Blue dices in orange background

No Dice

Retired Booth professor Waverly Deutsch shares how Dungeons & Dragons inspired entrepreneurial simulations in her course Building the New Venture.

Portrait image of Waverly Deutsch

Waverly Deutsch joined the Booth faculty in 2001. An angel investor and advisor to startups and venture-capital firms, Deutsch launched the UChicago Global Entrepreneurs Network before her retirement from Booth in 2023. In this recollection, she talks about the novel approach she took to Building the New Venture, the MBA course on entrepreneurship that she created and then taught for 15 years.

As a kid I played Dungeons & Dragons, the game in which you assume a character and operate in a world with challenges. A roll of the die dictates whether you accomplish those challenges or not.  

I thought, “I can adapt that to an entrepreneurial simulation”—not a computer simulation with strict guidelines and rails, but much more like Dungeons & Dragons, where the gameplay was in the mind. You had to create the story as you went.  

I made a set of assignments that imagined the first 18 months of running a business, from forming your team and getting your initial funding to going through a product-prototyping phase, doing customer research, finding a market, making early sales, and building processes.  

I told my students, “In a written paper, tell me what happened in your company during those months. And the way that you figure out what happens in building the company is you go out and do research. Go learn what it takes to sell as a tiny startup by talking to salespeople, by looking at case studies.”

The other piece that I borrowed from Dungeons & Dragons was fate. Luck. The students would turn in their papers and they’d say, “We hired this experienced CEO to join our company who’s going to bring us all his connections in the industry for customers, and he’s going to invest $250,000 in our company.”

And I’d say, “OK, come on down in front of the class and tell us how you did that. How did you recruit the senior guy to come to your little startup? How did you meet him? What kind of compensation package did you offer him?” 

I had these software calculators based on Bayesian probability analysis. My teaching assistant would put pluses and minuses into the calculator based on what they said, and it would spit out a percentage: 60 percent chance you were able to hire that CEO given that method.

Then they would have to roll a 10-sided die, the way you do in Dungeons & Dragons. If they got one to six, great—they had their CEO with his connections and investment. They could continue on. But if they got seven, eight, nine, or zero, it didn’t happen, and they had to write a backup plan.

That was my way of simulating the market and the pitfalls of entrepreneurship for them. My goal was to get them to learn how to research, how to be an entrepreneur, and to experience the tension of, “Are we going to make payroll this month?”


—Speaking with Ram Shivakumar, adjunct professor of economics and strategy, in March 2024 for his video series, Pivotal Moments. Watch the full conversation and view more episodes on YouTube. Remarks have been edited for space and clarity.

Did Your Startup Plan’s Fate Rest on a Roll of the 10-Sided Die?

Or perhaps another novel teaching tool has stuck with you from your time at Booth. We’d love to hear about it. Write to us at editor@chicagobooth.edu and tell us your story. We may share it in a coming issue.

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