Dear SaaStr: What Are The Best and Worst Parts of a Startup?

The best parts:

  • Having a great team. Once you really have a great team, not just some great individuals — magic happens. It’s truly special.
  • Lifelong relationships with the team. Building long-life friendships grounded on a multi-year journey together. Pretty powerful.
  • Relationships with other CEOs. The ones you went through it all together with.
  • The victories. The first $1m ARR. The first $1m day. The first $1m customer. We don’t celebrate these victories enough, but they never get old.
  • Always something important to do. You’re never bored. It’s more than this, but when you’re on that journey together, truly building something — you’re never bored. Sometimes tired. Even a little burnt. But never bored.
  • Always challenged. This can be stressful, and tiring. But if you’re scaling a tech business, the pace of change always challenges you.
  • Builders gotta build. My most unhappy stretches have been when I haven’t been building. Being a founder solves this.
  • Not working for “The Man”. The benefits here are real. You’re in charge of your own destiny, at least in part.
  • Keeps you young at heart — and curious. A curious mind keeps it all going.

Toughest parts:

  • Being let down. The co-founder that quit. The partner that threw you under the bus. The VC that never believed.
  • The big mistakes. Blowing a huge deal. Make 1 or 2 truly bad decisions. They haunt you. The 1000 small mistakes, you move on from. But there are a few big decisions each year you just gotta get right. And you won’t get them all right.
  • When you can’t. When you just can’t get that feature built. When you just can’t get there fast enough. A lot of this is part of the journey. But when you come up truly short a few critical times, that’s beyond tough.
  • Recruiting is always hard. It never really gets easier.

(Note: an updated SaaStr Classic answer)

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