Kevin Ryan reclines in a designer chair in his Park Avenue office, wearing a Luciano Barbera suit and a vintage Rolex watch. A picture of Ryan with PresidentBarack Obama is on the wall and an ornate Oscar de la Renta gown hangs from the door.
This is not a man who would blend in among the sneaker-clad startup ranks of Silicon Valley. Yet Ryan, chief executive of the Gilt Groupe and a founder of several prominent Internet companies, is one of the technology world's most influential people, with a career trajectory that mirrors the rise of New York's tech scene.
Ryan and Dwight Merriman run a startup factory called AlleyCorp, after Silicon Alley, a nickname given to New York's answer to Silicon Valley. It has churned out companies that have almost nothing in common, from e-commerce to publishing to database software.
When asked about this startup grab bag, Ryan smiled and said, "Are you saying I have a focus problem?"
Gilt.com, which sells luxury goods like designer clothes and vacation packages, is considering going public next year. Business Insider, another AlleyCorp company, is a blog publisher with 19 million readers a month, run by Henry Blodget, the infamous former Internet stock analyst. And 10gen, which makes MongoDB, open-source database software that is used by companies like Disney and Foursquare, was valued at $500 million by venture capitalists who invested $50 million in May.
These companies contribute to New York's growing role as an Internet hub, particularly for the new generation of online media and retail companies. Last year, 256 New York tech startups raised $2.2 billion in investment, up from 149 and $1.3 billion five years ago, according to the National Venture Capital Association.
"Silicon Valley is on their fifth generation," Ryan said. "We're on our second or third generation of New York entrepreneurs, combined with a bigger and better infrastructure to support it, so the scene is just mushrooming."
Ryan made his name during the first tech boom as chief executive of DoubleClick, the digital advertising company that Google bought for $3.1 billion in 2007.
"He doesn't fit into the Valley mold as much, but he's definitely one of the most prominent people here," said Chris Dixon, a New York tech investor and entrepreneur. "He went off and did this thing that entrepreneurs fantasize about, starting multiple companies and having them be really successful."
Other veteran entrepreneurs are doing variations on the idea of a factory for startups, including Evan Williams and Biz Stone, two of Twitter's founders, who now run a startup lab called Obvious, and Craig Walker, who developed the technology that became Google Voice and now runs Firespotter Labs. Kevin Rose, co-founder of Digg, started a similar company called Milk before joining Google in March.
Ryan compares his formula to dating - try out a bunch of startups and see what sticks. He and Merriman started the companies and then hired people to run them when they began to take off. In the case of Gilt, Ryan hired Alexis Maybank and Alexandra Wilkis Wilson as co-founders, then returned to run it himself once it became big.
He now spends most of his time at Gilt but splits 10 percent of it between Business Insider, where he is chairman, and 10gen, where he is a board member. Merriman is chief executive of 10gen.
Two other AlleyCorp companies, ShopWiki for comparison shopping and Panther Express for delivering content over the Web, were acquired, but not at prices high enough to make the deals profitable.
Ryan's ideas are not novel. He borrowed the idea of flash sales at Gilt from vente-privee.com, a flash-sale site in France. Business Insider followed blog networks like Gawker Media, and 10gen's software is similar to Oracle's MySQL.
"Hardly anything is a really brand-new idea on a global scale," Ryan said. "What makes companies successful is a different version of something."
He considers his greatest skill to be hiring the right people. And increasingly, those people are in New York instead of the Bay Area.
When tech meant only hardware and chips, Silicon Valley, home to Stanford's computer science department and large swaths of land for big factories, was the obvious epicenter. But today, a new tech company is more likely to be in retail, media or advertising - all industries based in New York.
"If you want financial journalists, the reality is there are more in New York," Ryan said. "If you want people who know fashion, there's got to be 10 times more in New York. If you want to be selling to ad agencies, you're in New York."
He added, "You're already seeing huge sectors of the Internet dominate in New York, not competing with San Francisco but dominating."
Ryan does not venture to Silicon Valley very often, mostly because he says it is not relevant to his businesses, even for raising money, which he said had changed since the first tech boom in the 1990s.
Of the 16 rounds of financing he has raised for his companies in the last five years, just two came from a West Coast venture capital firm, Sequoia Capital.
If he did show up in Silicon Valley, he would certainly stand out. Unlike founders in the mold of Mark Zuckerberg, Ryan, 48, is married with three children in junior high and high school. Then there are his suits. The Internet world in New York is slightly more formal, he said, and the valley's hoodies and jeans would not fly at New York cocktail parties.
"For me, the jacket, tie-less look goes anywhere," he said. Also, unlike most tech entrepreneurs, Ryan does not know how to write software code. Merriman, who was co-founder and chief technology officer at DoubleClick, provided the technical brains for the companies, Ryan said.
His ambition extends to his personal life. He trains for triathlons and plays competitive table tennis (people who work at Gilt warn new employees to stay away from Ryan at the table). There is also his borderline obsession with Halloween. A couple of years ago he dressed up as a flash sale, wearing no pants and a flasher's overcoat that he opened to display pictures of things Gilt offers, like watches, underwear and stays at a Paris hotel.
After spending a few years on Wall Street and working in finance and operations at Disney, Ryan landed at United Media when the Internet was taking off. In 1995 he started the Dilbert website, which took off quickly because early users of the Web were often Dilbert fans.
"When I was here in 1996, everyone was asking me, 'Why aren't you in San Francisco? Why aren't you in Boston?"' Ryan said. "Today, no one asks that."
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