To understand the root of Montreal gambling mogul David Baazov’s success, you’d have to have somehow stumbled upon him roughly twenty years ago, at a Dunkin’ Donuts at three o’clock in the morning. There he would have been: sitting in a booth under the glare of 24-hour florescent lights, droopy-eyed, trying valiantly to keep his head off the table. Trying, and failing.

He was 16. He was living on the streets. And he was exhausted.

Driven by a powerful instinct he did not yet understand, he had dropped out of Cégep after a single semester. His father was not impressed, and promptly threw him out of the house. Baazov was cold, hungry and dejected — and too damn proud to go home. So there he was, in an all-night donut shop, stubbornly saving face.

Young, uneducated guy brazenly goes after the biggest player in the online gaming industry…and wakes up a billionaire before his 34th birthday.

While Baazov would soon mend fences with his family and get an apartment on his own, that brief two weeks of homelessness proved pivotal. “It honed some part of me,” he says. The ordeal planted the seeds for the character that would later make Baazov famous. And, not for nothing: very, very rich.

The CEO of Amaya is on the line from his office, a modest converted warehouse in Pointe-Clair, an industrial suburb just west of Montreal’s Trudeau Airport. The space is low-key, adorned mainly with family photos and sports memorabilia from charity auctions. Not exactly the lavish global headquarters you’d expect of a man who’s become the digital version of Sheldon Adelson.

Baazov’s firm has, after all, become a giant in online gambling. Amaya owns mega-brands like PokerStars and Full Tilt Poker, with a combined registered user base of 93 million people. The company Baazov founded in 2005 is now the largest publicly-traded online gaming company in the world. It’s worth $10 billion dollars, or roughly a quarter of the industry as a whole. His personal net worth? Somewhere in the neighbourhood of $800 million.

“On the one hand, the story of Amaya’s takeover of the Rational Group under Baazov’s leadership is the stuff of MBA mythology,” says David Weitzner, Assistant Professor of Strategy at the Schulich School of Business. “Young, uneducated guy brazenly goes after the biggest player in the shadowy online gaming industry with nothing more than attitude and charisma, convinces one of the biggest private equity funds in the world to finance him, and wakes up a billionaire before his 34th birthday.”

But there’s always another hand.

At 35, Baazov is having his Master of the Universe moment, with the leadership awards, speaking engagements, panel invitations — and intense insider scrutiny, including a potentially crippling insider trading investigation — to prove it. Here he is at the top of his cinematic rise. But how’d he get there? At some point, he had to bet the house.

Picture Baazov at 17, standing in a Montreal restaurant, trying desperately to sell its much-older male owner on his first business, a coupon venture called Discount Pack. At the time, he couldn’t afford to put gas in his car, had no capital to his name and no entrepreneurial experience whatsoever. But he was certain his new scheme would work.

“I still remember my first meeting,” Baazov recalls with a laugh. “He asked me for a business card, and I didn’t have one. And he asked me for pricing. I didn’t have the answers…He looked at me and said, ‘Son, go do your homework and come back.’” The next day Baazov printed ink-jet business cards and ran his numbers. He closed the deal — and never looked back.

Born in Haifa, Israel, Baazov was raised in the west island of Montreal, in a conservative, Modern Orthodox Jewish home. His construction worker father laboured at several jobs to support the family. “I maybe didn’t have the nicest Nikes,” Baazov admits. Being the second youngest of six siblings, he wore a lot of hand-me-downs.

I don’t let people see any doubt on my side. Even though I may have some.

It was a close, family-focused household — busy, noisy, full of life, full of people. A highlight of the week was walking to synagogue on Saturdays with his father.

But Baazov had his eyes on the wider world. School often didn’t go so well. There were calls from principals. He was smart, especially in math. But he strained his relationships and soon got booted out. “At the time, I felt like I wasn’t learning anything,” he explains. “I wanted to do something that was impactful. I wanted to see a tangible return — to feel like I’m accomplishing something. I didn’t want to invest a few years to then get a degree, to then have to go and do something. I wanted to do something now.”

After Discount Pack ran its course, Baazov moved on to a computer re-selling business, eventually winning a coveted contract from the Montreal Public Library that transformed the venture into a $20-million business. “It was a massive milestone,” he recalls. “I’m walking into this meeting and I am the only one who doesn’t own a suit. But I walked away with it. I delivered it. It was huge.”

***

Fast forward 15 years, to 2013. By now, the computer outfit had had legal issues and gone bankrupt — and Baazov had moved on to found Amaya, a tech gaming company he successfully took public in 2010. He’d been steadily acquiring assets in the gambling industry, and was now bringing in $146 million in revenue.

Baazov had his eye on the Rational Group; it owned the absurdly profitable site PokerStars and raked in $1.1 billion a year in revenue. He was after its zealous customer base (then 89 million users). The acquisition was so unlikely, so pie-in-the-sky, that when he went to his CFO, Daniel Sebag, with the plan, his reply was: “Please do not waste one minute of your time on this.” To Baazov’s ears, that sounded a lot like: “Why not give it a shot?”

So he approached Rational’s owners — the reclusive Scheinberg family — again and again. They didn’t take him seriously. At all.

“Most entrepreneurs fail when doubt sets in,” Baazov reflects. “Doubt actually kills more deals than economics.” So Baazov put on his game face. “I don’t let people see any doubt on my side. Even though I may have some.”

His persistence paid off in early 2014, when the Scheinbergs were finally ready to make a deal.

“The Scheinberg family were no fools,” says Weitzner. “They unloaded a company that was facing serious legal problems and were being shut out of markets, thus hampering opportunities for growth in an industry already facing decline.”

This is not the end of the story, of course. The online gaming industry is fraught with legal, moral and financial hurdles to overcome, many of which Amaya is just now facing.

“Generally, online gambling is seen as a somewhat sleazy business,” says June Cotte, Scott & Melissa Beattie Professor in Marketing at Ivey Business School. “It makes gambling access available every moment of every day, in any jurisdiction it operates in.”

Baazov argues that there’s “a stubborn old idea that the gambling industry has a bad reputation, but we don’t see it [reflected] in the statistics — we don’t see it in people’s day to day actions and we don’t see it in government legislation.” He sees gambling as a form of entertainment, like any other: “People go to the movies, concerts, watch TV and people go to casinos to be entertained in the same way.”

But image isn’t the only problem. The issue of regulation looms large too, particularly in the US, as GOP presidential hopeful Marco Rubio makes a congressional, anti-online gaming push (championed by none other than casino kingpin — and Republican donor — Sheldon Adelson, who’s keen to defend his territory). This bill takes the moral argument out of business circles and into the mainstream. It harms the poor, Rubio et al. say, and encourages gambling addictions.

People go to the movies, concerts, watch TV and people go to casinos to be entertained in the same way.

Baazov is, not surprisingly, undeterred. Rubio and his allies can hardly claim to be the moral police, he says. And of course he’s happy for each market to decide for itself how it wants to handle online gaming.

As it turns out, the largest, most pressing issue is at here at home. According to a Globe and Mail report, Baazov is now the subject of “the largest insider trading investigation in Canadian history” by Quebec’s securities regulator, the Autorité des marches financiers (AMF), in conjunction with the RCMP, American and British regulators and the Ontario Securities Commission. According to the Globe, the central question is “why so many investors bet on a minnow-sized online gambling company months before news broke about its improbable $4.9-billion (U.S.) takeover last summer of online betting whale PokerStars.” The newspaper notes that authorities have not made any allegations of wrongdoing to date.

When asked about the investigation, Eric Hollreiser, Amaya’s head of corporate communications, stresses the fact that there have been no charges filed. “We have done an internal review — conducted by the former head of the RMCP — which found no wrongdoing at Amaya,” he says. “We’re confident the AMF will come to the same conclusion.”

Money is not a driving factor in my motivation.

Perhaps it’s not surprising that despite the fame — and the insane influx of cash that the Rational mega-deal gave him — Baazov has maintained a low profile. His team says he runs the business frugally, with an eye ever-trained to the numbers.

His relationship to this newfound wealth and power and influence is at heart a conservative one. “Money is not a driving factor in my motivation,” he says. “Challenges motivate me. The more someone says I can’t do something, the more it pushes me to do it.” He drives a Range Rover, sure, and he collects watches. He travels frequently, and last year he flew 23 people in his extended family to the Bahamas for Christmas. But he still lives in the same neighbourhood he grew up in.

It’s still possible for Baazov to stay on his winning streak – if he plays his cards right. “If he can distance himself from the insider trading allegations, or quietly settle, and return to his persona as an ambitious relationship builder,” says Weitzner, “maybe by crafting new partnerships with players in the provincial government who have expressed interest in the potential tax revenue offered by online gaming, he may yet prove to be the savior of an industry that appears to be in decline,” Weitzner says.

For his part, Baazov remains characteristically optimistic, in spite of the mounting pressures. He is, instead — as usual — focused on the horizon. On the next move. He promises it will be a big one.