We had an entrepreneur in this week who, one of my partners said admiringly, “owned the room.”
He was not a jerk, or shameless, or a “bad boy,” as many of the entrepreneurs we see are. If you grant me that chutzpah is the golden mean between self-effacement and shamelessness, they slosh over into shamelessness.
This guy didn’t do any of that stuff. He just thought he was pretty good and made us think it, too.
How? Humor, for one thing. He poked fun at some of his early assumptions building his company, and did so in a way that brought us in on the joke. He made fun of VCs a bit, too, but, unlike jerky entrepreneurs, it didn’t sting. Again, we were in on the joke.
Also, he made persuasive arguments with logical steps in them to show us why he believed he was doing well (his potential is good but his numbers aren’t there yet). And, unlike jerky entrepreneurs, he didn’t try to mislead us. He told us all his trial installations were just that: trials. The logical arguments made sense, and made us think he was sensible even though the proof isn’t there yet with his company.
A lot of people seem to think chutzpah means “win/lose”: you grab at something before I can grab at it and take it away from me.
By being funny and sensible, this entrepreneur made his nerviness “win/win”.
Hope we get the chance to work with him.