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 other co-founder without telling me. That was tough. Hard to walk that one back.
- Almost running out of money, having to work for $0 salary “again”. Working for $0 is not a big deal in beginning, but it’s much tougher later.
- Key / top customer telling you your product doesn’t work — and they won’t reconsider buying it for at least 3 years. Man.
- 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 VP of Engineering I really needed.
- 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 …