Mike Brown’s short-lived time in the NFL made him grateful for one thing: that his mum 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.
“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.
“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 it only ran for one season.
Brown loved it.
“I came out of Draper very confident,” he says. “Ideas are coming out Draper’s head like crazy. As wacky as the program seems to be, it changed my life.”
He vowed to himself, “I’m going to move to Silicon Valley and I’m going to start my own startup.'”
Cold calls and working hard
But he didn’t have a job in the expensive Bay Area, so he went back to Houston, determined to return.
Brown’s wife finished up her master’s degree in education (while she was pregnant) and got hired at California State University as a counselor.
“My wife believed in me. We moved to the Bay Area the next year. My job was to get a job,” he said.
Once in the Bay Area, he contacted everyone he could think of. He sent a cold email to a guy at a startup called Kiip who graduated years after him, but remembered the star football player.
Kiip is a mobile advertising company known in its early days for its young founder, Brian Wong, who landed $200,000 of seed funding at age 19. He was one of the youngest people to ever land funding back then, in 2010.
Brown was offered an entry-level, cold-calls sales job. He worked his way up to a full sales job within four months and started making “good money,” he says. He also had another kid on the way. “We moved to a bigger place. I became the tech guy for my friends. They started pitching me ideas. It was funny. I was in a really good place.”
While at Kiip, his co-workers talked him into joining their Fantasy Football sports league, his first time playing. They convinced him it wasn’t about winning the money at the end of the season but about teasing each other all season long.
That was the same season that FanDuel and DraftKings were smothering the airwaves with ads, which got Brown thinking. Why weren’t the players tweeting about the daily fantasy?
“I called players that I knew and they told me two things: they didn’t care enough to have an opinion or they flat out didn’t like it,” he said. One player, Pierre Garcon of the Washington Redskins even sued FanDuel for using his image repeatedly on an infomercial without permission or compensation. (They settled out of court.)
Replace gambling with charity
It gave Brown a “light bulb moment,” he said. If fans were really just playing for fun, not money, why not let the money go to the player’s charity, something “that is more impactful and more important to an athlete? And in exchange you would be able to win something that money can’t buy,” like hanging out with the athlete.
He asked the players if they would be willing to donate their time or other stuff if it raised money for their causes and “100% of the time, ‘Hell, yeah’ was the answer. Because they didn’t even have to do anything. They didn’t have to host a golf tournament or a benefit dinner,” he said.
Brown was laid off from Kiip in November and founded his company, Win-Win in January, just in time to attend the Fantasy Sports Trade Association (FSTA) conference in Dallas.
That’s where he pitched his startup idea to a panel that included Mark Cuban.
Cuban didn’t invest, but the exposure helped him land a bunch of other angels who put in about $1 million, he says.
“Within nine months, I had built a small team, raised a good chunk of money for a first time founder and launched on time,” Brown says. Win-Win currently employs four full-time people and three contractors, he says.
The first tournament was launched in September at the start of football season. The prize was a trip on a private jet with Arizona Cardinals cornerback Patrick Peterson to watch the LSU vs. Alabama game with him. The tournament raised money for the Louisiana flood victims via the Baton Rouge Area Foundation on behalf of Peterson.
Other tournaments gave away sideline tickets to Cardinals and San Francisco 49ers games, and prizes ranging from signed jerseys to discounts at the sports retailer, Fanatics. Brown wants everyone who plays to win something.
Currently, Win-Win makes its money by taking a small percentage of the entry fees but he says he’s exploring other fees, too, perhaps on the marketing/advertising side.
For his first year, he’s attracted about 3,500 players and had over over 65 athletes express interest. He’s now ramping up to launch for the NBA season and launching other ways to play, like bracket games.
While there’s no telling if Win-Win will ultimately succeed, the concept is intriguing. Because all the money goes to charity, Win-Win may not face the kind of “is-this-gambling?” scrutiny that originally plagued FanDuel.
And Brown is living his second dream of being a tech entrepreneur.