Play Games You Can Keep Playing

Most people leave the table too early.

In 2008, Elon Musk wired his last $20 million into Tesla. He was already borrowing money from friends to pay rent. SpaceX had just failed its third rocket launch. Both companies were weeks from dying.

It worked. Obviously. He’s now the richest person on the planet.

I think about stories like that sometimes. Not with envy. More like the way I think about free soloing a cliff. I can appreciate the insanity of it. I’m just not built for it.

I don’t want to be that rich. I know that sounds like something people say to make themselves feel better. But I mean it. Past a certain point, the money creates problems I don’t want to have. I like my life small. I like knowing my neighbors. I like time on the river. We also have wildly different opinions on the ideal number of partners and children necessary.

I’m also not smart enough to solve problems at that scale. I’m not being humble. I’m being accurate. I’m a guy who built an interview site on WordPress and put the profits into ETFs. That’s probably near my ceiling.

The real reason I don’t make bets like that is simpler than strategy.

I’d stop sleeping well.

I know this about myself because it’s happened. Anytime the stakes get too high, my body keeps score before my brain catches up. The anxiety comes first. Then the bad sleep. Then everything else starts to slide. My health. My patience. My ability to be a decent person to the people around me.

So I stopped playing games I could lose badly.

Not games I could lose at all. Everything has risk. But I started asking a different question before every bet. Can I keep playing if this doesn’t work?

If IdeaMensch never made a dollar, I’d have lost some weekends. If the ETFs dipped, I didn’t need the money anyway. If a rental sat empty for a month, the other income covered it. Every bet was structured so that the worst-case outcome was merely annoying, not devastating.

Play games you can keep playing.

IdeaMensch is a good example. For years, it made money, but nothing crazy. I kept it running, kept it lean, kept showing up. Then AI changed the game. Not because I automated everything. Even though I mostly did. Because suddenly everyone wanted to be interviewed. Having a presence on established sites began to matter for how AI models found and cited people. Demand went up. I didn’t do anything different. The world just caught up to what was already there.

But here’s the thing. That only mattered because I was still at the table.

If I’d quit in year three when it was making $100 a month, I would have missed it entirely. The timing wasn’t something I could have predicted. I just had to still be there when it showed up.

People talk about luck like it’s random. It’s not entirely. Hard work plus time increases your surface area for luck.

I just made sure I was still at the table.