Hate the game (Ricky Weekly #64)

This is where I share 3 things every week with my friends and anyone else interested.

A picture from my life:

Went to dinner with friends last night and decided to go to an escape room on a whim. It was so fun!

A thing on my mind:

I’ve been a startup founder for more than a decade without being particularly successful. I still suffer from self-doubt, and the older you get, the more people question your life choices. I think this is very healthy. The more I question myself, and the more others question me, the more clear I have to be about why I do what I do. I’ve definitely noticed my resolve growing more firm over the years, and the intentionality has made me more confident as a founder.

I see my friends go through the same process and end up in different places. We all started out thinking that we want to play this startup game because there’s something we want from it, but as time goes on, we see the game more clearly. It becomes clear how elusive product market fit really is, how fundraising is stupid and rigged, how high the opportunity cost is, how privilege some of the players actually are, how people made way more money as early employees or from crypto, how so-and-so we used to hang out got lucky and became a billionaire, how many terrible people there are, how bootstrapping feels way more freeing, how working for someone else is so much easier, how being an investor allows you to be more diversified, how SF/SV location is overrated…the list goes on and on.

All of this clarity feels healthy to me. For every feature of this game you identify and every comparison you make to the alternative, you figure out if you actually want to play this game or exit. All of the nasty features were true when we started, the only difference is we didn’t really understand them and we thought we could win. Maybe the startup game has gotten more “elevated” so doesn’t feel like a niche game anymore, and that loses some appeal. Maybe the money got way bigger, so more people you know have gotten a taste of winning, and attracted more riff raff to play. But most of the features…rigged funding, elusive PMF, opportunity cost, luck, bad people, etc. they were there when we started.

Many friends have exited the game, but they’re not always more fulfilled. You can bootstrap a business, but it’s still hard. Maybe you can dictate the terms and define success a little more, but it could be hard to reach that custom definition of success. Becoming investor is just playing yet another kind of game. They’re all games, I feel like, and all these games suck to an extent. Ultimately, you negotiate with yourself to what extent you want to play and figure out how you the game can serve you.

A piece of content I recommend:

738: Good Grief! and 737: The Daily - This American Life

I thought the last two episodes of This American Life were stellar, so I’m recommending both. Episode 738 documented how different people experience grief, and reminded me of when I dealt with the passing of a dear friend and I felt bad that I didn’t cry for him. Episode 737 talked about daily routines and took me on an emotional rollercoaster ride.


As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.