How the Second City Pivoted to Become a Startup at 60

By relying on its improvisational ethos, the Second City made a quick pivot to virtual offerings that is already showing signs of long-term benefits.

Written by Kelly Leonard
Published on Apr. 23, 2020
How the Second City Pivoted to Become a Startup at 60
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My first gig out of college was as a dishwasher at the world famous Second City comedy theatre in Chicago. It was 1988, and the resident stage cast included Bonnie Hunt, Mike Myers, Joel Murray and Jane Lynch. Chris Farley and Tim Meadows had just been hired into the Second City Touring Company (basically the AAA squad to the resident stages’ big leagues). Within a year, I had worked my way up to a job in the Second City’s box office.

At that time, we had no computers, just one Brother electronic typewriter. We didn’t take credit cards, only cash. A few years later, I have a very distinct memory of the Second City being wired to join a new thing called the internet. A member of one of our teen improv ensembles by the name of Simeon Schnapper was doing the wiring. Today, Simeon is a wildly successful tech entrepreneur.

I eventually made it out of the box office, and, in 1992, I became producer at Second City. I got to work with such talent as Stephen Colbert, Tina Fey, Amy Poehler, Steve Carell, Keegan-Michael Key, Amy Sedaris and many others. In 2015, I wrote the book Yes, And: Lessons From The Second City, which focused on the principles of improvisation and how we take those skills and bring them to the business world. “Yes, and” is the idea that, when people are making something out of nothing, they don’t get far saying “no,” and they don’t get much farther saying just “yes” by itself, either. In improvisation, you say “yes, and” as a way to affirm others and contribute to the piece in order to explore and heighten new, creative ideas within your ensemble.

Essentially, the Second City is a content and education company: We deliver a variety of entertainment products and we teach people a variety of skills that can make them more creative. And while the Second City has become more and more reliant on web-based platforms for the business of running the theatre, the core of our work  the day-to-day products and services that pay the bills  is distinctly and profoundly live. We offer live shows and live classes in our theatres and classrooms, on cruise ships and at conferences and in venues all over the world.

And then, on March 15, 2020, it all shut down.

Now, as I write this a little over a month later, the Second City is a virtual entertainment and training company. Over the course of one month, we pivoted to become a tech startup at 60 years old.

Although we weren’t prepared for this, we did have three things that gave us a bit of a head start. The first was that the Second City Training Center had been offering online writing classes for many years. Though this wasn’t a huge part of our business, at least we had some content that was built to be delivered online. Second, at the time of the shutdown, we had already been in discussions with a contact at Zoom about the potential to use their service to reach the various corporate audiences that are consumers for Second City Works, the business-to-business division of the Second City that brings our content and training to thousands of organizations all over the world. The third, and most important of all, is that we are the foremost global experts in improvisation.

Expertise in improvisation provides a bunch of skills that have proven useful as we’ve made this transition. For instance, through improv, you practice leading groups of people to make something out of nothing, the ability to see all obstacles as gifts, a mindset that plays the scene we’re in instead of the scene we want to be in, and a kind of jocular resilience that holds to the “yes, and” philosophy of improvisation. We aren’t interested in “no” or “yes, but.” When operating from “yes, and,” you can rapidly prototype creativity and innovation. So that’s what we did.

By March 17, each division  our theatres, our training center, and Second City Works  figured out how and when we could move our business units from live to virtual. This was never a matter of “if.” An improvisational mindset assumes that, if you do enough experiments, you can make the thing that needs to be made. We took our own medicine. In improvisation we say that all of us are better than one of us and that we need to bring a brick, not a cathedral when collaborating to create something new.

Since the Second City Training Center already had a leg up on the rest of the company, it went first. All the live writing classes were immediately switched over to virtual formats. Check. Moving acting classes to a virtual setting really wasn’t such a stretch either, given how many actors are already doing their work on tape for casting directors on each coast. Done. Our Harold Ramis Film School was able to transition online, as was our Comedy Studies program at Columbia College, through a mixture of Zoom sessions and taped lectures. With these segments of our training secured, we had to turn to another question: how do you teach improv online?

Our faculty went into action testing out platforms, including Google, Zoom and Skype. We quickly discovered that Google Meet was the most easily accessible platform for our students. Our faculty started sharing discoveries about leading various improv exercises in an online format with each other, talking about what works, what doesn’t, and what exercises could be adapted to fit this new, digital classroom.

Two weeks after ending in-person classes, we’ve been able to retain 85 percent of our current students at the Second City Training Centers. Because innovation so often happens at gunpoint (to borrow a phrase uttered by my friend Steve Kakos about businesses’ response to crises), we began thinking of customized programming that could be created to meet this moment. In the world of shelter-in-place, many people find themselves being parents and homeschool teachers while simultaneously attempting to work their professional jobs. So we launched weekday camps for kids ages seven through 18. Offered from 10 a.m. to 3 p.m. in three time zones, these camps give parents a bit of help in keeping the young ones occupied during work hours.

The line “never waste a crisis” has been attributed to everyone from Winston Churchill to Rahm Emanuel, but we began to see more opportunity inside this particular crisis. So we also decided to begin offering low-cost, drop-in improv classes that could attract new students. In our first week offering the drop-ins, we had 100 registrants. In week two, that number grew to 400 registrants. This week, we even launched an improv class in Japanese. Despite all the disruptions that come with a global pandemic, it’s fascinating to discover what becomes possible when you are no longer forced to be tethered to one common physical space. When you are no longer stuck in a certain building, in a certain city, in a certain country, the world can become your classroom.

At Second City Works, we dialed up our friends at Zoom, who immediately leapt to help us in any way they could. For instance, a client asked if we could provide a virtual improv show for them, simply as a morale booster for their employees. Another asked us if we could take the live collaboration workshop we were supposed to lead for them in a few weeks and instead deliver that virtually. Of course, we responded with a “yes, and.” The fine folks at Zoom expanded our existing licenses to expand our potential audience to 10,000 people and provided the kind of tech support we needed to move our new ideas forward.

As we started discussing how we would have all our talent improvising from their home computers, we realized that there was a certain segment of The Second City family that wasn’t home alone. An interesting aspect of working at the Second City is realizing just how many people met and married their significant other at the theatre. When we started figuring out how we would create the improv show, we asked ourselves, “What if we used three Second City couples who were quarantined together?” When we reached out to the alumni, the response was overwhelmingly positive. Everyone wanted to get in on the act. We set up a series of rehearsals so we could get used to all the elements of Zoom technology and experiment with which improv games could work in this new medium.

While this was happening, our sales team talked to the dozens of clients who had upcoming live sessions booked with us. Although many of them decided to cancel, a handful discussed the idea of having us create sessions that could be delivered online.

Unlike our Training Center, where in person classes are conducted with no more than 18 students, the corporate workshops are often done with hundreds, if not thousands, of employees. It’s not unusual for us to send a dozen facilitators to Austin one day, Los Angeles the next, and then back to Chicago as we deliver live, interactive workshops on how to collaborate, create and navigate change more effectively. These corporate workshops are often as much a performance as they are a learning session, as we have to keep these large crowds engaged and laughing in order to get our learning objectives through. Here was another “yes, and,” moment, albeit one that we were not as confident about until we started to get our hands dirty.

Based on the Training Center’s experience, we knew we could translate the exercises online. Keeping the attention of hundreds of corporate team members, all sheltering in place and sitting at their computers, was a bigger challenge though. This is where the “content” part of being a “content and education” company became a distinct advantage. In addition to the exercises, we have access to thousands of filmed scenes from our stages, as well as digital shorts that could be streamed as part of the workshops. That way, we can use our entertainment as another way to teach. Better yet, when the pandemic hit, we had just finished editing a new digital workplace series called The Feedback Loop as part of our “Improvising Radical Candor” partnership with New York Times-bestselling author Kim Scott. The core of the program is a five-episode sitcom set at a fictional company that is struggling to implement the elements of “radical candor.” The series is accompanied by cheat sheets and a playbook that help the end user to practice these elements in their own work lives. So we were lucky enough to already have a distance learning program primed to go.

So we brought all of these assets together: facilitator-led improv exercises, hilarious workplace content and an ever-expanding set of digital tools (chats, polls, Q&A, handraises), and we began delivering the virtual sessions to our clients just three weeks after our offices shut down.

After these successes, we wanted to try out everything we had learned in adapting to serve our student population and our corporate client base in a format that could appeal to our widest audience: the millions of individuals and groups that have attended our live comedy revues since we opened our doors in 1959.

We had no idea what to expect when we announced our first live virtual, improv show, called Second City’s Improv House Party. We announced our first Thursday night show just 24 hours before going live. By showtime, over 3,000 people tuned in to see alumni from Chicago, Los Angeles, and Toronto improvise for 40 minutes. One of my favorite parts of the experience was seeing everyone who joined the session sign in and say hi from where they live. We had audience members in Brazil, Nova Scotia, Mexico City, Frankfurt and London, among others. Our weekly show audiences continue to grow into the thousands. Previously, our largest theatre was limited to a physical capacity of 290 people.

So what does all of this mean for the Second City as a business? Well, we have been able to keep a core staff of 70 people or so on payroll, with their insurance intact, and providing them the chance to do meaningful work. While many of our profit centers are closed to us for now (we still haven’t figured out how to sell Long Island Iced Teas during the online shows), we have expanded our audience exponentially, and not just in the global sense. We’ve taken down many barriers that stood in the way of all the people who couldn’t interact with the brand, either by circumstance, disadvantage, or inequity. Right now, anyone with an internet connection can experience everything that the Second City has to offer.

We will always be masterful in our live domain. But now, when we reopen our physical doors, we won’t ever have to shut the new doors we’ve opened when we improvised our way through COVID-19.

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