‘My life is surreal. I can’t tell you how many propositions I get, it’s absolutely insane,” said Jason McCabe Calacanis, founder of the Silicon Alley Reporter , the New York Internet community’s version of People magazine. “It’s actually wound up hurting me on a personal level. I have two people I dated in the last three years who dated me specifically to leverage their careers.” The blond, baby-faced 29 year old, whose magazine is best known for its “Silicon Alley 100″ issue, in which Mr. McCabe Calacanis ranks the New York players, said, “I’m not used to women liking me. It’s depressing to think they like me for my Rolodex, or for what I can do for their dot-com.”
Welcome to the big leagues, Jason. Sure, you might have been one of the geeks who warmed the bench while the golden boys slam-dunked the financial markets, but now you and your Internet buddies have the power. Or, at least, the perception of power. Which, in New York, is the same thing. So get ready to be courted by the media, the venture capitalists, the politicians, the real estate brokers and, of course, the New York female. After all, why should a woman settle for a dull investment banker making a safe million a year when she could have a dot-com stud with $50 million in his pocket?
But how does the Internet bachelor differ from the Wall Street equivalent, with his dependable institutions–a Park Avenue eight, the Racquet and Union clubs, fast cars, wine and a well-mannered, well-heeled pliant woman on his arm? The Internet entrepreneur will tell you his passions run deeper. More cerebral. Or so he says. In recognition perhaps of the Net’s populist myth, his millions may indeed be linked to socially worthy causes. He wears Banana Republic instead of Brioni, jeans instead of J. Press. He didn’t come up through the Old Boy Ivy League network. He’s often middle class in origin. Also, unlike their I-banker predecessors, Internet studs must contend with the fact that women in their industry are increasingly laying claim to as much power as the guys. “It was always mostly men,” said Stacey Horn, founder of Echo, an on-line community. “Now it feels like women all over the place.”
But where men and money mingle, there will be ego. “A lot of these guys just had an idea and got funding and now have millions of dollars,” said a woman who is an Internet consultant. “A lot of them use it to their benefit in their pursuit of women. It’s not particularly pleasant.”
“Internet C.E.O.’s are getting groupies,” said Cecilia Pagkalinawan, the 31-year-old founder of the Internet company Boutique Y3K, which does e-commerce consulting for fashion companies. “You can see at parties and events that women who know them, or of them, are circling around them.”
Ms. Pagkalinawan said that one dot-com chief executive claims there is a sure-fire way to tell if a woman he meets is only interested in his money. “The women start talking to him about charities,” she said. “They want to be the next Melinda Gates.”
But like their Wall Street brethren, Internet bachelors don’t unplug. To do so would be to risk losing to the other guy. Or gal.
“It’s the constant ringing of cell phones and beepers–you are never away even if you are away,” said Ms. Pagkalinawan, who dates the chief executive officer of an Internet company. “Thirty minutes after the millennium, my boyfriend was back on the computer. We couldn’t even celebrate this once-in-a-lifetime event together. That is my nightmare.
“Every decision is a negotiation,” she said. “‘Where do we go this weekend? How much time will we have?’ Because it has to pull from their business time. Appeasing you could be worth serious bucks to them.”
“Are Internet entrepreneurs catches? To any fellow workaholic, sure,” said Genevieve Field, editorial director and co-publisher of Nerve.com, a Web site of highbrow erotica. “They tend to be smart, creative and disciplined. They have complicated personalities and they think in big, bold colors. But if you’re looking for someone who’ll be home by 7 to cook dinner with you after work–someone to share a sane, stable life–Internet people, men and women alike, are probably not for you.”
“The people in this industry are very goal-oriented. They have a checklist of things they need to accomplish before they get married,” said Ms. Pagkalinawan. “In this industry, it’s ‘After I’ve gone public’, or ‘After I’ve received $10 million in investments, then I’ll find a wife or make time for one.’ We’ll find these men not having offspring to hand their businesses to, we’ll find men who won’t be alive to see their kids’ high school graduation.”
The rewards of dating an e-millionaire can shift with a click of the mouse. As Ms. Field noted, “Although most of them are rich on paper, there are no guarantees that that money will ever become material.”
As savvy as these men are about business, the Internet entrepreneur may be clueless when it comes to a real woman. Ms. Pagkalinawan said, “They have some very unrealistic ideals for women. They’re working with a virtual environment, where every photograph can be Photoshop-ed; you can do virtual cosmetic surgery on line. They’re used to playing with Lara Croft from Tomb Raider. She’s worse than Barbie, her figure is more unrealistic than Barbie’s.
“So they want the physical stimulation and the intellectual stimulation and I think that’s a rarity. On line there’s so much extra heightened stimulation, there’s so much information and images that come to you on the Internet, that you sort of require the same challenges and interests off line.”
But above all, they just want to be loved.
‘There’s no reason why I can’t be the next Michael Eisner,” said Mr. McCabe Calacanis. “Somebody has to be the next M.E. I probably sound a bit delusional. People counted me out. People don’t think I’m going to do it when I say I’m going to be the next Michael Eisner. So that’s good, Michael Eisner’s not worried about me.”
Mr. McCabe Calacanis began as a technologist, later advised venture capitalists, then founded his fledgling media empire. The son of a nurse and a restaurateur, he was raised in Bay Ridge, Brooklyn, educated at Fordham University, and is a fourth-degree black belt in Tae Kwon Do. He has run the past 11 New York City Marathons. He said he loves the fact that many people on his staff went to better colleges than he did. He makes anyone who wants to work for him watch two of his favorite movies, All The President’s Men and The China Syndrome .
Rising Tide Studios, the parent company of The Silicon Alley Reporter, has gotten into on-line publishing, and organizes conferences for new media bigwigs. Mr. McCabe Calacanis’ mother and one of his brothers work for him.
He wears Agnès B. and eats almost exclusively at Gramercy Tavern, Nobu and Bond Street. (He named his bulldog Toro after sushi.) He has Knicks season tickets. (Though not courtside.) He is not pining for a relationship.
“There’s no line between personal and private, between job and free time, and that’s a good thing,” he said. “You have people who have found their mission; their work is not really work to them. Michael Jordan’s job was to play basketball, but how much of a job did he think that was?”
He has met some disappointment on the dating circuit. “There’s a famous story from two years ago,” he said. “A young lady who was very attractive and a C.E.O. started asking me to lunch and to movies, and after about five dates–we were at dinner at a French restaurant in SoHo–she said over dessert, ‘Why is this person in the “Silicon Alley 100″?’ and I justified it. And she said, “Do you know my company has twice as many employees?’ And I said ‘No. Congratulations.’ And it wasn’t until 45 minutes later that I realized what was going on, and then I was sick to my stomach. That was tough because I really liked the person and I felt so used.”
“Right now I just want to be in the game,” he said. “Just like the N.B.A., I may not be the top-rated team in the league, but I’ve got a chance at the table and I’m going to play my heart out. It’s well worth it, because you’re living. I don’t know if Orson Welles or Kurosawa had the healthiest personal lives but they changed the world. They did some good work.”
Dating while working so hard is “very, very difficult,” said Andrew Rasiej, a 41-year-old former nightclub owner who last year co-founded Digital Club Network, which cybercasts live music performances from nightclubs and keeps an archive of classic performances. But Mr. Rasiej’s heart is in the non profit Mouse.org (Making Opportunities for Upgrading Schools and Education), which he started six years ago and which has wired close to 50 public schools, utilizing a database of 1,500 volunteers.
“What’s the difference between $50 million, $100 million, $400 million? You can’t fuck your money,” he said. “How do you differentiate yourself from the next guy with a gazillion dollars? The new, new thing is how much of an agent of change can you be.”
At a recent Hillary Clinton “meet and greet” for 100 supporters, held in a Manhattan townhouse, Mr. Rasiej told Mrs. Clinton that wiring schools would only make sense if each school had a systems administrator on staff. He suggested she support college scholarships for people who would commit to becoming systems administrators for public schools. According to Mr. Rasiej, the Senate candidate gushed about the idea and the room broke into applause.
Mr. Rasiej, who grew up in Bogota, N.J. as the son of Polish-American immigrants, put himself through Cooper Union by renovating houses. After some time in the real estate business, he got into nightclubs. He owned Irving Plaza, the cutting edge rock hall downtown. Then he found the Web.
Weekends, he goes to a place he built himself on the Jersey Shore. He just went into contract on an old carriage house in the West Village. He said he wants to get married and that he prefers European women to American women because “they have a cultural sensitivity that I don’t usually find in the United States.” He’s dating a French journalist who recently moved to New York to be with him.
He also believes that women with divorced parents are trouble, at least for him. “The chances of success in marriage increase when the parents have stayed married,” said Mr. Rasiej, whose parents have been married for 49 years. “I’m shocked at how often I come across it. More often than not, their parents are divorced. Maybe I just pick them wrong…. You want to minimize the number of variables when you’re getting involved in a relationship. Adding the potential emotional baggage from a divorce doesn’t help.” Still, he said he wouldn’t totally rule out marrying a woman from a divorced family. “Empathy,” he said, is the quality he most desires in a partner.
In any case, he said, Web work gets in the way of marriage. “It’s just insane, unless you’re going to turn it into a strategical move, it’s impossible to spend any time on personal relationships,” he said. “It has to be a project in itself. When it becomes a priority, it will happen.”
“The ultimate holy grail is true cybersex,” he said. “The holy grail is having cybersex that is not actually masturbation.”
“My perfect woman? I liken it to experiencing the moon or the ocean,” said Murray Hidary, who is 28 and worth $40 million. “She is somebody who inspires me, and is inspiring enough so that I can look at her fresh every day in whatever form that takes.”
Mr. Hidary is the executive vice president of EarthWeb, a business portal for the information and technology industries, which he co-founded in 1994 with his older brother, Jack, who is chief executive officer. As a student at Columbia University, Jack Hidary had developed a computer network, ColumbiaNet. Later, when he was working at the National Institutes of Health, he talked with little brother Murray about the Rwandan refugees. They decided to use the Internet to publicize the refugees’ plight and created ReliefNet. Newsweek wrote them up. “We realized this was the future,” said Murray Hidary.
Which was a good thing. At the time, he was caught between his passion, music composition, and pressure from Dad to enter the family apparel business. After graduating from New York University and teaching music appreciation, he did end up at M. Hidary & Company. But then came ReliefNet. (He didn’t have to give up the music: He has a grand piano in EarthWeb’s Park Avenue offices, which occupy an entire floor and offer a sweeping, 360-degree view of the city.)
After ReliefNet the Hidary brothers started EarthWeb, which built Web-sites for the Metropolitan Museum of Art and other institutions eager to establish an on-line presence. Mr. Hidary describes EarthNet as “the leading business-to-business portal for the IT world”. The company does a lot of everything: providing content, hosting on-line community forums, e-commerce. In 1998 it went public.
“‘You never really achieve manhood until you’re successful in business’ is the Hidary family motto,” said Mr. Hidary. Raised in what he described as a “very closed-off community” near Coney Island, in a large Orthodox household, the Hidary children are expected to have Jewish spouses. But Mr. Hidary said that, for him, religion was not a priority. “Mom, please look away,” he joked. People call him daily to fix him up; he’s declared a moratorium on blind dates.
He’s having fun with his money: loft in TriBeCa, BMW motorcycle, Porsche 911, 1973 Volkswagen van. “You remember those peace vans? I fell in love with a bright orange one with a flower on it,” he said. He eats out at a different restaurant every night with friends, wears jeans every day, Prada when necessary.
“I haven’t had a steady girlfriend for a number of years,” said Mr. Hidary “Part of being a hopeless romantic makes it more difficult to find that. You’re always dreaming of that perfect person.”
But he said he’s become a shrewd dater. “What success does, it acts as a microscope. It creates a tremendous amount of clarity,” he said. “There is no time for six dates. You need to come to a decision quicker. It’s a question of investment.”
Omar Wasow was eating lunch at the Four Seasons recently when Matt Lauer came over to shake his hand. The Today show co-host told the 29-year-old Mr. Wasow that he was a big fan and would love to have him on the show. Mr. Wasow gave a slight bow and said he would be delighted. “That is so generous,” he said after Mr. Lauer left. Mr. Wasow is best-known to the public as “Oprah’s computer guy.” When Oprah Winfrey decided to document her initiation to the Internet, she chose Mr. Wasow as her on-camera guru. The first episode of the twelve-part Oprah Goes Online aired in February. But before Oprah, he had already made a big noise inside the industry. Last September he launched Blackplanet.com, now the most visited Web site geared to African Americans. He is also MSNBC’s on-air Internet analyst, and has consulted for Newhouse newspapers. He recently became an equity partner in Community Connect, which runs on-line communities for minority groups. He claimed to have no idea of his net worth. “I don’t know what the future holds. My net worth is a lot of credit card debt,” he said.
He was raised by two intellectuals, a Jewish father and African-American mother. The family moved a lot–Bangladesh, Nairobi–and squabbled as intellectuals will. “Family arguments were how you showed love,” said Mr. Wasow. They settled in New York, where his father became a professor of economics at New York University. Omar programmed his own computers and ended up at Stuyvesant High (his English teacher, Frank McCourt, wrote a college recommendation letter). He went on to Stanford University. (His mother is currently dean of continuing education at Bank Street College; his father works at the Century Foundation, a think tank.) About his waist-length dreadlocks, which he began growing 14 years ago, Mr. Wasow said, “It’s kind of absurd. I wanted to freak out my family. Now they’re scared I’m going to cut them. The family joke is that to rebel is to wear a suit and read George Gilder, which I’m doing now.”
He said his goals include writing and living in Cape Town, and being involved in school reform (he is on the board of a group that is applying to start a charter school in Brooklyn). But he’s also ready to make some dough. “I’m proud of my work and I’m working feverishly hard and we’re No. 1 at what we do,” he said. “So I hope we reach the promised land.” For now, he lives in Boerum Hill, Brooklyn, and avoids the Silicon Alley social scene. “The Brooklyn Bridge is the closest thing to religion to me,” he said.
He said he prefers coupledom to singleness, but he’s barely sleeping, let alone dating. His perfect woman, he said, “should be able to beat me up, verbally, she should have a sense of humor, she should be sort of a contrarian, she should like to dress, she should like hot sauce and pulpy orange juice.”
He doesn’t date in the industry. “I spend enough time as it is in the world of bits and take a certain pleasure in being drawn out of my geek cave. As difficult as it can be to juggle a heavy workload and a girlfriend who doesn’t eat, sleep, and breathe the Net, I’d rather have that balance in my life than be totally subsumed in ones and zeros.”
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