"I wanted to wait until I found something I really wanted," says Winnick, now 51, sitting in his spacious Beverly Hills office.
His ability to defer instant gratification for that "something" -- and going all out when it came -- has propelled Winnick to the rank of the wealthiest man in Los Angeles.
The title was bestowed on him in May by the Los Angeles Business Journal, which put his net worth at $6.2 billion. A cover story in Forbes magazine the previous month cited a figure of only $4.5 billion -- but, hey, who's counting.
Whatever the total, Winnick is also among the dozen richest men in America, in about the same league as media moguls Rupert Murdoch and Ted Turner.
Having made his pile in an astonishingly short time, Winnick is increasingly focusing on philanthropic endeavors, both in the Jewish and general communities.
Just announced is a $5 million pledge by the Gary and Karen Winnick Family Foundation to erect children's and changing exhibit galleries at the Skirball Cultural Center. He and his wife have also endowed Hillel centers at three East Coast universities and a children's zoo at the Los Angeles Zoo. They are also major supporters of the Jewish Federation of Greater Los Angeles, the Simon Wiesenthal Center and New York's Whitney Museum. A list of the foundation's charities includes 54 organizations and institutions, from the American Friends of the Israel Philharmonic to the World Relief Foundation.
His criteria for giving are simple: "I must believe in the cause, and I demand accountability from the recipient," he says.
It doesn't hurt if he knows and likes the person running the cause he believes in. "I have incredible respect for Uri Herscher [founder and president of the Skirball Center]. I must support his efforts," he says.
Gary Winnick's rapid rise to great fortune has become part of modern entrepreneurial folklore, illustrating both his personality as risk taker and the global revolution in telecommunications.
After a post-college stint on Wall Street, he got his start as a serious money man in the early 1980s, working with Michael Milken's high-yield trading operation at Drexel Burnham Lambert. Even among that group of workaholics, Winnick earned a reputation as a notably dedicated trader.
In 1985, Winnick set up his own investment partnership, now known as Pacific Capital Group, which proved a solid producer. Lightning struck in January 1997, when AT&T needed to raise $750 million in a hurry to lay an underwater fiber-optic cable across the Atlantic. Risking $15 million of his own money, he formed a new company, Global Crossing, and raised the total in record time. With the worldwide explosion in voice, video and data transmission -- spurred by the Internet -- the company's worth has grown exponentially, and its market value now is set at $22 billion.
According to Forbes, Winnick is the fastest among today's top entrepreneurs to make his first billion dollars. He did it in a breathtaking 18 months, while it took such laggards as Bill Gates of Microsoft 12 years and Michael Milken 20 years.
Global Crossing's plans for the future call for a worldwide network of fiber-optic cables that would link and provide telecom services for 180 cities in 50 countries, thus radically lowering costs for voice, data, video and Internet transmission.
As a major step in this plan, Global Crossing announced last month a joint venture with Microsoft and Japan's Softbank Corp. to build a high-capacity telecommunications network in Asia.
Winnick believes in spreading the wealth. Some 40 percent of the company's stock is held by employees, all of whom were given options ahead of the company's initial public offering. Three of Global's top executives also made the Business Journal's list of the 50 richest Angelenos, and even some secretaries are millionaires, at least on paper.
The Winnicks' housekeeper, Natie, gained fame as the wealthiest member of her profession, and other beneficiaries of early option offers are three rabbis, whom Winnick declined to name.
The future entrepreneur grew up on Long Island, N.Y., where his father owned a restaurant-supply business.
"I started working when my age was in single digits," he says. "I always had a lot of drive, and I never questioned my determination."
His parents were members of a Reform congregation, and Winnick attended Hebrew school -- unenthusiastically. "My mother had to shlep me on Sunday mornings, like I was going to be shot," he says.
He was inspired to "turn on my light as a Jew" with the birth of the first of his three sons, 24 years ago.
Winnick credits much of his interest in Jewish causes to Ed Sanders, then, as now, a major Jewish community activist. Winnick's Jewish ties grew when his kids enrolled at the Stephen S. Wise Day School. "The boys loved the school and loved being Jewish, something I didn't have as a child," Winnick says.
He illustrates his commitment to the Jewish community with an anecdote. "I have a friend who invested $300,000 in Global Crossing, which is now worth $50 million," he starts. "He called me up and said he wanted to buy me a Rolls Royce, with all the trimmings, as a token of his appreciation. So I asked him how much he planned to spend on that, and he said about $500,000. So I told him, 'Give the money to the Jewish community, to the elderly people on Fairfax Avenue; that'll be my Rolls Royce.' "
Recently, Winnick spoke at UCLA's Anderson Graduate School of Management and shared his three basic rules for entrepreneurial success.
* Persistence will almost always win over calculation. There is no better asset than persistence.
* Passion always trumps expertise. Passion drives success.
* Speed rules. Entrepreneurs are addicted to speed and are fixated on winning.
He closed the talk on an almost lyrical note. "At Global Crossing, we're building a new network for the new century," he says. "A highway of glass and light, along which will travel ideas and information for all the world to use."
When Global Crossing first started off, Winnick and his top executives worked 18 hours a day, seven days a week for six months. He has slowed down now to getting up around 5:45 a.m., checking at home on the Bloomberg financial news, placing calls to Europe and the East Coast, and driving to the office, which he leaves between 7:30 to 8 p.m.
If Winnick sounds like a driven man, he is a remarkably contented one. Asked where he wants to be 10 years from now, he responds that he would be happy "if I can freeze-frame my life now. I love my wife, Karen [a highly regarded writer and illustrator of children's books], we've been married 26 years, and I hope for 50 more.
"I love my kids. When they were growing up, I coached them in soccer and basketball, and I never missed a dinner at home. I love what I'm doing."
What is his ultimate ambition? "It's not about being the richest man in Los Angeles, or the world," he says. "It's about using what talents you have to your utmost."