Q: How do I prepare myself to become a successful startup CEO?

My list of 5+ things that will help:

  • Manage People. This is one of the best things you can do, because 50% of the job of a CEO is recruiting a team, leading a team, empowering a team, convincing a team. This team will include investors, the public, press, PR, etc. — but it’s all a team. Manage anyone you can, even if it’s not perfect. My first management job was managing HR. I didn’t want to learn HR as a function, I turned it down at first. And then I realized I was wrong, apologized, and went back and took the reports. I was lucky I got the opportunity.
  • Work for The Best One You Can. This may be obvious, but try to do this at least once if you can. The best way to do this is to join the management team of the best start-up that will have you. Even if you get topped 12-24 months down the road, it’s worth it to have reported to (and thus worked directly with) the best CEO you can.
  • Find One Great Mentor / Advisor / Coach. Once you become CEO, find one person you can confide it, that can push you harder, point out where you need to do more, and generally simply help. Someone that’s done it before. More here: SaaStr | I Don’t Know about CEO Coaches. But We All Could Use CEO Trainers.
  • Try to Care More About People. And Show It. This is one of the top mistakes I see in first-time CEOs. They care so much about the company, but they forget to care about the people, the team. They just assume everyone should be as committed as they are. But everyone else can’t be. You aren’t going to double your EQ overnight. But try a few things. Say “Thank You” more often. Give raises more often. Give spot bonuses more often. Give 20% more shares to your top 10% employees, without them asking. Take the team on outings. Do a retreat for the whole company when you hit $5m ARR. Do stuff together. Do dinners. Stay late with the sales team when they’re trying to close the last deals of the quarter, and take ’em out for drinks after. Do it all. Again — if nothing else — SAY THANK YOU!
  • Hire People Better Than You (and That Aren’t Your Friends). Whatever you do, don’t hire executives that aren’t better than you. You can hire up-and-comers, that’s OK. But as CEO the key is everyone on the team should be better than you if possible. This isn’t a threat. It’s a way to make your equity worth 100x more. Before you are a CEO yourself, experiment here. Don’t just hire your friends, and don’t hire people that make you look good. Hire people insanely better than you, that look, act, and feel different. But that you 100% believe in. Amazing things will happen. You will learn so much here.
  • Stay.  The more you job hop, the less you learn about how to be a leader.  Staying a decade may be risky.  There’s only so much time.  But if you leave everything after 12-18 months, you will see a lot.  But you probably won’t learn a lot.  And at the margin, take that promotion rather than move on.  Try to become that director, that VP where you are today.  It’s less risky, and a faster way to advance, more times than not.  When they already know you and believe in you.


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