Two founders sold companies for $28 million and $158 million respectively, yet both felt miserable after. They describe lingering insecurity and scarcity mindset that therapy couldn't fix, and discuss why money didn't deliver the happiness they expected.
I sold my first company for $28 million. By the time I split it with my ex, I ended up with a few million dollars. But the big win was probably selling L2, and I like thought, oh wow, I can buy a plane.
What'd it sell for? $158 million. I sold my company 2 or 3 years ago and I made a fair bit.
Enough that I'm naked here. What did you make? Yeah, let's go. He's hesitant because he's worried people will listen to me. Okay, go ahead.
At the end of the process, I walked away with about $20 million.
And how old are you?
I was 31 or 32.
Unless you really screw up, you should be much wealthier than I am by my age. Yeah, but I still feel shitty.
I'm boring. Shawn makes fun of me. I do 80/20 index and bonds.
That's exactly what you should be doing right now.
I think so. Shawn makes fun of me. He's like, how are you feeling insecure? And I'm like, dude, I'm broken. It doesn't matter how much therapy I go to when it comes to money. I have a scarcity mindset and I'm broken.
Yeah, I'm the same way.
