Though her earliest love was theater, Chicago Booth clinical professor of entrepreneurship Waverly Deutsch pursued business knowledge from the beginning of her academic career thanks to a high school teacher who told her she would never be a professional actor. After earning a theater history PhD at Tufts University, she got a crash course in entrepreneurship as a research associate at Forrester Research when the company was on the cusp of “rocket ship growth.” Deutsch later moved to Chicago, where she consulted and worked with a variety of ventures. At one, hoping to bolster their advisory board, Deutsch’s male colleagues encouraged her to get in touch with Ellen Rudnick, MBA’73, Booth clinical professor of entrepreneurship and executive director of the entrepreneurship center, now the Michael P. Polsky Center for Entrepreneurship and Innovation. (“They said, ‘You’re female. You guys have so much in common.’”) Rudnick joined the board, Deutsch confessed to Rudnick a desire to teach, and soon Deutsch was guest lecturing at Booth.

Thirteen years ago, after Booth built out its entrepreneurship curriculum, Deutsch came on full time. She now teaches the popular class Building the New Venture, using her award-winning YourCo simulation game, which allows students to develop and run a mock business through all phases of operation. Deutsch also advises students in Booth’s annual New Venture Challenge business plan competition. From 2006 to 2009, in conjunction with the University’s Collegiate Scholars Program, she designed and taught an intensive two-week summer seminar on entrepreneurship for promising high schoolers from Chicago public schools. The Magazine’s interview with Deutsch is edited and adapted below.

How does a theater history PhD end up teaching at a business school? My passion as a kid was theater. I knew I wanted to pursue a theater degree but thought I would also pursue a business degree just in case I would go into theater management. I had a smart guidance counselor my first year who said, “Don’t do an undergraduate business degree. It’s a watered-down MBA. Do something relevant to business but go deep.” So I took a computer science class and fell madly in love with it. I ended up doing two degrees at the University of Pittsburgh: computer science and theater. If I had listened to myself a bit better, I probably would have pursued computer science.

I knew what I really wanted to do was teach. I won the Mellon Fellowship in the humanities. I couldn’t convince anyone that computer science was a humanity, and I had this money to go do a PhD. So I ended up at Tufts. And what I learned was that being an academic in the humanities was not going to make me happy. I loved teaching, but the kind of research that I was doing was irrelevant to the world. I did my dissertation on a 19th-century theater manager named Laura Keene, who happened to have the misfortune that her troupe was playing Our American Cousin in Ford’s Theatre the night Lincoln was shot. She, in fact, identified John Wilkes Booth.

Did your background in computer science help you create YourCo? What informed this much more was the fact that as a kid, I was in love with Dungeons and Dragons. There is an element of the YourCo process where anything that their business accomplishes, the team can be called down on the carpet in front of the class to tell us how they did it. What was the step-by-step process you used to raise that seed funding? What was the process you used to land that first customer? While the students are telling us how their company did this, my TA will put pluses and minuses into probability calculators. Did they do it in a way that would make it more or less likely to succeed? The calculator spits out a probability. And then they roll a 10-sided die. We use that to discuss a lot of things that would be really boring to lecture on.

Do you still play Dungeons and Dragons? People don’t do Dungeons and Dragons the way they used to. The way it was played in high school, you had to have a really brilliant kid as the dungeon master. That person literally created their world. My dungeon master was a very odd guy. He was a college administrator who still played with high school kids, which was a little awkward, but he was a brilliant dungeon master. Now it’s all done by publishing companies and moved online. It’s World of Warcraft now.

You’re an angel investor. Are there any projects you’re involved in now that you’re particularly excited about? I just invested in a local company called the Stylisted, which was started by one of my former teaching assistants and her business partner. It brings independent stylists into a woman’s home before a big event. It’s funny that I invested in this; I don’t wear makeup. But they convinced me through their business metrics, their passion, their persistence, their hard work.

In many of your talks, you’re blunt about an entrepreneur’s low chances of success. Why that message? Entrepreneurship is very hard work. Failure is an essential, necessary part of the process, because if you’re being truly innovative, there’s risk involved. So I like to use scare tactics to make people think about why they want to be an entrepreneur. Then I teach them about principles and practices of experienced entrepreneurs that are different from what you read about in the press. Mark Zuckerberg taking his company public is the exception. Most companies that go public are on their third, fourth, fifth CEO, not the founder who had the original idea and grew the company.

One of the most gratifying things that happens during my class is when a student, in his or her final reflection paper, will say, “The best thing I learned in your class is that I don’t want to be an entrepreneur.” I say, “Good, because if everybody was an entrepreneur, who would the entrepreneurs hire?”

How did you get involved with the New Venture Challenge? Pretty much as soon as I started teaching at Booth, I was asked to participate as a coach. The first year I sat through it, the students were allowed to talk for 20 minutes and there was no structure to their presentations. Because I have a lot of public speaking experience, I created a presentation on giving a good business plan presentation. That became a lecture at the midpoint. So they have to struggle through their first round of presentations.

What’s the biggest lesson students typically need to learn? They think that because they’re so excited about their idea, that everyone will be excited. They don’t understand the challenges of behavior change or that there are problems in the world that we don’t pay to solve. So it’s getting them to learn how to tell a compelling story about an actual value proposition and convince the investor they have a clue how to build it, because you don’t just pitch a vision, you’ve got to pitch a step-by-step process to get to that vision.

What’s it like teaching this particular generation of students? Teaching is about improving the way people think. For an entrepreneur, 90 percent of what you need to know is in somebody else’s head. And you learn faster by talking to somebody than by Googling all day long. Because you can ask questions, you can interact.

Given that they’re the millennial generation, they don’t want to talk to people. They want to send out email surveys; they want to text someone. “He doesn’t respond to my emails.” Well, pick up the phone, you know? That way of learning is something that kids have lost. If I can teach a generation of entrepreneurs to jump-start their learning by involving more people from their network in the process, by finding people who have done it before and learning from them by adopting best practices, I’ve made a huge impact.