DraftKings founder Jason Robins, king of daily fantasy sports, got his start in Miami

Jason Robins founded DraftKings and turned it into a $1.5 billion corporation. Above, he speaks on a panel at the Global Gaming Expo in Las Vegas on Sept. 29, 2015.
Jason Robins founded DraftKings and turned it into a $1.5 billion corporation. Above, he speaks on a panel at the Global Gaming Expo in Las Vegas on Sept. 29, 2015. AP

There were clues, long before Jason Robins founded DraftKings and turned it into a $1.5 billion corporation, before he saturated the airways with commercials for his fantasy sports leagues, that he would make his money and his mark with statistics and computer games.

On the eve of Super Bowl weekend, Robins, a 34-year-old Miami Killian High graduate from Kendall, explained to the Miami Herald how he went from a sports-crazed self-described “tech geek” to No. 8 on Fortune’s latest “40 Under 40” list of the most influential young people in business.

Every morning, before heading off to Leewood Elementary School, Robins sat at the kitchen table and memorized statistics and boxscores from the Miami Herald Sports section. He would ask his mother, Susie, a schoolteacher, and his father, Philip, an economics professor at the University of Miami and diehard Hurricanes fan, to quiz him. He rarely got a question wrong.

He loved games. Of all kinds.

Robins started a chess club at the elementary school. He also loved Scrabble, like his maternal grandfather, who was a regional Scrabble champion. But sports were his deepest passion. His parents took him to UM football and baseball games from the time he was 4. They rarely missed a home game.

He played youth soccer at the Jewish Community Center. He played Khoury League baseball at Howard-Palmetto in Pinecrest. He took tennis lessons at the Montana Academy.

Like many young kids, he dreamed of becoming a professional athlete. But he realized by the time he reached Arvida Middle School that he was far better at memorizing statistics than he was creating them on the fields. He sheepishly admitted his most memorable athletic achievement was receiving an award from former UM baseball coach Ron Fraser at a summer camp for making a “heady” double play.

“There is one moment in particular, when I look back, when I should have known I was destined to be a fantasy sports geek and not a player on the field,” Robins said by phone Tuesday from the DraftKings headquarters in Boston, where he oversees 300 employees and this week launched their fantasy games in the United Kingdom. “When I tried out for one of my Khoury League teams, they published all the ratings of all the players and I was more successful at memorizing everyone else’s ratings and who got what than I was at actually playing baseball.”

He did manage to make the Killian High tennis team, which won a state title while he was there, but he rarely cracked the playing rotation. “Our team was really good, so I worked hard to be an alternate doubles player,” he said.

“By that point, I had become much more interested in the business side of sports, studying how general managers assemble teams, how they think about balancing salary caps. The Money Ball philosophy wasn’t out yet, but there was already for those like me really digging, the Billy Bean days, people talking about using statistics to figure out ways to outcompete other GMs and ballclubs. I just loved that stuff, ate it up.

“When fantasy sports hit the internet it was like love at first sight for me.”

He entered every fantasy league he could find. He played in more than 150 leagues as a teenager.

It was right about the time he got to high school, in the mid-90s, that personal computers and the Internet were going mainstream. Robins, a math whiz and admitted “tech nerd” was way ahead of the curve.

His father was “a huge technofile,” the first to get the latest gadgets, the first to upgrade software.

“From a very early age, technology was part of my life,” Robins said. “I got introduced to computers when personal computers were starting to hit the home. We always had the latest stuff. When you’re a kid who likes numbers and exploring and technology, and your parents have really cool toys that none of your friends have, it really draws you in.”

He taught himself computer programming at 13, “back in the days of Basic and Pascal. He used dial-up modems to sign onto message boards, where he connected with fellow tech junkies. But his interest in computers went beyond programming, nuts and bolts.

“I was more interested in what computers enabled, how they were changing people’s social habits, access to information, changing the way people could take tasks that were very cumbersome before and make them a lot easier and improve quality of life.”

Robins graduated No. 8 in the Killian Class of 1999. His pre-calculus teacher, Charles Innes, was delighted to learn of Robins’ success.

“It’s very rewarding when you hear that one of your students, a kid who went to a basic public high school like Killian, was able to get a good education and go on to a good college and then create a business like Jason has done,” said Innes, who now teaches at Hebrew Academy. “If you looked up all the pre-calc and calculus students I had in 45 years at Killian, I bet you’d be astounded at the success stories.”

Robins attended Duke University and majored in economics and computer science. His father suggested he go to graduate school. Robins had other plans. He was determined to be a tech entrepreneur. When he got to college, dot-com start-ups were mushrooming across the country. The speculative tech industry was booming, and Robins desperately wanted to be part of it.

“Tech start-ups were flourishing, raising capital, the whole Jeff Bezos and all those stories were happening, and I thought, ‘This is my calling,’” Robins said. “It brings together technology and innovation, which I love, and business.”

But by the time he graduated, in 2003, the bubble had burst. Investors were getting cold feet, and funding was drying up. He took a job as a marketing executive and analyst at Capital One, where he met eventual DraftKings co-founder Matt Kalish. From there, they both went to VistaPrint. They met Paul Liberman, who eventually became their third partner.

They came up with the idea of a daily fantasy sports league, rather than the traditional season-long leagues, and on nights and weekends began networking, putting together presentations and financial models and seeking investors. They were rejected by 40 to 50 investors before they found a firm to put up the $1.4 million seed money. In 2012, they quit their day jobs and DraftKings was born.

“We were off to the races,” Robins said.

By last summer, they had secured $375 million of funding and inked deals with Major League Baseball, Major League Soccer, NASCAR, ESPN, among others.

Robins said he tried not to get discouraged by the naysayers in the early days.

“You can’t get caught up in rejection, you’ll wallow in it,” he said. “There were points at which I asked myself because there were a lot of people saying we don’t think that’s a good idea, don’t think there will be a big audience for it, you do ask yourself, ‘Am I just drinking my own Kool-Aid here? Is this really a good idea?’ But I felt like my passion for fantasy sports, the work we put in sizing the market, I felt confident if we found the right investor we’d get there.

“I said, ‘I’m going to prove every one of these people who told us we had a bad idea wrong.’ I cannot tell you how gratifying it is when they have come back and said, ‘We were wrong.’”

His parents are thrilled he was able to combine his passions.

“We never imagined that business would incorporate his love of sports and mathematical and statistical abilities,” Philip Robins said. “ When Jason initially told us about his plans to start DraftKings with his two partners, we supported him 100 percent. We are proud that he started a business that not only is a perfect merger of his passion for sports and his great business acumen, but also delivers a fun game for millions of sports fans like Jason to play.”

Not everyone is as excited as the Robins family about the company’s success. The New York attorney general filed a lawsuit against DraftKings and competitor FanDuel, claiming they are running an illegal gambling operation. Five states have banned their leagues, saying they violate anti-gaming laws. Others might follow suit.

Both companies have argued that daily fantasy is a game of skill, not chance. They say their operations are legal because they technically don’t accept wagers and because the teams are invented by customers and real-game results play no part in the payouts.

Robins would not discuss the status of the legal proceedings. He is busy with his growing business and family — wife, Shannon, whom he said has been a huge help through his journey, two-year-old son, Levi, and two-week-old son, Charlie.

“The business is nerve-wracking, but it’s exciting, too,” Robins said. “You’re in a race and all you can focus on is how can I keep going and keep building this thing? If you can’t just zone in on what you’re doing, it’s going to be very hard to be successful because the ups and downs of starting and building a company are tremendous. The highs are high, the valleys are low, and they can switch day to day. If you get caught up in that and don’t just keep your eye on the ball, you can get distracted and get lost in the emotions of it all.”

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