You Probably Shouldn’t Work at a Startup

It's overrated—both financially and emotionally

TL;DR

  • This article is for someone trying to decide whether to work at an early-stage, venture-backed startup.
  • There is a romantic vision of startup employment that doesn’t hold up under close scrutiny. 
  • Business model risk is extreme and the financial opportunity cost is significant.
  • Typically we assume that a startup is a better overall employment experience, this probably isn’t true for most people
  • There are some circumstances working at a startup makes sense! But it is important to go in with open eyes.


If you work in Silicon Valley for long enough, you will have your own near miss story. This is when, through unfortunate circumstance or innate stupidity, you reject or ignore a startup opportunity that would have paid off big. We all have them. I blew off Allbirds in early 2017 (who needs more ugly sneakers? Turns out everybody, apparently). My editor Nathan did some freelance work for Coinbase in their first year, never really followed up (whoops), and asked to be paid in USD (double whoops).

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