With limitless will and immeasurable confidence and perseverance, Jason Robins leads DraftKings through chaotic storms to ultimate success

Jason Robins sat on a black sofa at DraftKings’ outpost on radio row on the Friday morning before the Super Bowl, his back to a partition covered in faux Wrigley Field ivy. A burgundy blazer dressed up the pale blue T-shirt he wore beneath it.

Two days before the game, Robins had whittled his to-do list down to something manageable. A live shot with a financial news outlet was done, and he had almost an hour before his last task. After that, he’d head back to his hotel to change clothes for a pickleball date with wide-receiver-turned-ESPN-analyst Larry Fitzgerald, a DraftKings evangelist and shareholder who would joke that they should “start playing for equity” after winning the first point.

Seasoned by a dozen years as co-founder and CEO of a company that weathered a highly publicized FBI investigation, outlasted cease-and-desist orders in at least a dozen states and hit the NASDAQ six weeks after COVID shut down sports, Robins has grown comfortable with probing questions from TV interviewers and stock analysts, polished, though more like a well-drilled student than a practiced salesman.

His ninth Super Bowl trip would offer yet another chance to elevate DraftKings’ profile. Bringing the biggest betting day of the year to Las Vegas was like taking a carload of trick-or-treaters to Willy Wonka’s chocolate factory. If CNBC and Fox Business wanted to put him on air to dive into that, Robins was happy to oblige.

Though the company has grown to $3.6 billion in annual revenue and a $20 billion market cap, Robins remains the stat-crazed math nerd who grew up devouring box scores at the breakfast table and making it to every University of Miami home football game with his father, an economics professor at the school, and his mother, a schoolteacher.

Sometimes, it feels like he’s watching someone else’s life unfold. Like when he rented out Gillette Stadium for his wife Shannon’s birthday party, hiring the Dave Matthews Band and David Spade to perform. Or sitting courtside with his family at a Boston Celtics game, looking up to the rafters, remembering choosing tickets in the top row so he could stand to get a clear view.

A father of four with a fifth on the way, Robins would have a small sidekick with him at the Super Bowl for the first time. His oldest son was joining his parents in DraftKings’ suite as a 10th birthday present.

“It’s like one big pinch-myself moment,” Robins said. “All of this.”

Still, he hasn’t forgotten what it was like when the pinch was more like a vice. Persevering has become core to Robins’ identity and the company’s ethos, so much so that if you forced him to rank the existential threats DraftKings has faced in its dozen years, a pandemic that shut down sports while he was taking it public wouldn’t make the medal stand.

“There’s actually a positive to all that adversity,” Robins said in the calm tone he holds through most conversations. “It gets people to focus on things or ask questions they wouldn’t have forced themselves to think about. And you learn to kind of embrace it, especially since it doesn’t feel existential any more.

“Every time something comes up, I can say, ‘This isn’t the hardest thing we’ve had to go through.’”

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DraftKings’ origin story begins with Robins and co-founders Matt Kalish and Paul Liberman in their early 30s, working in strategy and analytics at an online printing service based near Boston, commiserating over how they’d missed the last boom of tech startups and noodling on ways to be part of the next.

Early in 2011, after months of hatching and dismissing ideas over after-work drinks, Kalish suggested a website offering games that digested seasonlong fantasy leagues into a single day. Robins, who once considered dropping out of Duke to mine Silicon Valley gold, was immediately smitten.

When they found that others were already down the road on similar concepts, Kalish was crestfallen. But Robins saw it as evidence that they were onto something viable. They secured Liberman’s buy-in and pushed forward.

Working nights and weekends out of a spare bedroom at Liberman’s townhouse, they spent the next six months developing a business model and coding a prototype. Seeing progress, Robins suggested it was time they pool their money and start a company.

They scraped together $25,000, but hadn’t a clue what to do beyond that. A mentor recommended a lawyer who worked with startup companies, John Hession. He agreed to counsel them if they would meet at the crack of dawn on weekends at a greasy spoon diner. So long as they picked up the check, he wouldn’t bill them for his advice. They would take what they learned back to Liberman’s spare room and work for the rest of the day.

After a few sessions, Hession asked if they’d considered how they’d raise the money to fund the business.

“How are we supposed to do that?” Robins asked, dumbfounded. “We have a badly built prototype, a couple of PowerPoint presentations and some spreadsheets.”

Undeterred, Hession said he’d introduce them to some venture capital firms.

The first VC firm that agreed to listen said it liked the concept but wouldn’t invest until they had at least 1,000 customers. When Robins explained they couldn’t afford to launch without the seed money, it told them to come back when they’d worked that out.

Five minutes into their second pitch, they thought they’d struck gold. A venture firm partner named Alex Finkelstein took to their idea, but needed them to come back in three days to pitch others from the firm. Facing a larger audience, their three-headed presentation tanked.

So began a brutal succession of rejections. Robins approached every contact he had, asking for introductions to venture firms. He estimates he’d struck out with “30 or 40” of them when he went back to Finkelstein for advice.

After going over what his partners disliked about their presentation, Finkelstein asked who else Robins had met with. One by one, he went over the most recent dozen. “Every single one of these is a waste of time,” Finkelstein said. He showed Robins the disconnect. One had invested in solar energy. Another was chasing startups that developed SAAS software.

“Do you see any consumer tech on any of these guys’ lists?” he asked.

Robins devoured every nugget of advice. When they were done, he asked Finkelstein to connect him to a venture firm more inclined to bite. Finkelstein said he couldn’t help. But after work, Finkelstein had beers with a close friend from another Boston-based venture firm, Ryan Moore of Atlas Advisors. When the conversation veered to fantasy football, Moore launched into an impassioned, position-by-position assessment of his team.

Finkelstein thought Moore and the DraftKings trio might be right for each other.

Later that night, Robins got an email introducing him to Moore. When they pitched him, he liked the idea and the founders. It wasn’t so much that it was fantasy football, but that their focus was on creating something fans could play together every day using their smart phone.

“Let’s see what they can do with a million bucks,”  Moore thought.

They had their first yes after dozens of no’s.

“That’s the first resilience lesson of Jason Robins,” Moore said. “I know a lot of entrepreneurs who after 25 no’s would have said, maybe it’s not for me. Or maybe the market has told me something. Because it’s a portfolio of feedback, not one. That was the first lesson that these guys were in it to win it.

“That’s the beauty of venture. All you need is one person who says yes to fund your dream. I was that person at that time. I made a ton of other mistakes in my career, but I didn’t on that day.”

Three months later, at Moore’s urging, the co-founders quit their day jobs. Robins’ focus remained on raising capital, which didn’t get any easier. Hoping to infuse credibility, Moore volunteered to write the lead check on the next round, putting up more than $4 million of the $7 million they targeted for the series. Robins spent the next two months hustling around New York, cobbling together $25,000, $50,000 and $100,000 investments to finish it out.

It was on one of those trips in the first quarter of 2012 that Moore joined Robins for a meeting with Kenny Gersh, who then headed business development for MLB’s digital media company. Gersh was high on the potential of daily fantasy, both as a sponsor category and a vehicle to engage fans.

At that point, FanDuel was the clear leader in the burgeoning category, which made it the better fit for MLB. But when Gersh met with FanDuel co-founder Nigel Eccles, their views on deal structure differed dramatically. Gersh wanted a guaranteed sponsor fee. Eccles wanted to pay based on how many sign-ups MLB drove for his contests.

“We were going to make them the official DFS game of Major League Baseball, which I thought was a pretty big deal,” Gersh said. “Nigel couldn’t see it. Jason, on the other hand, got it right away.”

Robins believed an MLB sponsorship would add credibility for both his company and daily fantasy, which at that point still was seen as operating on the fringes of illegal gambling. In text exchanges with Moore and his partners, Robins described the meeting with MLB as a “chance to make history,” Moore said.

They negotiated a two-year deal that would test-drive DraftKings as the league’s official DFS game in exchange for a mix of cash and stock warrants. Moore’s firm would guarantee the cash.

“Jason was willing to put real money up, but at the time they didn’t have a lot of real money to put up,” Gersh said. “It was important that [Moore] was there to guarantee it that day, because back then we really didn’t know who these guys were.”

Robins was working to change that. He’d learned from the rejections that the thing venture firms most wanted to see was traction; a growth spike that indicated their idea was catching on. The fastest way to attract more customers was to run more contests, with larger prizes — so large that they’d give away more money than they took in. And the best time to do that was during the NFL season, which was only a few months away.

At this stage, raising money was far more important than making it. Robins approached Kalish and Liberman with a radical proposal.

“We worked so hard to get this money in,” Robins recalled telling them. “Now, we need to go spend all of it in the next five months.”

Robins chuckled when asked what they initially thought of his plan.

“They said I was insane,” he said.

They weren’t the only ones who thought so. Competitors who monitored the space and ran the math knew they had to be bleeding cash. But the strategy paid off. Bigger prizes, paid to more winners, led to more entries. Robins had a growth story to take to investors.

“I was being very pragmatic,” Robins said. “Are we going to try to get profitable on this money? Probably not. So that means we’re going to have to go raise more money.

“Being able to raise money quickly is going to be a competitive advantage as much as product or anything else is going to be. And maybe the most important thing. I’m up against a bunch of startups. So who is going to raise the money is going to be a huge part of the battle.”

This time, Robins turned his attention to Silicon Valley. A month of meetings yielded term sheets with four firms, bringing in $24 million at a valuation 4½ times higher than what they’d raised on three months earlier. That led to a fourth raise, this time of $41 million in the first half of 2014.

By the start of 2015, DraftKings had emerged as the sole realistic challenger to FanDuel, accelerated by the growth of its customer base and the acquisition of DraftStreet, a competitor that had been No. 2.

That spring would bring a pair of head-to-head bake-offs that would set the stage for a pivotal fall.

The first was for the official DFS rights with MLB, which incumbent DraftKings won over FanDuel, but at an exorbitant increase for a five-year deal that would grant vastly expanded promotion across MLB’s platforms.

The second was for exclusive rights as the official DFS provider of ESPN, a deal certain to require a massive ad spend, but also to deliver a substantial advantage over competitors. So fierce was the bidding on the ad commitment that the network eventually capped it.

“We finally said, ‘It’s enough money,’ because we didn’t want to create such an aggressive deal that it inhibited their chance to succeed,” said John Skipper, the former ESPN president who ran the process along with Disney executive Kevin Mayer. “So we said we’re going to call both parties in and see who we want to be in business with.”

FanDuel presented first, arriving at Disney’s Burbank offices with a team of four in suits and ties, each delivering a portion of a pitch around what the company could deliver along with its ad spend. Skipper recalled a “very buttoned-up” delivery that impressed them both.

Next came Robins, by himself, in a sweater and slacks.

“He didn’t have some big slick presentation,” recalled Skipper, who now counts DraftKings as the leading sponsor of Meadowlark Media, the content studio he co-founded in 2021. “He just looked at us and talked. And we bet on his drive and his brains. This is no denigration. We wanted to be in business with both of them. But Kevin and I, 30 minutes after he had presented, we said, ‘We’re going with this guy. Because this guy has got conviction. He’s got drive. He’s got brains.’

“We liked that he came in by himself and didn’t feel like he needed to make a presentation.”

There was no shortage of takers when Fox led DraftKings’ next capital raise of $300 million at a $1.8 billion valuation, strategically timed to close in time for the 2015 football season. MLB, the NHL, MLS, Madison Square Garden Co. and Legends all joined, as did DraftKings’ previous large investors.

“At that point, I could have thrown a rock and hit somebody that wanted to give us money,” Robins once said.

Again, Robins immediately weaponized the new funds, opening the football season with an advertising blitz that set off an arms war with FanDuel, with the two of them combining to spend an estimated $27 million for about 8,000 spots during NFL’s opening week, according to ad monitoring service iSpot.tv. 

His approach was the same as it had been after earlier rounds, only this time with enough fuel to not only mint more backward-cap-wearing millionaires, but to drop a brand bomb.

“We were in a category that was emerging,” Robins said. “But if it was going to have the potential I thought it had, somebody was going to have to break through the mainstream first. Or somebodies. So being aggressive was important. Having that money was an advantage. But if you don’t spend it, then it’s not an advantage.”

An all-out war with market leader FanDuel not only fit Robins’ calculus, it matched his personality.

He loves chess, where he can plot moves and test his foresight. And racket sports, where a lob or dink sends an opponent scurrying out of position. In the past few years, he has taken to golf. Having “hacked around” a few times, he knew the only way he’d improve was through hours on the driving range — hours he couldn’t spare.

He had a Trackman simulator installed at home.

“For a long time, there was a narrative created by our competitors that Jason is reckless, and he’s crazy,” Moore said. “That’s the picture they painted. He is not. He’s incredibly thoughtful. He’s incredibly calculating. He knows exactly what he is doing at all times and is in control. I think that narrative has moved away now. And I think that’s important.”

A month into football season, DraftKings had pulled even with FanDuel.

“Our deal was a big deal for them,” Gersh said. “And the ESPN deal was a big deal. It was a lot of money.

“And then shit sort of hit the fan pretty quickly after that.”

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In October 2015, allegations surfaced that DraftKings and FanDuel employees were trading inside information to win money on each other’s sites, raising questions about the legitimacy of their contests and attracting the attention of FBI investigators. A user in Kentucky filed a class-action lawsuit against both companies.

A month later, the attorney general in New York ordered both companies to stop taking bets in the state, saying their contests constituted illegal gambling, a ruling that triggered similar scrutiny in a string of states.

New York AG Eric Schneiderman accused the companies of “a massive, multibillion-dollar scheme intended to evade the law and fleece sports fans across the country.”

“When your mom reads on the front page of the New York Times that there’s a scandal in the unregulated fantasy world, and you know that every single person you know is reading articles … that takes a toll on you,” Liberman said. “I had twins that were 1 year old. We all had young kids. It was a tough time.”

Letters came from attorneys general and prosecutors. DraftKings continued to operate, confident in its interpretation of the law, but aware that the founders eventually could face charges.

“This was not just business. It was very personal in a lot of ways,” Kalish said. “It wasn’t like you go to work and work on the problems and then go home. We [the founders] had no money going into this. So there were questions about even the way we’d exist in the world. Pay bills. Whatever. And it was highly questionable if the company would even continue to exist.”

Robins said his low point came that winter. His wife was pregnant with their third child. The new house they were building wasn’t finished, so they were living with her mother.

“We were so in survival mode that I didn’t have time to process any of it,” Robins said. “The whole thing was kind of surreal. I knew what I needed to do in the next hour and that was it. You’d be thinking one fire was put out and three more would be burning around the corner.”

With the company hemorrhaging money, Robins turned to address upcoming debts. MLB agreed to amend its deal to take more equity in lieu of cash, at least while DraftKings worked through its legal and regulatory issues. Gersh sent him a bottle of good whiskey, with a note that said, “This too shall pass.”

When Robins called Skipper, he started by laying out all that Draft-Kings was facing. He painted a daunting picture, but did so cooly. He told him he wanted to make good on his deal with ESPN, but that it wouldn’t be prudent to spend at that level with the company under duress. Skipper agreed. They “worked out something highly satisfactory to both parties,” Skipper said. DraftKings would relinquish its hold on the category, and keep its money.

“He still was calm while dealing with more things than it is possible to imagine,” Skipper said. “I’ve never heard him be pessimistic. I’ve heard him be realistic. I’ve heard him be stressed. But I’ve never heard him be discouraged in any existential way.

“I have chosen to be in business with him now twice. So my first experience was clearly good.”

Even relieved of two large expense lines, Robins knew the company would need more funding to survive. So he hit the streets again, eventually accepting a $500 million valuation about seven months after raising money at $1.8 billion.

“I was less concerned with a much lower valuation and more concerned with, wow, are we going to make it out to the other side of this?” Robins said. “If anything, I’ll take whatever valuation I can get now just so we can get money into the company to try to survive here.”

As 2016 began, the tides turned. The two bitter DFS rivals worked together on legislation to regulate and tax daily fantasy, state by state. Virginia was the first to fall, passing a bill in February. “I remember thinking, well, at least I know there’s one state we’ll be able to be in,” Robins said with a high-pitched chuckle. Next came Indiana. In March, DraftKings and FanDuel agreed to stop running paid contests in New York while the state legislature worked on a bill, which was signed in August.

With the NFL season about to open, DraftKings announced another capital raise, this time for $150 million in a round led by venture firm Revolution Growth, co-founded by Washington Capitals and Wizards owner Ted Leonsis.

A month later, New Jersey Gov. Chris Christie would petition the Supreme Court to clear the way for states to allow sports betting.

“The ability he has to just maintain focus and hard work and get through any issue that pops up is a one-in-a-million differentiator with Jason,” Kalish said. “He never loses energy, never loses motivation. No way we would be successful without him having that quality.”

“One thing that’s extremely unique about Jason is his ambition,” Moore said. “I don’t know if it has a ceiling. And that is special. That’s my business. I’m meeting with thousands of entrepreneurs trying to find more Jasons in the world.”

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Late on a weekday afternoon in the spring of 2020, Robins made his way through the halls of his suburban home, seeking out a quiet corner to continue a phone conversation. His three children, the oldest of whom had recently turned 6, shouted and giggled in the background.

For the umpteenth time, he regretted putting off converting the empty space over the garage into a spare office. It didn’t seem an urgent need, until all of a sudden it became one. On video calls, he noticed others at the same desk or table each day. He was a work-from-home nomad.

Closing a bedroom door, Robins apologized for the disruption.

It was the sort of scene that played out in tens of millions of U.S. households that year, as families learned to balance work, school, internet bandwidth and the search for toilet paper. In Robins’ case, it coincided with taking a company public six weeks after closing its offices, with 2,500 employees working remotely, most of them for the first time.

That company was a sportsbook, and there were no sports.

Four years later, Robins recounts that period matter-of-factly. Like many, he was surprised work-from-home worked as well as it did, but that wasn’t unique to DraftKings. Yes, revenue cratered when there were no sports to bet on, but he was confident cash flow would resume when the games did, which seemed inevitable.

His co-founders don’t count that span as an especially trying time for the business, either.

“It wasn’t so different from other challenges we’d run into where you make a plan and do the plan,” Kalish said. “The fact that we didn’t just go down, down, down when there was no sports — that’s amazing. But Jason has always been great at telling the story of the company to investors, even in … very challenging circumstances.”

“There have been so many ups and downs and we’ve gotten punched in the face so many times,” Liberman said, “I feel like it was just status quo.”

As for many, there were spans of great sadness, and moments missed. The NASDAQ bell-ringing that founders traditionally celebrate when they go public was held virtually, a checkerboard of employees and board members shown applauding from their homes. A few weeks after the bell-ringing, Robins’ mother-in-law died. They sprinkled her ashes in a park, where she used to take their children.

“It feels like forever ago,” Robins said. “Like it was another world.”

Since then, DraftKings’ peaks and valleys largely have been functions of its stock price. When it was near its high of $71 in March 2021, the company took the opportunity to borrow against the stock, setting it up to continue slugging against FanDuel. When the market turned skittish a year later and the stock dropped to less than $10, Robins preached patience, arguing that if they turned steadily toward profitability, investors would come back.

Last Tuesday, it closed at $48.68.

The lone founder among the CEOs of the leading seven U.S.-based sportsbooks, Robins continues to espouse the long view.

Explaining that approach as the appointed time for his last pre-Super Bowl TV hit neared, Robins casually lifted his left arm over the back of the sofa. His jacket fell open slightly, revealing a narrow glimpse of custom lining; black, some neon green, and a sliver of orange. Were those letters, maybe?

Never a fan of fashion, or even collared shirts, Robins wouldn’t have thought to add a burgundy jacket to his mostly casual wardrobe, or to have it lined with dozens of DraftKings logos, as his wife did when she had it made for him.

But he liked it.