Flashy Entrepreneur Kevin Ryan

Most entrepreneurs put all of their eggs in one basket. Not entrepreneur Kevin Ryan.

The former DoubleClick CEO keeps having too many ideas and finding enough sophisticated investors to help finance all of them.

Using an umbrella company called AlleyCorp that Ryan co-founded with entrepreneur Dwight Merriman in 2007, Ryan has launched five businesses over the last four-plus years, and he says that he has probably raised “15 rounds” of venture capital during that time.

Much, but not all of it, has gone into Gilt Groupe, Ryan’s crown jewel, which he co-founded with two Chief Merchandising Officer Alexandra Wilkis Wilson and Chief Marketing Officer Alexis Maybank. Ryan serves as CEO.

The four-year-old, high-end shopping service—which sells everything from Marc Jacobs bags to artisan foods and high-end travel packages at discounted and full prices in flash sales—has already raised $236 million in funding, including a $138 million infusion this year from Draper Fisher Jurvetson, Goldman Sachs, General Atlantic, Matrix Partners and New Enterprise Associates, among others. The company reportedly enjoys a valuation of $1 billion and booked $500 million in revenue in the fiscal year ending July, though it remains unprofitable.

Ryan and Merriman also co-founded three-year-old 10gen, which offers enterprises a big, commercialized version of the open source, non-relational database platform MongoDB. 10gen has raised $31.4 million since its 2007 founding, including a $20 million round led by Sequoia Capital in September.

Ryan claims 10gen, run by Merriman, is worth at least a billion dollars. “If you compare MongoDB adoption to [open source database] MySQL, it’s faster, and MySQL sold for a billion dollars [in 2008 to Sun Microsystems],” he says.

Then there’s Business Insider, which Ryan and Merriman co-founded in 2007 and that has so far raised $13.7 million, $7 million of it coming in a September round that included Institutional Venture Partners, RRE Ventures and individuals, such as Marc Andreessen.

That’s saying nothing of the other companies that Ryan and Merriman have created and sold in recent years. Panther Express and ShopWiki were acquired, respectively, by CDNetworks and Oversee for undisclosed amounts. Together, the companies raised roughly $28 million from VCs that included Greylock Partners and Index Ventures.

Does he also invest in startups? “I invested in [high-end career site] TheLadders while at DoubleClick because I knew the guys starting it and I loved the concept. But in general,” Ryan says, “I’ve only made one or two angel investments ever. It takes a lot of time and I’m not looking for more distractions.”

He’s certainly accustomed to them, though. The 48-year-old father of three was born in Milwaukee, and raised as a toddler in Lincoln, Neb.

At age six, when his father joined the construction company Caterpillar as an executive, life turned itinerant. The family moved to Rome, then to Geneva, then to Sherman Falls, Ohio, then back to Geneva.

Eventually, Ryan returned to the United States and after graduating from Yale University, he worked briefly in investment banking at Prudential, followed by United Media, where he pushed the company to focus on Internet licensing. His biggest claim to fame during this period was launching Dilbert.com in 1995, based on the comical office character created by Scott Adams.

For a while, it looked like Ryan would follow in his father’s footsteps and become a career executive at someone else’s global conglomerate. Then DoubleClick came calling in 1996, and put him on another path entirely.

Ryan’s lucky break came during DoubleClick’s darkest hour. It was 2000, two years after the company had launched its IPO and one year after its value began a downward tumble from its peak of roughly $12 billion. As the company’s business of representing website customers began to shrivel along with its client base, co-founder Kevin O’Connor decided to step down. Ryan, then president, was made its CEO and used the role to refocus the company to offer online ad-serving and management technology.

Though it wasn’t enough to restore DoubleClick to a multibillion-dollar valuation, the shift made the company attractive enough to sell in 2005 for $1.1 billion to the private equity firm Hellman & Friedman, which turned around and sold DoubleClick to Google in 2008 for $3.1 billion.

Ryan says he didn’t want to sell in 2005. “I thought it was worth more,” he says.

I’ve only made one or two angel investments ever. It takes a lot of time and I’m not looking for more distractions.

Kevin RyanCEOGilt Groupe

But the experience gave him the wherewithal to strike out on his own. It also provided him with the contacts to do it.

Merriman, of course, was part of the picture. But Ryan also convinced much of DoubleClick’s former recruiting team to join him at Gilt Groupe, and he insists that more than anything, it’s those employees who’ve gotten the company to where it is today.

Success boils down to “hiring the right people,” Ryan says. “At Business Insider, we hired two people and they just started writing a blog, and now the company has 65 employees and 12 million unique visitors a month. Great people are the building blocks to great products.”

That seems easier said than done at a company such as Gilt Groupe, which already employs more than 750 employees and is hiring dozens more each month. Ryan insists that it’s key no matter how inconvenient, however.

“You might think, OK, it’s a big hassle factor to replace [this particular employee]. But a company is like a sports team. The Yankees don’t say, ‘This third baseman isn’t that great, but we should just keep him.’ You can’t win unless you have great people in every position. At an Internet company, all you have is your brand and people.”

Of course, having access to plenty of venture capital helps, says Ryan, who, when he has the rare free moment, sometimes advises young entrepreneurs who seek him out.

“What do I tell them? They all sound like platitudes. But I always say to raise more money than you think you need, and don’t worry about dilution.” It’s not nearly as important as “being able to move quickly.”

Constance Loizos can be reached at connie.loizos@thomsonreuters.com. She tweets at @cookie.Kevin Ryan at a Glance

Age: 48

Hometown: Milwaukee, Wis.

Degree: B.A., Yale University; M.B.A., INSEAD

Career: Previously worked in investment banking at Prudential; held various roles, including senior vice president of Euro Disney and United Media; CEO, DoubleClick; co-founder, AlleyCorp, Panther Express, ShopWiki, 10gen and Gilt Groupe

Did you know? Ryan’s brothers are also entrepreneurs. Brother Sean Ryan has headed up numerous companies and is currently director of games partnerships at Facebook. Brother Conor Kennedy is the founder of the New York-based modeling agency Muse Management.

Sample Investment

TheLadders

Mission: Online job service for the $100K+ job market

Location: New York

Funding: Not disclosed since 2004, when Matrix Partners invested $7.25 million in “expansion capital.”