Let me make a short list instead 🙂
- Having a critical co-founder walk out the door and never return. This happened to me once with a true co-founder, and once with a critical early employee (a critical COO). The learning is, slow down sometimes to go fast.
- Losing a very key customer — due to product not being ready. Did this both times. The learning is probably again, sometimes slow down to go fast.
- Losing a key business partner — due to pushing too hard and fast to hit milestones.
The common theme of these worst mistakes/memories seems to be moving too quickly on certain very key strategic hires and actions.
Move fast and break things on 99% of what you do.
But on the 1% that really matters, that is make-or-break — maybe slow it down. Get help from your mentors. Sleep on it. And if it doesn’t feel right … find another way.