Mike Tauiliili-Brown ’08 was the captain of the football team and a two-time All-American when he played at Duke.

Now, he’s at the helm of a different team: a Silicon Valley tech startup called Win-Win – named that because the users of the service have an enjoyable experience while simultaneously donating to charity.

Founded in January 2016, Win-Win partners with professional athletes and allows them to host sports tournaments, such as a Pick ‘Em Pool or a March Madness challenge. They can then invite their fans to play in the tournaments, with fans’ entry fees donated to the charity of the athlete’s choice. The grand prize is an experience money can’t buy, such as time spent with the athlete, but everyone who participates wins in some way – other prizes include autographed apparel or offers from brands.

Brown didn’t become an entrepreneur right away, though. A public policy analysis major while at Duke, he played in the NFL for a few years. Upon exiting the NFL, he knew he wanted to start something of his own, so he planned to go back to school to get his MBA – until someone told him about Draper University.

Brown knew nothing about Silicon Valley at the time, but he applied to be in the first batch of the program for aspiring entrepreneurs founded by venture capitalist Tim Draper.

After a full scholarship took him to a nine-week crash course that changed his life, Brown graduated at the top of his Draper University class. By then, he was hooked on Silicon Valley and knew he had to return. He moved back home to Houston and began to prepare for the transition, creating a curriculum that he would use to teach himself how to design and code. Although he knew he didn’t want to be a developer, he wanted to have a technical background to better communicate with developers he might work with.

“I had the same mentality as I had in the classroom at Draper and on the field,” he said. “I wanted to be the best. I spent all day every day just cranking it out, and I learned about five languages in eight months.”

Brown then moved to Silicon Valley with his wife. He had a young child and a baby on the way, but didn’t yet have a job. Although he was still determined to start his own venture, he knew he needed to work at a startup to learn how they worked from the inside out.

Being a Duke alumnus helped him connect with some of the biggest players in tech, including a cold email to a fellow alumnus who’d graduated four years after him and remembered him because of his football career.

That fellow alumnus worked at Kiip, where Brown found his first startup job. He started as a growth associate and worked his way up to head of growth within about five months. Kiip was focused on helping brands connect with customers while they’re using their favorite apps – a strategy Brown would later employ at his own startup.

While at Kiip, Brown was convinced by his coworkers to join a fantasy football league for the first time. At first, he saw it as throwing money away, but his coworkers said it was more about the friendly competition than the money.

Upon doing more research, Brown found that 99 percent of people were losing or breaking even when playing fantasy sports, meaning money really wasn’t a main driver for playing.

He started to ask athletes who he knew from his time in the NFL what they thought about fantasy sports. The resounding consensus: The players weren’t fans. Their likenesses were used, but they didn’t benefit from it at all.

Also around that time, legality questions were starting to surround fantasy sports. Was it gambling, and were there too many people gaming the system?

Brown left Kiip in November 2015 and incorporated his new startup, Win-Win, in January 2016. In eight months, he raised $925K, which included funding from the Duke Angel Network and the Duke Innovation Fund.

He also pitched at the DukeGEN Startup Showcase in June 2016, which also generated interest and support in his initial funding round (Brown’s pitch begins at 59:00).

Because Win-Win allowed fantasy players to contribute to charity, Brown decided to market the company as “fantasy you feel good about.”

However, he quickly realized Win-Win would need to pivot to reach a wider market. Many sports fans saw the value in the prizes Win-Win was offering and in giving to charity, but they weren’t necessarily interested in playing fantasy sports.

Brown knew he needed to meet people where they were and create games that they would already be playing in their offices, such as March Madness bracket challenges.

Now, the slogan behind Win-Win is “social games for social good.”

When a fan registers for a tournament, 100 percent of their donation goes to the nonprofit arm of Win-Win, meaning that their donations are tax deductible.

Twenty percent of the funds in the nonprofit arm are deducted as a service fee, creating a revenue stream for Win-Win. The rest is donated to the charities chosen by participating athletes.

Brown, who is now in the process of fundraising a second round, said Win-Win plans to scale vertically. The company has already launched a new initiative that involves prizes with retired athletes, and soon they plan to also include other entertainers and influencers outside of the sports world.

Win-Win is currently a team of two full-time employees and several contractors, but Brown sees that expanding to about nine full-time employees within the next six months. He said he’s hired Duke interns in the past and is open to employing more in the future.

Win-Win also just graduated from accelerator 500 Startups, which Brown called an amazing program that allowed him to receive mentorship and build relationships with other entrepreneurs.

To learn more about Win-Win, visit its website.

To read about more Duke Entrepreneurs, click here.