Through the Lookingglass: A founder’s journey with David Schwimmer

David Schwimmer ’88 can still taste the sashimi.

The meal represented the first bit of success for a Northwestern undergrad who had turned an avant-garde off-Broadway play into an off-campus cult hit.

“I used my Bar Mitzvah money — about $3,000 — and I found a theater off campus,” Schwimmer told an audience of 300-plus Kellogg students about his first entrepreneurial endeavor, self-producing an adaptation of “Alice in Wonderland.” “At the end of the run I had made enough money to take the entire cast out for sushi.”

His hunger to succeed has never left.

Before graduating in 1988, Schwimmer, classmate David Catlin ’88 — now head of acting at Northwestern’s School of Communication — and six other students formed the Lookingglass Theatre Company, an ensemble steeped in collaboration, transformation and invention on stage.

No one knew what was to come.

Months after forming Lookingglass, Schwimmer performed in a senior showcase and was told he had what it took to be a Hollywood star. His first stint in Los Angeles lasted just a year. Jealous of his friends making their mark in Chicago and demoralized by the repetition of auditions, rejections and small successes, Schwimmer returned to the Windy City.

Chapter 2: Raising capital

Like most startups, money remained an issue. Beyond ticket sales, the ensemble implemented a “reverse stipend,” where members would contribute 10 percent of their outside earnings … and be fined $1 for every minute they were late to rehearsal. 

“Over the years, what I found was that this group of people has made me feel the most like myself. They became the antidote to an often ego-driven industry."

And Lookingglass remained a nomadic company, seeking places to perform as they worked on a minimalistic and physical type of acting inspired by Jerzy Grotowski, Schwimmer recalled.

“I found it extremely meaningful to hear from and be able to humanize an individual who has achieved huge success,” says Mrin Bhushan ’26 One-Year Program. “What stood out to me is that at the end of the day, David began as a student dreamer at Northwestern and did what it took to keep doing what he loved.”

Chapter 3: From startup to showtime

Sitting on a stage in late April 2026 opposite Greg Hanifee, associate dean of degree operations, Schwimmer discussed the evolution of Lookingglass.

Deciding he would continue to pursue a mainstream acting career, Schwimmer spent the early ’90s balancing TV and film roles with the theatre ensemble that lived within his soul. In 1993 he filmed his first TV series, playing Henry Winkler’s son in a sitcom that would only air six episodes.

“I saved over $100,000 and moved back to Chicago and vowed I would never do TV again,” Schwimmer says. He was playing Pontius Pilate in the Lookingglass production of “The Master and Margarita” when the phone rang.

“Success is a combination of preparation, hard work and luck,” says Hanifee. “David discussed the role of luck in his talk, and we heard the same thing a week before from Ken Potrock ’84 MBA, president of Disney Partnerships. We’ve heard this motif from almost every alumnus that returns to the Hub; I think having David articulate the values and principles from his entrepreneurial journey — an actor and theater owner — reinforces that being true to your values matters.”

Chapter 4: Friends and ‘Friends’

“Over the years, what I found was that this group of people has made me feel the most like myself. They became the antidote to an often ego-driven industry,” Schwimmer says.

That ensemble mentality made its way to California, too. When renegotiating his own contract, Schwimmer encouraged the cast of “Friends” to unite so that each member would be paid the same. 

“What struck me most listening to David was how consistently he backed bold vision with real action. He didn’t just dream of taking his college production of ‘Alice’ to Scotland, he asked the dean for funding, and when the dean offered to match whatever he raised, he went out and raised it,” says Sally Minn ’26 MMM Program. “Rather than following conventional advice to negotiate the highest individual salary he could get on ‘Friends,’ he trusted his instincts, organized the entire cast and pushed for a collective raise instead.”

Chapter 5: Lookingglass finds a home

Nestled between Lake Michigan’s shoreline and Chicago’s landmark water tower, sits a small theatre just minutes from the school’s downtown campus.

While half of the building is used to pump water to Chicago’s north side, the other half has been home to the Lookingglass Theatre Company since 2003.

“We were enjoying a certain amount of stability at that time and were asked to apply to become tenants in this incredible landmark building on Michigan Avenue,” Schwimmer recalls. “Lois Weisberg, the commissioner of cultural affairs, had this amazing idea of putting a theater in that space, and we won the lottery. The city and state gave us $3 million, and we had to raise another almost $5 million to make it a reality.”

Schwimmer directed the first play in Lookingglass’ new home.

“At that time, I felt like I did what I set out to do. I felt like we had arrived,” says Schwimmer, who was still working in California. “I could feel that things had stabilized. We had a much bigger ensemble, we had a great staff and we had great board of directors.”

The stability allowed Schwimmer to think more fully about his personal life.

Chapter 6: New beginnings

“Today, I’m living in this post COVID-19 chapter in which I have a 15-year-old,” Schwimmer says. “There was a moment before my kid was born where I felt I could step back from Lookingglass, while still voting as an ensemble member and put trust in other individuals to lead.”

As a company, Lookingglass has survived the many changes in the world around it, including seeing its front porch, the Magnificent Mile, turn from the most-walked street in the Midwest to desolate sidewalks during COVID, to a now-budding cultural experience once more.

Schwimmer’s fireside chat at Kellogg culminated with a question-and-answer session, during which students asked about his motivations to continue to lead in the nonprofit space, his joy for acting and his love for Chicago.

“I really enjoyed his perspective on the ensemble mentality and how he has taken that with him from his early career all the way through today,” says Sargam Prakash ’26 Two-Year Program.

“I hope the students took away the need to follow passion but be realistic and adaptive about the journey to get there,” says Hanifee. “David had to make many trade-offs in becoming both a paid actor and director/lead for Lookingglass. We always see the accomplishments, but there’s a lot of sacrifice along the way.”

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