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Do you not know poker at all?



Poker is actually a good analogy. It is luck in the short term but skill over the long term. You can't confidently predict that you will win any specific upcoming hand but, given a particular set of opponents, you can reasonably predict whether you will be up or down over a number of hands. I may beat Chris Moneymaker on a hand or two but he's going to take all my money over the long haul.

The insight here is to only play in games that you have the advantage (or are at least evenly matched) and be very, very careful not to put yourself in a position to go bust on any one hand.


I completely agree with the sentiment, and as someone who’s mostly focused on a startup for pro poker players to study game theory more effectively (https://www.livepokertheory.com) , I find countless parallels between poker and entrepreneurship.

Also, people don’t realize that startups aren’t one single event. There’s a million events and each one has its own luck. For example, you make a piece of content marketing there’s luck in whether it performs well, but that luck can be managed and the risk spread across many events by doing lots of small pieces of content marketing.

I also wrote a blog post about how a popular psychology book oriented towards poker pros (The Mental Game of Poker) can be easily reframed for entrepreneurs:

https://writing.billprin.com/p/the-mental-game-of-entreprene...

With all that said, it’s highly ironic you picked Moneymaker as your example poker pro, since he’s famous in the poker world for being a very bad amateur player who got extremely lucky at the perfect time . It’s a bit like talking about the importance of hard work and deep technology skills for founders, and using Adam Neumann and WeWork as your example of that.


> it’s highly ironic you picked Moneymaker as your example poker pro, since he’s famous in the poker world for being a very bad amateur player who got extremely lucky at the perfect time

You may be overly generous in your estimation of MY poker skills! However bad Chris is, I am sure I am not anywhere close.


Yes, ive played professionally. To be charitable I’ll explain it to you. In poker you play a massive number of hands and if you are good you play a preplanned strategy and sometimes when following that strategy you lose but over the long run, assuming you are playing a winning strategy, you make money.

The luck is seen in the short term fluctuations but over the long run when executing your strategy there is no luck.

This requires proper bankroll management among other things.

Also starting a business is easier than poker, poker is zero sum (more often negative sum due to rake).

Business is positive sum. What this means is people will gladly hand you money if your product generates more value for them than holding that money does. In poker, every single hand is like a fist fight because there is always a loser in every hand.


In this analogy, the VCs are playing poker. The hands (or the cards dealt to the VC player in that hand) are individual startups.

Yes you can win if you are a VC. Less clear what to do if you’re just a card.


Founders can take multiple shots too. Everyone is playing poker to an extent. VCs are playing cash games and founders are playing tournaments.




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