The Polsky Center at the University of Chicago has begun a yearlong celebration marking the 30th anniversary of the Edward L. Kaplan, ’71 New Venture Challenge (NVC), a startup accelerator program. The first event in the NVC@30 Fireside Chat series featured Matt Maloney, MBA’10, cofounder of Grubhub and a past winner of the competition.
The discussion was moderated by Mark Tebbe, adjunct professor of entrepreneurship at Chicago Booth School of Business and entrepreneur-in-residence at the Polsky Center. Steve Kaplan, Neubauer Family Distinguished Service Professor of Entrepreneurship and Finance and faculty director of the Polsky Center, opened the event by recalling Maloney’s early attempts to enter the competition. “Matt first applied and didn’t get in,” Kaplan said. “He came into my office, explained how his business worked, and I said, ‘Well, you didn’t write that in your plan.’ So, with that, he got in—and as you all know—he then won.”
Maloney discussed Grubhub’s beginnings as an advertising platform for restaurants before shifting its model to focus on food delivery based on restaurant performance. “Once I could say, ‘I make a dime when you make a dollar,’ that’s when everything changed,” Maloney explained.
As a part-time student at Booth who had not previously taken business or finance classes, Maloney noted: “I had a business that worked, but I didn’t know how to run it properly and communicate it to investors,” he said. “That’s the reason I came to Booth.” He described relying on faculty and mentors for guidance after an unsuccessful initial pitch: “We bombed our first pitch,” he said. “After that, we went to every faculty advisor we could.”
Maloney highlighted how classroom lessons informed real-time decisions while running his company: “I was in a marketing class when the professor said the easiest conversion is a repeat customer,” he recalled. “Later that day, I sent an email to all our customers asking them to order again—and it ended up being the biggest day we’d ever had.” These experiences helped him refine his approach: “We won first place and I immediately went all in,” he said.
Winning NVC did not lead directly to investment. “We spent the whole summer pitching and got nothing,” Maloney stated. “One investor told me it was a great idea, but it would take a lot longer than I thought—and they were right.” Eventually securing funding in late 2007 allowed Grubhub to expand into other major cities such as San Francisco, Boston, and New York.
Data-driven decision-making played an important role as Grubhub grew. “We had a lot of data that strongly supported our scaling,” Maloney said. He added: “Because of that, we knew early on that Grubhub could be a good public company. And at that time, that was the typical goal for a startup like ours.” In 2014 Grubhub went public after merging with Seamless; Maloney led the company until its sale in 2020 for $7.3 billion.
Reflecting on his entrepreneurial journey spanning two decades, Maloney shared insights with current students: “Being an entrepreneur is about persistence,” he said. “There are massive highs and lows. The successful ones are the people who stick with it longest.” His advice for future participants was direct: “Just do it. If you believe, go all in,” he said. “It’s a hobby until you make it your job. Once you take that leap, you can’t ignore problems anymore—and that’s when real progress happens.”
This fireside chat is one among several planned events intended to showcase NVC alumni founders over the next year as part of ongoing efforts by Chicago Booth’s entrepreneurial community.