What was the biggest mistake you ever made in your life that you don’t want to happen again?
I’ve had many almost failures and the #1 thing I’ve learned from them is never quit. The others will quit. They will give up when it’s hard. They will give up when you finally have customers, but not enough of them. They will give up when the market size looks too small. They will give up when it’s Month 12 and no one has a paycheck.
Giving up after a certain amount of time is rational. But don’t give up, ever, if you have something.
My failures are more subtle but painful. The first “failure” was my first start-up job, where we sold to a recently IPO’d startup instead of Amazon “just” for a higher price. But the quality of that compensation was lower. I lost that $12m in paper money just a few months later. We should have sold to Amazon for all cash. While that’s only somewhat clear in hindsight, there was so much pressure and so many conflicting interests. What we should have done was slowed down the process.
The next almost failure I had was shipping a product that really was not ready to a mission-critical customer. This is always a tough trade-off, but in this case it was way too early. I almost destroyed the company. But I was under huge pressure. We were almost out of money, and the future looked grim. My co-founder told me it was highly risky. She turned out to be quite right. But I felt I had to roll the dice. Still, I should somehow have found another way.
You have to take risks, but the learning from that experience is speed up 95% of decisions, but slow down the 5% of decisions that really matter — especially where the answer is unclear.
Push down almost all decision making once you can, but hold on to the key decisions that will decide your fate. Get more advice. Mull over them. Most important, don’t get too worried about external time pressure. That deal, that term sheet, that customer will probably also be there tomorrow. If it isn’t, perhaps that’s OK. We assume more deals and opportunities are about to blow up and expire than really do.