Playbook of the Wealthy

What if you could own the S&P 500 and never see a negative year? That's the pitch behind buffered ETFs — and like every pitch that sounds too good, the fine print is where it gets interesting. The protection is real. So are the caps, the costs, and the ways to pick the wrong one.★ WHAT YOU'LL LEARN ★▸ What a buffered ETF really is — the "defined outcome ETF" that tracks an index, protects the downside, and caps the upside▸ How big this corner of the market has become: 420 products and $58 billion since 2018▸ How calls and puts actually create the buffer — walked through on a fake $100 stock, no rabbit holes▸ The 100%-protection trade-off: your return never goes negative, but your cap lands around 6–7% and resets every year▸ How a 10% or 15% buffer works in practice — what you really lose when the market drops 12%▸ Why "the stock market averages 10%" is the most misleading stat in investing — and what a cap actually costs you in real, lumpy markets▸ Dave's real-world strategy: splitting a retiree's S&P 500 allocation in half — roughly 75% of the upside with half the downside▸ Buffered ETF vs. annuity: the liquidity difference, the fee difference (about 0.8% vs. up to 3.5%), and the one promise only an annuity can make▸ How these products behaved during this spring's market temper tantrum★ CHAPTERS ★00:00 Cold open: best annuity product? Buffered ETFs all day01:02 If the market drops 20% right at retirement — what could you have done?01:21 Welcome — today you become a nerd like us01:40 Fair warning: this one's finance 4.002:02 The definition: what a "defined outcome ETF" is02:58 Not new: 420 products and $58B since 201803:40 The catch — protection isn't free and upside gets capped04:23 How they're built: calls and puts on a $100 stock07:10 Packaging the buffer: how much insurance do you want?07:33 Headline: Dave uses these, Heather doesn't (yet)08:17 Client one: Sally Smith and 100% downside protection09:37 How a 10% or 15% buffer actually works10:12 Client two: Joe Sample wants upside with a safety net11:25 Why "10% average returns" misleads — caps in real markets11:52 Why these have been a hard sell in a three-year bull run13:21 How Dave really uses them: split the S&P allocation in half15:01 Heather pushes back — modeling the trade-off honestly15:51 Who this is for (and who it definitely isn't)16:39 "You just explained an annuity" — the comparison everyone asks17:46 How buffered ETFs handled this year's volatility18:38 The one thing an annuity does that this never will19:24 Modeling buffered ETFs in a financial plan20:29 What they cost: ~0.8% — cheaper than an annuity, pricier than an index fund21:49 Final cautions: dual-direction products and buying the wrong one22:45 A quick ask — like, comment, subscribe23:17 The bow: terrified of volatility? This might be for you23:53 What Would You Do?24:00 Q1: Retiring in six months and scared of a drop — buckets, then buffers26:14 Q2: My insurance broker wants my 401(k) in a fixed index annuity28:41 Q3: 420 products — how do I pick the right buffered ETF?30:54 Caps, resets, and the new-product-every-month strategy33:21 Highlights33:27 Highlights: Dave is back in the credit-card points game35:23 Highlights: Heather survives the Scottsdale fair37:03 Wrap up

Ever wonder what your financial advisor is actually reading over morning coffee — and how those headlines quietly reshape the advice you get? This episode is that reading list, cracked open. No 4.0 level finance nerd-out, just the stories Dave and Heather think you should know about, with opinions attached.In this Playbook of the Wealthy episode, financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial run through the news they've been tracking this quarter — the "Trump accounts" landing at Robinhood, AI getting the math wrong on people's retirement plans, $14 billion walking out of a single brokerage house, a "new retirement number" that leapt 16% in a year, private-credit funds telling investors "you can have half," and a wave of wealth-tax proposals from California to the Netherlands to Washington. Plus highlights: parenting a kid who just got their license, and an inspiring Costa Rica trip straight out of Die With Zero.▶ Listen on Apple, Spotify, or visit https://playbookotw.com★ WHAT YOU'LL LEARN ★▸ Why the new "Trump accounts" are landing at Robinhood — who's really running them, and the one-account-per-kid rule that trips up well-meaning grandparents and parents▸ The thing AI still gets dangerously wrong in a financial plan — and why one bad math number can quietly break your whole retirement▸ Why $14 billion walked out of UBS in a single year, and what advisors fleeing the big brokerage houses means for the advice you actually receive▸ The survey number that jumped from 38% to 68% in 16 years: when paying for financial advice is genuinely worth the fee — and when it isn't▸ Why "the new retirement number" leapt 16% in one year to $1.45M — and why that headline number almost certainly isn't yours▸ The buffer most retirees skip — and why 40% of households can't cover a single year of surprise expenses▸ How a "gray divorce" can wreck a retirement plan that worked perfectly fine for two▸ The illiquidity trap, explained plainly: what happens when you ask a private-credit fund for your money back and the answer is "half, maybe"▸ The wealth-tax experiments brewing in California, the Netherlands, and Washington — including the one that already got reversed after public outcry▸ Why a slowing job market might be an AI productivity story, not a recession story — and why the hosts aren't panicking about either★ CHAPTERS ★00:00 Cold open: getting (a little) political on taxing the wealthy00:59 What financial advisors actually read in the news01:10 Welcome — today we're reading the headlines01:22 Why we picked these stories (finance 2.0, not 11.0)02:02 The "Trump accounts" are coming — and they're at Robinhood06:08 AI can't do math — verify before you trust it08:05 Why advisors are leaving the big brokerage houses09:46 68% of wealthy investors now say advice is worth the fee11:54 Hiring is the slowest since Covid — recession signal or AI?12:50 Dave's take: the AI fear-mongering is overblown15:20 The "new retirement number" jumps to $1.45M17:33 Retirement confidence hits its lowest in a decade19:22 Unexpected expenses, buffers, and the case for buckets22:21 Gray divorces are wrecking retirement plans24:38 Private-credit redemption gates — the illiquidity trap27:25 California, the Netherlands & Washington: taxing the wealthy34:33 A quick ask — like, comment, subscribe34:44 Highlights34:54 Highlights: Dave on parenting a newly-independent teen37:24 Highlights: Heather's inspiring Costa Rica trip39:33 Wrap up★ LISTEN ON ANY PLATFORM ★Apple Podcasts: https://podcasts.apple.com/us/podcast...Spotify: https://open.spotify.com/show/21LrI3I...Website: https://playbookotw.com★ CONNECT ★Submit a question for a future episode: https://playbookotw.comEmail: [email protected] Grant on Instagram:   https://www.instagram.com/davegrant82Heather Townsend on Instagram:  https://www.instagram.com/heather.townsend.financial

Four CPAs can take the same set of numbers and hand you four different tax returns. That's not a knock on accountants — it's how tangled the tax code has become. And this year, Dave and Heather caught a stack of expensive mistakes on returns that clients and other preparers had already called "finished."In this Playbook of the Wealthy episode, financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial run through everything they saw in this tax season — the under-withholding, the mutual funds quietly throwing off capital gains, the backdoor Roth that got taxed twice, the S-Corp set up with no salary, the W-2 that never made it onto the return — and then, more importantly, exactly how to avoid each one next year. Plus a "What Would You Do?" mailbag on withholding after a raise, refund envy at the office, and what to do when a too-big refund makes you nervous.▶ Listen on Apple, Spotify, or visit https://playbookotw.com★ WHAT YOU'LL LEARN ★▸ Why "I adjusted my W-4" almost never fixes an under-withholding problem on its own▸ The capital gains distributions line on your return — and the one portfolio swap (mutual fund to ETF) that can nearly erase it▸ Why an out-of-state 529 plan can quietly cost you a state tax deduction you were owed▸ The S-Corp mistake that costs owners thousands: a salary-vs-distribution split that never got set up▸ Why piecemeal, drip-fed paperwork wrecks a tax return — and the checklist habit that fixes it▸ How a missing W-2 or a forgotten high-yield-savings 1099 turns into an IRS matching notice▸ The backdoor Roth error that makes a non-taxable $14,000 suddenly taxable — and why it traces back to Form 8606▸ Why business owners can't do real tax planning without clean books — you're taxed on profit, not gross▸ The fall tax review every complex household should be doing, and why most investment advisors skip it▸ When to actually switch CPAs — summer, not the December scramble★ CHAPTERS ★00:00 Cold open: the mistakes we caught this tax season01:09 Welcome — a tax season recap01:25 Into the mistakes we saw02:33 Mistake: clients badly under-withheld03:45 Mistake: investments throwing off capital gains distributions04:31 Mistake: out-of-state 529 plans and the missed state deduction05:16 Mistake: an S-Corp set up with no salary split06:10 Mistake: disorganized, piecemeal paperwork07:08 Mistake: missing tax documents — a whole W-2, a forgotten 109907:51 Mistake: the backdoor Roth reported as taxable (Form 8606)08:46 Mistake: incomplete or incorrect business books09:16 Mistake: HSA contributions the CPA never knew about09:29 Mistake: projections thrown off by late switches and new tax law10:27 This isn't about slamming anyone — catching mistakes is the job11:06 Fixes for next year: the fall tax review13:34 The capital gains line you can almost erase with one portfolio tweak14:23 The older couple whose tax bill got cut in half16:31 Review business income every quarter19:05 Build your own tax-document checklist20:16 Inside the Townsend household's 2026 tax folder21:41 Business owners: keep your books clean year-round22:53 When to actually switch CPAs (hint: not December)23:47 K-1s, curveballs, and when to just extend25:58 The bow: reflect on your tax season26:33 A quick ask — and YouTube's new "hype" button27:03 What Would You Do?27:08 Q1: I adjusted my withholding for a raise and still owe — why?29:34 Q2: Why do my coworkers get refunds and I don't?31:41 Q3: I'm getting a huge refund and it scares me — should I get a second opinion?33:01 Highlights33:05 Highlights: Heather's lifting progress and the creatine debate35:25 Highlights: Dave on the summer slowdown and a new designation36:23 Wrap up

Two different advisors should differ in their financial advice - should they?One was broke living off a teacher's salary the day he got married. The other watched her Mom's country-club life evaporate after a divorce. Today they're in the virtual boxing ring — same questions, different answers, no script.In this Playbook of the Wealthy episode, financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial run through seven questions originally asked of Heather by people outside her client base — the kind of basic-but-loaded questions you don't always get a straight answer to. What sparked you into finance? What's the one habit everyone should practice? When is it actually time to hire an advisor? Are annuities a trap or a tool? Plus a bonus they didn't prep for: the wildest thing a client has ever bought. Spoiler — it's a $1M off-road RV.▶ Listen on Apple, Spotify, or visit https://playbookotw.com★ WHAT YOU'LL LEARN ★▸ The two very different money origin stories that shaped how Dave and Heather practice today▸ Why Dave Ramsey's baby steps lit Heather's spark — and the Ramsey advice she's grown out of▸ The family-money story that pushed Dave into financial planning (and away from his dad's pattern)▸ Saving vs. avoiding debt: which "cornerstone habit" each host will fight for▸ Why Dave says small business owners need revenue first — and why Heather says "know your numbers" first▸ Bookkeeper vs. CPA: which one belongs at the front of the queue and why▸ The most common financial mistake — a budget no one tracks, or money fragmented everywhere▸ The reframe Heather uses on someone who thinks it's too late to start (no slap required)▸ When DIY finance stops working and a real advisor starts paying for itself▸ Why "my wealth got too big to manage" is a legit reason to hire help, not a brag▸ The wildest thing a client has ever bought — an RV pumped full of steroids that doesn't need a road▸ Annuities, honestly: where they actually fit, the SPIA Dave likes, and the questions to ask before you buy one▸ Why "I don't trust insurance companies" should make you look twice at your current portfolio★ CHAPTERS ★00:00 Cold open: two money origin stories01:11 Welcome to the virtual boxing ring02:11 Q1: What first sparked your interest in finance?02:21 Dave: broke living off a teacher salary and the Dave Ramsey baby steps04:11 Heather watching Mom's lifestyle disappear after the divorce06:46 Q2: One financial habit everyone should practice06:54 Heather: save first, on autopilot07:16 Dave: avoid debt, or make it a very smart decision08:59 Q3: Where should small business owners seek help first?09:07 Dave: build a real business and real revenue first09:54 Heather: know your numbers — bookkeeper before CPA11:10 Q4: The most common financial mistake11:19 Dave: not understanding your monthly cash flow11:40 Heather: fragmented accounts with no plan and no purpose13:32 If this is helping you — like, comment, subscribe, share13:49 Q5: What to say to someone who feels it's too late14:15 Dave's tough love: start now, tomorrow is later14:54 Heather's reframe: better off in 10 years if you start today16:02 Q6: When should someone hire a financial advisor?16:13 Dave: when DIY and free advice stop being enough17:28 Heather: when you want the next level — or your wealth got too big to hold18:13 Bonus question: the wildest thing a client has ever bought — a $1M off-road RV20:36 Q7: Annuities — love them, hate them, or it depends?21:23 Where Heather lands (and where she'd consider one)22:13 Dave on SPIAs and why annuities are almost always "sold" versus "bought:23:32 The $10,000-a-year-more annuity shop and the "I don't trust insurance companies" comeback24:34 Highlights24:48 Highlights: Dave's love letter to Matthew, our editor26:13 Highlights: Heather's new girls group and the Ferrari art show27:54 Wrap up

You should probably learn "How NOT to Invest" as well as learning the right things to doBoomers were supposed to be broke. The Apple Store was supposed to fail. The dollar was supposed to crash. The people making those calls had decades of experience and the cover of major magazines, and the market did the opposite anyway.In this Playbook of the Wealthy episode, financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial unpack the lessons Heather pulled from Barry Ritholtz's new book How Not to Invest. They run through the famously wrong predictions (Michael Burry post-Big Short, Robert Kiyosaki on Twitter), the magazine covers that aged badly (Cisco, BlackBerry, the Apple Store, real estate 2005), the 96% the dollar has lost in purchasing power, and why a market-cap weighted index beats almost every stock picker once taxes are in the picture. Plus the ugliest cautionary tale in the book: a billionaire family that rode Belco Petroleum into Enron, Bernie Madoff, and finally FTX.▶ Listen on Apple, Spotify, or visit https://playbookotw.com★ WHAT YOU'LL LEARN ★▸ Why expert forecasts are statistically indistinguishable from random guesses (the Philip Tetlock study of 28,000 predictions)▸ Michael Burry's record after The Big Short, and why being right once doesn't make you right twice▸ Robert Kiyosaki's recent fearmongering and what the S&P actually did instead▸ The magazine covers that called Cisco, BlackBerry, and the Apple Store dead wrong▸ Why the dollar has lost 96% of its purchasing power and what that means for cash-heavy business owners▸ The 9% vs. 12% stock trader: how taxes quietly erase the alpha you thought you earned▸ Why roughly 1% of public companies drive nearly all market returns, and why guessing them is near impossible▸ Market-cap weighted indexing: the boring formula that's nearly impossible to beat▸ The librarian who left $5 million to her library, and why "average" compounds into "exceptional"▸ The Belco Petroleum family: an immigrant billionaire dynasty that lost it all to Enron, Madoff, and FTX▸ John Foley, Peloton, and the cost of leverage plus a $55M Hamptons mansion at the top▸ Barry Ritholtz's 12-point investor's "bow" — from fees to cycles to long-term thinking★ CHAPTERS ★00:00 Cold open: boomers, the dollar, and the monkey with the dartboard01:06 The book Heather had to share: Barry Ritholtz's How Not to Invest01:54 Who is Barry Ritholtz?03:30 Lesson 1: Forecasts and predictions are more wrong than right04:51 Michael Burry's track record after The Big Short06:22 Robert Kiyosaki, fearmongering, and what the market actually did08:40 The Tetlock study: 28,000 forecasts and what they revealed09:44 Lesson 2: The media is just as bad as the pundits10:01 Cisco 2000, the Apple Store, and BlackBerry vs. iPhone11:16 The 2005 real estate cover (and the crash that followed)12:16 Lesson 3: Cash is for spending, not saving — the 96% dollar story13:25 Heather's grandmother-in-law, the CD ladder, and the Great Depression13:58 The best stock trader and why 12% turns back into 9% after taxes15:04 Most stocks don't matter — and why indexing wins17:11 Average performance turns into outperformance: the librarian story17:42 The boring bucket vs. the fun bucket20:19 Lesson 5: People brag about wins and hide their losses20:33 The Belco Petroleum family: Enron, Madoff, and FTX in one bloodline22:27 Peloton, John Foley, and the $55M Hamptons mistake25:08 Barry Ritholtz's 12-point investor's bow26:08 Heather's bow: a plan, a diversified portfolio, and ignoring the noise27:32 Highlights: Heather's hard Q1 hiring lesson29:21 Highlights: Bridgerton and The Pit — Dave's TV recommendations31:41 Wrap up

The buy vs. lease debate is older than the cars themselves, and most people pick wrong because they never run the math. The right answer depends on the brand, the miles, and what you actually do with the car when the term ends.In this Playbook of the Wealthy episode, financial advisors Heather Townsend of Townsend Financial and Dave Grant of Retirement Matters break down when leasing wins, when buying wins, and the exact framework Heather uses with clients. Heather walks through a real lease vs. buy comparison on a $100K Porsche Macan, the 6,000-lb SUV depreciation play for business owners, and the BMW maintenance trap that turned her from a lifelong leaser into a buyer. Dave shares the frugal-to-Tesla journey, why he gave his 16-year-old the family Chevy Malibu, and how a switch in insurance brokers cut his auto premium in half.▶ Listen on Apple, Spotify, or visit https://playbookotw.com★ WHAT YOU'LL LEARN ★▸ The mileage cap question that kills most leases before the conversation even starts▸ Why a BMW out of warranty is the most expensive "deal" in the driveway▸ How leasing actually works as a rental, including what's covered, what's not, and what you owe at turn-in▸ Why customizing a leased car (tints, body kits) almost never pays you back▸ Why Porsches are the rare luxury car that can make more sense to buy than lease▸ The 6,000-lb SUV bonus depreciation play for business owners driving 50%+ for work▸ The buy-vs-lease math on a $100K Macan over six years▸ Why "leasing all four cars" with four drivers in the house is almost always the wrong answer▸ How adding a teen driver impacts insurance, and what a good broker can do about it▸ The decision framework Heather uses with clients: mileage, then brand, then math★ CHAPTERS ★00:00 Cold open: a $17,000 BMW maintenance bill and the question that won't go away01:09 Welcome: the buy vs. lease debate that never dies01:54 Why this question comes up so much (and why Heather is "the car girl")03:05 Lease basics: it's a rental, not ownership03:58 The mileage cap that kills most leases before they start05:36 Maintenance under warranty: lease's quietly biggest value06:57 Customizing a leased car (and the body kit you'll never see again)08:16 The pros and cons of leasing, summarized08:33 Why getting out of a lease is harder than getting out of a marriage09:27 Heather's lease story: $5K, age 16, and a "Beemer Check" plate13:06 Business owners: the 6,000-lb SUV depreciation play14:43 The pros and cons of buying outright16:48 Longer payment terms and the trade-in trap18:42 You buy it, you own it, you fix it18:53 Buy vs. lease math on a $100K Porsche Macan21:25 Dave's frugal years: used cars until kids forced new23:40 Trump, EV credits, and the day after the Tesla call25:03 The decision framework: mileage, then brand, then math26:18 Q&A: $120K sports car, lease or buy?27:34 Q&A: 4 drivers, 4 cars, should I lease them all?31:14 Highlights: the day Eli got his license (and our insurance bill)33:09 Highlights: a one-car household and the tariff that killed the GT 6336:07 Wrap up★ LISTEN ON ANY PLATFORM ★Apple Podcasts: https://podcasts.apple.com/us/podcast/playbook-of-the-wealthy/id1787630097Spotify: https://open.spotify.com/show/21LrI3IB2wMsOOJLiGsRJKWebsite: https://playbookotw.com★ WATCH NEXT ★The 5 DIY Money Mistakes That Quietly Cost You Years | EP065: https://www.youtube.com/watch?v=s4zprAatOtoDividends Are Lying To You: The Outdated Retirement Income Strategy | EP066: https://www.youtube.com/watch?v=P3B5rw6VPSU★ CONNECT ★Submit a question for a future episode: https://playbookotw.comEmail: [email protected] Grant on Instagram: https://www.instagram.com/davegrant82Heather Townsend on Instagram: https://www.instagram.com/heather.townsend.financial#BuyVsLease #CarBuying #PlaybookOfTheWealthy

Retirement timing matters more than most people realize. The right month to retire can be worth six figures in bonus, RSU, pension, and tax savings.In this Playbook of the Wealthy episode, financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial break down 5 things you must lock in before you hand in your notice, using a case study of Jeffrey, a $400k-a-year executive with a base salary, bonus, RSUs, and a pension. They cover 401K and HSA frontloading, the NUA strategy, COBRA vs marketplace healthcare, IRMAA Medicare planning, zero-income years for Roth conversions, and pension service credit timing.▶ Listen on Apple, Spotify, or visit https://playbookotw.com★ WHAT YOU'LL LEARN ★▸ How to max out your 401K and HSA in 2-3 months and capture a full year of tax-deferred savings▸ The NUA (Net Unrealized Appreciation) strategy for company stock inside a 401K▸ Why leaving one month before your bonus or RSU payout could cost six figures▸ Clawback provisions, where to find them, and how they change your exit timing▸ The real cost of COBRA, marketplace alternatives, and how income unlocks premium tax credits▸ IRMAA: how Medicare premiums in retirement are based on your income from two years earlier▸ Why a zero-income year is the ideal window for Roth conversions▸ When Roth conversions are oversold online, and when a lopsided pretax portfolio makes them essential▸ Pension service credit: how six months can mean thousands per year for life▸ What to do when your bonus, RSU, 401K match, and pension credit all fall in different months★ CHAPTERS ★00:00 Cold open: losing an 11-month bonus and Roth conversion traps01:26 Why retirement month planning beats retirement year planning02:26 Case study: Jeffrey, $400k total comp executive03:47 Point 1: Max out 401K and HSA in the first 2-3 months06:21 The NUA strategy: company stock in a 401K explained07:37 Point 2: Capture your prior year bonus and RSU payout08:55 Clawback provisions in your employment agreement10:43 Point 3: Healthcare coverage from retirement to Medicare11:06 COBRA vs marketplace insurance costs compared13:09 IRMAA explained: Medicare premiums based on income from two years ago16:50 Point 4: Zero-income years for tax-free Roth conversions19:48 Pension and Roth: convert before your pension sets your tax bracket20:33 Point 5: Pension service credit timing23:44 The 5-point retirement timing checklist25:02 Q&A: Bonus in April, pension credit in October, when do I retire?27:15 Q&A: Wife retires at 62, I'd lose pension. Should I delay?28:41 Q&A: 401K match spread monthly, retire in spring or year-end?30:21 Highlights33:58 Wrap up★ LISTEN ON ANY PLATFORM ★Apple Podcasts: https://podcasts.apple.com/us/podcast/playbook-of-the-wealthy/id1787630097Spotify: https://open.spotify.com/show/21LrI3IB2wMsOOJLiGsRJKWebsite: https://playbookotw.com★ WATCH NEXT ★The 5 DIY Money Mistakes That Quietly Cost You Years | EP065: https://www.youtube.com/watch?v=s4zprAatOtoDividends Are Lying To You: The Outdated Retirement Income Strategy | EP066: https://www.youtube.com/watch?v=P3B5rw6VPSU★ CONNECT ★Submit a question for a future episode: https://playbookotw.comEmail: [email protected] Grant on Instagram: https://www.instagram.com/davegrant82Heather Townsend on Instagram: https://www.instagram.com/heather.townsend.financial★ ABOUT THE SHOW ★Playbook of the Wealthy is a podcast that makes wealth planning and retirement simple, clear, and approachable. Hosted by financial advisors Dave Grant of Retirement Matters and Heather Townsend of Townsend Financial, the show covers Social Security, tax strategies, IRAs, 401(k)s, Roth conversions, RSUs, executive compensation, job changes, inheritance, and more.#RetirementPlanning #RothConversion #PlaybookOfTheWealthy

Rapid-fire questions, real-world answers.In this mailbag episode, Dave Grant and Heather Townsend go straight into “What Would You Do?” and tackle a stack of listener and client questions, from charitable giving and Roth conversions to AI in financial planning, inheritance tax strategy, and whether you should change your investing plan based on what markets might do next year.  What you’ll learn… • QCDs explained simply, and why they don’t work the way many people think for Roth conversion “room”   • 529 vs 529 ABLE: who they’re for and what the money can be used for   • How Dave and Heather actually use AI, and where it still gets financial planning wrong   • Market forecasts for 2026: why “big institutions” disagree, and why no one actually knows   • The timeless advice when markets feel uncertain: keep contributing anyway   • Inheritance strategy: step-up in basis explained, and which accounts can be best to leave to which people   • HSA inheritance rules and why they treat HSAs differently in estate planning   • Partnership buy-ins: when “buying in” is a bad idea if you don’t have the cash flow   • How often a DIY plan should be reviewed (and why a periodic check-up can save you big money)  Chapters00:00 Cold open: market predictions, noise, and why no one knows  01:12 Welcome: mailbag episode (straight into questions)  01:58 Q1: QCD strategy to “enable” a bigger Roth conversion  06:18 Q2: 529 vs 529 ABLE (who qualifies and what it’s for)  08:01 Q3: Do you use AI as a CFP? Pros, cons, and what it gets wrong  11:14 Q4: How will AI change investing and the role of a financial planner?  16:12 Market forecast chart: what big institutions think for 2026 (and why to ignore it)  19:00 Q5: Inheritance planning: step-up in basis and which accounts to leave to whom  21:50 Q6: Becoming a shareholder/partner without extra cash (should you go into debt?)  25:05 Highlights  29:14 Wrap up  29:38 Disclaimer  I’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff, just real talk about what matters most to your financial future.On this channel, we cover Social Security, tax strategies, IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit playbookotw.com or email [email protected]: All opinions expressed by Dave Grant and Heather Townsend are solely their own opinions and do not reflect the views of their respective wealth management firms. This podcast is for informational purposes only and should not be relied upon for investment decisions. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Clients of Retirement Matters and Townsend Financial may maintain positions of the securities discussed in this podcast.

A lot of people were taught one rule for retirement: never touch the principal. Just live off dividends and interest.In this episode, Dave Grant and Heather Townsend explain why that “dividends and interest only” portfolio is outdated, often forces you into riskier investments, and can literally cut your spending in half. They break down what actually drives long-term returns, why dividend chasing can backfire in recessions, and the cleaner alternative: a diversified portfolio with a sustainable withdrawal strategy and buckets. What you’ll learn… • Why living off dividends only can be a “pay cut” compared to a normal withdrawal plan • The real source of growth in the S&P 500 (and why dividends are a small piece) • What changed from the 80s/90s to today: bond yields and dividend yields are way lower now • Why dividend investors tend to chase riskier stocks, MLPs, and junk bonds to boost income • The recession problem: dividends get cut, and companies can go bankrupt • The inflation trap: when your portfolio does not grow, your “income” buys less every year • The tax control issue: dividends and interest hit on their schedule, not yours • The better model: index funds/ETFs + a sustainable withdrawal rate + buckets for downturns • Real examples: GE and Citigroup dividend cuts, and what that would do to a retiree’s paycheck • A book recommendation if you want the data: Income on Demand by Jonathan Bird Chapters00:00 Cold open: “You’re giving yourself a pay cut” 01:08 Why the dividends-and-interest model is outdated (and we’re ripping it apart) 02:05 The money story: “Never touch the principal” 03:36 Surprise: it’s not the best way to do things 04:13 What changed since the 80s/90s: bonds 6–10% vs today 3–5% 05:00 Dividends then vs now: 4–6% vs today 1–2% 05:21 The S&P return breakdown: most return is price growth, not dividends 06:34 The math: $1M at 2% dividends is $20k vs a normal withdrawal strategy 07:00 “You’re giving yourself a pay cut” headline explained 08:21 The behavior problem: chasing yield pushes you into worse investments 10:17 Junk bonds and risk: higher yield usually means higher risk 11:11 Dividends get cut and companies go bankrupt 12:04 The business analogy: great companies reinvest, they don’t always pay dividends 14:21 Inflation: when your portfolio doesn’t grow, your income shrinks 15:20 Warren Buffett and why Berkshire doesn’t pay dividends 15:48 Taxes: control, qualified dividends, interest income, and timing 18:58 The “bow”: the better way to do retirement income 20:18 Book plug: Income on Demand (Jonathan Bird) 21:37 What Would You Do? Market drops 30%, do I have to sell? (buckets) 23:22 Q&A: Aren’t dividends safer? (GE + Citigroup examples) I’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff, just real talk about what matters most to your financial future.On this channel, we cover Social Security, tax strategies, IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit www.playbookotw.com or email [email protected].

Financial mistakes happen more often than you think.DIY financial planning is not just “hard.” It’s easy to build something that looks fine on paper, but is actually fragmented, outdated, and full of hidden risks.In this episode, Dave Grant and Heather Townsend walk through the top five mistakes they see in DIY financial plans, from vague goals and messy portfolios to bad insurance coverage and outdated strategies. They also get into the deeper truth most people miss: money can’t fix a life you don’t feel excited about, but it can be a powerful tool to help you rebuild direction and fulfillment. What you’ll learn… • Why most DIY plans are fragmented: money “over here,” accounts “over there,” and no single purpose • Mistake #1: no real goals (or goals with no cost, timeline, or plan) • How to turn vague goals like “remodel the house” into SMART goals with parameters • Mistake #2: poorly designed portfolios (too much in a 401(k), overlapping funds, random target date mixes) • Why multiple advisors often multiply the mess (and can wreck tax optimization) • The dividend trap: ordinary dividends taxed at the highest bracket for high earners • Mistake #3: cash drag (especially for business owners with feast-or-famine cash flow) • Mistake #4: bad insurance “defense” (state minimum auto coverage, missing umbrella, outdated life/disability) • Mistake #5: the deeper one: being unfulfilled, and trying to use money to fix it • Q&A: how often to get a DIY plan reviewed, and what to tell a spouse who doesn’t want an advisor Chapters00:00 Cold open: state-minimum insurance with high net worth assets (and getting heated) 01:05 The premise: you can’t DIY taxes, insurance, estate, investing, and everything else forever 01:44 Mistake #1: money with no goals (no direction, no purpose) 02:15 “People are floating”: why most goals are too vague to plan around 03:06 The ultra-wealth example: no goals means no plan (even with experts in the room) 04:30 The SMART goal example: house remodel with cost, timeline, and order of operations 07:16 Adults stop dreaming (and why that matters for your money) 08:01 Mistake #2: poorly designed portfolios (401(k) only, overlap, and randomness) 09:48 The overlap problem: picking the “best funds” that are basically the same 10:38 The target-date fund mess (2035 + 2040 + 2045 + 2050 all at once) 12:02 Two advisors managing the same thing (and why it breaks optimization) 12:47 Dividends without tax context: “Are you kidding me?” 13:14 Mistake #3: cash drag (Roth and brokerage money not invested, too much cash held) 14:18 Mistake #4: bad insurance coverage (state minimums, missing umbrella, outdated coverage) 16:27 Defense first: why insurance is “defense” before offense investing 20:26 Mistake #4 continued: outdated approaches (tax law, Roth/529 changes, inefficient investments) 23:39 State estate tax story: why your state rules can cost heirs big money 25:13 The teaser: “ILITs” and outdated planning (and why they’re saving it for another episode) 25:59 Mistake #5: unfulfilled life, money can’t fix it (but it can help as a tool) 30:45 The recap “bow”: goals, defense, account titling, allocation, accountability 32:10 What Would You Do? Q1: How do I keep a DIY plan accurate and up to date? 33:21 Q2: Convincing a spouse to hire an advisor (the best argument) 35:18 Q3: How often should I get my plan reviewed if I’m DIY? 36:54 Highlights On this channel, we cover Social Security, tax strategies, IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit https://playbookotw.com or email [email protected].

Credit card points can feel like a gimmick... until you realize people are quietly turning everyday spending into free hotel nights, business-class upgrades, and $2,000 stays for $0.In this episode, Dave Grant and Heather Townsend break down the credit card points “game” in plain English: how to do it without spending more or going into debt, why travel points often beat cashback, how to avoid the biggest traps, and the simple system they actually use at home.Note: The first minute is a DOAC-style intro made from clips pulled from later in the episode.What you’ll learn...• How the credit card points game really works (sign-up bonuses, multipliers, and redemptions)• The #1 rule: never carry credit card debt, pay it off monthly• A real example: a hotel booking that instantly gave $400 value, plus “five free nights” bonuses• Why they’re not fans of cashback for most high earners, and when it still makes sense• The 3 main card types: airline cards, hotel cards, and flexible travel cards (Chase/Amex/Capital One)• How they decide when to use points (big trips) vs when to pay cash (small flights)• The “too many cards” problem, and why simplicity usually wins• The Chase 5/24 rule and why hoarding points can backfire• Are points taxable? The nuance most people miss• What Would You Do? How to start from zero, which card to pick, and how much points can really be worthChapters00:00 Intro montage (clips from later in the episode)01:09 Welcome + today’s topic: credit card points01:35 Credit card points explained (no overspending, no debt)02:30 A real example: Marriott booking bonus + $400 value03:05 The “five nights free” offer and how the math becomes a $2,000 stay04:11 Why cashback is usually the wrong play (and why points go farther)04:33 Shoutout: Colin Stroud (Go Somewhere) and why outsourcing point-redemption saves time05:43 The 3 card categories: airline, hotel, and flexible travel cards06:29 When cashback does make sense (2% cards +Amazon example)08:10 Why points can change behavior (and get you to take the trips you actually want)10:07 Their rule: use points for big trips, not small flights11:36 The “spreadsheet era”: signing up for too many cards (and why they stopped)13:33 Simpler system: mortgage points + Chase Sapphire setup14:23 Business points tip: transfer points to personal (don’t waste them)15:16 Watch the annual fees (and how perks can justify them)16:12 Hidden benefits: protections, rental insurance, weird emergencies18:00 “Chase is the Mack Daddy” + why flexibility matters19:11 Hilton vs Hyatt vs Marriott: why point value keeps changing20:06 Transfer partners (British Airways example) and why strategy matters21:51 The Chase 5/24 rule + why hoarding points can be risky23:26 Are points taxable? The real answer24:18 Tools: Points platforms that help you planredemptions25:12 The “bow”: the simple 3-step system to do this without chaos26:19 What Would You Do? Q1: How do I start the points game?28:47 Q2: Do cards really differ that much?30:07 Q3: How much can points really be worth per year?31:41 Bonus: why they hate debit cards for spending (fraud + protections)32:20 Highlights36:49 Wrap up + where to watch37:10 DisclaimerWant to collab?: [email protected] more about Retirement Matters, or to contact us, visit our website: https://www.retirementmatters.co/

High income and high net worth does not protect you frombad decisions. In fact, it can make the mistakes bigger.In this episode, Dave Grant and Heather Townsend breakdown the 4 most common mistakes financial advisorssee in wealthy clients, based on insights gathered fromfamily offices and advisors across the country, and how toavoid them before they quietly drain your cash flow andlong-term freedom.What you’ll learn...• Why “personal real estate” can become a liability(especially second homes)• The hidden cost of maintaining multiple properties (taxes,insurance, repairs, utilities, staff)• Lifestyle inflation at the top end, and why it is hard to undoonce you raise the floor• The warning sign: income rises but your savings stay flat• Why illiquid investments can trap wealthy investors (privateRE, PE, hedge funds)• The “investment club” ego trap, and why sellers often win• Why estate and tax planning is not set-and-forget, and howbig dollars magnify small misses• Q&A on buying a family second home, lifestyle creepthresholds, and how often to review estate docsChapters00:00 Intro01:12 Welcome + how the show is structured01:33 Why this episode exists (what advisors across thecountry see)02:42 Mistake 1: Overload on personal real estate05:03 The “heat bird” story and why second homes createstress07:22 The real test: what % of your resources goes tohousing?08:17 Mistake 2: Lifestyle inflation (yes, even for the ultra-wealthy)10:13 The advisor framing: have it, but be able to keep it10:58 Mistake 3: Overload to illiquid investments11:58 The trap: big houses + illiquid funds + a downturn13:39 Mistake 4: Lack of estate and tax planning16:43 The 4-point recap (the “bow”)17:50 What Would You Do? Buying a family second home18:56 What Would You Do? How to gauge lifestyle creep20:32 What Would You Do? Estate planning: how often toreview21:07 Highlights: parenting taxi driver life + airport clientstory25:57 Wrap up26:22 DisclaimerI’m here to make wealth planning and retirement simple,clear, and approachable. No jargon, no fluff, just real talkabout what matters most to your financial future.On this channel, we cover Social Security, tax strategies,IRAs, 401(k)s, job changes, inheritance, and more so youcan feel confident about your retirement plan and preparedfor the risks that could affect your money along the way.Want to submit a question for a future episode? Visitplaybookotw.com or email [email protected]: All opinions expressed by Dave Grant andHeather Townsend are solely their own opinions and do notreflect the views of their respective wealth managementfirms. This podcast is for informational purposes only andshould not be relied upon for investment decisions. Nothingin this material constitutes a solicitation for the sale orpurchase of any securities. Clients of Retirement Mattersand Townsend Financial may maintain positions of thesecurities discussed in this podcast.

If you had a baby between 2025 and 2028, the government may be offering $1,000 into a new minor investment account. But there’s a catch: you have to open the account and file the form to get the money.In this episode, Dave Grant and Heather Townsend break down what “Trump Accounts” are, who qualifies, when they launch, how contributions work (including employers), what the money will be invested in, and the biggest thing people might miss: the tax tracking and reporting could get messy if you mix pre-tax and after-tax contributions.What you’ll learn…- Who qualifies for a Trump Account, and who qualifies for the $1,000 government contribution- Why you must open the account yourself to receive the $1,000- Contribution rules: up to $5,000/year, plus who can contribute (parents, grandparents, friends, employers)- Launch timing: why they think it will go live between July 4–6, 2026- The form you will need to file, and how it may be submitted- What it will likely be invested in (US stocks, low-cost index funds, and what is still unknown)- The tax wrinkle: why this may resemble a non-deductible IRA with basis tracking- When withdrawals are allowed, penalties, and exceptions (education, first home, starting a business)- Why a 529 may still be better for college savings, plus the new flexibility they mention- The compounding math that makes the $1,000 potentially powerful over decadesChapters00:00 Cold open: “Take the free money” and what’s the catch?01:04 Welcome + what we’re covering today01:27 What Trump Accounts are and why they exist02:57 The $1,000 government contribution and the 2025–2028 window03:25 You must open the account to receive the $1,00004:31 Contributions: who can add money, and the $5,000 annual limit05:18 Who can open one, and who gets the $1,000 (plus a quick correction)06:18 Launch timing: July 4–6, 2026 and what you can do now07:16 Filing the form (and the “45/47” moment)08:22 What it may be invested in: US stocks, index funds, and unknowns10:11 Taxes: why this gets complicated (after-tax vs pre-tax)11:39 Withdrawals: age 18 rules, penalties, and exceptions14:31 No earned income needed (compared to Roth IRAs for kids)16:13 Qualified expenses: education, first home, starting a business18:49 Employer contributions and discrimination testing for business owners21:29 Dell and Ray Dalio contributions: what they mention and who may qualify22:32 Compounding example: $1,000 at 18 vs $1,000 at birth24:23 The bigger planning question: Trump account vs 529 vs brokerage vs Roth IRA26:28 What Would You Do? Prioritize this over a 529?27:41 What’s the catch? The tracking and unknown investment details29:21 Personal: are they opening accounts for their kids?31:51 Highlights36:50 DisclaimerI’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff, just real talk about what matters most to your financial future.On this channel, we cover Social Security, tax strategies, IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit playbookotw.com or email [email protected]: All opinions expressed by Dave Grant and Heather Townsend are solely their own opinions and do not reflect the views of their respective wealth management firms. This podcast is for informational purposes only and should not be relied upon for investment decisions. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Clients of Retirement Matters and Townsend Financial may maintain positions of the securities discussed in this podcast.

If it feels like your Social Security check does not go as far each year (even after the cost-of-living adjustment), that’s not just a perception.In this episode, Dave Grant and Heather Townsend break down how inflation actually works, why inflation hits some categories way harder than others (hello, healthcare), and why Medicare premiums can take an increasingly bigger bite out of Social Security over time. Then they walk through the real solution: building a portfolio designed to outpace inflation without chasing quick fixes.  What you’ll learn… • What inflation really is (and why 2–3% is normal, but spikes matter)   • Why inflation is an average, and not evenly distributed across goods and services   • The categories that have exploded since 2000 (hospital and medical services)   • Why Social Security COLA generally tracks inflation, but Medicare premiums do not   • The eye-opening data: Medicare Part B as a % of the average Social Security benefit (3.6% → 9.4% → 11.5%)   • Why your “raise” can get eaten, and what that means for retirees on fixed income   • The simple antidote to inflation: growth assets, plus how to think about cash, TIPs, and equities   • Q&A: Should you redesign your portfolio for inflation? Can Medicare ever wipe out Social Security? Is Social Security going away?  Chapters00:00 Cold open: “Can I juice my portfolio?” (and why that’s emotional investing)  00:48 Social Security vs Medicare: why it feels like your check shrinks  01:13 Welcome + how the show is structured  01:47 “Beyond Finance 101” + chart episode warning  02:04 Inflation explained simply (the $10 to $10.30 example)  03:28 Chart 1: inflation is not evenly distributed (medical, college, TVs)  06:27 Chart 2: inflation by presidential term (it doesn’t care who’s in office)  07:18 Chart 3: Social Security COLA vs inflation  07:46 Chart 4: Medicare premiums and the problem retirees feel  08:22 The data breakdown: Medicare as % of Social Security (3.6% → 9.4% → 11.5%)  11:22 The “40% of the raise” example (how COLA gets eaten)  12:15 Health insurance increases beyond Medicare (why it’s bigger than one program)  14:25 What to do about it: why investing is non-optional  14:47 The coffee test: $1,000 becomes $107 in cash vs ~$323,000 invested  16:30 Practical portfolio basics: cash, bonds/TIPs, and equities for inflation protection  18:31 How retiree withdrawals adjust with inflation  20:40 What Would You Do? Q&A begins  20:45 Q1: If SS is squeezed by Medicare, should my portfolio be different?  21:20 Q2: Can Medicare ever fully erase my Social Security benefit?  22:34 Q3: Is Social Security going away?  22:54 Q4: Should I change my portfolio when inflation changes?  24:29 Highlights: show recommendations (The Night Manager, Land Man)  26:00 Highlights: the car seat inflation story (and the upside of earning more)  27:12 Wrap up  27:41 Disclaimer  I’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff, just real talk about what matters most to your financial future.On this channel, we cover everything from Social Security and tax strategies to IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit playbookotw.com or email [email protected]: All opinions expressed by Dave Grant and Heather Townsend are solely their own opinions and do not reflect the views of their respective wealth management firms. This podcast is for informational purposes only and should not be relied upon for investment decisions. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Clients of Retirement Matters and Townsend Financial may maintain positions of the securities discussed in this podcast. 

(We skipped a couple of episode numbers to keep it current with our YouTube channel!)Most people “diversify” by owning stocks and bonds, but then stop there.In this episode, Dave Grant and Heather Townsend break down what bonds actually are, why bond diversification is a thing, and how the real pros think about bond strategy: active vs passive, bond duration, where bonds should live for tax efficiency, and what 2008 taught investors about owning the right bonds.What you’ll learn… • Bonds explained simply: loans, interest, maturity, and why they stabilize portfolios   • “Loan vs growth”: the cleanest way to understand bonds vs stocks   • Why diversifying within bonds matters (Treasuries, corporates, munis, international, and more)   • Why bonds are not optional for retirees and anyone living off their portfolio   • The rebalancing advantage: how bonds can help you buy stocks cheaper during downturns   • Active vs passive in bonds, including why it depends on the bond type (TIPs vs other fixed income)   • The “lock in the rate” story: why high-rate long bonds can be a forever hold   • Tax drag in plain English, and why bond placement (asset location) matters • Municipal bonds basics, plus the tax angle they discuss   • 2008 bond confusion: what actually failed, what held up, and why bond type matters  Chapters00:00 Welcome + what “bond diversification” really means  00:49 What is a bond? (the simplest explanation)  02:06 Bonds vs stocks: loan vs growth  02:19 Is building a bond portfolio “that easy”?  03:43 Bonds are not optional for retirees (and why)  04:07 Rebalancing: the underrated reason bonds exist  05:13 Active vs passive bond strategy (and what the data suggests)  05:43 TIPs explained, plus why inflation hits retirees hardest  10:35 The 10% bond story: when you lock it in, you never sell  12:09 “That’s how the bond game works” (locking CD rates)  13:47 Asset location vs asset allocation (quick definitions)  15:58 The relationship banter break (then straight back to strategy)  16:42 Tax drag explained + why bonds often belong in retirement accounts  17:30 Municipal bonds and the taxable account conversation  28:43 2008: “bonds weren’t a diversifier” (what investors are really asking)  29:14 The 2008 context + what has changed since  30:06 “Naked short selling” and why bond type matters (Treasuries vs MBS)  31:43 Highlights  I’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff, just real talk about what matters most to your financial future.On this channel, we cover everything from Social Security and tax strategies to IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit playbookotw.com or email [email protected]: All opinions expressed by Dave Grant and Heather Townsend are solely their own opinions and do not reflect the views of their respective wealth management firms. This podcast is for informational purposes only and should not be relied upon for investment decisions. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Clients of Retirement Matters and Townsend Financial may maintain positions of the securities discussed in this podcast.

Subpar investments can be bad luck, but most of the time they come down to concentration, complexity, and no exit plan.In this episode, Dave Grant and Heather Townsend break down how to avoid “good investments” turning into disasters, why single stocks and flashy alternatives can wreck real portfolios, and the simple rules they use to keep risk contained (without killing your upside).  What you’ll learn… • Why diversification and avoiding concentration can prevent most “investment blowups”   • The single stock risk nobody thinks about until it happens (BP, Harley Davidson examples)   • Alternative investments explained simply, plus why the “sexy returns” pitch is usually the trap   • The hidden cost of illiquidity: tender windows, redemption delays, and “blank stare” moments when you want out   • The “rodeo account” rule: keep the risky stuff small (5 to 10% max, often less)   • Why you should decide your exit price or exit plan before you buy   • What to do if your advisor recommends a non-traded REIT   • How to rebuild confidence after losing 40% and panic-selling   • How to avoid a bond bankruptcy scenario (and when bond funds beat individual bonds)  Chapters00:00 When “good” investments go bad  00:17 Welcome + how the show works  00:48 Single stocks: the concentration problem (BP, Harley)  02:07 What counts as “alternative investments” (and why people chase them)  03:11 The data: alternative fund mortality rate (and why it matters)  04:28 The “hotel pitch” story: how alternatives are sold  06:10 Real client example: tax deductions, oil and gas, and the return reality  09:02 Trying to get out: tender offers, SEC filings, and missing the window  11:00 Why you need an exit strategy before investing  11:50 The real driver: greed and “get rich quick” behavior  13:24 Ultra-wealth story: late repayments and being asked for more money  15:53 Active managers: buying vs selling problem, and why loss stories are rare  17:34 The rule: set your exit price before you buy  18:06 How much is too much? 5 to 10% max for “rodeo money”  21:07 What Would You Do? Non-traded REIT recommendation  23:05 What Would You Do? Lost 40%, sold everything, now scared to invest  24:27 What Would You Do? Individual bond went bankrupt  26:39 Highlights: Dave’s Bitcoin ETF mistake (and what he learned)  28:29 Highlights: hosting chaos in the new house  30:17 Where to watch + how to submit a question  31:09 Disclaimer  I’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff, just real talk about what matters most to your financial future.On this channel, we cover everything from Social Security and tax strategies to IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit playbookotw.com or email [email protected].  Disclaimer: All opinions expressed by Dave Grant and Heather Townsend are solely their own opinions and do not reflect the views of their respective wealth management firms. This podcast is for informational purposes only and should not be relied upon for investment decisions. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Clients of Retirement Matters and Townsend Financial may maintain positions of the securities discussed in this podcast.

For many wealthy people, the problem is not saving and investing. The problem is actually spending the money after you’ve built it.In this episode, Dave Grant and Heather Townsend unpack the psychology behind “wealth guilt,” fear of going backward, and why so many retirees and high earners end up gripping their portfolio instead of enjoying the life it was meant to fund. Then they share a simple framework to create clarity, build confidence, and spend with purpose.  What you’ll learn… • Why this show is “beyond Finance 101,” and why this topic is more common than people admit   • The wealthy dilemma: fear of going back to square one after you’ve reached freedom   • A key stat: many people fear running out of money more than death, and inflation makes it worse   • The real drivers of underspending: lack of clarity, control, and the emotional weight of volatility   • Why outdated goals create stagnation, and how to redesign what you actually want next   • Legacy planning in plain English: put a number on it so you can live too   • How to break through the fear: better questions, “why” conversations, and small experiments   • Why buckets help retirees spend confidently even when the market drops   • “What Would You Do?” Q&A: parents who won’t spend, the retirement sports car, and leaving a big inheritance  Chapters00:00 The wealthy dilemma: why spending feels scary  00:37 Welcome + how the show is structured  01:09 Not Finance 101: “Finance 202”  02:02 The dinner story: the $3,000 gym equipment struggle  04:58 The data: fear of running out of money, inflation anxiety  06:03 Why people won’t spend: unknowns, control, and fear  07:20 Market volatility and the emotional scars of 2000 and 2008  09:59 When goals get stale, spending disappears  10:21 Legacy: “How much is the legacy?”  11:10 How to overcome the reluctance: clarity, planning, and life design  14:12 Regret vs fear + Die With Zero  15:54 A powerful story: the inheritance loss that changed everything  19:15 The “why” questions that unlock spending  21:09 The market will crash again: normalize it, plan for it, then live  23:00 The bow: talk it through, build a plan, spend with purpose  23:50 What Would You Do? Parents retired but won’t spend  26:21 What Would You Do? The retirement sports car you can’t buy  28:47 What Would You Do? Big inheritance coming, how do I spend now?  30:20 Highlights: the gratitude app for your relationship  33:07 Highlights: money dates, rebalancing, and practicing what you preach  34:54 Wrap up + where to watch  35:34 Disclaimer  I’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff, just real talk about what matters most to your financial future.On this channel, we cover everything from Social Security and tax strategies to IRAs, 401(k)s, job changes, inheritance, and more so you can feel confident about your retirement plan and prepared for the risks that could affect your money along the way.Want to submit a question for a future episode? Visit playbook.com or email [email protected].  Disclaimer: All opinions expressed by Dave Grant and Heather Townsend are solely their own opinions and do not reflect the views of their respective wealth management firms. This podcast is for informational purposes only and should not be relied upon for investment decisions. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Clients of Retirement Matters and Townsend Financial may maintain positions of the securities discussed in this podcast. 

Stop Guessing Your Savings RateHigh earner or not, you should never be guessing how much you “should” be saving. You need a plan that ties your savings target to your real goals, and the right accounts to fund them.In this episode, Dave Grant and Heather Townsend break down how to set the right savings target (without generic internet percentages), how to build SMART goals, and how to balance living today with building tomorrow.  What you’ll learn… • Why goals come first, and why “I’ll retire when I hit X” is not a real plan   • The SMART goal framework (with real examples)   • How short-term goals and long-term goals can conflict, and how to balance them   • Why tax brackets and “wrong buckets” can wreck an otherwise good savings plan   • Dollar targets vs percentages: when each works, and why most people get confused   • How to handle irregular income (bonus, stock comp, commission, business owners) with simple rules   • A full case study: Joe and Susan, the lake house goal, and the surprise result (they may be saving too much)   • “What Would You Do?” Q&A on 401(k) over-reliance, couples who disagree on saving, and pensions vs Roth  Chapters00:00 Welcome + what this episode is about  00:38 Start here: goals drive your savings plan  01:24 The SMART goal framework (with examples)  04:13 Short-term vs long-term goals, and the tension between today and tomorrow  05:28 Back into the goal: assets, income, and tax planning  07:32 The “lopsided portfolio” problem (all pre-tax, no flexibility)  08:39 Irregular income: how to set targets when bonuses and stock swing  10:03 Saving targets: why they use dollar amounts, not generic percentages  11:59 Why percentages break down (gross vs net, bucket confusion, payroll realities)  14:44 When a percentage is still a good starting point  17:04 Case study: Joe and Susan, retirement in 7 years, and buying the lake house  21:01 The secret weapon: accountability (and what if returns are flat?)  21:49 What Would You Do? Q1: “I only max my 401(k). Am I doing it right?”  23:57 What Would You Do? Q2: Saver vs spender in marriage  25:30 What Would You Do? Q3: Pension + great match… traditional or Roth?  27:35 Highlights  32:08 Where to watch + how to submit a question  32:35 Disclaimer  

You saved well. Now comes the part everyone underestimates: turning your portfolio into a reliable paycheck.In this episode, Dave Grant and Heather Townsend walk through how they design an optimal retirement income stream, starting with the question every retiree asks: “Do I have enough?” Then they break down how to build income buckets, choose the right withdrawal mix across accounts, and avoid the biggest trap they see: trying to live off dividends alone.  What you’ll learn… • Why “Do I have enough?” starts with your monthly spending number, not a random retirement goal   • The 4% rule: why it’s a useful starting point, and why real retiree plans rarely stay flat   • The key factors that change your withdrawal rate: risk level, Social Security timing, pensions, and more   • How Heather plans for long-term care and higher end-of-life medical costs (without relying on insurance)   • The 3-bucket strategy (cash, fixed income, growth) and why it improves peace of mind and plan success   • Where those buckets should sit (IRA vs brokerage vs Roth) to keep taxes under control   • Why creating some taxable income can be smarter than showing “$0” income in retirement   • The problem with “living off dividends and interest”, and why it can create risk and tax drag   • Why paying yourself monthly in retirement helps spending discipline and reduces stress  

In this episode, Dave Grant and Heather Townsend go rapid fire through a stack of real listener questions in a special “What Would You Do?” format. No deep dive, just straight answers, real-world trade-offs, and the money conversations high earners actually have behind closed doors.What you’ll learn...• The truth about the short-term rental “tax bill to $0” claim, and when depreciation can actually offset W-2 income• Why cost segregation matters, and why the land value (like beachfront property) can kill the strategy• How to figure out what’s pre-tax vs after-tax when you’ve rolled multiple401(k)s into an IRA (and what happens if you cannot prove it)• What to do if your phone (with cards attached) gets stolen, plus why credit cards beat debit cards for fraud protection• Why freezing your credit can be a pain, but worth it• Hedge funds, limited partnerships, and long-short funds explained simply, including the biggest risks: fees, complexity, and illiquidity• How to keep a future inheritance separate in a second marriage, and why an estate attorney matters before the money hits• The “huge bonus” playbook: taxes first, emotions second, then intentional spending and saving• What to do when a surviving spouse inherits complex real estate, including the step-up-in-basis angle and the “would you buy this today?” test• Plus: the unexpected “Would you rather?” showdown (Bitcoin vs Birkin)

In this episode, Dave Grant and Heather Townsend break down The Retiree’s Wealthy Playbook for 2026, including how to plan your spending, manage taxes, and actually enjoy the money you worked so hard to build.  What you’ll learn…• The real foundation of a “rich retiree” plan: priorities, monthly needs, and the bucket list• The hardest trade off in retirement: spending enough now vs preserving assets for later• Why underspending can be a bigger threat than running out of money• How to think about inflation, and why health insurance can blow up your projections (especially early retirees)• The “why” behind big purchases (cars, trips, second homes) and how to plan them without wrecking your tax bracket• 2026 tax items to know (charitable deductions, standard deduction boosts for 65+, and more)• Roth conversions in the “gap years”, plus how timing (like market dips) can help• When simplifying accounts can make your tax season way less painful• IRMAA in plain English, and how to think about it without letting it run your life• Q&A: IRMAA letters, funding big trips, and planning for a large inherited IRAChapters00:00 Setting up 2026 for retirees00:49 The foundation: priorities, monthly needs, and bucket list planning03:24 Peace of mind, inflation, and the risk of underspending04:44 Health insurance reality check (especially pre Medicare)06:09 Big purchases: the “why” test, trade offs, and keeping your plan intact10:09 Is your plan actually designed for the life you want this year?11:10 Health planning and the “go go years”14:11 2026 tax updates retirees should know16:06 Roth conversions: when, why, and how to avoid tax bracket mistakes20:10 Simplify accounts, simplify taxes21:37 IRMAA explained, plus when to appeal25:30 Q&A: IRMAA letter, big trips, and inheriting an IRA30:41 Highlights (personal and professional)33:08 Wrap up33:33 DisclaimerI’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff... just real talk about what matters most to your financial future.On this channel, we cover everything from Social Security and tax strategies to IRAs, 401(k)s, job changes, inheritance, and so much more. My goal is to help you feel confident about your retirement plan, so you not only have enough, but you're also prepared for the risks that could affect your money along the way.Let’s take the mystery out of retirement and build a plan you can feel good about.For more about Retirement Matters, or to contact us, visit our website: https://www.retirementmatters.co/

High earner? 2026 could quietly change how much you keep.In this episode, Dave Grant and Heather Townsend break down the tax playbook for 2026. What you'll learn:• Why “it’s not how much you make, it’s what you do with it” (and why high earners still feel broke)• The core foundation: cash flow is the engine of wealth, not returns• How to create intentional surplus without killing your lifestyle• 2026 planning priorities (accounts, savings targets, and timing decisions)• How to think about income spikes, bonuses, and planning ahead• The money conversation most couples avoid (and why it matters)• The single most important step: know your numbers, know your goals, then execute Chapters: 00:00 Setting up 2026 for high earners00:55 Foundation: it’s not how much you make01:19 Cash flow is the engine of wealth03:14 Emergency fund + lifestyle design04:31 2026 contribution limit refresh05:58 Pre-tax vs Roth decision framework08:14 2026 tax changes to watch10:39 Housing decisions and cash flow reality check14:10 Bonuses, vesting, and irregular income planning23:26 Know your savings targets23:59 Money conversations with your spouse26:21 Q&A35:15 Disclaimer I’m here to make wealth planning and retirement simple, clear, and approachable. No jargon, no fluff... just real talk about what matters most to your financial future.On this channel, we cover everything from Social Security and tax strategies to IRAs, 401(k)s, job changes, inheritance, and so much more. My goal is to help you feel confident about your retirement plan, so you not only have enough, but you're also prepared for the risks that could affect your money along the way.Let’s take the mystery out of retirement and build a plan you can feel good about.For more about Retirement Matters, or to contact us, visit our website:https://www.retirementmatters.co/

Remodeling your home is going to take money. There are several options and we're discussing them today. We explore the benefits and drawbacks of using cash, HELOCs, margin loans, and credit cards, emphasizing the importance of planning and understanding personal debt sensitivity. The conversation also touches on family loans and the psychological aspects of managing debt, providing listeners with practical insights and personal experiences related to home financing.00:00:00 Introduction to Home Remodel Financing Options00:00:46 When to Pay Cash for Home Projects00:04:01 Understanding HELOCs - Benefits and Mechanics00:07:00 HELOC Drawbacks and Considerations00:09:40 Margin Loans Against Investments00:12:27 Cash-Out Refinancing and Other Financing Options00:17:17 Special Considerations for Retirees00:19:12 Practical Advice and Rules of Thumb00:25:17 Announcement and Personal Highlights

Episode 50 - Sell your business for more - Heather Townsend and Dave Grant share the secrets and discuss the intricacies of business transition and exit planning. They explore the importance of team dynamics, the emotional aspects of selling a business, and the various strategies for maximizing business value. The conversation delves into the four C's of business valuation, tax strategies for business sales, and the challenges of family business transitions. Real-life examples illustrate the impact of proper planning and the necessity of having a clear exit strategy. The episode emphasizes the need for business owners to prepare for transitions at all times and to align their personal and financial goals with their business objectives.00:00:00 Introduction to Business Exit Planning00:01:04 The Wealth Trapped in Businesses and Why Exits Fail00:04:02 Business Dependency and Valuation Challenges00:06:21 The Four C's Framework for Increasing Business Value00:08:16 Industry Multiples and the Value Gap00:12:13 Derisking Your Business Before Sale00:15:13 Growth Strategies and Strategic Acquisitions00:17:14 The Long Timeline and Complexity of Business Sales00:17:49 Seller's Remorse and Identity After the Sale00:18:48 Planning for Life After Business and Family Transitions00:23:22 Q&A - Calculating Business Worth Without a Full Valuation00:24:25 Q&A - Minimizing Taxes and Managing Sale Proceeds00:26:53 Personal Highlights - School Tours and Taking Time Off00:30:40 Closing Remarks and Disclaimers

In this episode, Heather Townsend and Dave Grant discuss the upcoming changes to 401k plans in 2026, focusing on the implications for individuals over 50 and the new rules regarding catch-up contributions. They explore the impact of these changes on retirement planning, tax strategies, and the importance of adapting to new regulations.

RMDs are complicated. Heather and Dave discuss the complexities of RMDs from retirement accounts, including the rules surrounding inherited IRAs. They break down the nuances of RMDs, the implications of tax laws, and strategies for effective management to avoid unnecessary tax burdens. The conversation emphasizes the importance of understanding RMDs for both personal retirement planning and for those inheriting retirement accounts, highlighting the need for proactive tax planning and the potential pitfalls of mismanagement.

Managing uneven cash flow is complex. In this episode, Dave and Heather discuss the complexities, particularly for business owners and W-2 employees. They emphasize the importance of knowing living expenses, setting financial goals, and having a plan for unexpected income. The conversation also touches on strategies for creating a financial runway, the significance of separating business and personal finances, and the need for continuous financial education. The hosts share insights on how to achieve financial stability and success through effective cash flow management.

Dave and Heather discuss the critical role of cash in retirement planning, emphasizing the balance between cash reserves and investments. They explore how much cash is necessary for different life stages, the importance of emergency funds, and strategies for managing cash effectively. The conversation also touches on the implications of inflation on cash holdings and the necessity of investing to maintain wealth. Listener questions provide further insights into practical cash management strategies.

Health Savings Accounts (HSAs) are worth obsessing over! Dave and Heather discuss their benefits, eligibility, contribution limits, and unique rules. They share personal anecdotes and practical advice on how to maximize the advantages of HSAs, especially in relation to tax savings and medical expenses. The conversation also touches on the implications of HSAs after age 65, employer contributions, and estate planning considerations.

Dave and Heather delve into the intricacies of benefits enrollment, discussing various types of insurance including health, disability, and life insurance. They emphasize the importance of understanding health plans, the nuances of flexible spending accounts (FSA) and health savings accounts (HSA), and the significance of long-term disability coverage. The conversation also covers deferred compensation, legal benefits for estate planning, and employer discounts that can lead to substantial savings. The hosts provide practical advice for listeners to navigate their benefits effectively and maximize their financial well-being.

In this episode, Dave and Heather discuss various investing strategies, emphasizing the importance of understanding market changes, historical data, and the need for portfolio diversification. They analyze the performance of cash versus investments, the relationship between international equities and currency fluctuations, and the historical performance of different asset classes. The conversation also covers the pros and cons of target date funds versus ETFs, and the significance of rebalancing portfolios to manage risk and optimize returns.

Critical mistakes can be made when creating your estate planning documents. In this episode, hosts Dave Grant and Heather Townsend emphasize the importance of funding revocable living trusts, updating estate documents, and understanding beneficiary designations. They share personal experiences and insights on how to navigate the complexities of estate planning to avoid probate and ensure family protection. The conversation also includes a Q&A segment addressing common questions about estate planning, making it a comprehensive guide for listeners.

The critical topic of asset protection includes various forms of insurance including disability, life, and property insurance. Dave and Heather discuss the importance of legal structures like LLCs and trusts in safeguarding personal and business assets. The conversation emphasizes the need for comprehensive coverage to mitigate risks and protect wealth, especially for high-income earners and business owners. Heather shares personal anecdotes and insights on the complexities of insurance and legal protections, making the topic accessible and engaging for listeners.

Proactive tax planning: In this episode, Dave and Heather discuss the importance of proactive tax planning, especially for business owners and retirees. They emphasize the need for understanding tax withholding, navigating life changes, and avoiding penalties. The conversation also covers strategies for high-income earners and the significance of working with a CPA to optimize tax situations. The hosts share personal anecdotes and professional insights, making the topic relatable and informative for listeners.

What are the hot topics in finance today? From the controversy surrounding Wells Fargo's handling of fraud cases to the Treasury's shift away from paper checks, they cover the hot topics that impact your financial planning. Discover why property and casualty insurance rates are soaring and how the economy and stock market are not as linked as you might think. Tune in for insights, stories, and practical advice to navigate today's financial landscape.

Crypto and private equity: in this episode, we delve into the evolving landscape of 401k plans, focusing on the integration of cryptocurrencies and private equity. Discover the challenges investors face, from regulatory hurdles to liquidity concerns, and explore the opportunities these assets present for diversification and potential growth. Join us as we navigate the complexities and uncover strategies to optimize your retirement portfolio.

Hosts Dave Grant and Heather Townsend discuss the importance of hiring a financial advisor and the criteria to consider.Not everyone needs a financial advisor so it's important to understand when it's necessary. They discuss the value of fee-only, fiduciary, and CFP-certified advisors. They offer real-life examples of when to seek financial advice. The role of financial advisors in enhancing portfolio returns. The importance of transparency and accountability in client-advisor relationships.Personal Insights: Heather shares her passion for cars and how financial planning feels like a sport to her.Send your questions to [email protected]#FinancialAdvice #RetirementPlanning #WealthManagement

Heather Townsend and Retirement Matters discuss various retirement plans available for business owners, including Solo 401k, SEP IRA, and defined benefit plans. They explore the advantages and disadvantages of each plan, emphasizing the importance of understanding tax implications and the role of financial advisors. The conversation also highlights real-life applications and personal experiences with retirement planning, aiming to provide listeners with practical insights and strategies for effective financial planning.

In this episode of "Playbook of the Wealthy," hosts Heather Townsend and Dave Grant dive into the intricacies of managing your 401k when leaving a job or retiring.They explore the options available, including rolling over to an IRA, the rule of 55, and the potential pitfalls of tax withholdings. With personal anecdotes and expert insights, Heather and Dave provide a comprehensive guide to making informed decisions about your retirement savings. Tune in to learn how to navigate these financial waters and ensure a smooth transition into retirement.

Discover how placing investments in the right accounts can lead to significant tax savings and better returns. From understanding the nuances of IRAs and Roth IRAs to exploring the benefits of municipal bonds, this episode is packed with insights to help you optimize your investment strategy. Whether you're a seasoned investor or just starting, tune in to learn how strategic asset location can enhance your financial future.

The Conversation You Didn’t Know You Needed-Some of the most valuable conversations start with a simple question. This week, we’re taking yours and exploring the ideas, strategies, and perspectives that matter most right now.

This is a follow up episode with more information on selling real estate and what you need to know.

Big changes to the tax code could mean big consequences -or big opportunities - for retirees.In this episode, we break down key updates from Trump’s proposed “Big Beautiful Bill” and what they mean for your retirement strategy. From new estate tax exemptions to the evolving rules around Roth conversions, we cover it all.🔹 How Social Security taxation could shift your income planning🔹 Charitable giving strategies that work under the new code🔹 Expanded state and local tax (SALT) deductions🔹 What the $15M estate tax exemption means for legacy planning🔹 The pros and cons of Roth conversions under new limits🔹 Why proactive planning matters now more than everWhether you’re already retired or just planning ahead, this episode will help you better understand how to protect and grow your retirement nest egg. Our hosts also share personal stories to illustrate just how much thoughtful planning can shape both your financial and personal future.🎧 Tune in—and be sure to talk with your financial advisor to put these changes to work for you.#RetirementPlanning #TrumpTaxPlan #RothConversion #EstatePlanning #FinancialFreedom

The hosts discuss the implications of the new tax bill on high-income earners and business owners. They explore various tax planning strategies, including deductions for retirees, charitable contributions, mortgage interest, and estate taxes. The conversation emphasizes the importance of proactive tax planning and understanding the evolving landscape of student loans. They delve into various aspects of retirement planning, focusing on tax implications for retirees, high-income earners, and business owners. They discuss estate tax exemptions, the impact of the new tax bill on charitable contributions, and strategies for maximizing tax benefits through Roth conversions and business deductions. The conversation also addresses listener questions, providing insights into navigating complex tax scenarios and planning for future financial stability.

In this episode, Heather Townsend and Dave Grant discuss the complexities of passive losses in real estate investment, particularly focusing on the nuances of taxation and the implications for investors. They share personal updates, delve into the intricacies of the tax code, and provide insights on how to strategically approach real estate investments. The conversation also includes a Q&A segment addressing common questions about real estate and taxation, emphasizing the importance of having a solid plan and understanding the rules surrounding passive income and losses.

Heather and Dave discuss various financial planning topics, including investment projections, rebalancing strategies, client engagement, personal finance decisions, debt management, the role of 529 plans, home ownership versus renting, entrepreneurship, behavioral finance, college education funding, and retirement planning.

Dropping this episode early so you can enjoy it before the holiday!In this episode, Heather Townsend and Dave Grant discuss the intricacies of tax optimization in real estate, touching on various topics such as the emotional impact of money, the importance of fiduciary duty, and the risks associated with fix and flips. They share personal stories and client successes, emphasizing the need for strategic planning in real estate investments. The conversation also highlights the significance of understanding depreciation and its implications, as well as the emotional aspects of financial decisions.

Hosts Heather Townsend and Dave Grant explore the complexities of real estate investing. They discuss personal experiences, the pros and cons of various investment strategies, and the importance of market timing. The conversation delves into the intricacies of property management, tax implications, and the emotional aspects of real estate transactions.

Hosts Heather Townsend and Dave Grant discuss significant updates to Social Security, including changes affecting government employees and divorcees. They explore the complexities of claiming benefits, the impact of longevity on retirement planning, and the importance of financial literacy in navigating these changes. The conversation also touches on personal anecdotes and highlights from their lives, emphasizing the balance between professional advice and personal experiences.

Dave Grant and Heather Townsend discuss the complexities and strategies surrounding concentrated stock positions. They explore the risks associated with having a significant portion of one's wealth tied up in a single stock, share personal anecdotes, and provide insights into effective management strategies for such investments. The discussion emphasizes the importance of diversification and the emotional challenges investors face when dealing with concentrated stock holdings. The conversation also includes real-life scenarios where they provide insights on how to handle significant gains from investments in major companies like Apple and Amazon.