Matt Maloney (Grubhub) & Mark Tebbe

Matt Maloney admits he had a bit of an ego when he entered the New Venture Challenge. He had already launched Grubhub, had a few customers, and had landed at a top business school.

But during his first presentation to the NVC judges, he fell on his face.

“You could tell mid-way through, the blank stares, people were expecting unit model economics,” Maloney, MBA ’10, recalls. “They’re expecting financial plan. What do you need to invest? What’s the runway? What’s the outcome? What’s the next round? What’s your marketing plan? What’s your hiring plan? We weren’t even doing a good job of explaining the technology and the product itself.”

Maloney followed the advice to speak to all of the Booth advisors he could in order to gain insights on everything from marketing to quantifying the opportunity. Grubhub ended up tying for first-place in the 2006 NVC and the following year secured a $1.1 million Series A.

“We didn’t change the product. The opportunity didn’t change. The solution didn’t change. It was completely about how did I go about communicating to potential investors the opportunity, the solution, and the potential payout,” Maloney said.

Chicago-based Grubhub, which went public in 2014, has since become a mammoth food delivery company. A deal to be acquired by Amsterdam-based Just Eat Takeaway for $7.3 billion is set to close June 15.

In this episode, Maloney, who continues as Grubhub’s CEO, speaks with Mark Tebbe, an adjunct professor of entrepreneurship at Booth who calls Maloney the “poster child” for the NVC.

They discuss the leadership challenges at a fast-growing company, why some markets were not successful for Grubhub, and the difficulty of learning how to sell.