What are the signs that an entrepreneur will always be small time?

I answered this question on Quora recently and thought I’d post a variant of that answer here.

There is lot of good information in the other Quora answers, so check those out. I’m going to come at it from a little bit lower level, a more personal and personality perspective.

I’ve worked with a lot of early stage tech. startup CEOs over the years, seed, pre-seed, and ground floor. Everyone knows the numbers, where by far most fail or at least never achieve “home run” success.

A few traits that are immediate red flags for me are:

  1. Unable to learn or listen. They already know everything. This is by far the worst trait and means run away. Investors want to see confidence but it can cross over to stubbornness and arrogance. Sure, you have the Steve Jobs’ and Elon Musk’s of the world that get away with it but they are just too rare to make it a good strategy to pair up with these kinds of people as a rule.
  2. No innate respect for contributions from team. A CEO with a strong tech background that can’t appreciate sales and marketing or a sales-oriented CEO that can’t appreciate product development are both recipes for disaster. If the CEO has to be reminded to thank the team, walk away. If they don’t value the contributions of people, intrinsically, they wont attract and retain good people; and that is one of the main jobs of a good CEO, as noted below.

Again, there are so many good perspectives in the other answers, and I won’t repeat them here. The final thing I’ll add is: avoid CEOs that don’t know what the job is. At a startup, the two main things CEOs need to do are raise money and recruit and retain talent. If they aren’t good at these things, if they don’t absolutely live for these things and love doing them, they will probably fail as CEO — they might be valuable and thrive in some other role but they shouldn’t be CEO.

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