Dear SaaStr: What’s Hard About Being a CEO?

A few learnings:

  1. The pressure ebbs and flows, but it never ends. Once you ship, you’re always under the gun. In the earlier days, it’s under the gun to make the cash last. Later, cash doesn’t matter as much as growth. But you always have to grow. In fact, each year, you often have to add as much in bookings as all the prior years combined.
  2. The others can quit, but you can’t. This isn’t that bad in reality, but it can feel that way in tougher times. That you can’t quit. The rest all can. You always have to be there.
  3. Lack of appreciation. This has weighed on me more and more as the years have gone by. One of the most rewarding parts of being a founder is enabling careers. Its tough when folks don’t appreciate it, or don’t appreciate it much. You can’t say it aloud, but it’s tough.
  4. When the best leave. I know many CEOs and founders say it’s great to see their top folks move on to even bigger and better things, but man it’s tough.
  5. There’s always some CEO that has it a bit easier. OK, this one is subtle, but it’s real. There’s always some hotter startup, growing faster. That finds it easier to raise capital, and recruit. It not that CEOs mostly need to beat folks that aren’t the direct competition. It’s more than it weighs on you. That say Notion or Calendly or whomever is just killing it, seems to be doing with about the same amount of energy as you are putting in. It’s just, they are going even further. You can’t help but sort of wonder, “Man, if only I was CEO of Notion”. At least a little bit.
  6. It never gets easier.  Yes, you get better.  But it never gets easier.  By contrast, a lot of “ordinary” jobs do get easier as you get better and better at them.
  7. Your family probably won’t really understand.  They may be there, they may not.  They may drift away over time.  The intensity of being a CEO, of always being responsible for everything, for always — most folks won’t get it.

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