It’s Good to Be King

Work-life balance comes hard for Paul Liberman. Sure, he knows the standard tricks: Go for a drive with the family. (Oh look, a DraftKings billboard.) Catch up on the news. (“DraftKings Takes Market Share Lead,” reads the headline.) Maybe kick back and take in the game? (Nothing less than a busman’s holiday—a term coined in the early 1900s for downtime that involves what you do for work.)

Call it an occupational hazard or the cost of success, but Liberman is hard-pressed to escape the ubiquity of DraftKings, the online gaming colossus he co-founded in 2012. Little more than a decade after launching the company from his apartment, Liberman and his partners Jason Robins and Matthew Kalish stand at the helm of an international brand that shows no signs of flagging. Valued at just over $14 billion, DraftKings edged out its competitors for the largest market share of online gaming in 2023.

Of course, as the saying goes, “Uneasy lies the head that wears the crown.” Although the three co-founders have experienced stratospheric success, they have also encountered their share of challenges in growing DraftKings to a thriving company with offices in six countries. However, it takes more than a few intractable problems to discourage Liberman—in fact, as an electrical engineering and computer science major, he was trained for it.

Find a young engineer-in-the-making and you’ll likely discover a nearby pile of dismantled electronics. In that respect, the young Liberman fit the mold famously. “As early as I can remember, I was a tinkerer,” he says, recalling the IBM 386 DX his father bought for him and his brother—which they promptly stripped down, rebuilt, and otherwise modified. “I used to like this QBasic game, Nibbles BAS. We’d open it up to see how it was programmed and write little programs of our own.”

Without the benefit of plug-and-play algorithms, the MQP team members needed to train their program to decode each user’s voice and then retrieve the correct track. To make the project even more challenging, the team chose a Christina Aguilera song with an especially hard-to-pronounce title as their test subject.

Though Liberman’s MQP team succeeded at building a technical solution, he found the greatest satisfaction in creating a program that a driver might actually use—foreshadowing his future work. “The interesting part for me was the human-computer interaction,” he says. “How easy could we make it for a driver to interact with the system without being distracted? Although I was an electrical engineering major, a lot of our project involved making the customer experience better and more productive, not just solving a technological problem.”

His passion for systemic problem solving drove him through his undergraduate work, and following his graduation in 2005, Liberman accepted his first job as an applications engineer at a Massachusetts-based firm that built semiconductors and closed circuits for electronics devices. He was disappointed to discover that the position required a much narrower skill set than what he previously used to tackle open-ended challenges at WPI; however, what the job revealed about Liberman’s interests proved to be invaluable. “A lot of my time was spent optimizing existing work, or doing mechanical stuff, like soldering,” he recalls. “And I realized that I preferred the problem-solving aspect of engineering: tinkering, building, and constantly working on new projects.”

Liberman soon moved to a new position at VistaPrint, an e-commerce firm, that allowed him to dig into customers’ user experiences when navigating the company’s website. This new role brought him back to the methodical approach to problem solving he’d learned as an undergraduate, letting questions that arose organically guide his work. “How do people navigate the website? How do I measure that? How do I leverage data to make the experience better?,” he recalls.

Liberman’s experience at VistaPrint provided a critical eureka moment. “Whether you’re facing an engineering problem or a business problem, you’re using data, a hypothesis, and logic. The same approach applies, just in a different framework. It’s a mindset, and, as I realized, that’s my passion,” he says. Although he had been trained in the technical aspects of electrical engineering, it was the methodical approach to problem solving—the engineering mindset—that was his greatest superpower. This epiphany freed him to think beyond the boundaries of electrical engineering to the broader world of entrepreneurship. In fact, with a proven approach to problem solving that transcends disciplines or industries, the sky was the limit. And in a few short years, that’s exactly where he and several like-minded friends would be headed.

Nearly a year into his job at VistaPrint, Liberman began meeting up with Kalish and Robins, friends and fellow VistaPrint employees, to finesse their fantasy leagues and bat around their latest entrepreneurial ideas. Over time, the two activities merged and the trio envisioned a fantasy sports platform that allowed players to opt in for one or two games, rather than sign up for an entire season. The DraftKings concept began to take shape. Of course, there was the little problem of building a platform from the ground up—but little problems happen to be Liberman’s area of expertise. “I thought, ‘Ok, awesome; here’s a problem to solve,” he says. “Let’s build this. I’ll take on the tech side.’”

In 2012, Liberman and his co-founders officially launched DraftKings, a few weeks into Major League Baseball’s season. The startup won thousands of customers in its first few months, and the three friends watched trades turn to dollars. As with most startups, the owners held onto their day jobs, spending nights and weekends building and tweaking the new platform before quitting to focus on it full-time shortly before launch day. They soon committed to a five-month run, and scraped together $25,000 among themselves to do so.

For many entrepreneurs, leading with intuition is the key to their success. “Intuition is a very powerful thing, more powerful than intellect, in my opinion,” Steve Jobs told his biographer, Walter Isaacson. Other business moguls, including Jeff Bezos, Richard Branson, and Elon Musk have shown a similar inclination to let their gut be their guide, with varying results. For Liberman, intuition needs to be paired with data for success—both are critical; good data leads to good decisions.

As he moved from one side of the business to the other in DraftKings’ early days, Liberman consistently applied the analytical approach to problem solving he’d learned as an engineer to business challenges. “I have filled a variety of roles at DraftKings, but in each one I asked, ‘How can we make this department revolve around data? How can we bring it back to basic problem solving?’”

In 2015, DraftKings faced its first major headwinds as an emerging industry leader. Questions arose nationally about the legality of fantasy sports, with some arguing that it constituted gambling and others defining simulation sports as a game of skill. Additionally, The New York Times ran a story accusing an employee of DraftKings of insider trading related to bets placed on a competitor’s website. The controversies proved to be temporary, albeit painful, bumps in the road to industry dominance. An internal review definitively confirmed that the employee in question did not have access to insider information prior to placing the bet. A 2018 decision from the U.S. Supreme Court resolved the legality of fantasy sports by allowing states to decide for themselves whether to allow sports betting. That same year, DraftKings announced its first online sportsbook in New Jersey; today, DraftKings Sportsbook is live with mobile and/or retail sports betting operations pursuant to regulations in 25 states and in Ontario, Canada.

When remembering this difficult phase in DraftKings’ history, Liberman remains as analytical as ever; for him, these hiccups simply provided more invaluable data. “My mentality is that a failure is just another problem to be solved,” he explains. “The reason we’re here today—as a public entity, a regulated company, and even the gaming industry as a whole—came from what we learned in 2015. You can look at those experiences as failures, but we became a much better company because of it.”

In the summer of 2023, a study from Eilers & Krejcik Gaming revealed that DraftKings had taken the national lead in online gaming, commanding a 31 percent share of overall gaming revenue. In just 11 years, Liberman and his two co-founders had turned their modest idea into an international juggernaut. As impressive as their growth has been, DraftKings’ meteoric rise has also posed personal and professional challenges for Liberman. Among them is the high visibility that comes with reaching the top of the proverbial mountain. “The scale changes. When something goes wrong, it’s on the front page of ESPN, or there’s 50,000 Tweets about it,” says Liberman. He adds with a chuckle, “If there’s a bad news story, I’ll say to my friends, ‘I know you guys all saw that article, because you all sent it to me within 30 seconds.”

Not that he’s complaining—in fact, most of the pressures attendant to his success aren’t related to him at all. “The pressure is a lot higher because your employees rely on you,” he notes. “But that’s also the best part of the job. I love going into the office on Sunday when football starts and seeing all the amazing people here, focused on making this organization a better place.”

Liberman sees another upside to having built an international team of high-caliber professionals: more problems. “We have such a great team right now, which gives me leverage to focus on the next thing we do. How do we grow? How do we scale?” he says. “You never run out of problems, which is what keeps me motivated.”

In fact, according to Liberman, all three co-founders thrive best when naysayers underestimate their abilities. Since becoming a publicly traded company in 2020, the company has discovered a new proving ground in the stock market, with financial gurus hailing their stock alternately as the next great buy or significantly overvalued. “Whether it’s Wall Street or our competitors, our challenge is to prove them wrong, beat their expectations, and launch a better product,” says Liberman. “When I get together with my co-founders, we always say, ‘We haven’t achieved everything; we’ve got more to prove.’ And that’s a huge driver for me.”