Here’s what I’ve learned, on start-ups #3 and #4:

Pros of Experience:

  • Better at Hiring. You now know what makes a good VP of most things. This doesn’t mean you are always a better recruiter. Recruiting takes a ton of energy and you do lose some as you age. But you get much better at knowing who can do the job well. And when you do make hiring mistakes, you don’t keep believing people can do a job that they clearly can’t. Rookies do that all the time.
  • Fewer Terrible Mistakes. The terrible mistakes you make in a startup almost destroy you. Everyone makes them. Making fewer of them really does help. I made several Very Almost Company Killing mistakes in my youth. I make fewer of them now.
  • Better Ability to Go Long. If it’s your first job or first startup, it can be hard to know how long to commit. Later you learn, it sort of has to be for forever to build anything that matters. It’s hard to plan much further than the length of time you’ve already done something.
  • Better Network. This really helps a lot. From mentoring, to advice, to customers and prospects, to partners. It takes a village. It helps a lot to already have at least some part of that in place.
  • You’ve Seen it Before. You know when to freak out and worry, and when not to. What to share. How to experiment, and when to go for it. Most importantly, you know when you have something. You can now see and feel the moment something starts to break-out, even when outsiders and even other insiders can’t see it. That’s when you pounce and push on the accelerator.


  • You Know Why Things Won’t Work. While this is a tactical asset, it can be a strategic liability. All of the companies I’ve started, the smart, experienced folks told me the markets were too small, or other great reasons why it wouldn’t work. They were right at the time, but wrong in seeing the future.
  • You Do Get More Tired. Maybe Not Everyone Does, But Most of Us. It’s not the hours, it’s the constant low-level stress. It does wear on you. And it’s harder to get on that next jet, to be away from the family, to cram your legs into coach. You have to make up for this with more efficiency with your time. And more help.
  • You Can Tolerate Failure. Maybe this is just me, but one of the one reasons my first two startups succeeded was because I couldn’t bear to fail. At this point in life, I don’t want to fail, but am more zen about it. I’m not sure that’s an asset.
  • Harder on Your Family. Family matters, and while it comes first, it often doesn’t really once a startup takes off. When you don’t have much of a family, the conflicts and trade-offs here are small. They aren’t small later.
  • You’ve Seen It Before. Related to the first point, but this means you kill things maybe you shouldn’t. Like, all the time. The art of entrepreneurship is also seeing why small things can grow big, not just why they are small and don’t work well today.

I’m not sure which mix is better. But I do know if you evolve your playbook, both stages of entrepreneurship can work well.

2 years ago, “SaaStr Inc” had $0 in revenue. We’ll do $14m in bookings this year. Without experience, that couldn’t have happened. But perhaps, the younger version of myself could have done something crazier.

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