Dear SaaStr: Is it Bad to Leave a Failing Startup?

It can be a tough situation.

If you’re a critical resource and leave a struggling startup — would that increase the odds it fails? If so, do you have an obligation of some form to stay?

I’ve never failed as a CEO but I sure have come close. And most of the best folks stayed, but not all. All I can share is from that perspective:

  • Talk to the founders first. At least let them know you are thinking of moving on. They may at first react emotionally, but they’ll get it and may try to give you their best pitch to stay.
  • The beauty to startups is its OK if they fail and it won’t hurt your resume, not usually. So it’s worth it often to stay and see one more card played out — if you still believe in the founders. In the early days of Apple, Steve Jobs made this pitch. He told the best engineers there was a chance they might not make it, but worst case, there would be 10 other tech companies that wanted to hire them.
  • Is it really failing — or just struggling? Again, ask the founders for data. How much runway does the startup have? What will it take to succeed?  So many iconic startups have come close to failing in the early days — but pulled it out.

In the end, at least give notice. Ideally, twice as much as you otherwise would. If you just up and quit, the founders will likely be hurt, and likely never forget. Even if they say nothing. But if you tell them first you are thinking about it … and if you decide to go, give them 30 days notice … the relationship probably will be strong.

That oftentimes leads to something else great down the road.

A great session with the CEO of $30B+ Veeva on how in the early days, they almost always failed, so only set goals for just the one quarter ahead:


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