A few that I’ve seen across the handful of investments I’ve made … that didn’t work out:

  • Not really committed to going long. This doesn’t so much make you a “bad” CEO as one that likely won’t get much past $2m-$10m in ARR. If you aren’t committed for 10+ years, you tend to exit one way or another … earlier.
  • Too reactive and emotional. Yes, you do need to care to be a great leader, at least generally speaking IMHO. But if you are too reactive to all the downs and bumps, you will overreact to them. Again, you gotta go long.
  • Dishonest or at least, a B.S. artist. The CEOs I’ve lost money in many cases lied about something, or at least, weren’t honest about something.
  • Can sell but can’t build great software. This one is a bit of a shame, but it happens. Sometimes, a non-technical CEO is so great at sales and the vision that sheer force of will allows them to sell several million of a product that just isn’t there, or isn’t very good. A great CTO usually can solve this problem just in time to save the customers, but without one, revenue stalls.
  • Too slow. The best CEOs and founders are just fast. Fast to iterate, fast to learn, fast to fix. Sometimes, in a new or emerging category you can be slow at first. But you usually at least have to speed up after that.

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