What’s the Link Between Improv & Entrepreneurship?

Welcome to BW Missions Newsletter 24

Finishing my final class at DC Improv last Saturday was bittersweet. Six weeks of embarrassing myself for two hours in a row every weekend. Between you and me, I had no idea what to expect when I first signed up. I felt an urge to try something totally new and leaped in headfirst. 

When I called the local improv center, they told me they had 2 spots left. Scarcity tactics or not, I signed up that same day. After, I called my parents and played the upcoming birthday “card” to get my mom and dad to each pay for half. If you don’t know, I call this the perks of divorced parents: Us kids get the same perks twice, from birthday presents to Easter egg baskets. 

But seriously, why does improv matter, especially for this big-ideas audience? I learned so many lessons from improv, but my biggest takeaway comes down to the level of human connection. Everything is about building on top of a solid foundation, including launching a company. In our personal lives, it’s about finding the people who can make things better and improve upon what you have in place. It’s not just about saying “Yes” but also “Yes … And.” The best people you’ll meet are the ones with an unquenchable desire to carry ideas forward.

On the contrary, in college, I also know a lot of “Yes… but” people. They tended to point out the challenges, roadblocks, and obstacles, which made it feel like they were stifling my ideas in their tracks. On the flipside, critiques can be really helpful. These two types of mindsets are why the world works so well. Acknowledging critiques and finding improvements help lay out the steps to get from idea to reality. We need people whose thinking styles are both contrary and complimentary.  We need people who can dream big and overcome challenges, and also practical people who push us to be better by expanding our worldview.

On an existential level, the game of entrepreneurship is about embracing the “Yes … and” mentality. It’s about rolling with the punches and even making them a part of your story, rather than hiding the times you struggled or even failed. Fighting your way through in the short term makes you better by the end of the process. 

I’ve taken many risks over the past 6 years, so I’m no stranger to the vulnerability that comes with exposure. I’ve wondered, “Will I be good at this?” countless times.  In these improv classes, I often felt a familiar timidness tinged with the discomfort and even fear as I challenged myself. The first half-hour of each session, believe it or not, felt just like an entrepreneurial warmup. 

Even though improv was a new endeavor, these sensations were no different than anything I’ve felt before. It was just a different environment with new people. As I reflect on the community we built together,  I realize we were ultimately a team of 20 united under one mission. We were the builders of ideas, connection and conversation. In those moments, anything was possible.

Chris Ulrich: Newsletter 24 Featured Mission

Chris Ulrich has made his life’s work helping people get out of their own heads and see their true potential. When we feel comfortable in our skin, we can convey our true identities with pride and carry ourselves with confidence and ease. This is no easy feat, but it’s absolutely within reach.

His company, CU in the Moment, provides body language training and improvisation techniques that help people think on their feet and take action faster. This training program also involves developing active and mindful listening skills, critical thinking, and creative problem-solving.

Chris has empowered executives, salespeople, government staffers, lobbyists, and small business entrepreneurs to transform their executive presence simply by changing their body language. He’s a regular face on major media outlets like CNN, Good Morning America, Fox Business News, MSNBC, and ESPN. Chris was my improv coach at DC Improv and made the class incredibly enjoyable. Connect with him on Linkedin 

Growth: Newsletter 24


The COVID-19 pandemic has shocked our systems, posing threats not just to our health, but also our relationships, jobs, and the future. In just a matter of weeks, the coronavirus has stretched us all thin. We all need some guidance right now, so I reached out to thought leaders, founders, and executives to share their stories of resilience. Read about their unique experiences at the links below:

Opportunities: Newsletter 24


In 2008, Brandon Green was hit by the economic downfall and almost lost everything in the process. His story of overcoming the past decade from both a leadership and financial perspective is one for the ages. To respond to COVID, he’s been working with entrepreneurs in two ways:

  1. Accessing any of the government financial assistance programs requires navigating complex loan and grant applications. Many small business owners are under-prepared and overwhelmed by these processes and requirements, which means they won’t be able to secure the resources needed to survive Q2.
  2. Many small business owners don’t have complete, accurate, or organized financial reports — exacerbating the near-term problem and exposing a vulnerability that, if not fixed, could tank their business later.

This is personal for him: Brandon lived this experience in 2008.
 If this resonates with you, feel free to connect with him here.


A Rising Tide Lifts All Boats
My friend Jake Hurwitz whipped up a fascinating project connecting volunteers in NYC to entrepreneurs. I’ve been really impressed with Jake since I first met him, and this project is one that can help so many. trying to keep their dreams afloat. Check out the website here

Book Recommendation of the Week
Our body language can speak volumes about who we are without us saying a word. Think about comics like the cast of SNL; sometimes the parts of improv skits we laugh the hardest at are physical comedy. Learn how to align the message you physically communicate with the impression you want to make in author Janine Driver’s book You Say More Than You Think.

One Teacher Away From Understanding Humanity Beyond the Transaction 

Kevin Schafer exemplifies many of the strengths and skills I consistently focus on improving in my own life. His inspiring leadership and community-building skills are something to be admired by anyone working in this space. Listen to his full story on the One Away Podcast, and learn my top five takeaways from our thought-provoking discussion.

Taking Memorial Services to the Digital Realm During the Pandemic

The Coronavirus pandemic has resulted in countless losses of every kind for so many people, from careers to housing, to the ultimate tragedy: loss of loved ones, and loss of life itself.  After facing down the pain of losing his mother, Dave Kerpen has created a solution to temporarily replace traditional funerals with an online platform that’s custom-built. Learn more about Remembering.Live here. 


Next Gen HQ is teaming up with Dell on Thursday, April 16th at 1 PM EST to host a series of entertaining webinars with incredible entrepreneurs and leaders designed to ignite inspiration for entrepreneurs stuck at home. 

Join them for Igniting Inspiration LIVE! – a series of entertaining, engaging, and enlightening interviews alongside empowering entrepreneurs! 

My improv instructor started off the final class by saying this line. On the micro-level, he was talking about how the small pieces of improv are what really help you stand out and make people laugh. The funniest sketches come to life when you can make the “big stuff” lighthearted and give some weight to the “small stuff” in life.

“Make the big stuff, little.”

After my last class, I thought about how this quote applied to the greater context of my life. Without asking the hard questions and facing the ‘little” challenges head-on, they will inevitably turn into more significant issues down the road.

Conversely, as overwhelming as the “big stuff” might feel in the moment, all of these questions, actions, and decisions are actually composed of minor ones packed together. Once we break them down, they become so much more manageable. Try this strategy and see for yourself.

The Pathfinder
Catherine Kushan

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