What’s the toughest part of running a startup?   A partial list:

  • Recruiting.  This is always hard, forever.
  • Co-founder Conflict.  Hopefully, you don’t have this.  If you do, boy it’s hard.
  • Almost running out of money.  Happens to almost all of us. Not fun.
  • Loneliness at the top.  Tough indeed.
  • Having to rebuild the team every few years.  Man.
  • Falling behind the competition.  Painful.
  • Losing momentum.  It’s so, so hard to get it back.

That’s a lot of tough stuff 😉

But one visceral memory I had was of a celebration dinner with friends after Adobe acquired my last startup.  I was so tired, I barely made it to the restaurant.

And then I had to choose between 3 open parking spots.  But I couldn’t chose.  I just sat there.  

It had been 5.5 years of mission-critical decisions.  Many of which I got wrong.  I just didn’t want to, I couldn’t, make those decisions anymore.

I’ve of course bounced back since.  And what I’ve learned is you have to find someone to help share this load.  I had a lot of help here, a great VP of Sales and VP of Product to help.  But it was not quite enough.  Not as much as I needed.

As CEO, you have to make a few big decisions right a year, and maybe 20-30 tough decisions a year on top of that.  And many others every day, that you have to make.

Delegate where you can, push down the decisions that can be un-made.  But get more help, as much as you can, on the bigger ones.  Because you’ll get some of them wrong.  And just the pressure of getting most of them right, it’s more than we realized.

It was the biggest weight of all for me.

A related post here:

Dear SaaStr: I Sold My Company And Made Real Money, But I Still Feel Like A Loser. What Should I Do?

(image from here)

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