ThimbleberryU

Hosted by Amy Walls

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169

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Oct 2026

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About the show

Financial planning is all about vision - what do you want for the rest of your life? Amy Walls of Thimbleberry Financial helps clients paint that picture every day. And it's what we will do in this podcast.

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60 recent

October 12, 202619 min

Should I Annuitize my 403(b) When I Retire?

If you're in healthcare or academia and retirement is coming into view, you've probably gotten a form asking whether you want to annuitize your 403(b), and it's not obvious what you're actually agreeing to. This episode breaks down what annuitizing really means, why it's usually permanent, and how it compares to keeping the account invested instead. Amy Walls walks through why not every 403(b) can be annuitized in the first place, the mechanics and irreversibility of the ones that can, why your own health and life expectancy belong in the math, a hypothetical showing how annuitizing doesn't have to be all-or-nothing when you hold more than one 403(b), and how this decision connects to the pension lump-sum-versus-monthly choice so many healthcare and academic households face in the same window. You'll learn: Why not every 403(b) can be annuitized, and how to find out which kind you have Why annuitizing your 403(b) is usually an irreversible decision How staying invested, whether through a rollover or by simply leaving the account in place, compares to annuitizing it, in taxes and in control Why your health and life expectancy are part of the annuitize-or-not math Why you can combine required minimum distributions across multiple 403(b) accounts, but not with a 401(k) or an IRA How a pension lump-sum decision and a 403(b) annuitization decision connect, and why they're worth deciding together (00:00) Intro (00:08) Should You Annuitize Your 403(b)? (01:16) TSA vs. Other 403(b) Plans (02:04) Do You Need More Guaranteed Income? (03:38) How 403(b) Annuitization Works (05:14) The Deal or No Deal Example (09:19) A Retirement Example (10:35) Comparing Two 403(b) Accounts (13:33) How Pension Decisions Fit In (16:38) Spouses, Longevity, and Survivor Benefits (17:38) Looking at the Whole Retirement Picture To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

September 28, 202615 min

How Do I Recover the AMT Credit After Exercising ISOs?

If you're in tech and exercised incentive stock options, you may have discovered that holding the shares can trigger Alternative Minimum Tax, even though you never sold anything and never saw a dollar of cash. Amy Walls breaks down why that phantom income creates a real tax bill, and why that bill isn't gone for good, it becomes a credit you can recover. This episode walks through how the minimum tax credit tracked on Form 8801 actually gets recovered, why the 2026 changes to the AMT exemption phase-out under the One Big Beautiful Bill Act pull more tech professionals into this exact situation, and why some people recover their full credit while others end up with a portion permanently stranded. You'll learn: Why exercising and holding ISOs can create a tax bill even with zero cash proceeds How the minimum tax credit on Form 8801 carries forward and what triggers recovery Why the 2026 AMT phase-out threshold and rate changes pull more tech professionals into AMT exposure Why the AMT rate you pay and the capital gains rate you recover against don't match, and what that means for your credit Why the size of an ISO exercise should be planned across multiple years, not decided in isolation (00:00) Intro (00:54) Why AMT Can Become a Future Tax Credit (02:22) Why You Owe Tax Without Selling Shares (02:30) Understanding the ISO Bargain Element (05:11) Why AMT Matters More in 2026 (07:12) Priya’s $200,000 AMT Example (09:47) Do You Always Recover the Full AMT Credit? (10:53) Qualifying Dispositions and Capital Gains (11:51) Understanding a Stranded AMT Credit (12:31) How to Plan Before Exercising ISOs (12:40) Why ISO Planning Should Be Multi-Year (15:06) How to Contact Thimbleberry Financial To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

September 14, 202616 min

Do I Need a Financial Advisor If I Already Have a CPA?

If you’re in healthcare or academia and you already have a CPA, it’s easy to assume your tax and financial picture is fully covered. It isn’t, and this episode explains exactly where the line falls. Amy Walls breaks down the real difference between tax preparation and tax planning, why accounts spread across multiple hospital systems or universities, 403(b)s, 457(b)s, and pensions, need someone coordinating them across institutions, and where CPAs and financial planners have to work together instead of separately. You’ll learn Why tax preparation and tax planning are different services, and why a financial planner’s tax projections are not the same as official CPA tax planning Why a 457(b)’s early-access advantage matters when you’re coordinating multiple retirement accounts What can go wrong with a Roth conversion when a prior IRA rollover wasn’t done as a clean, direct transfer Why a pension lump-sum versus monthly-income decision is a planning question, not just a tax question Why the real question isn’t whether your CPA offers tax planning, it’s whether they’re willing to work with your financial planner as a team (00:00:00) - Intro (00:00:22) - Do I need a financial advisor if I have a CPA? (00:00:59) - Backward looking vs forward planning (00:02:37) - Tax preparation vs tax planning (00:06:05) - Multiple retirement accounts in healthcare (00:08:10) - Where coordination breaks down (00:08:19) - Roth conversion coordination example (00:10:21) - Pension lump sum vs monthly income decisions (00:12:40) - Making advisor and CPA work together (00:14:06) - The key question to ask your CPA (00:15:18) - Wrap up and contact info To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

August 24, 202620 min

Should I Pay Off My Mortgage or Invest When Interest Rates Are High?

Higher mortgage rates quietly changed the math on one of the most argued questions in personal finance. If you’re in tech, with a mortgage, RSUs, and real money to deploy, the answer isn’t as obvious as it used to be, and the stakes are higher than a simple rate comparison suggests. In this episode, Amy Walls walks you through how to weigh a guaranteed return against an uncertain one, what extra mortgage payments actually compete with (it’s not your 401(k) match), how your equity comp and concentration picture change the call, and how to set a decide-once rule so you stop relitigating it every month. You’ll learn: Why higher rates made this an open question again, and what actually changed How to compare a guaranteed payoff return to an uncertain investment return What extra mortgage payments should, and shouldn’t, compete with How taxes and the standard deduction can change your math Why liquidity and concentration matter before the mortgage question does How to set a split strategy that respects both the numbers and how you’re wired Why paying down the mortgage and investing aren’t symmetrical choices (00:00) Introduction (00:16) Should You Pay Off the Mortgage or Invest? (00:57) The Basic Decision Framework (02:26) Why Higher Mortgage Rates Change the Math (03:19) Guaranteed Returns Versus Expected Returns (05:59) Why Personal Behavior Matters (06:09) Common Mortgage Payoff Mistakes (09:02) Using RSUs and Bonuses (09:18) Liquidity and Concentration Risk (12:20) The Value of Peace of Mind (12:34) Lower Fixed Costs and Employment Uncertainty (14:58) When Psychology Changes the Best Decision (15:50) What to Prioritize First (18:47) Choosing a Lane Intentionally (19:07) How to Contact Thimbleberry Financial To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

August 10, 202612 min

When Can I Retire? Academic Healthcare Professionals

This episode focuses on a question that follows many professionals in academic medicine, healthcare, and research: “Can I actually retire?” Jon Gay and Amy Walls explain that the stress behind this question often does not come from a lack of money. It comes from a lack of visibility. Retirement accounts, pensions, 403(b)s, 457 plans, IRAs, and Social Security all produce separate statements. But none of those statements show how everything works together. That leaves people with pieces of information, but not a complete picture. Amy explains that the common instinct is to start with a number. People want to know how many millions they need before they can retire. But a number by itself does not answer the real question. Retirement planning has to start with life. What does life cost right now? What expenses will go away after retirement? What expenses have been postponed for years and will finally appear? For people whose identity is closely tied to their work, retirement can also feel like a loss before it feels like freedom. That makes it important to define the next chapter before deciding what financial number is enough. Retirement planning is more complicated for people in healthcare academia. A pension can be the centerpiece, but it often requires an irreversible decision between lifetime monthly income and a lump sum. That decision depends on health, a spouse, other income, investment accounts, and taxes. Amy also explains that 457 plans are often misunderstood. Governmental 457 plans can usually be accessed after separation from service without an early withdrawal penalty, while non-governmental plans work differently. That difference can change the order in which accounts should be used. Real confidence comes from testing the plan. Retirement readiness should not stay a feeling or a hypothesis. The plan needs to be stressed against hard questions. What happens if the market drops 30 percent in year two? What if someone lives to 97? What if long-term care is needed? When the plan still works under pressure, the question shifts from “ Am I ready? ” to “ I am ready. ” We share the example of a physician researcher who believed she was behind because her peers in private practice had built business equity. Once her full financial picture was mapped against her actual life and goals, she was comfortably on track. Nothing changed financially in that conversation. What changed was her relationship to the information. A retirement plan is not a one-time snapshot. Life changes, tax laws shift, markets move, and planning needs a rhythm. Annual reviews and updates help keep the plan connected to real life. The relief does not come from hitting a magic number. It comes from finally seeing the whole picture. (00:00) Intro (00:54) Why retirement uncertainty is really about visibility, not just money (02:31) Why starting with a “magic number” is usually the wrong approach (02:50) How to build retirement planning around actual life costs (03:25) Why retirement can feel like a loss before it feels like freedom (04:05) How pensions, 403(b)s, and 457 plans need to be viewed together (07:15) How stress testing turns “Am I ready?” into “I am ready” (10:06) Why retirement planning needs regular review, not a one-time snapshot To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

July 27, 202613 min

"Set It and Forget It" or Just Forgetting It?

In this episode of ThimbleberryU, Jag and Amy talk about the difference between simple investing and ignoring your portfolio. This is especially for those of you working in tech, where it is easy for much of your financial life to become tied to the same industry without realizing it. Your paycheck may come from tech. Your RSUs or stock options may depend on your company’s performance. Your future career growth may depend on the same sector. Then, on top of that, your investments may also be heavily weighted toward technology through index funds or individual stocks. Amy explains that many investors want a “set it and forget it” approach because they want peace of mind. That is understandable. The problem is that simple and unattended are not the same thing. A target date fund may feel passive to the investor, but there is still a process behind it. Your fund is being rebalanced and adjusted over time. That is very different from building a portfolio once and then never checking whether the risks still fit your life. The biggest issue for you could be concentration risk. This is when too much of your financial life is exposed to the same company, industry, or type of investment. This risk often builds slowly. It may not come from one bad decision. It can come from you saving consistently, investing responsibly, holding company stock, and buying familiar tech names on the side. During strong markets, that can feel great. But when layoffs, downturns, or sharp drops hit, your risk becomes much more obvious. Jag compares it to gambling, where early success can make someone feel like their strategy is working even when they are taking on more risk than they realize. Amy agrees: success itself can quietly create concentration. A stock or sector does well, becomes a bigger part of the portfolio, and starts to feel normal. That is exactly why rebalancing matters. Rebalancing is not about you trying to predict the market. It is about managing risk. It keeps yesterday’s winners from becoming tomorrow’s overexposures. For tech professionals, this can be especially important because strong performance in the sector may increase both your confidence and concentration at the same time. We also talk about the emotional side of company stock. Amy explains that once shares vest, they become part of your investment portfolio. At that point, holding them should be an investment decision, not just an emotional one. One helpful question we ask clients is this: I f your company paid you the same amount in cash instead of stock, would you use that cash to buy company shares? For many people, the answer is no. Your long-term investing should feel calm, simple, and intentional. It does not require reacting to every headline. But it also should not mean abandoning your portfolio for years at a time. A healthy strategy includes periodic reviews, rebalancing, checking concentration risk, and making sure your investments still match your goals. Calm requires attention, not abandonment. (00:00) Intro (00:49) Why tech workers want simplicity and peace of mind. (02:00) Target date funds vs portfolios that are built once and ignored. (03:42) A seemingly diversified portfolio can have concentration risk (05:52) How success can quietly create concentration risk. (06:44) Rebalancing (08:22) The emotional attachment people can have to company stock. (10:39) The healthy middle ground: calm, simple, and intentional investing To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

July 13, 202620 min

Reducing Chaos for the People You Love

In this episode of ThimbleberryU, you'll hear why reducing chaos for the people you love is one of the most practical and caring financial steps you can take. It is not a topic most people want to face, but it is one almost every family eventually has to deal with. For healthcare professionals, financial life can get complicated quickly. You may have old retirement plans from different hospital systems, HSAs, deferred compensation, insurance portals, stock plans, passwords, apps, and accounts spread across many places. It is easy to assume your spouse or family member will know who to call, but that only works if they actually know where to start. You are not avoiding this because you are irresponsible. You may be avoiding it because life is busy and the topic feels emotionally heavy. But your loved ones should not have to become detectives during a crisis. They already have to deal with fear, grief, logistics, and decisions. The goal is not perfection. The goal is enough clarity so someone can take the next right step. This can be especially important for healthcare professionals because they handle complexity every day at work. That can make you more tolerant of complexity in your personal life. Over time, financial life becomes layered. One person in the household often becomes the default organizer, and that works until that person is unavailable. This is operational planning for your family today, not just estate planning for someday. A good starting point is simple: who to call, where things are, and what matters first. You do not need a giant binder with every detail of your life in it. Your family needs important contacts, major accounts, insurance information, legal document locations, and a basic explanation of how bills are paid. A one page summary sheet can make a huge difference. You'll also hear about password managers, emergency access, and the importance of testing access before there is an emergency. Email and phones often act as master keys to financial life, so you need to think carefully about both security and usability. If your system is so secure that no trusted person can get in during a crisis, it fails the people it was meant to protect. Amy also addresses households where one spouse handles most of the finances. The answer is not mastery. It is familiarity. Regular household CFO meetings can help both people understand income, accounts, insurance, contacts, and emergency processes. After a sudden death or medical crisis, families often freeze, move too fast, close accounts too early, miss deadlines, or let insurance lapse. Amy recommends slowing down, stabilizing first, and thinking in phases: 30 days, 60 days, 90 days, and the first year. The real message is that a simple system is far better than no system at all. You are not trying to predict a crisis. You are giving the people you love enough clarity to breathe, think, and take the next right step when they need it. (00:00) Intro (00:56) Why people put off emergency planning (01:45) Progress over perfection (02:21) Why healthcare professionals face added complexity (04:04) Where to start when there is no system (04:49) The three essentials: who to call, where things are, what matters first (05:47) Password managers and emergency access (08:53) Balancing security and accessibility (11:00) When one spouse handles the finances (14:50) Common mistakes after death or medical crisis (17:20) Thinking in 30, 60, and 90 day phases (18:20) Making life easier for the people you love (19:41) How to contact Thimbleberry Financial (20:03) Disclosures To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

June 22, 202610 min

What Do Giant IPOs Like SpaceX Mean For Your Portfolio?

In this episode of ThimbleberryU, we talk about what a giant IPO like SpaceX could mean for a personal investment portfolio. The conversation starts with common questions many investors ask when a major private company gets ready to go public. Am I missing out? Is my index fund going to own it? Am I exposed to something I do not understand? Amy explains that many people assume an index fund owns the biggest companies in the market, but that is not always true. Index funds follow rules. For example, a company in the S&P 500 usually has to meet certain requirements around profitability, public trading shares, and time as a public company. So a company can be huge and still not appear in an index fund right away. That distinction matters, but probably not as much as the headlines make it feel. For most investors, one company being absent from an index now or added later is a small part of a diversified portfolio. The bigger risk is behavioral. A headline can create fear of missing out, and that fear can push someone to chase a single hot stock. That reaction can do more damage than the index rules themselves. Amy also explains where this can show up in real accounts. Broad index funds may be held in taxable brokerage accounts, 401(k)s, or IRAs. If those funds are designed to track an index, then the rules of that index shape what the investor actually owns. An index fund does not necessarily mean the investor owns everything. It means the investor owns what the index includes at that time. The episode also explains the difference between active and passive investing. An active fund has a manager making ongoing decisions about what to buy and sell. A passive fund tracks an index mechanically. That does not mean no decisions were made. It means the decisions are built into the index rules rather than made day to day by a fund manager. Amy thinks this is not a one-time issue. Large private companies have been staying private longer and going public at larger sizes. That means investors may keep seeing a large gap between when a company becomes enormous and when it appears in an index fund. The practical takeaway is not to reshuffle a portfolio because of a headline. The better move is to understand what your funds actually own and why they own it. Investors should check whether their index exposure reflects their goals, either with an advisor or through careful research. The calm, fact-based review is more useful than reacting to news. (00:00:00) - Intro (00:00:57) - Do index funds automatically own the biggest companies? (00:01:54) - Does SpaceX's absence actually matter for investors? (00:03:14) - Where this shows up in real accounts (00:04:43) - Active versus passive fund management explained (00:06:15) - Is this a pattern we'll keep seeing? (00:07:23) - What investors should actually do (00:09:18) - Closing and contact info To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

June 8, 202618 min

Beyond the Paycheck: Building Wealth When You’re Already Comfortable

In this episode, we talk about what it means to move beyond simply earning a strong paycheck and start building wealth with real intention, especially for people in tech who are in the middle or later stages of their careers. We start with the idea that success can remove urgency. Early on, financial decisions feel obvious because everything is new and growing. Later, income is steady, accounts are already set up, and the basic systems are running. On the surface, everything looks fine. But that can create a quiet risk because passive financial habits keep shaping the future without anyone stopping to ask where it is all leading. We focus on the importance of clarity. Saving a large amount each year can look impressive, but that does not automatically mean the long term outcome matches someone’s goals. Rising spending, overreliance on employer stock, or disconnected decisions across accounts can slowly push someone off course. The key is not that anything is broken. The issue is that many people have never paused to see the full picture. Once they do, they can compare where they are headed with where they actually want to go. We also spend time on equity compensation, which can become one of the largest opportunities and one of the largest risks in a financial life. We make the case that equity comp should be treated as real money when it is close enough to affect cash flow. Without a plan, it can get handled like a windfall, spent too casually, or allowed to build into a dangerously concentrated position. A simple plan such as selling shares on a schedule, reviewing vesting decisions regularly, and coordinating with taxes can turn that uncertainty into something durable. Another big theme is defining what enough means. We explain that the right starting point is not a target net worth pulled from a headline or a commercial. It starts with lifestyle. We need real numbers for what life costs today, what expenses are fixed, what is flexible, and what actually adds value. From there, the idea of enough becomes personal and measurable. That clarity can replace pressure, comparison, and vague anxiety with perspective. We close by bringing it back to purpose. Intentional wealth building does not mean adding more complexity. It means making sure income has a role, equity compensation has a plan, risk is understood, and there is a regular rhythm for checking in. The goal is to move from something that is working okay to something that is working on purpose. (00:00) Intro (00:08) Why success can remove urgency (01:18) How passive money habits shape outcomes (04:23) What gets missed when nothing feels urgent (05:17) Example of concentrated company stock risk (07:09) Treating equity compensation as real money (09:53) How to know if you are actually on track (12:00) The pressure of comparison and feeling behind (14:21) Where to focus when you do not have time (16:20) What intentional wealth building actually looks like (17:36) How to contact Thimbleberry Financial To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

May 26, 202619 min

The Hidden Costs Of Doing Nothing

Today, Amy and Jag look at a financial risk that is easy to ignore because it does not feel urgent in the moment: the cost of doing nothing. In this episode, we focus on how delays in financial decisions can quietly create long term consequences, especially for healthcare professionals who are used to acting quickly at work but may postpone choices in their own financial lives. The central idea is simple. Inaction is still a decision, and over time it can carry a real cost. Amy explains that many financial delays do not come with immediate pain. Income is still coming in, accounts still exist, and nothing appears broken. That makes it easy to leave cash uninvested, skip HSA contributions, ignore open enrollment changes, or delay insurance decisions. But time is often the thing being lost, and time can translate into large amounts of money. A $100,000 cash balance left sitting too long can mean missing tens of thousands of dollars in growth. Missed HSA contributions can reduce both tax savings and long term wealth. Idle cash spread across accounts may not seem serious until the total missed opportunity becomes clear. The episode also highlights timing windows that matter. Open enrollment, tax planning before year end, lower income years that create Roth conversion opportunities, and insurance decisions made while health is still favorable can all have meaningful financial impact. Amy gives several examples where waiting leads to higher taxes, less retirement savings, or insurance that becomes more expensive or unavailable. She also notes that rule changes can remove options people assumed would still be there later. A major theme in the conversation is that the biggest mistakes are often basic ones that never get revisited. People repeat the same benefits elections, forget to update beneficiaries, let cash build up unintentionally, and miss planning opportunities because nothing forces action. Amy stresses that beneficiary designations override a will, which makes that one of the fastest and most important items to review. She also emphasizes income protection through insurance and the importance of identifying unintentional cash balances. The practical advice is to start small and focus on what matters most. Review beneficiaries. Check insurance coverage. Look for idle cash. Make a short list of what has a deadline, what affects family, and what becomes more expensive if delayed. Amy suggests one or two intentional financial reviews each year, along with a pre year end tax check and regular check ins on the biggest issues. The message is not to do everything at once. It is to notice what has been sitting too long and move it forward. Doing nothing feels neutral, but it is often where the biggest hidden costs begin. (00:00) Intro (00:16) Why financial inaction feels harmless (01:50) The real cost of waiting (03:10) Missed HSA contributions and idle cash (04:29) How to triage financial decisions (05:00) Tax timing and lower income years (06:14) Why insurance gets riskier to delay (06:51) Decisions that get more expensive over time (10:05) Common mistakes people make when they delay (12:18) Where to start fixing it (17:57) Key takeaways To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com . The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/