Uploaded June 2026 | Updated September 2026, 2 weeks ago
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 — bit.ly/49BQugd
Oblivious Investor — bit.ly/4oeIacs
We're Talking Millions! (free PDF and audio) — paulmerriman.com/free-books
If You Can by Bill Bernstein (free PDF) — paulmerriman.com/free-books
PlanVision — Mark Zoril — planvisionmn.com
/rhe Bessembinder study — "Do Stocks Outperform Treasury Bills?" morningstar.com/personal-finance/hendrik-bessembinder-do-stocks-outperform-treasury-bills
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 — bit.ly/49BQugd
Oblivious Investor — bit.ly/4oeIacs
We're Talking Millions! (free PDF and audio) — paulmerriman.com/free-books
If You Can by Bill Bernstein (free PDF) — paulmerriman.com/free-books
PlanVision — Mark Zoril — planvisionmn.com
/rhe Bessembinder study — "Do Stocks Outperform Treasury Bills?" morningstar.com/personal-finance/hendrik-bessembinder-do-stocks-outperform-treasury-bills
