Keeping More of What You Earn- Mike Piper and Paul Merriman

In Session 3 of the 2026 Bainbridge Community Foundation Spring Financial Education Series, Paul sits down with Mike Piper — CPA, Personal Financial Specialist, and the voice behind the Oblivious Investor blog and the free Open Social Security calculator — for one of the warmest, most practical conversations of the series. Mike has a rare gift: taking the topics that intimidate most investors and making them feel obvious. Over the course of the hour, he and Paul work through the handful of decisions that genuinely shape a retirement. Mike opens with a quietly radical idea: if you've prepared well, "more than enough" isn't the exception — it's the most likely outcome. Because we have to plan for long lifespans, poor markets, and high medical costs that usually don't all come to pass, most disciplined savers end up with leftovers. From there, he explains which dollars to spend first each year, how age and capital gains should steer whether you draw from taxable or retirement accounts, and why the step-up in basis matters more than most people realize. The conversation turns to the human side of money, too — how to talk a couple through it when one spouse is aggressive and the other can't stand the thought of the stock market, why both positions are almost always driven by fear, and how framing the trade-offs around the people you love often brings them closer together. Mike and Paul also tackle the spendthrift-child dilemma, the case for matching a young person's Roth IRA, and why small gifts early can dwarf an inheritance received at 70. On Social Security, Mike makes the point that most people get the risk exactly backwards: delaying benefits isn't a gamble — it's insurance against the scary scenario of living a very long time. He walks through what really happens if Congress does nothing before the trust fund shortfall around 2033 (hint: the program doesn't disappear), and the range of fixes on the table. Throughout, both men return to the same theme — simple, low-cost, broadly diversified portfolios keep beating the clever alternatives, and the Bessembinder research helps explain why. Stick around for the closing exchange on using AI to learn from the "Truth Tellers" — and Mike's cautionary tale about a chatbot that invented an entire tax-code provision, word for word and completely convincingly, that simply does not exist. CHAPTERS 00:00 Intro — Matt Longmire, BCF 03:03 Paul introduces Mike Piper 04:48 Mike's blog and books 06:00 CPA vs. PFS and why taxes matter 08:00 What fiduciary duty really means 09:45 How Mike started writing 11:32 "More Than Enough" and the 4% rule 13:10 Why most retirees end up with more than enough 15:20 "Just enough" vs. "more than enough" 17:10 Which dollars to spend first 19:40 Age, gains, and the step-up in basis 21:00 Pushing back on too much risk 23:00 When spouses disagree on risk 26:20 The real trade-off of playing it safe 27:55 Mistakes that leave people short 31:20 Bernstein's 20% rule 34:20 Matching your kids' Roth IRA 36:45 Age 60: the most common age to inherit 38:30 The spendthrift child 41:30 Why Mike pushes back on SPIAs 44:00 Q&A: American expats abroad 46:50 One habit investors and advisors should change 48:50 Small-cap growth, Tesla, Bessembinder 51:00 What advisors should do differently 53:40 NAPFA, AUM, and hidden agendas 55:30 Sole practitioner vs. a firm 58:00 Mike's one-fund portfolio 01:00:00 The "Mind the Gap" study 01:03:00 Paul's 12 favorite Vanguard funds 01:04:30 Getting 20-somethings investing 01:05:30 When to claim Social Security 01:09:45 Will benefits be cut? The 2033 trust fund 01:18:45 Risk parity and "golden butterfly" 01:20:50 What a good planner should cover 01:24:10 Withdrawals for early retirees 01:27:00 RMDs at 75 and Roth conversions 01:28:35 Using AI to learn — and its limits 01:33:10 Closing — Bill Bernstein next week LINKS: Mike Piper's blog — ⁠obliviousinvestor.com⁠ Open Social Security — ⁠opensocialsecurity.com⁠ Mike's books on Amazon — ⁠https://bit.ly/49BQugd⁠ Oblivious Investor — ⁠https://bit.ly/4oeIacs⁠ We're Talking Millions! (free PDF and audio) — ⁠https://www.paulmerriman.com/free-books⁠ If You Can by Bill Bernstein (free PDF) — ⁠https://www.paulmerriman.com/free-books⁠ PlanVision — Mark Zoril — ⁠planvisionmn.com⁠ /rhe Bessembinder study — "Do Stocks Outperform Treasury Bills?" https://www.morningstar.com/personal-...