I Asked 40 Millionaires Their Biggest Regret

We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wr

Why do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.

I asked 40 millionaires their biggest regret. One answer was just two words: "withholding love."

This episode started with a simple survey: 40 millionaires, one question — what's your biggest regret? The answers ranged from $22K a year dumped into life insurance instead of Bitcoin ($11M of upside gone) to hundreds of bitcoins sold at $300 to make payroll. But cross-referenced against 100+ Moneywise conversations, every answer collapsed into just three regrets: I can see the life I almost had. I didn't become the person I thought I could become. I thought I had more time.

Then it gets into the science. Why bronze medalists look happier than silver medalists. Why finance is only 2.5% of most people's regrets but dominated this survey. Why the person you never became can bother you longer than any mistake you actually made. Why an $80M exit sent one founder to rock bottom. And a three-question Regret Test to figure out whether your regret is still useful — or just expensive entertainment.

Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mw

Timestamps:
00:00 — The survey: 40 millionaires, one question, and the answers that looked completely random
01:02 — Every regret collapses into three buckets
01:24 — Regret vs. disappointment: why regret needs an alternate reality
02:25 — The brain science: patients with orbitofrontal damage don't feel regret
03:14 — Your brain uses regret to change future decisions before you make them
04:02 — Bucket 1: "I can see the life I almost had" — "the stock market is basically a regret calculator"
05:23 — The Olympic study: why bronze medalists look happier than silver medalists
06:27 — Finance is only 2.5% of most people's regrets — so why was this survey drowning in them?
07:36 — The Opportunity Principle: agency creates regret, and rich people have had a lot of agency
08:25 — Bucket 2: "I didn't become the person I thought I could become"
09:08 — Ought self vs. ideal self — and why ideal-self regrets never get closure
10:26 — "The unlived version of you never has a bad quarter"
11:02 — The famous "you'll regret what you didn't do" stat — and the 2,600-person study that broke it
13:04 — The 23-year-old already in the "never enough stage," and the moving goalposts from $10M to $1B
13:56 — Bucket 3: "I thought I had more time" — kids, health, and the $80M founder who hit rock bottom
14:52 — Why priorities flip when time feels scarce (and Daniel's midlife crisis at 30)
16:13 — When to engage with a regret and when to let it go — what the research on older adults found
17:21 — The Harvard study: relationships at 50 predicted health at 80 better than cholesterol
19:45 — The Regret Test: three questions to ask about your biggest regret
20:44 — "Regret in 4K": why money doesn't eliminate regret — it makes it higher resolution

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