When I enrolled in my first improv class back in 2012, I told people that it was because comedy exercised parts of my brain that my day job as an entrepreneur did not. Five years later, I take that back. It turns out doing improv and starting a business have a lot in common.
In 2009 I co-founded an analytics startup called RJMetrics. We ended up growing to over 100 team members, raising over $20 million in venture capital, and being acquired by Magento Commerce in 2016. The experience of building a business, growing a team, and learning to lead — even over this past year as an acquired company — was all new for me.
So was improv. Just as RJMetrics was taking off, I began regularly performing with Big Baby, a house team at Philly Improv Theater. Over the years, I’ve come to appreciate the complementary nature of the skills I’ve built in the office and on the stage. Here are three things improv comedy has taught me about starting, and running, a company.
Always say “Yes, and…”
It’s the first lesson in Improv 101 and the foundation of all good improv: When in doubt, say “Yes, and…” to the new ideas your scene partner puts on the table. Acknowledge the reality of the scene you’re in, whether you created it or not, and accept it as the basis on which you’ll build something new. The same principle holds true in business. The best entrepreneurs pay close attention to the realities of their industries, then say, “Yes, and…” to build from there.
This technique is all about discovery, and entrepreneurs who understand, accept and add to their realities are more likely to discover a competitive edge. Disruptive companies like Venmo, Square and Stripe didn’t achieve their goals by working in isolation or starting from a blank slate. Instead, they looked at existing financial institutions and consumer behaviors to build a better, more valuable reality for us all.
It’s important to note that “yes, and” is not about blind acceptance. It’s about listening and incorporating new information, a process that often sets boundaries rather than expanding your universe. In running a company, this approach ends up being quite powerful. For example, when customers make unrealistic asks, framing your response as a constructive “yes, and…” statement can help reframe the reality without dismissing their perspective. “Yes, your business is important to us, and so we need to set clear expectations about what is and isn’t realistic. If we lose money on deals like this, we won’t be here to serve you. And if we try to deliver on this ask without repricing the deal that’s what will happen.” You’re agreeing, but reframing the facts of the situation to bring both parties into a shared reality.
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Develop customer (and audience) empathy
No two crowds are the same, and as an improv team we must master the art of reading feedback and adjusting in real-time. In one recent performance, I realized our 20-minute show had been happening for at least 10 minutes, but my character hadn’t said a word. There I was, silent on stage, and the audience was likely thinking, “Who is this dude, and what’s he even doing up there?”
By empathizing with the audience — putting myself in their shoes — I was able to call out the uncomfortable situation and make it a source of comedy. “Is my time-out over yet?” I blurted out. My savvy teammates quickly used “yes, and…” to justify that my character, indeed, had been forbidden to speak for ten minutes. This unlocked a fun new game of exploring the circumstances that led to my time-out in the first place, raising the stakes and adding new information and context to the ongoing scene.
An entrepreneur has the same responsibility, because failure to empathize with customers and acknowledge what’s on their minds will quickly put you out of business. Customer sentiment can turn on a dime, but it’s easy to get ahead of these changes — good and bad — when you invest in a deep understanding of what customers care about. As an improviser, you do this by going to see other shows and sitting in the seats of an audience member on a regular basis. As an entrepreneur, you do this by using your own product, knowing your competitors’ products, and talking to your customers all along the way.
Play the long game
Longform improv sets typically run between 20 and 25 minutes, and Big Baby performs a style known as a “bunker monoscene” in which the entire show is a single scene in a single location. Without scripts or props, you need to think critically about how to make the most of that time in a way that keeps the audience engaged. It comes down to making thoughtful investments in character development and details early on, allowing for relationship growth, steadily increasing stakes, and emotional investments that build to a satisfying crescendo at the end of the show.
Performers think about this obsessively when shaping their characters in the opening minutes of a scene, because that groundwork is what tees up satisfying outcomes later on. One of my favorite starting points is to play an old grandfather, because there is so much richness in how their personality can be revealed over time. While he may start out in a chair blurting out incorrect Jeopardy answers at inopportune times, that seemingly one-note trope can evolve as you realize that he has a unique relationship with every member of the family, memories from a 30-year career, and untold wisdom that arrives when you least expect it. And then he screams at the TV again. Doing the upfront work to create flexibility and options for your team provides you all with a powerful utility belt to pull from when things get slow.
In business, the balancing act is similar. In an evolving economy, every entrepreneur’s early investments are key to his or her team’s future success. These are core business investments: Mission. Vision. Values. And they extend to include anything from the principles you adopt to the products you develop, and the way you go out to market and sell. Like improvisers, the best companies define their values and core beliefs early on, but preserve optionality for discovering new opportunities as they explore the world from within that framework. In both cases, taking the time to do this right will leave you with no regrets when the show reaches the end of its run.