Dear SaaStr: What Were Your Toughest Times Before Breaking Out?

My toughest times:

  • COO pulling out after signed term sheet — VCs then pulled term sheet. This of course was my fault — I hired the “wrong” COO. But boy it was tough. I had 9 employees on payroll and $0 in the bank.
  • Co-founder walking out the door. Man that’s tough.
  • Co-founder firing my other co-founder — without telling me. That was tough. It was hard to walk that one back.  I did, but things were sort of broken after that a bit.
  • Almost running out of money, having to work for $0 salary “again”. Working for $0 is not a big deal in the beginning, but it’s much tougher later.  More here.
  • Key / top customer telling you your product doesn’t work — and they won’t reconsider buying it for at least 3 years. Man.  Ship early, but not too early.  Especially to bigger customers.
  • Not being able to get the team to build something truly mission-critical, losing hugest deal because of it. You can’t do it all on your own.
  • Doing customer support for Europe every night for 3 months. Never really slept.
  • Not closing the epic VP of Engineering I really needed.  I tried 5 times, maybe 10.  I offered him half my equity and the largest salary in the company.  But looking back, I should have tried even harder.
  • Selling when you already have $10m+ ARR, growing 100% YoY, and are cash-flow positive. Even if the deal was fair.

As tough as all these were …

You are always one truly great VP hire away from solving them.  That’s my biggest lessons of all from these mistakes.

A related post on that here:

If You Don’t Think You Need a VP of Product, VP of Marketing, Etc. — Then You Haven’t Worked With a Great One

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