Yes, And

When asked what’s required to be a great investor, I often suggest a willingness to learn improv. That’s not to suggest that you have to be funny or comedic. Rather, an ability to lean in, listen, and play on a team. Improv and its “Yes, And” approach is dynamic; it’s collaborative and constructive.

I learned in the 2nd grade that I’m a terrible singer when my music teacher shared with the class that “the noise Rick is making was a scream, not music.” She then suggested that I learn the violin instead (which I failed at too). 

Thanks Mrs. Collins!

So you’ll understand how mortified I was when in my first Improv class that I reluctantly joined (see: I blame Jeff) included a singing scene. For 5 excruciating seconds, I screamed to a room full of strangers. 

I was terrible. 

And no one cared. The class’ attention shifted to the next performer instantly. Improv asks you to be in the moment. And then leave it behind.

The most powerful rule of improv is: “Yes, and.” The class circled up and was asked to construct a story using sitcom personality references. I was so eager to drop a Jazz from Fresh Prince comment that I ignored the prior student’s cue and broke the flow of the story. What was more important: proving that I’m funny or improving the story? “Yes, And” asks you to accept the reality that is presented and build it up. Or pivot in a collaborative way versus promoting an agenda or tearing it down. 

We were asked to play a parent / child scene. My improv father asked me why I dropped out of school. I said “because school was boring and I can’t believe he was making me go.” Our teacher cut the scene and proposed: “whenever you can, choose awesome! How about dropping out of school because you founded a social network and are worth a billion dollars? Live in the positive.” Life’s more fun when you squint your eyes.

Improv is theater, yes, and (see what I did there?) and has become a  development framework for me. I often struggle with imposter syndrome and improv is a reminder that getting things wrong is just as important as getting something right! And it’s defined how I work with founders. There is no VC without entrepreneurs founding ventures, so let’s build them up — not tear them down. 

I’m working on improving my balance on the advocacy/inquiry scale (I lean heavily on advocacy) and improv reminds me to squint my eyes and see the awesome future they see. This is about them, not me. Listen more, talk less. 

“Yes, And” is dynamic; it’s collaborative and constructive. I see it when Jeff asks  “yes, and if everything goes right, what will your business be in 5 years?” When Brentos says, “it’s amazing and tell me more.” And when Joele offers, “What’s cool about the brand is X and how do you feel about why?” We can simultaneously lean in on the dream and reveal how many “ands” — how many things need to go right to make it a reality. 

So, all that to ask: who wants to take another Improv class and hear me sing?