Itzler’s father, Lenny Sylk, is the son of the founder of the Sun Ray drugstore chain. The Sylks lived outside Philadelphia in a 120-year-old mansion with an eighteen-car garage, a helicopter pad, and maids and butlers who attended to domestic chores. But Ronnie and Lenny’s marriage had unraveled by Jason’s second birthday.
After the divorce, Lenny dropped out of the picture and Ronnie got custody of Jason. She moved back to New York, where she met and married a bankruptcy lawyer named Ron Itzler. A partner in the powerful Manhattan law firm Fishbein, Badillo, Wagner & Itzler, Ron raised Jason from then on. Jason would later acknowledge this by changing his name to Itzler.
Jason Itzler was shuttled through a series of exclusive private schools. The only thing he recalls about his early academic years is his celebrity classmates: Mira Sorvino (“tall with big boobies”) and Brooke Shields (“really pretty, classy, and elegant”). Curiously, though, he left them behind and graduated instead from a public high school in Tenafly, New Jersey. “I wanted to experience the real world,” he explains.
In 1985, Itzler enrolled at George Washington University. Born a Sylk, he had inherited expensive tastes. Now, living away from home for the first time, he felt liberated to indulge them-he drove a 280 ZX, appreciated fancy restaurants. To finance his lifestyle, Itzler says, he exploited the collegiate demographic in every way he could think of. He promoted fraternity keg parties and wet-T-shirt contests. He did a brisk business in fake IDs and scalped concert tickets. (“It was a little shady,” he admits.) And he dabbled in publishing. His most memorable title was The World’s Greatest Pick-up Line. Advertised in the back of Rolling Stone for $5, the book contained exactly one page, printed with a fill-in-the-blank exercise:
“Do you know____________________? Hi, I’m ____________________.”
After graduation, he bowed to pressure from his parents and went to law school. During his first year at Nova Southeastern University in Fort Lauderdale, Itzler launched 1-900-REVENGE (“Press 1 for revenge on a wife. Press 2 for revenge on a teacher…”). The take-$5,000 a month-wasn’t much by the standards of an industry then at its peak, but it did give Itzler a vision of his future life. “My whole attitude was, anything’s easier than being a lawyer,” he says.
Soon after REVENGE folded, he was approached by an investor who wanted to start a 900 number offering legal advice. Itzler’s eyes glazed over. He countered with a proposal to do a sex line, something that had been percolating in his mind for months. His money-man acquiesced. Christened Boss Entertainment, this would be Itzler’s first big score.
What set Boss Entertainment apart from the competition were the ads, which ran in Penthouse and Hustler. Instead of listing the 900 number, Itzler promised a “free live call.” Prospective customers would dial a toll-free number and talk to a woman who pretended to be in the same town. After chatting up the lovesick chump for several minutes, she’d then ask him to call her back at a 900 number, where the meter would run at $5 a minute.
It was the first time anyone had used the “free live” rubric, an angle that made Itzler’s ads “fifty times more profitable than a standard 900-number ad,” according to one industry expert. Within sixty days, Boss Entertainment was grossing $600,000 a month. Although there were many larger players in the industry, Itzler, ever the self-promoter, declared that he was the “Phone-Sex King.” But just as Boss was hitting its stride, Itzler says, he was edged out of the business by his partner.
Itzler graduated from Nova in 1993 with a 2.03 grade point average. Since he had no intention of practicing law, he bypassed the bar exam. (Still, a remarkable number of people seem to be under the impression that Jason is a lawyer, including, at times, Jason himself.) Instead, he would ask his stepfather to help stage his triumphant return to the phone-sex business. According to Jason, Ron Itzler told one of his bankruptcy clients, Mel Roslyn, about his son the phone-sex king, and Roslyn cut a check for $100,000. M2 Communications was launched in 1993, and within three years, Jason claims, it was grossing between $1.2 and $1.4 million a month.
As the money poured in, Jason Itzler gave his college sweetheart a six-carat heart-shaped engagement ring from Harry Winston. They flew to Las Vegas and were married at the Little White Chapel, but the union would last only nine months. Lenny Sylk blames his son for the breakup. “The first thing he did was get her a nose job,” Sylk says. “The second thing he did was get her a boob job. And then he made her crazy. We just felt bad for her, because she was such a lovely, sweet girl.” He sighs. “Jason’s a sick kid.”
To fill the void in his life, Itzler dated strippers, leased exotic sports cars (including a $400,000 Aston Martin Virage), gambled (blackjack at the Hard Rock Casino), shopped for real estate (a luxury high-rise apartment in the Oceania on Collins Avenue in Miami Beach). He says he was making $2 million to $3 million a year and spending half of it on “lifestyle.”
All true, says a former M2 employee: “Jason spent 80 to 100 grand a month on his Platinum Amex card alone. The kid would go into the Disney store and spend $13,000 on ceramic statues of the Seven Dwarfs. He’d spend $1,000 a night in strip clubs. His place in the Oceania was decorated with a waterfall and a smoke machine. It was like a Vegas show.” One friend who visited Itzler at the Oceania describes the decor as “early-nineties Miami coke den. There were low-rent models and blow everywhere.”
Women were a significant expense. For Itzler, there was no such thing as a cheap date. He showered them with gifts: Cristal champagne. Chanel frocks. Bulgari jewelry. Breasts. By one ex-girlfriend’s estimate, Itzler referred at least ten girls a year to Lenny Roudner, a local plastic surgeon whose flair for breast implants has earned him the nickname “Dr. Boobner.” Itzler praises Roudner as an “amazing artist;” Roudner, returning the compliment, billed Itzler the preferred-customer rate, $3,500 a set.
During Itzler’s shopping spree, Mel Roslyn was told M2 hadn’t turned a profit yet. He was starting to wonder whether he would ever see a return on his $100,000 investment, so he did some investigating and discovered that M2 was a raging success. The silent partner suddenly became very vocal. He sued not only Ron Itzler but his law firm as well. Needless to say, the firm was not pleased that one of its partners was involved in a phone-sex service with a client, and Ron resigned.
The legal fees cut into M2’s profits, and that wasn’t the only drain. The company was bridging the gap between accounts payable and accounts receivable with loans that carried exorbitant interest rates-as high as 36 percent. Even with its torrential cash flow, M2 couldn’t keep up. Itzler lost the company and all his business assets, including his most prized possessions. Back when the Internet was still a gleam in Al Gore’s eye, Itzler had had his minions registering every dirty domain name they could think of. “He was a visionary in that respect,” one employee says. Now, with M2 in ruins, he had to give up the rights to blowjobs.com and pussy.com.
In 1997, Itzler left Miami, acutely depressed. Some time later, he turned up in New York and began to ponder his next move. He’d been toying with the idea of breaking into the Internet-sex business, selling video feed to online porn sites. All you needed were naked girls, web cams, and a T1 line. And the field had its perks. While operators at 900 lines were hired for their voices, not their bodies, Internet-sex girls were hot.