By Julie Bort


Michael Tauiliili-Brown, founder CEO of Win-Win

Mike Brown’s short-lived time in the NFL made him grateful for one thing: that his mom made him keep his grades up in order to play sports.

Thanks to that, today Brown has another dream job, as CEO of a year-old startup called Win-Win.

But back in 2009, when the two-time all-American linebacker from Duke University got picked up as a free agent for the Indianapolis Colts, he thought his dreams of an NFL career had come true. It didn’t. The Colts cut him from the roster at the end of training camp.

He kicked around for a few years in the United Football League, best known for its fast failure and low salaries. UFL went defunct after a few years.

“I didn’t play football for as long as I wanted to. I didn’t make it to retirement/pension. I was there for a Hollywood second, bounced around. Never able to get to big contract,” he told Business Insider.

In 2013, after four years, he was done as a pro player. He planned to go get his MBA. That’s when he, quite literally, got the calling to go to Silicon Valley and do a tech startup instead.

“I was getting ready to go to Rice University and a friend of mine in the Bay Area told me about this program that he heard about called Draper University. I didn’t know anything about Silicon Valley. All I knew that Facebook was here,” he said.

On a lark, he applied to the program but didn’t think he’d really do it.

Tim Draper comes calling

Soon after, billionaire VC Tim Draper personally called Brown. Draper is known for his eccentric, boisterous, confident personality. He’s hard to say no to.

Tim Draper

Business Insider

Tim Draper

“If anyone else would have called, I probably would not have changed my plans to go back to school. But he said, “Hey, Mike, this is Tim. We loved your application. You’re in. Full scholarship. We’ll see you in March. And I was like, “Uh. I guess I’ll change my plans.”

Draper University, as the program is called, isn’t a university but a two-month boot camp for wanna-be tech entrepreneurs. It had launched the year before as Draper’s brainchild to teach people leadership skills in unconventional ways.

While other accelerator programs focus on building a product, Draper U does things like military survival training (Draper calls it “hero training”) where students spend days in the wilderness foraging for food and shelter. They compete in offbeat contests too, like “to sell something embarrassing, or go to San Francisco and come back with a job offer, on paper, in 24 hours,” Draper previously told Business Insider.

At one point, Draper even turned his university into a reality TV show, Startup U, that aired on ABC Family, though