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Pep Rosenfeld hosts a corporate event
Pep Rosenfeld hosts a corporate event - Credit: Pep Rosenfeld / Pep Rosenfeld - License: All Rights Reserved
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Thursday, 24 April 2025 - 06:10

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Pep Talk: Boom Chicago's Pep Rosenfeld on improv comedy, and why work should be funny

Boom Chicago established the city of Amsterdam as a comedy hub in Europe. The theatre, monumentally situated on the Rozengracht in the capital's Jordaan neighborhood, is home to the improv comedy group of the same name. Notable alumni include Late Night host Seth Meyers, filmmaker and Key & Peele star Jordan Peele, Have I Got News for You panelist Amber Ruffin, and Ted Lasso star Jason Sudeikis.

Pep Rosenfeld co-founded Boom Chicago when he and his close friends, Andrew Moskos and Ken Schaefle, were trying to figure out in the early 1990s how they could spend more time in Amsterdam. Despite a lack of any support from the municipality and the live theater world in the Netherlands, the improv comedy venue became a hit with tourists and locals.

Rosenfeld developed and still leads Boom Chicago for Business, the side of the company which tailors trainings and hosts events for businesses. He recently authored his new book, Work-Laugh Balance which indicates how humor can make people more successful professionally. Rosenfeld sat down with the Dam Yankee podcast, in partnership with NL Times, to discuss the book, his tenure on the American legacy comedy show Saturday Night Live, and why he’s chosen to call the Netherlands home.

Dam Yankee: For a lot of comedians, corporate gigs are just a way to pay the bills while they pursue other dreams. You, on the other hand, are really successful in and passionate about this space. So much so that you wrote the book on how comedy is advantageous for business. How did you end up cornering this market?

Pep Rosenfeld: There are a couple of reasons. I was an economics major. I run my own business. I'm interested in business. I like coming into companies and seeing what makes them tick. I like hosting business events and learning what thought leaders are thinking and what the trends are.

I think your average comedian probably isn't genuinely interested in these things and doesn't have to be. Most comedians want to do their act and then walk away. And that's not what we do at Boom Chicago. When we do a show, we learn about the company, we find out what makes them tick, we write jokes about that, and then we perform our material. Every comedian likes it when they make jokes and the audience laughs. We make jokes tailored for these people so they laugh extra hard.

We're doing it differently. We have a different model. We're not the mountain climber that comes in and tells you about their mountain climbing story. We talk about you and make jokes about you. It's a great business model. We come in, we learn about a company, we make jokes, we make fun of them to their faces, we drink their wine and we send them an invoice. It's a great gig.

DY: You live in Amsterdam now, but after you co-founded Boom Chicago in the 90s, you briefly moved back to the States. Why did you move and why did you ultimately return to Amsterdam?

PR: We started Boom Chicago in 1993. In 1998, the company was looking like it was going to really grow. But, I still had some wild oats to sow. So, I went to Los Angeles and did stand-up, and tried to do some writing as well. I was friends with Rachel Dratch who was on Saturday Night Live for a while. She is super hilarious and also a very kind and helpful person. She told me they were going to be looking for staff and that I should come. And so that's how I got the job writing at SNL.

We got nominated for an Emmy for that season and the ceremony was going to be in L.A. Then, I woke up on September 11th, 2001 in New York City and everything was crazy. I spent a week in the city before I could rent a car and get out. I went to Chicago for a couple of weeks, and finally I went to L.A. where I had lived before.

I thought, you know, I've lived in all three of these cities. I've worked in all three of these cities. I liked it better in Amsterdam.

DY: What is it that you love so much?

PR: I just like life here. I like biking places. I like that people are chill. I like that it's not a 40-minute drag to get anywhere and everywhere. I like this concept of “gezelligheid”. Maybe when I first arrived in Amsterdam I'd get furious because it took so long for dinner and I had a movie to catch. But I got used to it.

I like that there are not TVs everywhere you go. I like that there is not advertising in my face everywhere I go. It's a good life that we have in Amsterdam. It's easy to forget that, but we've got it good here.

Pep Rosenfeld’s book can be purchased online in English or Dutch for 24.99 euros as a paperback, or 13.99 euros as an e-book. The agenda for Boom Chicago includes information about tickets for their in-house improv shows, local performers appearing on their stages, and the touring acts they host at the theater.

Listen to this entire episode of Dam Yankee wherever you get your podcasts, or watch the full videos on YouTube. Rosenfeld goes on to dispel who speaks better English: him or Queen Maxima, and what exactly he said to get a laugh out of President Obama.

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