — it's one of the most misunderstood products in personal finance, largely because people wildly overestimate what it costs. David breaks down why term, not whole life, is the right starting point for most families, how to calculate a real coverage number instead of relying on a lazy "10x income" rule, and the three mistakes that quietly leave families underinsured: relying on employer coverage alone, never revisiting the policy after major life changes, and cutting coverage because of sticker shock instead of shopping it properly. "A healthy 35-year-old can often get $1,000,000 of 20-year term coverage for the cost of a streaming subscription or two per month." The Living Benefit Nobody Explains Correctly (~8:00) Here's the part of the episode that surprises almost everyone: modern life insurance can pay out while you're still alive. Drawing on his CLTC (Certified in Long-Term Care) designation, David explains how a long-term care or chronic illness rider lets you access a portion of your death benefit if you survive a stroke, a serious diagnosis, or another disabling health event — the kind of moment traditional life insurance does nothing for, because nobody died. This isn't a retiree-only conversation; it's relevant the moment you have a family depending on your income. "Don't just ask 'how much life insurance do I have?' Ask 'what happens if I get sick and don't die?'" Not sure what's actually in your policy? If you don't know whether your coverage includes living benefits — or whether it still fits your life — that's a five-minute conversation, not a five-month project. Book your free Vision Call . When Life Insurance Becomes a Business Strategy (~14:30) For business owners, life insurance stops being a safety net and starts being a strategic tool. This segment covers two scenarios every co-owned business needs to plan for: a properly funded buy-sell agreement that lets a surviving owner keep control of the business instead of unexpectedly co-owning it with a deceased partner's estate, and key-person insurance that funds the runway to recover if someone critical to revenue is suddenly gone. "If my partner died tomorrow, what happens? In most cases, their ownership stake doesn't just evaporate." Estate Liquidity: The Wealth Trap Nobody Warns You About You can be genuinely wealthy and still face a liquidity crisis the moment you die. When a large share of net worth is tied up in a business, real estate, or concentrated stock, an estate tax bill can come due with almost no cash available to pay it — forcing a rushed sale of assets at a discount. David explains how life insurance, often held inside an irrevocable trust, creates exactly the liquidity needed to pay that bill without touching the underlying assets — and how it can be used to equalize an inheritance when one child takes over the business and the others don't. Curious how ready your business actually is for a transition? Get your free Sellability Score . The "Properly Structured IUL" Red Flag (~21:00) Permanent insurance — including indexed universal life (IUL) — has a legitimate use as a tax-advantaged savings and growth vehicle, for the right person, in the right situation. But David draws a hard line around a specific phrase circulating on social media: "properly structured IUL." If someone leads with that phrase, treat it as a warning label, not a credential. This segment covers what illustrated vs. guaranteed rates actually mean, why "no market losses" isn't the whole picture, and the one question to ask before you ever sign an IUL application. "When someone leads with the phrase 'properly structured,' that's usually the tell, not the reassurance." Frequently Asked Questions How much life insurance do I actually need? A useful starting framework is DIME — Debt, Income, Mortgage, Education — which totals what it would take to eliminate debt, replace income for a meaningful runway, pay off the house, and fund your kids' education. It's a strong starting point, but a real needs analysis that reflects your specific family and goals will always beat a formula. What's the difference between term and permanent life insurance? Term life covers you for a defined window at a much lower cost. Permanent insurance (whole life or IUL) lasts your entire life and builds cash value, but costs significantly more and serves a different purpose: savings, estate liquidity, or wealth transfer rather than pure income replacement. What is a long-term care or chronic illness rider? It's a feature that lets you access a portion of your death benefit while you're still alive if you experience a qualifying health event — a stroke, a serious diagnosis, or a need for long-term care. It addresses a risk traditional life insurance ignores entirely: surviving, but with a serious financial disruption. What is a buy-sell agreement and why does my business need one? A buy-sell agreement is a contract, funded by life insurance, that determines what happens to a business owner's stake if they die. Without one, that ownership stake typically passes to the deceased owner's spouse or estate — leaving the surviving owner unexpectedly co-owning the business with someone who may not want to run it, and may need cash instead. Is "properly structured IUL" a real thing, or a red flag? IUL can be a legitimate planning tool, but the phrase itself — used as a blanket reassurance on social media — is usually a sign to slow down. The real question isn't whether it's "structured properly," it's whether you've seen the guaranteed rate, not just the illustrated one, and whether the person recommending it is held to a fiduciary standard. Wherever you landed in this episode — that's exactly what a Vision Call is for. Whether you need your first policy or a real review of what you already have, it's a free 20-minute conversation, not a sales pitch. Book your free Vision Call .

August 28, 202620 min

Ep 278: Readiness 360 for Exit Planning

73% of business owners who say they're ready to sell are missing at least one of the two numbers required to know if a sale will actually work. In this episode, David breaks down a new data study of 10,548 business owner assessments and lays out the Readiness 360 — the three questions every owner has to answer honestly before they sit across from a buyer. Are you personally ready to let go? Is your business actually ready to be sold? And does the math even work? What You'll Learn The two numbers every owner needs before they can know if a sale will work — and why 73% of owners are missing at least one Why even owners who did the homework still get bad news: 1 in 5 discover their business is worth less than they need The “pushed vs. pulled” problem — why burnout and stress are driving more exits than actual planning Why 25% of owners can't name a single thing they're excited about after the sale, and what that means for a deal The eight drivers that determine whether your business survives buyer diligence — separate from how much cash it generates Timestamps 0:00 — Cold open: You've decided to sell. Here's why you're not ready. 0:45 — Intro: framing the Readiness 360 2:30 — Segment 1: Are you financially ready? The two numbers 9:30 — Mid-episode: the Sellability Score 10:00 — Segment 2: Are you personally ready? Pushed vs. pulled 16:30 — Segment 3: Is your business ready to be sold? 21:30 — Wrap-up: putting the 360 together 24:00 — Where to start: Sellability Score and PREScore Key Takeaway “Wanting to sell is not the same as being ready to sell.” Only 27% of business owners have both a minimum number and a recent valuation — the two things required to know whether a sale will fund the life they want afterward. And even among owners who have both, roughly 1 in 5 find out the business is worth less than they need. Readiness isn't a feeling. It's a diagnosis, and the earlier you run it, the more options you have. Ready to Find Out Where You Stand? Start with the free Sellability Score — a 15-minute assessment that shows you where your business stands on the eight drivers that determine what it's worth: weeklywealthpodcast.com/sellabilityscore Want to go deeper on personal readiness? The PREScore assessment measures whether you — not just the business — are ready for what comes next: weeklywealthpodcast.com/prescore

August 21, 202623 min

Ep 277: Advanced Financial BASICS

Advanced Financial Basics Success is boring. That's not a knock — it's the whole point. The best tennis players in the world don't win with highlight-reel shots; they win by making almost every easy shot and missing almost nothing. Wealth-building works the same way. This week, David Chudyk, CFP®, breaks down BASICS — a six-letter framework covering the unglamorous, "advanced" fundamentals that actually move the needle for people who are already building real wealth. What BASICS Actually Stands For B — Budget. Not a lecture about canceling subscriptions. The real question isn't "can I afford this," it's "is this appropriate for my current situation." For some listeners — especially those with a solid nest egg — an appropriate spending plan means spending more , not less. A — Allocation. Where should your money actually live — checking, real estate, retirement accounts, an emergency fund, speculative positions? "Should I buy the hot new IPO?" is really an allocation question in disguise, and there's no universal right answer without knowing the full picture. S — Systems. We don't rise to the level of our goals, we fall to the level of our systems. This segment covers the financial habits — recurring money check-ins, subscription audits, auto-pay, systematic investing — that quietly determine whether goals actually happen. I — Insurance. Insurance isn't exciting, and David doesn't pretend otherwise — but its job is simple: it protects your money, nothing more, nothing less. Includes a breakdown of life insurance, liability coverage, and why finding a great local independent insurance agent is real advice, not a throwaway line. C — Caring. Tying back to David's core philosophy — how we handle our money should positively impact our lives and the lives of those around us — this segment covers generosity beyond the tax-deductible check, and a candid look at whether your spending actually reflects what you say you value. S — Support. Borrowing from Dr. Benjamin Hardy's Who Not How , David makes the case that the right question isn't "how do I figure this out myself," it's "who already knows how to do this." Financial advisors, CPAs, attorneys, fractional CFOs, and mastermind groups all make the list. Bonus Content: Allocation, Round Two Stick around after the outro for a bonus deep-dive on allocation: why the goal of investing isn't always the highest possible return, how David solves for the required rate of return needed to hit a goal, and why a 79-year-old getting a lucky 40% return doesn't mean their money was allocated correctly. Resources Mentioned Free E-Book: The Rainmaker's Dilemma — for business owners stuck as the primary revenue driver in their own company Book Referenced: Who Not How by Dr. Benjamin Hardy Related Episode: "The Richest Corpse in the Graveyard" (referenced in the Budget segment) Where Are You Strong? Where Are You Weak? Leave David a voicemail at weeklywealthpodcast.com and tell him which of the six basics you need to work on. Or skip straight to a conversation: Book your free Vision Call .

August 14, 202633 min

Ep 276: Peyton Hoppes

Guest: Peyton Hoppes, ProVest Wealth Advisors (Spartanburg, SC) Episode Summary David sits down with longtime friend and fellow financial advisor Peyton Hoppes to talk shop. Peyton recently joined ProVest Wealth Advisors in Spartanburg, SC, where he and colleague Gabe are stepping in to take over the client relationships of a retiring advisor. The two dig into what they're seeing with clients day-to-day: how busy families in their "formation years" actually manage cash flow, the real difference between Roth and pre-tax retirement accounts (and when each makes sense), and — for anyone who's ever dreamed of owning a beach house — a breakdown of the smartest (and riskiest) ways to actually pay for one. Key Takeaways Purposeful money management beats default money management. Peyton runs a system of segregated accounts (savings, taxes, vacation/project fund) so every dollar has a job — and vacations get booked only once the savings cover them. Family formation years (roughly age 28–47) are the most expensive of your financial life. Most people's spending peaks here, then tapers as kids move out. Wealth isn't a number — it's time. Peyton's definition: wealth is the amount of time you can spend not working, not a dollar figure on a screen. Roth vs. pre-tax isn't a "which is better" question — it's a "which serves this purpose" question. Younger earners in lower tax brackets often benefit more from brokerage/Roth flexibility than maxing out pre-tax accounts; higher earners in higher brackets benefit more from pre-tax now with planned Roth conversions later. The three-bucket strategy: pre-tax, Roth (post-tax), and brokerage (post-tax, flexible) — where you focus your dollars should shift as your income and life stage change. Funding a dream property (like a beach house) has real tax tradeoffs. David and Peyton walk through three scenarios: cashing out a brokerage account (and eating the capital gains tax), a HELOC against your primary residence, and a securities-backed line of credit — each with very different risk profiles. Late-in-life cash flow planning is about spending well, not just accumulating. For those in their late 60s+ with fixed income covering expenses, the conversation shifts to strategic giving and enjoying wealth now rather than only growing net worth. About Peyton Hoppes Peyton recently joined ProVest Wealth Advisors in Spartanburg, SC, focusing on families with busy lives and high financial complexity — business owners, medical professionals, and families with special-needs children. He and David worked together for several years before Peyton's move. Connect with Peyton: Email: peyton@provestwealth.com LinkedIn: Peyton Hoppes Website: provestwealth.com 📅 Want to Talk Through Your Own Financial Situation? Book a complimentary 20-minute Wealth Optimization Call with David — a CFP® who works with successful individuals and business owners. 👉 Book Your Call → weeklywealthpodcast.com/vision 📧 Questions? Email david@parallelfinancial.com The information presented on this podcast is for general educational purposes only and does not constitute financial, investment, legal, or tax advice. Parallel Financial is registered with the U.S. Securities and Exchange Commission (SEC) as a registered investment advisor. Registration does not imply a certain level of skill or training, nor does it constitute an endorsement by the SEC. All investing involves risk, including the potential loss of principal. Please consult a qualified financial professional before making any financial decisions.

August 7, 202625 min

Ep: The Richest Corpse in the Graveyard

The Richest Corpse in the Graveyard If you ran out of money, when would it happen? For a growing number of retirees — paid-off home, pension, Social Security, a seven-figure portfolio sitting quietly in the background — the honest answer is probably never. And yet study after study shows this exact group is still the most hesitant to spend a dollar of it. In this episode, David uses a composite family — paid-off home, $3 million invested, pension and Social Security covering nearly all of their monthly expenses — to unpack why disciplined savers keep saving long after saving has stopped being the point, what the research actually says about it, and what to do instead: fund a business start for someone who needs it, launch a scholarship, or hand your grandkid the keys to a car while you're around to watch her drive it away. Why So Many Retirees Underspend Research from the Employee Benefit Research Institute found that roughly one-third of retirees still have 100% or more of their original retirement assets remaining by their mid-80s . Married couples 65 and older withdraw, on average, just 2.1% of their portfolio per year — well below the roughly 5% that current research considers a safe withdrawal rate. David calls this FORO — Fear Of Running Out — the retirement version of FOMO, except what you're missing is your own life. The people this happens to aren't reckless with money — they're the most disciplined savers in the room. As advisor Zach Teutsch puts it, "Overspending is risky. But underspending is risky too." David — who holds the CLTC designation alongside his CFP® — also draws a hard line between vague, unfocused fear and one actual, named risk worth planning for: an extended long-term care event. Solve that risk on purpose, and the rest of the portfolio is free to be used. Money That Moves vs. Money That Sits David's core mission for the show: how we handle our money should positively impact our lives and the lives of those around us. A growing balance doesn't do that on its own — it only matters once it moves. Fund a business start. More than a quarter of people who've helped fund someone's business gave to a close family member. David's practical note: decide up front whether it's a gift, a loan, or an equity stake, and put it in writing. Start a scholarship. A scholarship is legacy you get to watch unfold now — not legacy that waits for a will to activate. Buy the car, watch them drive it. Cash left invested usually outperforms a depreciating asset financially — but if the goal is connection rather than optimization, watching your grandchild's reaction beats a line item in probate. Give with a warm heart, not a cold hand — it doesn't need a tax deduction to be worth doing. Episode Timestamps 0:00 — Cold open: one grandfather, two very different versions of the same gift 2:15 — The data: why one-third of retirees barely touch their savings 6:30 — Why disciplined savers are the most likely to underspend 10:30 — The one legitimate fear worth naming: long-term care 13:30 — The mission statement, and why a growing balance isn't the goal 14:15 — Funding a family member's business start 17:00 — Starting a scholarship while you're alive to see it work 19:30 — The car in the driveway, and the tax-deduction question, answered directly 23:30 — Permission to spend: why the gap only closes with a real plan 27:00 — Wrap-up and next steps Have You Already Won the Game? If your expenses are mostly covered and your portfolio is quietly growing untouched, you don't need a guess — you need an actual answer. Book a free 20-minute Vision Call with David: weeklywealthpodcast.com/vision Related Episodes Ep. 267: What If You Have Already Won? — the Freedom Point episode this one builds directly on. Ep. 261: Six Retirement Philosophies — a broader look at the mindsets that shape how people actually spend, or don't, in retirement.

July 31, 202637 min

EP 274: A Refresher... check it out!

Replay Episode — This one's a "blast from the past." David originally recorded this conversation in the last quarter of 2022, right in the middle of heavy recession fear and a rough year in the markets. He's bringing it back now because 2026 has had its own share of ups and downs, and the mindset underneath this conversation hasn't gone stale. Joining David is Mike DiJoseph of Vanguard's Investment Advisory Research Center, whose team studies why investors make the decisions they make — and how a good advisor changes the outcome. In This Episode Why financial news functions more like entertainment than information Vanguard's "Advisor's Alpha" research: the roughly 3% net-return value a good advisor adds over time A real 2020 case study: bailing out at the bottom turned $1M into $800K, while staying the course turned it into $1.2M Why the political party in power has a surprisingly weak relationship with market returns The behavioral finance reason your brain forgets years of gains the moment there's one bad year Reframing downturns: lock in the loss on the portfolio, or lock in the loss on the goal Meet the Guest Mike DiJoseph works within Vanguard's financial advisor services division, on the Investment Advisory Research Center team. He and David connected through the Financial Planning Association. Key Moments Approximate timestamps — this is a replay, so times are estimated from the conversation flow. 00:00 — Why David is replaying this episode now 03:30 — Meet Mike DiJoseph and Vanguard's research team 06:00 — Is a recession actually bad for the stock market? 10:30 — The Tesla thought experiment 13:00 — How one word turns a headline from bullish to bearish 16:00 — Staying the course doesn't mean standing still 19:00 — Does the party in power actually move the markets? 24:00 — The recency bias problem 27:00 — The 2020 case study: $800K vs. $1.2M 33:00 — What a good advisor is actually worth 37:00 — Insurance and estate-planning blind spots 41:00 — Personal definitions of wealth Quotable "You can either lock in the loss on the portfolio, or you lock in the loss on the goal." "There is never going to be an all-clear signal. And to the extent that there is one, it's probably too late." "When your values are clear, your decisions are easy." Not sure if your portfolio — or your plan — is actually built for moments like this? Book a free 20-minute Vision Call: weeklywealthpodcast.com/vision Connect with David directly: david@parallelfinancial.com If this episode helped reframe how you're thinking about the market right now, share it with someone who needs to hear it — and follow the show so you don't miss what's next.

July 24, 202620 min

Ep 273: The Mid-Year Money Checkup: 9 Things to Check Before the Year Slips Away

The Mid-Year Money Checkup: 9 Things to Check Before the Year Slips Away You change your oil every 5,000 miles or so. Nobody waits for the engine to seize up on the highway to think about it. Your finances deserve the same treatment — and we're right at the halfway point of the year, which is exactly the moment to pop the hood before a bunch of December deadlines sneak up on you. This episode is nine things, no long story, no single deep dive. Some apply if you're a business owner, some don't — but almost everyone listening will hear at least three or four that apply directly to them. "A fifteen-minute check-in in July is a lot cheaper, financially and emotionally, than the same conversation happening in a panic in December." The 9-Item Checklist 1. The Roth Conversion Window — a lower-income or down-market year can make this the best conversion opportunity you'll get. 2. Charitable Giving Strategy — bunch giving or fund a donor-advised fund now, not in the last week of December. 3. Retirement Contribution Pace Check — are you actually on track to max out by December 31st? 4. Buy-Sell Agreement & Valuation Freshness Check — business owners: does that document still reflect reality? 5. The Mid-Year P&L Sit-Down — with your CFO, CPA, advisor, or just yourself and a cup of coffee. 6. The Zombie Subscription Audit — find the charges you forgot you were paying for. 7. Portfolio Drift Check — your allocation has probably wandered from target, even if you never touched it. 8. The Net Worth Snapshot — recalculate it and compare to January. Fifteen minutes, real data instead of a vibe. 9. Did Anything Big Happen This Year? — marriage, divorce, a new kid, a home purchase, a sale. Any of these should trigger a full plan review, not just a line-item update. Episode Timestamps 00:00 — Cold open: the oil change analogy 02:15 — 1. The Roth Conversion Window 04:15 — 2. Charitable Giving Strategy 06:15 — 3. Retirement Contribution Pace Check 08:15 — 4. Buy-Sell Agreement & Valuation Freshness Check 10:15 — 5. The Mid-Year P&L Sit-Down 14:00 — 6. The Zombie Subscription Audit 16:00 — 7. Portfolio Drift Check 18:00 — 8. The Net Worth Snapshot 20:00 — 9. Did Anything Big Happen This Year? 22:30 — Close: pick two, put a date on the calendar Got a question raised by this list? Book a free 20-minute Vision Call: weeklywealthpodcast.com/vision Know someone who needs this list more than you do? Send them the episode — it's more useful than another group text about the weather. Resources Mentioned Sellability Score — for business owners revisiting their buy-sell agreement or valuation Book a Vision Call

July 17, 202620 min

Ep 272: You Don't Need to Become a Financial Expert (Do This Instead)

I cut my own grass every week. I don't mind it — it's mindless, it's outside, I like the hour. Plenty of people I know, just as busy and just as capable, pay someone else to do theirs. Neither one of us is wrong. We just decided differently about where we want to spend that hour. Turns out we all make that same call, constantly, in every part of our lives — we just never name it out loud. This episode names it: the DIYer , the Partner , and the Delegator , and the honest question of which one you actually are when it comes to your money. "My job was never to know something you couldn't Google. My job is to make sure the right thing happens even on the day you don't feel like doing it." What You'll Learn This episode breaks down the DIYer / Partner / Delegator framework and applies it directly to your money — using ideas borrowed from Bill Bachrach's values-based financial planning and the "Who Not How" mindset from Dan Sullivan and Dr. Benjamin Hardy. Episode Timestamps 00:00 — Cold open: the lawn story and the three types 02:30 — Segment 1: DIYer, Partner, Delegator, defined across everyday life 07:00 — Segment 2: Information is free. Your time isn't. 10:00 — The Bachrach question: what would you do with the time back? 11:00 — From "How" to "Who": the Who Not How mindset shift 13:30 — Segment 3: Implementation is the whole game 17:00 — Segment 4: The cost of small mistakes (the beneficiary story) 20:30 — Close: the honest question to ask yourself The Question Worth Sitting With If you no longer spent your evenings and weekends researching stocks, reading up on IRA rules, or checking your portfolio — what would you actually do with that time? Coach your kid's team without half your brain on the market? Sleep through the night instead of running numbers at 1am? Whatever you just pictured — that's the actual return on delegating. Not a better return than the S&P. Your life back. "The DIYer instinct is to ask 'how do I do this.' The Delegator instinct is to ask 'who can do this for me.' Neither question is wrong — but only one of them gives you your evenings back." The Mistake Nobody Talks About It's rarely a market crash that quietly costs a family everything. It's a beneficiary form filled out once, years ago, and never updated through a marriage, a divorce, or a new kid. That account doesn't care what your will says — it pays out exactly according to the form. That's not a knowledge gap. That's an implementation gap, and it's exactly the kind of thing accountability is built to catch. Not sure which one you are with your money? Book a free 20-minute Vision Call: weeklywealthpodcast.com/vision Know a Delegator who's still white-knuckling their own portfolio out of guilt? Send them this episode — it might be the permission they've been waiting for. Resources Mentioned Who Not How by Dan Sullivan and Dr. Benjamin Hardy Bill Bachrach's values-based financial planning approach Book a Vision Call

July 10, 202618 min

Ep 271: Are TRUMP accounts a gimmick?

Everyone's talking about the free $1,000 the government just dropped into Trump Accounts. Almost nobody's talking about the fine print — or the backdoor Roth IRA strategy hiding inside it. In this episode, David breaks down Trump Accounts, 529 plans, UGMA/UTMA custodial accounts, and custodial Roth IRAs side by side: what each one actually does, where the real catches are, and the one advanced move that could turn a modest Trump Account into a six-figure Roth IRA by your kid's mid-20s. The Numbers You Need to Know $1,000 — one-time federal seed deposit for eligible kids born 2025–2028 $5,000/year — combined annual contribution cap for a Trump Account (individuals + employer) $2,500/year — max employer contribution, counted within the $5,000 cap 0.10% — expense ratio cap on Trump Account investments Age 18 — when a Trump Account unlocks and converts to a traditional IRA $7,500 — 2026 contribution limit for a custodial Roth IRA (requires earned income) 10% — early withdrawal penalty on taxable IRA distributions before age 59½ Episode Timestamps 0:00 — Cold open: the free money everyone's talking about 2:30 — What a Trump Account actually is 8:00 — The 529 comparison 12:30 — UGMA/UTMA: the no-restrictions account (and its biggest risk) 17:00 — Custodial Roth IRA for kids with earned income 23:00 — The backdoor Roth conversion strategy hiding inside a Trump Account 27:30 — So which account do you actually use? 31:00 — Wrap-up and next steps What Is a Trump Account? A Trump Account (formally a Section 530A account) is a new type of custodial-style traditional IRA for children, available starting July 4, 2026. Any U.S. citizen child under 18 with a valid Social Security number can have one opened on their behalf — and children born between January 1, 2025 and December 31, 2028 qualify for a one-time $1,000 federal seed deposit. After that seed money, parents, grandparents, and other individuals can contribute up to $5,000 combined per year, with no earned-income requirement. Employers can add up to $2,500 of that total, tax-free to the employee. During the account's "growth period" — birth until January 1 of the year the child turns 18 — the money is locked, invested only in low-cost U.S. stock index funds, and cannot be withdrawn for any reason. "The Trump Account is not a replacement for a 529. It's not a replacement for a custodial account. And for some of you, it might not even be the best of the four options we're about to walk through." Trump Account Quick Facts No earned income required to contribute $1,000 government seed for eligible children (does not count toward the $5,000 annual cap) Locked until January 1 of the year the child turns 18 Converts to a standard traditional IRA at that point — ordinary income tax + 10% penalty on early withdrawals apply thereafter, with limited exceptions Trump Account vs. 529 Plan A 529 plan is purpose-built for education. Many states offer a tax deduction for contributions, and—unlike a Trump Account—qualified education withdrawals come out completely tax-free , not just tax-deferred. Contribution ceilings are also far higher than the Trump Account's $5,000 annual cap. The tradeoff: flexibility. If the money isn't used for qualified education expenses, you're facing taxes and penalties to access it for anything else. (Some limited 529-to-Roth rollover options now exist, but they come with their own caps and rules.) Bottom line: Trump Account = flexible use, locked for 18 years. 529 = bigger tax break, locked into education as the purpose. Trump Account vs. UGMA/UTMA UGMA and UTMA custodial accounts offer something neither of the accounts above can: zero restrictions on how the money gets used. Braces, a car, a business — anything. But that flexibility comes with two real costs. First, it's a fully taxable account — no tax-deferred growth, and the "kiddie tax" may apply, sometimes taxing gains at the parents' rate rather than the child's. Second, and more importantly: the money legally belongs to the child from day one. At 18 or 21 (state-dependent), every dollar becomes theirs, with no conditions and no say from the adults who funded it. "I've had conversations with clients who funded one of these accounts for a decade and then watched their 18-year-old empty it out for something the parents very much did not sign up for." Trump Account vs. Custodial Roth IRA For a child with real, documentable earned income — a W-2 job, self-employment, or legitimate pay through a family business — a custodial Roth IRA quietly beats all three other accounts on pure math. Contributions grow completely tax-free, not just tax-deferred, and the contribution ceiling ($7,500 in 2026) is higher than the Trump Account's $5,000 cap. The catch: it only works if the earned-income requirement is met, and the documentation needs to be handled correctly — especially if the income comes through a family business — or it can create a bigger problem with the IRS than it solves. The Backdoor Roth Strategy Hiding Inside a Trump Account Here's the piece almost nobody talks about: once a Trump Account converts to a traditional IRA at 18, it becomes eligible for a standard Roth IRA conversion — meaning some or all of that balance can be moved into a Roth IRA by paying ordinary income tax on the converted amount today, in exchange for tax-free growth and tax-free withdrawals for life. Because Trump Accounts never required earned income to fund in the first place, this creates something that wasn't possible before: a path to real Roth IRA money for a child who never worked a single job. "You could have a kid who never worked a single job, walk into age 18 with real money in that account, and convert it into a Roth IRA — something that was never possible before without earned income. That's the backdoor." The timing matters enormously. Converting during a low-income year — often the late teens through mid-20s — means paying tax on the conversion at a much lower bracket than the money would likely be taxed at later in life. Some financial planners have modeled modest Trump Account balances compounding into six figures in a Roth IRA by a young adult's mid-20s, and well over $1 million by retirement. Landmines to Know Before Converting Kiddie tax risk: converting while the child is still a full-time student or dependent can trigger taxation at the parents' rate, undercutting the strategy Basis tracking: government seed money, employer contributions, and charitable deposits are fully pre-tax and taxable on conversion; money contributed by parents or grandparents was already after-tax and shouldn't be taxed again The five-year rule: each conversion starts its own five-year clock before it can be withdrawn tax- and penalty-free Evolving guidance: the IRS has not finished writing all the rules around this strategy So Which Account Should You Actually Use? The honest answer: it's not "pick one." These accounts serve different goals, and stacking them intentionally — rather than by accident — is where real planning happens. 529: earmarked money for a specific outcome — education UGMA/UTMA: flexible, no-restriction savings, with real loss-of-control risk Trump Account: long-horizon retirement head start, with free seed money and a potential backdoor Roth play Custodial Roth IRA: the strongest long-term math, once a child has earned income None of these are wrong on their own. But four accounts with four different rule books, contribution sources, tax treatments, and control timelines is exactly how families end up with a pile of savings and no actual strategy behind it. Ready to Map It Out? If you've got a Trump Account, a 529, an old UTMA, and a kid with a summer job all in the mix — and you're not sure they're actually working together — that's exactly what a Vision Call is for. We'll map out every account you've got for your kids or grandkids and make sure they're pulling in the same direction, including whether a Roth conversion strategy makes sense for your family. Schedule your free Vision Call → Know a parent or grandparent who just opened a Trump Account without thinking through the other three options? Send them this episode — it might save them from a decision that's hard to undo. Topics covered: Trump Accounts, Section 530A accounts, 529 plans, UGMA accounts, UTMA accounts, custodial Roth IRA, Roth IRA conversion, kiddie tax, IRA contribution limits, saving for kids, tax-free growth, financial planning for children, retirement accounts for minors, backdoor Roth strategy