The Two Games You Can Play at a Startup

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Short thread on something I wish I had understood much better 10 years ago:

If you are ambitious, there are basically two games you can play at a startup. Many people early in their careers (especially those from big tech, consulting, finance) play the wrong game, and lose both.

  • Game 1: Optimize for company outcome. Spend all of your time finding and fixing the highest leverage problems you can

  • Game 2: Optimize for career outcome. Seek external signals like title, scope, and team size. Make sure you’re “learning the right things”

The more your personal outcome and the company outcome are synonymous, the more obvious it is that Game 1 is the right choice. Founders and people at startups with <10 people almost always play Game 1. At the largest companies, it’s more natural (and probably actually in your best interest) to play Game 2. This is close to the definition of why it is so awful to work at very large companies.

But at most startups, even those with hundreds or thousands of people, it’s almost always the right choice to play Game 1. Doing so will result in a better outcome for the company, but also a better outcome your career, for two reasons:

  1. Startups are an iterated game. Earning a reputation for playing Game 1 opens doors

  2. It’s actually very hard to know what is good for your career. Being pulled by the intersection of what the company needs and what you’re good at works better than any “20 year career plan”

As a result, the right move is to focus on putting yourself in the best companies with the best teams you can, and then playing Game 1.