Improv and Entrepreneurship

I have two degrees from Stanford University and an MBA from Harvard Business School, but I often tell audiences that my work in improvisational comedy has been more impactful on my career than any of those diplomas.

I feel very fortunate that I came across improv when I was a freshman at Stanford. Unlike some of my friends who had planned out their entire college careers and lives before arriving on campus, I saw college as an opportunity to try new things. During my very first quarter, I took an introduction to Acting class from the legendary Patricia Ryan Madson, followed by her Improv class the following term. I had, of course, participated in various school plays and musical performances when I was younger (I’m an all-time great at memorizing lines, but I never got cast in any big roles), but neither I nor those endeavors were particularly serious. In contrast, Patricia and her classes were, and I found myself learning principles and exercises to change my instincts.

After those classes, I joined one of Stanford’s improv comedy performance troupes, Spontaneous Generation (AKA SponGe) and after a diligent apprenticeship, was awarded my official SponGe uniform shirt and added to the performing company.

We held performances all over campus, and even hit the road to perform at college comedy festivals (to much acclaim, at least as I saw it!). We were good enough that some of our members ended up going into show business full-time (one good friend and frequent scene partner of mine was even nominated for an Oscar a couple of years back).

Looking back, those nights performing on stage were one of the best preparations imaginable for an entrepreneurial career.

First, my improv experience taught me how to be comfortable on stage. But there’s a difference between being comfortable on stage on performance 37 of a musical that you’ve spent months rehearsing, and being comfortable on stage not knowing what’s going to happen next. People who have seen me speak at various conferences and events often admire my ability to adapt to unexpected technical difficulties and hiccups; these seem like minor obstacles in comparison to improvising an entire musical number on the spot!

Second, improv taught me to stay in the moment and really pay attention to what’s happening around me. It’s comforting to make plans, but many planful people lose some of the benefit of their diligence by being reluctant to deviate from those plans, even as circumstances shift around them. Improv focuses on building on what is actually happening in the moment, which is critical for entrepreneurship.

Finally, my time as a performer taught me how to win an audience over. Improv is one of the few performance art forms where the performer can completely revamp their performance on the fly. An orchestra won’t improvise a new movement if the crowd seems restless. Even a standup comic is going to use crowd work rather than shifting to completely new material. Whether I was pitching a VC, recruiting a potential employee, or striking a deal with a business partner, I could tell when my audience was and wasn’t buying in, and could keep trying different approaches until I either succeeded in winning them over or ran out of time.

Even today, one of the standout bits from my standard workshop on storytelling is when I take volunteers from the audience, and after hearing their startup pitch, immediately pitch their company back to them, only 10 to 100 times more effectively. I’ve never seen anyone else in Silicon Valley do that, and I can credit my willingness and ability to improvise a new startup pitch on the fly to my experience as an improv performer.

P.S. Here is my favorite improv scene of all time. If you watch it, you *will* laugh!

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