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
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
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
“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
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
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.
“Life was also happening. I got married. We had a child,” he
said. “During that time, I taught myself how to code, how to
design. Knowing how to code or at the very least know how to talk
to developers is important. So all day, all night, laying in bed,
Brown’s wife finished up her master’s degree in education (while
she was pregnant) and got hired at California State University as
“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
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
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
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
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