An improv comic, an NHL player and a Fortune 500 CEO walk into a theater … but it’s no joke, it’s big business.
The Second City, the venerable Chicago-based improvisational comedy institution, has quietly built out a surprising side-hustle: Using the fundamentals and tactics of improv to teach corporate executives and professional athletes how to be better communicators.
That division, Second City Works, is not new. In fact it has been around for decades, but the rise of social media, where brands, executives and athletes are all expected to have a presence, has put a renewed emphasis on the skills necessary to succeed in 2025.
“We don’t teach people how to be funny,” says Tyler Kempf, creative director of Second City Works. “Humor exists in our programs because they’re fun, because we have a good time, because it gets a little silly, but we’re not there to teach people how to be funny. We’re there to teach people how the skills that we use to create comedy on stage directly apply to those skills in their real-life experiences.”
Second City Works has become a centerpiece of Second City’s business, which, under the ownership of Strauss Zelnick’s private equity firm ZMC, has already expanded to include new improv training facilities and theaters in New York and Toronto, alongside their Chicago home base.
Terms of the 2021 sale to ZMC were not disclosed, but reports at the time pegged the deal at around $50 million. Second City, like many similar companies, struggled amid the COVID-19 pandemic. And while live events have rebounded since then, many companies in the space have leaned into alternative revenue streams, corporate training being a unique one.
Kempf says that Second City Works now has more than 80 facilitators in the U.S. and Canada, all trained in the art of improv, and that the division has held more than 650 events in the last 18 months, with a client list that includes Uber, Adobe, the NHL and Chicago Cubs.
“No matter what sector we’re in, I will always ask, ‘how many of you are scared right now to be here?’ and hands just shoot up,” Kempf says. “The idea of improvising is fear-inducing.”
But the skills of improv, including what Kempf calls the “cornerstone philosophy” of “Yes, and…” has proven itself to work for both corporate executives looking to do team building or media training, and pro athletes wary of engaging with reporters or posting on platforms like TikTok or Instagram.
“I would argue that while many people know what that phrase [Yes, and…] is, they don’t truly understand what that philosophy is. For us, it’s about accepting the reality in front of you and then building upon that reality. It’s not saying yes to everything,” Kempf says. “It is about giving them the ability to ‘yes, and…’ so they can move that conversation forward, and to do it in an authentic way that connects with their audience.”
Second City knows a thing or two about that world, having helped build the foundation of improv comedy in the U.S. through its improv classes and performance groups, with an alumni list that reads like a who’s who of comedic legends, from Bill Murray, Joan Rivers and Gilda Radner to John Candy, Tina Fey and Stephen Colbert.
In the case of pro athletes, the skills being developed often manifest around the nature of media today. Journalists want more access and coverage than ever, while athletes are expected to become media personalities themselves. It may come naturally to some younger players that grew up with Instagram, but for others it takes some teaching, and Second City Works has developed a formula for that audience.
“What we focus on has developed over time as the skills that they need continue to develop or change … right now, social media is a big part of that,” Kempf says. “We did this program last week, and there were some players who asked, ‘what if I don’t want to be a personality on social media? What if I don’t want to talk to press?’ And we have realistic conversations around how that could negatively impact their career by not leaning into that part of their job, or how to find the authentic version of themselves in that space so it doesn’t feel like they’re performing or being anything other than what they actually are.”
“As we look each year to enhance the curriculum at our annual NHL/NHLPA Player Orientation Program, the importance of Second City’s participation and presence is never questioned,” NHL deputy commissioner Bill Daly says. “Whether it’s hosting the NHL Hot Stove; getting the Players engaged in the morning energizer sessions or delivering our media training, they always play a critical role in helping us connect with the Players in meaningful ways.”
“The Second City has become an important part of our NHL/NHLPA Player Orientation Program, bringing the perfect mix of energy and humour to create an impactful and engaging experience,” adds Marty Walsh, executive director of the NHL Players Association. “Working closely together, the Second City aligns their approach with our objectives, understanding the importance of making each session resonate with the players.”
And whether the client is a Fortune 500 CEO looking to improve their public speaking, a mid-level ad sales exec doing team-building or an up-and-coming NHL star hoping to figure out TikTok, Second City Works will hone their classes and seminars to meet the moment, and goals, of each group.
“Improvisers have to listen thoroughly to their scene partners and their audience. We can’t get in our heads thinking about what we’re going to do next. We can’t preplan, otherwise we might miss a detail, and then we’ve lost the scene, and then 300 drunk people are mad at us,” Kempf says. “It’s the same when you’re working in media, you need to be a great listener to that person who is interviewing you, so you understand the questions that are being asked, and while you might have some pre-planned elements ready to pull out of your back pocket, the thing that audiences or fans connect to the most is authenticity.”
This story appeared in the Oct. 22 issue of The Hollywood Reporter magazine. Click here to subscribe.
