Roxy Butner joins the show to break down practical retirement saving strategies—especially for entrepreneurs who struggle to pay themselves first. The conversation covers foundational options like IRAs and Roth IRAs, then moves into more powerful tools such as Solo 401(k)s, SEP IRAs, and SIMPLE IRAs for business owners. They highlight the enormous impact of starting early through compounding, common planning mistakes (like neglecting retirement and estate planning), and current client concerns around market volatility and geopolitical risk. Listener questions tackle HSA asset allocation and whether bonds belong in a portfolio nearing withdrawal, along with a comparison between money market funds and bond funds. The episode reinforces a core theme: ignore the noise, build a plan, and stick to it.

0:09 Show intro and Roxy joins; focus on practical, common-sense advice
0:50 Entrepreneurs and the challenge of saving vs reinvesting in business
1:14 Getting started: traditional IRA basics and tax deferral
2:41 Roth IRA advantages and contribution limits
3:41 Retirement options for self-employed: overview
4:20 Solo 401(k): high contribution potential and dual-role benefits
5:17 SEP IRA: flexible contributions for variable income
6:40 Contribution discipline and “pay yourself first” strategy
7:44 SIMPLE IRA for small businesses with employees
8:22 The power of compounding and starting early
9:12 Early vs late investor example—time beats total contributions
10:29 Common mistakes: not planning early, ignoring estate planning
12:00 Tax season behaviors and last-minute contributions
13:15 Listener question: HSA allocation—100% equity vs adding bonds
14:03 Suggested shift toward 80/20 or modest fixed income allocation
15:34 Risk considerations and need for stability nearing withdrawals
16:00 Listener question: money market vs bond fund performance
16:51 Apples-to-apples comparison and limits of historical data
17:57 Role of bonds vs money markets in long-term portfolios
18:49 Client fears: market drops and volatility concerns
19:49 Geopolitical risk and sticking to a long-term plan
20:17 Importance of real financial planning vs guessing returns
21:57 What listeners get from a free advisor consultation
23:16 How to connect with an advisor and submit questions

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Don and Tom tackle the idea that retirement isn’t what it used to be—and maybe shouldn’t be at all. From historical retirement ages (when most people never made it) to today’s longer, healthier lives, they explore why many people aren’t eager to stop working. The conversation shifts to purpose, identity, and the growing trend of “phased retirement,” where people scale back instead of quitting outright. They also answer listener questions on using the TSP’s G Fund as a stable anchor in a portfolio and the smartest way to time withdrawals from 529 plans for future medical school costs. Along the way, there’s the usual banter, skepticism of industry nonsense, and a firm reminder: retirement is no longer a finish line—it’s a design problem.

0:05 Don’s “retirement strategy”: Don’t
1:13 Should anyone actually retire anymore?
2:06 Financial vs. psychological reasons people keep working
3:15 History of retirement ages and why they were set
4:39 Longevity trends and aging populations
5:04 Why modern retirees want purpose and engagement
6:14 Companies encouraging phased retirement (Microsoft example)
7:48 Planning the “what will I do?” side of retirement
8:28 Why experience makes you better (especially in media)
10:12 Retirement identity and self-awareness
11:01 Real-world example: professionals scaling back instead of quitting
12:34 Don’s evolving “never retire” plan
14:55 The importance of knowing yourself before retiring
16:22 Retirement today vs. historical necessity
17:14 Rethinking retirement as continued contribution
17:58 Listener question: Using TSP G Fund in retirement allocation
20:19 Risks and logistics of split-account rebalancing
21:26 Listener question: When to use 529 funds for med school
23:17 Why delaying 529 withdrawals maximizes tax advantages
24:52 How to submit listener questions
26:19 Free advisor meetings and fiduciary pitch (without the noogie)

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A wide-ranging Q&A episode tackles the real-world tradeoffs investors actually face: whether Paul Merriman’s aggressive small/value “ultimate” portfolio is worth the complexity and risk, how much stock to put in scary online bank reviews versus FDIC reality, and how to find advice when you don’t want someone managing your money. Don also explains why FAFSA tricks with traditional IRA contributions don’t work, how to control capital gains taxes using specific share identification, and—somehow—confirms he was the voice behind a powerful Auschwitz exhibit. Practical, skeptical, and very Don.

0:05 Friday Q&A intro and how to submit questions

1:49 Merriman 10-fund portfolio vs “owning the market”

5:21 Don confirms Auschwitz exhibit voiceover work

6:54 Bread Savings reviews, withdrawal limits, and FDIC reality

9:38 Finding tax-only retirement advice (CPA vs hourly planner vs EA)

12:05 FAFSA myth: traditional IRA won’t lower aid eligibility

13:55 Selling ETFs: minimizing taxes with specific lot selection

17:01 Podcast hosting quirks and MP3 download workaround

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