Startups, Improv, and the Character of You
I’m often asked what skills I think aspiring startup founders should pick up. And beyond the obvious response that no one should be taking advice from me about anything, my answer is always improv.
More than coding or Photoshop or Excel or what have you, improv is the skill from my past that has felt the most relevant to my life as a startup founder.
I was obsessed with improv in high school; I studied and taught it through all four years and sucked down every improv-related book and manifesto I could get my hands on.
I ended up completely losing my taste for it in college, and I haven’t performed or even seen real improv — Don’t Think Twice notwithstanding — in years. But I still use the things I learned every day.
My job involves doing a million different things I don’t know how to do and being a million different people I don’t know how to be. And I can’t always learn how to do those things or how to be those people.
But if I have to, I can play any of those characters. Improv is my shortcut to learning how to do anything: just pretend you’re someone who already knows how to do those things, and the skills themselves will follow.
Sales pitch? I’m playing the character of a charming and confident salesperson. Sales comes very unnaturally for me: I don’t like asking people for things, and my impulse is to be self-deprecating at every turn. But when you’re pretending to be someone else, it doesn’t matter what comes naturally.
Call with an angry customer? This character is contrite and determined to make things right, no matter what it takes. He’s deferential, but not obsequious, and he always understands.
He’d make a great butler — an Alfred-from-Batman type, the kind who developed a genuine emotional bond with his employer.
Investor meeting? This character is steely, focused, and unafraid. He works incessantly, but when he does go out, he’s capable of knocking back a few beers without acting even the slightest bit tipsy, and he’s at home in the fanciest of restaurants.
He’s going to succeed with or without you, so he doesn’t care if you invest or not — he’s just excited to be sharing his vision.
And the real me? The real me can never feel ashamed when a customer yells, because the real me never gets yelled at. The real me can never be stung by rejection, because the real me never gets rejected. And the real me can never blow a sales pitch, because the real me never makes sales calls.
The real me is just an actor playing a scene where my character is yelled at, or gets rejected, or botches a pitch. And when my scene partner leaves the room, the character disappears, and the real me is the same as he ever was.