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I recently participated in an “Improv for Entrepreneurs” workshop run by Mary Lemmer, a founder-turned-VC who now teaches improv to companies and professionals. I’ve done a couple of these types of workshops over my career and seen a few improv shows — they’re really fun. Improv is like freestyle rap or live jazz: it might not be as polished as a studio album track, but it’s impressive and enjoyable to watch someone make stuff up on the fly.

If you like comedy but haven’t seen any improv before, I’d highly recommend it. Try taking a class or a workshop too. It’s hard to explain why improv is so funny, but here’s a 3 min scene (i.e. a contained performance) of first date where two actors play the guy together by “speaking with one voice“. It’s hilarious and also clearly challenging.


1. In our session, Mary had us write down leadership challenges we were facing. We started with a few exercises like Zip-Zap-Zop and Alliteration Intro. Similar to how you stretch and do a light jog to warmup before a run or workout, improv requires an emotional and mental “warmup” to get people in a chatty, creative, and open state of mind.

Then we did some improv scenes, which had as their prompts the leadership challenges we outlined earlier. I was in a 4 person group and our prompt was the one I had written down (launching and iterating on a new product). Except in the scene it was a sex toy, a much more salacious topic.

2. The first and perhaps only true rule of improv is “Yes, and“, meaning when your scene partner says something like “Isn’t it such a nice day outside?” you don’t negate them and say “No, it’s freezing and awful.” but instead build on it by saying “Yes, and the snow outside is perfect for skiing” (if you wanted to avoid the cliche sunny day situation).

But one of the other lessons / rules Mary introduced was “Play the scene that you’re in”, which similarly means, play the role that you’re in. If you’re not the “main character” of the scene, don’t try to force yourself into that position. That doesn’t mean be passive, but play the “supporting” role you’re in to the best of your ability. And in short order, you’ll probably see a moment to really shine / reshape the dynamic.

3. They say that doing a startup is like jumping off a cliff and building an airplane on the way down. You have to make up a lot of things along the way. In that regard, there are a lot of similarities to startups. Time is urgent—you can’t stop for 2 minutes to think about what you’re going to say next in a scene any more than can you deliberate for 6 months on how to go to market with your product.

Fundraising is very much a dance of improv. You play hundreds of scenes with roughly the same prompt (pitch yourself and your company) but a different partner and varied settings. You have to adjust on the fly based on how your partner is responding to you.

4. We played a game that night where you had to deliver “a report” to someone with a specific tone / energy (excited, disappointed, scared, angry, up to you) and you then had to swap place and receive the report from someone else, while maintaining your original emotion.You quickly realize that emotions are contagious. If you start out happy but the report deliverer is angry, you either become angry too or scared. Learning to both stay in character and respond to someone else’s emotions is tough. But probably valuable.

Similarly, I remember a pitch meeting where the partner looked completely bored with what we were doing, had no questions and it was really hard to stay excited during the pitch. My cofounder and I thought the meeting was a bust, but they ended up investing! I guess the lesson is that your enthusiasm matters even if you aren’t getting much back from your partner.


If you’re a founder or work in a field that’s going through a lot of change, it might make sense to get better at making shit up. Improv might be one way to shake yourself loose from old patterns and get more comfortable taking social risks that can pay huge dividends in the marketplace.

Photo by Simon Migaj from Pexels

Published by Jason