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King of hearts?

Semyon Dukach places another bet

NEWTON -- When introduced in ''Busting Vegas," Ben Mezrich's bestseller about a renegade band of MIT blackjack players who made millions outwitting casino dealers in the 1990s, Semyon Dukach is in full James Bond mode, hobbling toward a burning airplane to retrieve a bundle of cash.

Many hair-raising -- and lucrative -- escapades follow. In the book's epilogue, composed roughly a decade after Mezrich's tale ends, Dukach steps forward and tosses a few firebombs of his own, calling the casino industry ''evil" and plugging an instructional DVD of his on winning blackjack, MIT-style. Now meet Dukach in an autobiographical blurb posted on

''I'm a bit crazed, sentimental, spontaneous, successful former nerd," writes the 37-year-old divorced dad and Internet entrepreneur, ''ambitious, loving, emotional, liberal, intelligent, non-conformist . . . I try to view life as a series of escalating challenges, but I also try to listen."

Though he is best known for his blackjack prowess, Dukach goes on, ''my heart is really in my latest project, which is"

Whoa. Sentimental? Emotional? A good listener? Gotta-what-dot-com? Isn't he the ''nerd" who was once labeled the Darling of Las Vegas -- by casino bosses, and not as a term of endearment? How did he go from Bond to lonely hearts club blogger? And, seriously, is he really reinventing himself as the Darling of Web Dating Sites?

One of Dukach's current business partners, Vadim Yasinovsky, was asked as much during an interview at his Newton home recently. Yasinovsky pondered the question and laughed.

''Semyon is totally nuts," he said as Dukach sat a few feet away, not disagreeing. ''We all have crazy back stories here. There are no normal people in this company."

Next to Yasinovsky sat Mitch Russo, the third partner in Officially launched today, the site -- a prototype of which has been running since March -- combines aspects of an online dating site with an interactive ''Bachelorette"-style game.

''We've all been chasing dreams; now we're chasing the same dream," Russo commented. All three partners are rich guys who are divorced or separated and have been frustrated with Internet dating sites, he went on. ''We know how this works from personal experience, unfortunately."

Not exactly by the book
In a separate interview at his Brookline home, which he shares with his three daughters, aged 12, 7, and 6, Dukach admitted being a single guy is not all bad when you're wealthy, an MIT grad, and the hero of a best-selling book. Still, he said, finding true love, much like living up to his swashbuckling image in ''Busting Vegas," is often harder than it might seem.

''The book is not historically accurate. It's written like an airport novel," said Dukach. Most characters in the book are composites, distilled from a much larger cast of players than the handful Mezrich writes about. ''Ben did get my essence right, though," Dukach said. ''And his descriptions of how we beat the casinos are very accurate."

So where did Mezrich take liberties, exactly? ''I'm no math genius, for one thing," Dukach said, shaking his head. ''I'm good at it, but I've been around math geniuses -- and I'm not one of them."

He's no gambler, either, continued Dukach, even though conducting blackjack tutorials ($800 a pop) and hawking instructional videos (the $40 basic model and the $170 advanced version) has turned into a nice side business.

''I hate gambling," Dukach said emphatically. ''I've never gambled in my life. Gambling is waiting to get lucky. It's turning off your brain. It's deceitful and disengaged from reality, a tax on stupidity -- and a regressive one at that."

If the MIT team glamorized anything, he went on, it was science, not gambling.

''The casinos aren't gambling with their money, and neither did we. What we did to control the game was analogous to what the casino owners do, that's all."

Concerning his own celebrity status -- besides the Mezrich book, Dukach and his MIT teammates have been profiled in several TV news programs and documentaries -- Dukach said that having once desired to ''move on" from his colorful past, he's now embracing it, even reveling in it. Why?

''I believe in open information," Dukach said. ''Let the casinos try to defend themselves. Blackjack is a game that can be beat. Casinos want it to be beat. They just don't like the players who do it systematically."

Gamblers who buy his DVDs or take his seminars may think they're taking the shortcut to guaranteed riches, he said, but the reality -- there's that word again -- is strikingly different.

''You have to work your butt off." Dukach said. ''The funny thing is, it's not really worth it. You could start any business you wanted to if you applied yourself with the same intensity."

Focusing on the cards
In ''Busting Vegas," Dukach is a master of disguise: a slick, cool customer with wads of cash and nerves of steel who can change personae at will (high-rolling dentist, trust-fund preppie). Threatened at gunpoint and hounded by a special investigator employed by the casinos, he's both a romantic figure and an endangered one.

''Semyon is very charming, with tons of charisma, but he's also got an edge to him that makes him a little scary," says Mezrich, who met Dukach at a 2003 MIT panel discussion and made him the central character in ''Busting Vegas," the sequel to his bestseller ''Bringing Down the House." ''He is crazy -- a little bit," Mezrich says. ''But Semyon came from a very hard place in life, an immigrant kid living in a black neighborhood who got beaten up a lot."

If Mezrich's book accurately captures the Dukach of a decade ago, however, today's version is tamer. Off the page, Dukach comes across more like a concerned suburban father than a riverboat gambler. Raising three daughters occupies much of his energy and attention, more than burnishing his Robin Hood Meets Rocket Science image does.

When asked to speak at MIT these days, Dukach says, ''I feel a little foolish when Nobel laureates draw 15 to 20 listeners and I get hundreds for telling what's essentially a pop-culture story."

Nobel-worthy or not, his story is enlivened with Hollywood elements.

Born in Moscow, Dukach left Russia with his family as Jewish refugees and moved to Newark when Dukach was 9. His childhood hobbies included collecting comic books and playing video games, at which he demonstrated unusual skill. After moving to Houston, where his father repaired electronic gadgets, Dukach earned a degree in computer science at Columbia University and a master's from MIT in electrical engineering and computer science. His thesis on e-commerce and money exchange on the Internet was among the first comprehensive studies of the burgeoning field.

''It wasn't very good," Dukach says, ''but it pointed in the right direction." Had he not played so much blackjack, Dukach says with considerable regret, he might well have founded an Internet company worth billions today, given what fellow students at the MIT Media Lab went on to do. ''Financially, it was the worst thing I've ever done," says Dukach.

Starting out as a salaried player for the MIT team, which was managed by a group of investors and run as a limited partnership (players received about 10 percent of the team's profits), Dukach formed his own team when the original squad disbanded. The second team won between $4 million and $6 million over the next couple of years, but heat from the casinos and internal dissent eventually robbed the enterprise of much of its romance.

''Did greed play a part? To some extent, sure," says Dukach. ''We're human, after all."

Cool, different, and fun
Four years out of MIT and with a wife and young family to support, Dukach turned to making money a more traditional way. He first launched Fast Engines, a Cambridge-based software firm, then sold it in 2000 for $36 million, most of which evaporated when the dot-com bubble burst. In 1999 he started Vert Inc., a wireless media company specializing in taxi-top advertising, and from 2001-02 served as interim CEO of AccuRev, a Lexington-based firm specializing in software tools.

Three years ago, Dukach and his wife divorced. A year and a half ago, he, Yasinovsky, and Russo met over lunch to discuss ideas for new tech-oriented ventures. Several were considered, including a business converting VHS tapes to DVDs for home-movie buffs. Finally they settled on online dating and with $300,000 in seed money began designing

''I wanted to do something cool, something different, something fun -- no more enterprise software," Dukach reflects. ''Dating sites are OK for serious spouse hunting, but to me they're more like clothes shopping. The two things I love about this one are (a) the woman gets to make the rules, and (b) it's not fair. Well, it's supposed to be not fair."

Whether the website is a winner or a bust won't change Dukach's reputation as the Darling of Las Vegas. Both he and Mezrich have fielded complaints from other MIT players about their casino-busting techniques being revealed publicly. There's also some jealousy, Mezrich acknowledges, that Dukach has become a cult hero while others remain anonymous.

''Semyon is front and center for two reasons," says Mezrich. ''One, he wanted to be there. And two, he genuinely hates the casinos."

Joseph P. Kahn can be reached at

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