Power Lunch: DraftKings’ Jason Robins, Paul Liberman, and Matt Kalish

The biggest players in sports are lining up to invest in DraftKings. But what's next for Boston's billion-dollar startup?

draftkings power lunch

From left, Matt Kalish, Paul Liberman, and Jason Robins celebrate DraftKings’ new round of funding at the Beantown Pub. / Photograph by Ken Richardson

Four baseball seasons ago, the daily fantasy-sports company DraftKings launched its website out of a Watertown condo. This year, its millions of customers are competing for $1 billion in prizes. And the stakes may soon get even higher: This past July, DraftKings announced a new $300 million round of funding, with partners including Fox Sports, the NHL, and Major League Baseball. It’s a deal that reportedly values the company—headquartered in downtown Boston—at more than $1 billion. We met CEO Jason Robins, 34; chief operating officer Paul Liberman, 32; and chief revenue officer Matt Kalish, 33, for drinks and apps at the Beantown Pub on the day of the big funding announcement.

How did the idea come to you?

MK: It just clicked one day: The draft is always people’s favorite part of season-long leagues. What if you just could do that every day?

JR: The parts of the season-long fantasy experience that we all enjoyed the most were picking your team, watching your scores, and winning money. We cut out the whole notion that you have to stop playing when the regular season ends and playoffs begin. We focus on the part everybody loves and do it over and over again.

How is this legal?

JR: Across almost every state, skill games are classified in a different category than chance-based games. Fantasy is not a chance game—you’re not throwing the dice or guessing a number. If you really put the effort into it, if you really understand sports better than your competition, then you can win very consistently.

How did you figure out who would take which role?

JR: Paul is able to execute and design a process in a way that none of us can. We usually put Paul on whatever’s the most important thing going on for the company. Matt oversees the product operations, the promotions and contests, and the content we produce. He has the best understanding of the customer.

PL: Matt’s the brains. He’s like a scientist.

MK: Jason definitely had the best grip on the vision, early on. He thought bigger
than anyone.

What does the deal you announced today mean for DraftKings?

JR: It’s another validation that the company has enormous potential. We’re going to use the proceeds to expand internationally, starting with the U.K. later this year, and ultimately through Europe and Asia. We’ll continue to do a lot of special partnerships with sports leagues and teams. We’ll expand into new sports games and e-sports.


MK: A competitive circuit of video-game players. Some example games are League of Legends and Counter-Strike. Teams compete against one another worldwide. There’s 100-million-plus viewers.

JR: People who are really, really good are becoming like celebrity athletes.

PL: At some point there will be a fantasy of fantasy players.

Is this bigger than you thought it would be?

JR: We had this vision, but the speed with which it happened is blowing all of our minds. Three and a half years ago, we were still working out of Paul’s spare bedroom, still at our day jobs, slaving nights and weekends trying to get this thing off the ground. We thought it would take us
a decade or more to get to this point.