To placate his parents Sylk decided to put his grade point theory to the test. After being rejected by
Pepperdine, his first and last choice (he thought it would be cool to live in Malibu), his stepfather suggested
Nova South Eastern in Fort Lauderdale. When the acceptance letter arrived in the mail this man was
dumfounded. What he didn't know at the time was that Nova didn't reject anybody, as long as the check
cleared. Although he loathed the idea of attending a bottom feeder Law school, the prospect of living in
Florida did appeal to him. Relocating to The Sunshine State would irrevocably change his life. During
his freshman year, with the 900-number craze at its peak, Sylk launched 1-900-REVENGE ("Hit 1
for revenge on a wife. Hit 2 for revenge on a teacher…"). The project wasn't successful by industry
standards, grossing a mere $5,000 a month. But it did provide an insight into an industry that could yield
staggering profits. "My whole attitude was anything's easier than being a lawyer," says Sylk, explaining
the impetus for his initial foray into a business he knew absolutely nothing about. Soon after REVENGE
folded, he was approached by an investor who wanted to start a 900-number offering legal advice. Sylk's
eyes glazed over. He countered with a proposal to do a sex line, something that had been percolating in
his mind for months. Although the sex category was the most competitive field in the 900 industry, it also
provided the greatest rewards. His money man acquiesced. Christened Boss Entertainment, this was the
first big score.
What set Boss Entertainment apart from the competition were the ads, which ran in the back of Penthouse
and Hustler. Instead of listing the 900 number, Sylk promised a "Free Live Call." Perspective customers
would dial a toll-free number and hear a woman reading from a script who pretended to be living in the
same town as the caller. After chatting him up for several minutes, she'd then ask the love-sick chump to
call her back at a 900 number, where the going rate was $3 a minute. It was the first time the "Free Live"
rubric was ever used. The new telemarketing angle was brilliant and, according to one industry expert,
made Sylk's ads "fifty times more profitable than a standard 900-number ad." Sixty days after the ads
started running, Boss Entertainment was grossing $600,000 a month. Eventually the monthly gross hit $1
million. Although there were many larger players within the industry, Sylk, ever the self-promoter, dubbed
himself the "phone sex king." "I was excited because I learned a great way to make money," he says
proudly. "Who the hell pulls in 600 grand their third month in business ? Remember, this was before
the Internet. It was ridiculous money."
But just as his 900 gravy train was hitting it's stride, Sylk claims he lost the business to an unscrupulous
Miami lawyer he took on as a partner. During the six months the business was generating money Sylk
underwent a drastic transformation. With money in the bank for the first time -- he started spending
recklessly and plunged into the decadent South Beach party scene. He began experimenting with drugs,
especially cocaine. He became a strip club habitue. He ran up four-figure tabs at trendy restaurants, and
was on a first-name basis with all the doormen in town. This modest success was followed in 1990 by a
cookie-cutter operation called Lipstick Communications. The venture capitalists who put up the $250,000
to jump start this new sex line were, according to Sylk, a "Canadian father-son scam-artist team." Making
money in the phone sex business was simply a matter of plugging numbers into a formula for Sylk at this
point. Once again, the business flourished. And once again, Sylk went bust. According to him, it was the
investor's fault again. He says investors have always fleeced him and left him holding the bag. And that
bag, he says, is chock-full of misery: legal fees, back taxes, angry mobsters, unpaid bills… But Lenny
Sylk, Jason's biological father, says it's Jason himself who is to blame for his string of business misfortunes.
"Jason is always coming up with these great ideas, and saying that his partners screwed him out of his
money," says Lenny Sylk. "But what happens is that when it gets close to finalizing the deal he wants
more money and tries to change the contract because he thinks he's worth more."

ToTaLLy CoOL ®
written by Rene Chun


Sweat Shop"

No part of this Works, may be published or
reproduced in anyway without expressed
permission: in writing from the copyright
holders. c. 2002 All rights reserved.
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