A good colleague of mine recommended 2 years as the maximum time to stay in a startup. You should know at that point whether it’s going to do well.

Ignoring any early pivots for pre-A startups, after 2 years you should be well on the way to a real product, have grown the team, and even have potential customers trying out the product.

Try to avoid falling into the trap of “just 6 more months”, or “I’ll wait for it to end”. You really want to avoid getting Startup Stockholm Syndrome.

Reasons to Leave

  1. Too much work.
    • This isn’t “too many hours”, but rather the remaining work for the company to be ready with a product.
    • Maybe the product was mis-scoped, maybe the team didn’t grow, maybe the team isn’t executing.
    • If everyone is working 80 hour weeks, but the product is still over 2 years away, that’s not going to be fixed without hiring.
  2. Not enough professional growth.
    • Remember that this is one of the key reasons for joining, so when it’s over, it’s time.
  3. Not enough influence over direction.
    • This can be frustrating if you were in early. You thought you were getting this role, but unless you are a CxO you really aren’t.

There’s other odd reasons as well. In a big company, there’s a team for everything, and that can be frustrating. In a tiny startup, there isn’t a team for everything, so you may be the IT admin, you may have to do the mundane tasks. That really eats into the time when you could be doing interesting work.

The corollary to all the new possible experiences, is that you may often have to start from scratch on your own to learn something. This can be fun, but is slow. It’s exciting to not know about anything, to become the company expert by the end of the week. It’s frustrating to have to self teach everything from scratch.

Like working with other people? Then a tiny startup may not be for you. You’ll interact at the high level probably daily, but on the low level technical details you’ll be on your own, for days to weeks at an end.