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