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)  

Chapters

00:00 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  

Chapters

00:00 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 Rate

High 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  

Chapters

00:00 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 IRA

Chapters

00:00 Setting up 2026 for retirees

00:49 The foundation: priorities, monthly needs, and bucket list planning

03:24 Peace of mind, inflation, and the risk of underspending

04:44 Health insurance reality check (especially pre Medicare)

06:09 Big purchases: the “why” test, trade offs, and keeping your plan intact

10:09 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 know

16:06 Roth conversions: when, why, and how to avoid tax bracket mistakes

20:10 Simplify accounts, simplify taxes

21:37 IRMAA explained, plus when to appeal

25:30 Q&A: IRMAA letter, big trips, and inheriting an IRA

30:41 Highlights (personal and professional)

33:08 Wrap up

33:33 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/

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 earners

00:55 Foundation: it’s not how much you make

01:19 Cash flow is the engine of wealth

03:14 Emergency fund + lifestyle design

04:31 2026 contribution limit refresh

05:58 Pre-tax vs Roth decision framework

08:14 2026 tax changes to watch

10:39 Housing decisions and cash flow reality check

14:10 Bonuses, vesting, and irregular income planning

23:26 Know your savings targets

23:59 Money conversations with your spouse

26:21 Q&A

35:15 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.