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.