Show notes
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.
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
The Bessembinder study — "Do Stocks Outperform Treasury Bills?" https://www.morningstar.com/personal-finance/hendrik-bessembinder-do-stocks-outperform-treasury-bills
Watch the Video- https://www.youtube.com/watch?v=bB2ccYRLSOI&feature=youtu.be
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