Playbook of the Wealthy

The mistakes we saw in tax season | EP072

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 [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa19PemdNekRoN2NtbzRRemV2R2ZyNEFsR1FyUXxBQ3Jtc0tsV3UzajVKRXNmdEhRbVhxdEQ4T0xBYnp3TjdVNzQ4MFVkX2xpZWlxUURCRTNINTJ3VUF1anV5dWxtREkxLXJiUmFMRHU3MWdpSFljNU5IOTdBejlMWUJsMzhHNVl4RzJWbFlUZ3VqRlpLQWFZNEdRSQ&q=https%3A%2F%2Fplaybookotw.com%2F&v=GXNL0ed2IpI]★ 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 [https://www.youtube.com/watch?v=GXNL0ed2IpI] Cold open: the mistakes we caught this tax season01:09 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=69s] Welcome — a tax season recap01:25 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=85s] Into the mistakes we saw02:33 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=153s] Mistake: clients badly under-withheld03:45 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=225s] Mistake: investments throwing off capital gains distributions04:31 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=271s] Mistake: out-of-state 529 plans and the missed state deduction05:16 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=316s] Mistake: an S-Corp set up with no salary split06:10 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=370s] Mistake: disorganized, piecemeal paperwork07:08 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=428s] Mistake: missing tax documents — a whole W-2, a forgotten 109907:51 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=471s] Mistake: the backdoor Roth reported as taxable (Form 8606)08:46 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=526s] Mistake: incomplete or incorrect business books09:16 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=556s] Mistake: HSA contributions the CPA never knew about09:29 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=569s] Mistake: projections thrown off by late switches and new tax law10:27 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=627s] This isn't about slamming anyone — catching mistakes is the job11:06 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=666s] Fixes for next year: the fall tax review13:34 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=814s] The capital gains line you can almost erase with one portfolio tweak14:23 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=863s] The older couple whose tax bill got cut in half16:31 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=991s] Review business income every quarter19:05 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1145s] Build your own tax-document checklist20:16 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1216s] Inside the Townsend household's 2026 tax folder21:41 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1301s] Business owners: keep your books clean year-round22:53 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1373s] When to actually switch CPAs (hint: not December)23:47 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1427s] K-1s, curveballs, and when to just extend25:58 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1558s] The bow: reflect on your tax season26:33 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1593s] A quick ask — and YouTube's new "hype" button27:03 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1623s] What Would You Do?27:08 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1628s] Q1: I adjusted my withholding for a raise and still owe — why?29:34 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1774s] Q2: Why do my coworkers get refunds and I don't?31:41 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1901s] Q3: I'm getting a huge refund and it scares me — should I get a second opinion?33:01 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1981s] Highlights33:05 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=1985s] Highlights: Heather's lifting progress and the creatine debate35:25 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=2125s] Highlights: Dave on the summer slowdown and a new designation36:23 [https://www.youtube.com/watch?v=GXNL0ed2IpI&t=2183s] Wrap up

Where does our financial advice differ? | EP071

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

How Not to Invest (Book Review) | EP070

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

To Buy or Lease a Car | EP069

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 away 01:09 Welcome: the buy vs. lease debate that never dies 01:54 Why this question comes up so much (and why Heather is "the car girl") 03:05 Lease basics: it's a rental, not ownership 03:58 The mileage cap that kills most leases before they start 05:36 Maintenance under warranty: lease's quietly biggest value 06:57 Customizing a leased car (and the body kit you'll never see again) 08:16 The pros and cons of leasing, summarized 08:33 Why getting out of a lease is harder than getting out of a marriage 09:27 Heather's lease story: $5K, age 16, and a "Beemer Check" plate 13:06 Business owners: the 6,000-lb SUV depreciation play 14:43 The pros and cons of buying outright 16:48 Longer payment terms and the trade-in trap 18:42 You buy it, you own it, you fix it 18:53 Buy vs. lease math on a $100K Porsche Macan 21:25 Dave's frugal years: used cars until kids forced new 23:40 Trump, EV credits, and the day after the Tesla call 25:03 The decision framework: mileage, then brand, then math 26:18 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 63 36:07 Wrap up ★ LISTEN ON ANY PLATFORM ★ Apple Podcasts: https://podcasts.apple.com/us/podcast/playbook-of-the-wealthy/id1787630097 Spotify: https://open.spotify.com/show/21LrI3IB2wMsOOJLiGsRJK Website: https://playbookotw.com ★ WATCH NEXT ★ The 5 DIY Money Mistakes That Quietly Cost You Years | EP065: https://www.youtube.com/watch?v=s4zprAatOto Dividends 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.com Email: hello@playbookotw.com Dave Grant on Instagram: https://www.instagram.com/davegrant82 Heather Townsend on Instagram: https://www.instagram.com/heather.townsend.financial #BuyVsLease #CarBuying #PlaybookOfTheWealthy

Five reasons why the MONTH you retire MATTERS

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 traps 01:26 Why retirement month planning beats retirement year planning 02:26 Case study: Jeffrey, $400k total comp executive 03:47 Point 1: Max out 401K and HSA in the first 2-3 months 06:21 The NUA strategy: company stock in a 401K explained 07:37 Point 2: Capture your prior year bonus and RSU payout 08:55 Clawback provisions in your employment agreement 10:43 Point 3: Healthcare coverage from retirement to Medicare 11:06 COBRA vs marketplace insurance costs compared 13:09 IRMAA explained: Medicare premiums based on income from two years ago 16:50 Point 4: Zero-income years for tax-free Roth conversions 19:48 Pension and Roth: convert before your pension sets your tax bracket 20:33 Point 5: Pension service credit timing 23:44 The 5-point retirement timing checklist 25:02 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 Highlights 33:58 Wrap up ★ LISTEN ON ANY PLATFORM ★ Apple Podcasts: https://podcasts.apple.com/us/podcast/playbook-of-the-wealthy/id1787630097 Spotify: https://open.spotify.com/show/21LrI3IB2wMsOOJLiGsRJK Website: https://playbookotw.com ★ WATCH NEXT ★ The 5 DIY Money Mistakes That Quietly Cost You Years | EP065: https://www.youtube.com/watch?v=s4zprAatOto Dividends 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.com Email: hello@playbookotw.com Dave Grant on Instagram: https://www.instagram.com/davegrant82 Heather 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