BUSTING OUTTA VEGAS

Geeky local blackjack genius Semyon Dukach wants to fly you to Panama and get you laid
PAUL MCMORROW

Semyon Dukach, the self-professed “Darling of Las Vegas,” made millions playing blackjack. His play was so prolific, in fact, that it got him banned from every casino in the world, and landed him a starring role his own MIT-geek-takes-Vegas-by-the-balls book, Busting Vegas, by bestselling author and Harvard grad Ben Mezrich.

That’s why it’s surprising when the directions to Dukach’s Brookline home take me past the million-dollar properties on top of Summit Avenue and down a steep hill, to within a stone’s throw of some Allston slums, the lumbering B Line and a mini-mart famous for blowing out Busch Light on the cheap. Sure, Dukach’s home is nice—suburban neighborhood, yard, garage—but it certainly doesn’t look like the home of an international blackjack hustler. There’s no gold leaf trim, no butler, no Rolls Royce—not even a Benz—in the driveway. When he goes to offer me a drink, we both discover that, with the exception of some condiments and a bottle of wine, his fridge is entirely empty.

Then again, Semyon Dukach is no longer a blackjack kingpin. It’s this fact that brought me to his empty kitchen in the first place.

***

Dukach, the son of Russian immigrants, grew up in rough sections of Newark and Houston. He’s gotten his ass kicked more times than he can remember, or would care to. While earning his master’s in computer science from MIT, he hooked up with the blackjack team that would make him rich, and later, famous. Together, they ravaged casinos from Vegas to Monte Carlo.

In Busting Vegas, Dukach (through Mezrich) brags that his team was the world’s most successful because they didn’t stoop to card-counting. Instead, Dukach mastered innovative techniques—never before seen by casinos—for legally manipulating the game and steering cards into favorable hands. These card-steering techniques earned Dukach his millions. But they also earned him looks down gun barrels, visits to Vegas’s back rooms and threats of defenestration. Eventually, he became so successful at working the high rollers’ tables that the casinos stopped trying to intimidate him, and threw him out altogether.

So what do you do if you’re Semyon Dukach, you’re the world’s best blackjack player, and you’re no longer allowed to ply your trade?

You start a dating service. Obviously.

OK, maybe it’s not entirely obvious—at least it wasn’t to Dukach.

***

For him, playing blackjack wasn’t just a way to grab quick money—it was also a personal vendetta against what he saw as a reprehensible institution. Even today, when he talks about the business of gambling, he slips into seething.

“It’s based on a dishonest nature of business,” he argues. “They get people addicted and take their money, and they pretend it’s glamorous. They trick you. They lie to you. They feed you drinks. You’d think that, when one percent of the population, through hard work and dedication, figured out how to beat the system, and they still beat the other 99 percent, they’d write it off as a cost of doing business. No. They want to beat everyone. They’re in the business of fleecing everyone for everything they’ve got.”

It was this hatred that led him to Mezrich in the first place. He believes that, despite being banned from casinos, he could, theoretically, still play blackjack by proxy, teaching others his techniques and managing blackjack teams from afar. But such an arrangement would not deal a crippling blow to the casinos, nor would it cure his creeping boredom with the game. On the other hand, by telling his story and explaining his techniques in Busting Vegas, Dukach hoped to spawn an open-source blackjack revolution—the masses are now empowered to learn, innovate and win with alarming frequency.

Of course, Dukach himself has a stake in this blackjack revolution, albeit a small one. His own review of Busting Vegas on Amazon.com sends people to BlackjackScience.com, where Dukach sells DVDs that explain card-counting ($39.99) and advanced sequencing ($159.99) techniques; visitors can also book a spot at one of Dukach’s blackjack seminars ($475). BlackjackScience could be a full-time job, but the game that pulled him out of poverty has long since lost its grip on his attention.

“I gave up blackjack long ago,” he explains. “I have career ADD. I get bored easily. Maybe in 10 or 20 years, I’ll slow down and actually run a company. But I love starting something from scratch.”

In the years since being blackballed by casinos, Dukach’s ADD has involved him in a rapid succession of tech startups. His business card lists only his name, the title “Entrepreneur,” and a litany of current projects.

Since graduating MIT, Dukach started and sold off a web software company; founded e-mail delivery companies EMUmail and smtp.com; and co-founded Vert, an electronic taxi-top advertising company. He also mentions that he very nearly invented e-commerce: His master’s thesis laid out a first (failed) protocol for doing business on the web. “I’m not Al Gore—I’m not claiming I invented it,” he says. “It just happens that my protocol was the first one.” In the same breath, he adds that those who actually did invent e-commerce worked off his flawed protocol.

Not that Dukach is solely mired in computer science geekery. The former darling of Las Vegas is also exploring the possibility of launching a Panamanian airline. “I took a three-week bike ride through Costa Rica and Panama, even though I don’t bike and I don’t speak Spanish,” he explains. “I don’t know. Those are just the kinds of things I do. So because I’m not a biker, my legs gave out, and I started flying.” Dukach was unable to fly from Limón, Costa Rica, to the Panamanian resort islands of Bocas del Toro; when he found a local who was bitching about the same transportation gap, they decided to partner and explore founding a small airline themselves.

Dukach’s wildly fluctuating attention span—shuttling himself between Boston and New York instead of retiring to the Caribbean; dumping colossal amounts of time and money into one project, only to move on to something stranger a year later—may be a vestige of Dukach’s blackjack mindset, as an entrepreneur always looking for an opportunity or an opening to exploit. Or maybe it’s just a personality defect. But he’s pretty sure he didn’t pick it up at MIT.

“A lot of entrepreneurs come out of MIT,” he muses, “but if anything, MIT graduates tend to be conservative. They get steady jobs. I’m not close to that. I think that’s why when I’m speaking at MIT, I always sell out. They want to see someone who’s bent the rules. They’re surrounded by Nobel Laureates, but they come out for me. The lines are embarrassing. I feel stupid.”

***

In a sense, it’s no more strange for a former blackjack king to launch a dating service than it is for him to start up an e-mail company or a Panamanian airline. GottaFlirt.com, the internet dating startup that Dukach plans to unveil later this month, arose from the same Why the fuck not? attitude that spawned Dukach’s previous projects. What else is a guy who bores easily and who’s not allowed to gamble anymore supposed to do?

“I think about it all the time. It’s bigger than anything I’ve done before,” Dukach says, considerably more animated than when discussing blackjack, e-mail or MIT. “I’ve never tried to build something cool before.”

But there are also indications that, as he careens towards his 40s (Dukach is 37), the gambler’s sensibilities are softening a bit. He describes GottaFlirt not just in terms of market positioning, but also as a way to create value, to finally make something tangible.

“I want to be a good guy,” he says. “I want to create value for my customers. What we’re after is creating something real. It’s not a product you can sell to a guy at a corporation—it’s entertainment, it’s fun.”

“We’re cooler than the casinos—they don’t produce anything,” he continues. “They’re still fleecing people. I want to create value. If we’re successful, I might make millions, but people will ultimately, in aggregate, gain more and get the real benefit. I want to run into somebody on the street and have them say, ‘I really enjoyed using your site.’ That’s what blackjack lacks—nobody ever said thanks after playing for five years.”