He beat Vegas in blackjack. Now, he’s helping golf (and golfers) cash in

Jeff Ma is famously adept with numbers, but his quantitative skills go only so far on the course.

It’s a sun-kissed morning in the Napa Valley, and Ma is taking stock of his approach on a snaking par-5 at Silverado Resort. The proper club is 9-iron. Ma knows that. And the better miss is long. Ma is certain of that, too. But strategy is one thing. Execution is another. 

“I understand the analytics,” Ma says before pushing his approach into a greenside bunker. “I just don’t have the ability to pull off the shots.”

He smiles and shrugs. Ma also understands where his strengths lie in the game.

Even golfers unfamiliar with his name have likely heard about his expertise. In the early 1990s, as an undergraduate studying mechanical engineering at MIT, Ma was a key player on a team of card counters that swooped in regularly on Las Vegas casinos to cash in at the blackjack tables. Their exploits — think “Ocean’s 11” meets “A Beautiful Mind” — inspired a best-selling book, “Bringing Down the House,” which begat a high-grossing movie, “21,” in which Ma had a cameo as a casino dealer.

Where he didn’t make appearances back then was on the tee. Raised in New England, the son of Chinese immigrants, Ma didn’t touch a club until after college and didn’t fully convert to golf until Covid. But in a plot twist befitting a Hollywood script, he has since become a prominent industry player, enlisted to help lead innovation at Troon, the largest golf-course management company in the world. 

Troon’s hiring of Ma as its chief digital officer, in late 2023, came at interesting time for both parties. After a successful and varied career in which he’d traded stocks, launched (and sold) several startups and filled high-ranking roles at such tech juggernauts as Twitter and Microsoft, Ma, now in his early 50s, married with young kids and living in Northern California, was ready for a new challenge. Golf, meanwhile, was at an inflection point, as forward-minded industry leaders, fresh off a pandemic-era boom that had begun contracting, pondered how to best respond to a changing market while preparing for challenges ahead.

“We, of course, recognize that’s there’s been a demographic shift in the game, that that shift tends toward a greater use of technology and that we need to be out in front of it,” says Troon CEO Tim Schantz. “Jeff’s reputation as an innovative thinker preceded him. He also happens to be passionate about golf. As we thought about our evolution as a company, and how we wanted to position ourselves, our conversations with him continued, and a lot of things just converged.”

Says Ma: “As much as I liked playing the game, there was probably even more of an intellectual motivation to what made golf so interesting to me. There were so many inefficiencies. The industry was obviously ripe for disruption, though I don’t like that word. It has a negative meaning. I would rather talk about opportunities.”

Phrasing aside, the point was plain: Ma saw cause to question the status quo.

“It happens in any industry that has done things in a certain way for some time,” he says. “If you ask why are we doing it this way, and the answer is because that’s how it’s always been, there’s a good chance you should be doing something else.”

A lot of this was evident to Ma in golf. Take tee-time reservations. Why, in an age of ubiquitous online commerce, did so many golfers still call to book? The explanation was partly generational. But not all the callers were older and tech-wary. The online experience was often so bad, Ma says, that people preferred to pick up the phone.

And then there was the cumbersome check-in process, which, even if you’d paid online, required a visit to the pro shop to pick up a receipt, which you then showed to the starter.

“That’s like me calling to make an airline reservation then walking to the front desk to get an actual piece of paper,” Ma says. “We’ve largely moved away from that in air travel. But it’s still happening in golf.”

There was more. And while not every issue could be resolved overnight, nearly all could be addressed through tech.

“The whole idea was to take that startup mentality, an entrepreneurial mindset, and apply it within an existing company,” Ma says.

Ma’s first move at Troon was to take a page from the MIT playbook and assemble an A-team of engineers, software whizzes with backgrounds at bleeding-edge outfits like Robinhood and Microsoft. Atop their to-do list was to be build a platform for what was meant to be the largest rewards program in golf. In Silicon Valley-style, Ma and his squad worked quickly. Within 10 months, Troon Access was up and running at full speed. 

Like Troon Card before it, the program offers discounts at Troon courses. But it is more than an analog idea updated. Along with tee-time savings of 15 percent, the $249 annual membership (a $400 annual membership delivers up to 50 percent discounts within 78 hours of play) comes with guest passes, partner perks (such as discounts on Ship Sticks shipments, fee-free tickets to NBA games and entry into tournaments and other members-only events).

“The idea is to allow members to do all kinds of fun things with their rewards points,” Ma says. “Maybe it’s something like playing a round with Justin Thomas or another top Tour pro. We’re talking about experiences that are second-to-none that we can roll out on the back of a best-in-class booking system.”

Troon Access has enrolled more than 10,000 members; the goal, Ma says, is to grow that number to at least 40,000. If he’s feeling bullish, that’s in part because he knows that he’s getting a head start. In contrast to many of his past ventures, he isn’t trying to create a business from scratch. Troon’s portfolio of 850-plus courses represents a vast, built-in brick-and-mortar inventory, ready to be leveraged with virtual tools.

Ma is brimming with ideas for how to do so, some of them inspired by other industries. The most obvious comparisons, he says, are the restaurant and hotel sectors, both of which have undergone a digital-age transformation reflected in such services as Resy and the Marriott Bonvoy app, click-of-the-button platforms that drive demand.

The Bonvoy comp is particularly apt, Ma says, because what he and his team are building is not third-party but in-house, which means that all the revenue stays in-house, too.

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As Ma sees it, even the busiest courses could do better by thinking differently. They could, for instance, make more effective use of dynamic pricing and offers of more flexible ways to play. 

“If I get off work and want to squeeze in six holes, I can only really do that if I’m a member of a private club,” Ma says. “Or even if I want to practice, at a lot of courses, I can only do that if I have a tee time. There’s no reason we can’t get some of our properties to work together to make those experiences available to our customers.”

Opportunities abound, including on the Troon-managed grounds where Ma is playing today. The North Course at Silverado is an annual stop on the PGA Tour that, like its sibling, the South Course, operates as resort private, with non-member times available to overnight guests only. Its conditions are pristine. Its fairways are uncluttered. It sits in the heart of a marquee tourist region, close to a major metropolitan center. And yet it flies under the radar.

“It’s sad to think about a course like this not having more people experience it,” Ma says.

Not that he’d want to fling its tee sheets open wide, as that would alienate the membership and alter a key feature of the property’s appeal. But Ma can envision a middle ground that would preserve Silverado’s country club feel while boosting revenue for the resort: for example, by giving Troon Access members tee times in windows that do not infringe on member play. There is room, he says, to accommodate all parties.

And don’t even get him started on the untapped potential of Napa itself. Though the area is home to a cluster of fine courses, it isn’t widely thought of as a golf destination. Why not stitch those courses into a regional coalition, creating a product — and marketing power — beyond what any single property could muster?

“In some cases, you obviously have different constituents who you have to make happy,” Ma says. “I’m not saying that there aren’t challenges. But these are all solvable problems.”

Ma’s challenge at the moment is the greenside bunker in which his approach has landed. Digging in for a stance, he blasts a sand wedge to about eight feet, a respectable play for a double-digit index. The greens are pure and Ma’s stroke is smooth, but his par bid goes begging.

No matter. As he knows, even pros miss such putts nearly half the time.

“And I’m not clearly not a pro,” he says.

He taps in, snatches up his ball and walks to the next with the unbothered look of a man with bigger targets in mind.