I’ve done two start-ups to at least some success, and I wish I could do a third.
But I can’t.
The reason is my current inability to intensely, completely commit 24x7x365 to succeeding no matter what it takes, period.
Being a founder of a successful start-up is so hard. There is infinite, or at least intense, competition. Whoever you are disrupting wants to kill you. Recruiting talent is a never-ending struggle. Until you have a true brand, you have to convince customers to buy from a vendor they have never heard of and have no reason to trust. There’s never enough money. You might have to mortgage your house and max your credit cards just to make payroll. You might not even make some payrolls. You are always X months away from bankruptcy. Your family doesn’t really understand, so it takes a toll there. Once you finally get somewhere, the next generation of start-ups is ready to eat your lunch — and doesn’t have a dated tech stack. Etc. Etc. Etc.
I’ve done it twice and 50% of the reason I had some success was that I never quit, no matter what the odds, no matter what anyone said. And that I obsessed about not failing and succeeding every millisecond of the day.
The intensity of that for me is hard to sustain infinitely. You can take breaks in a start-up, and let your team carry the ball for a while once you are at Initial Scale. It does get easier once you have a great management team. But that 24x7x365 intensity — it never goes away.
I wish I could do a third one. I know the playbook now, the right team, the right people, the way to really build an enduring unicorn. But … it’s harder now.
I did it for 10+ years as a founder, which is nothing like doing it as a VP or an investor. It’s harder now.