Sebastian Rivas (Andes STR) interviewed by 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.

Coco Meers’ career has centered on helping women look and feel their best. When she caught the entrepreneurship bug and looked for a pain point to solve in that space, she kept remembering a long flight delay she had when traveling between Paris and New York and how she wished she could spend the time getting an eyebrow wax in town – if only she knew what salons were good, nearby, and available.

Her idea for PrettyQuick was to offer a marketplace for booking beauty services much like OpenTable does for restaurant reservations. She chose to attend Chicago Booth so she could take the idea through the New Venture Challenge, where in 2011 she tied for third place and received $10,000.

She recalls presenting to the panel of judges, which at the time was overwhelmingly male, and feeling that they couldn’t quite identify with the problem.

“With the emergency of eyebrow and bikini wax booking, I didn’t get a lot of confirmatory nods at the time,” Meers, MBA ’14, laughed.

Meers, who sold PrettyQuick to Groupon in 2015, has since committed to helping improve gender diversity among startup founders and investors. She launched Rebelle Collective, an angel fund that invests in women-owned companies, and through that platform cofounded Equilibria, a premium CBD company targeting women.

In conversation with Starr Marcello, deputy dean for MBA programs at Chicago Booth and former executive director of the Polsky Center, Meers discusses the times PrettyQuick nearly failed, why marketplaces are so difficult, and why she made the tough choice to sell to Groupon.