Better Beats Best

Four months ago, I was sitting around a poker table with my friends, losing all my money.

I’d never really played poker. I thought it was a game for gamblers and degenerates. But San Francisco has a way of pulling you into poker nights (turns out investors LOVE poker), so since April I’ve found myself around many felt tables.

But there was an obvious problem. I was extremely bad at poker.

After a month of regular games, I became a common trope:

“How much money did Gabe lose this game?” (Mom, if you’re reading, it was only $60… each game)

I’d show up, have a great time with my friends, and hemorrhage money because I didn’t understand a single principle of the game.

But during a long run through Golden Gate Park, I decided that would change. On the way back from Ocean Beach, feet pounding the pavement, I opened my Claude app.

Panting, I told it to build me a poker training program:

Make me the best poker player I physically can be. Write yourself instructions on how to coach me and feed me problems. Design it for mastery. Set it up so I can just log in every day, start a chat, and get better. And I like visuals! So build in instructions for that too.

POV of my daily scolding from Claude

I love the game of progress. I’ve loved it since I was 17, when I committed to shedding my 210-pound bag-of-milk body (and finished just in time for college!)

Now, I realize that a “growth mindset” is a default personality trait these days. Especially in SF! The city is littered with founders and grad students itching to be the best.

But here’s my big hot take: Being the best is overrated.

It actually kinda stinks. Constant betterment is a much more pleasurable goal.

The pursuit of the best comes with constant self-criticism.

If you’re not on top, nothing is good enough. And when you do make it? There’s only a momentary blip of joy before the fear of falling to number 2 crawls up into your chest.

I remember the first time I was top dog. I was 20, and the only sophomore in my major to land a Big Name internship (Boeing). My ego was massive. But when recruiting season rolled around the next year, I could feel the target on my back.

I started hating on my friends. “Oh, you got an interview with Microsoft? They talk to a lot of people. We’ll see if you make it to the next round.”

You could smell the insecurity through my clothes.

Those years, all I could think was: if I don’t land something bigger this year, everyone will see me as a failure. The guy who lost the lead.

So I went bigger. Junior year I went to Starbucks corporate. And after college, Microsoft.

And every time I landed one of those jobs/internships? I barely relished the glory of winning.

I was just relieved I didn’t lose.

Now the pursuit of better? It doesn’t work like that.

There’s no one to beat but the memory of who you once were. You’re just a logarithmic graph, climbing for all eternity.

The graph may slow, but it always goes up!

Some VCs and founders may call me weak for thinking like this. I’d call them insecure.

Maybe we’re both right.

But one thing I do know: three weeks ago, I absolutely dominated at a poker game, and it was no fun at all.

Now, my poker skills have been forged in the fire of Claude. At the same friendly game, I found myself winning almost every hand I played.

As the chips grew in front of me, I had less and less fun. All those nights before, the fun came from getting better. I had never even imagined the top!

I caught myself letting up, half-hoping someone else would win just to keep the game friendly.

Because I don't play to be the best. I play to be better.