Why Leave DoubleClick? Kevin Ryan’s Journey From Ad Exec To Wiki Master

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What would possess the founder of successful online advertising network to step down and set off on an odyssey to re-create the comparison shopping paradigm? In 2005, then-DoubleClick CEO Kevin Ryan, along with CTO Dwight Merriman, and R&D software developer Eliot Horowitz, left their lucrative online advertising company to build a comparison shopping business called ShopWiki.

It’s never easy to walk away from your creation. Ryan, always the restless entrepreneur built DoubleClick way back in 1996 as a marketing and ad serving company. He nurtured it as it grew. And by 2005, what had started as a 20-man company had become a 1500 employee global ad-serving power house with 21 offices around the world.

“You look around the office space, and you look around at the people, and you remember when each one of the joined, and all the great things that happened, and the challenging times in 2001 and 2002,” Ryan observes. “In ’96 the internet was still very small, there were doubters. We went out to raise money at times and people didn’t think it was going to work. So to have overcome that and then to have it turn into a huge success is a great feeling.” DoubleClick was later purchased by Hellman and Friedman, a private equity firm.

As consumers, Kevin, Dwight Merriman and Eliot Horowitz all had experience with comparison shopping sites. And as Kevin noted, they all pointed out ways they could be improved upon. “In a conversation with Dwight and myself,” says Ryan, “I remember about two years ago just thinking, ‘you know what, there’s a better way to do this.'” Having already made his millions, and not content to stay where he was, Kevin and his compatriots set out to do change the industry. “I was really ready to do something else from a product point of view. DoubleClick was the world leader in what it does, very profitable, very successful, but I was excited to start a consumer company.”

Kevin and company also saw the advertising potential of a comparison shopping site. Unlike news sites, where it isn’t always clear what sort of advertising fits and what doesn’t, comparison shopping sites and advertising go practically hand-in-hand. “If you were doing a search for “coffee maker,” on a comparison shopping engine, what are the odds that you’re going to buy a coffee maker in the next 30 days?” Ryan asks. “Either you really have nothing to do with your life, or you’re going to buy a coffee maker… The conversions are astronomical.”

For the first year of ShopWiki’s development, Kevin, Dwight and Eliot (a man Kevin describes as “one of the most brilliant engineers that we had ever seen at DoubleClick”) have been working alone and without outside investors. Right now they’re entirely focused on developing a quality product and developing ShopWiki’s search algorithms, which are designed by Eliot. “Our focus right now is actually not even so much on the revenue side as it is on the product side,” explains Ryan. Currently ShopWiki isn’t selling ad space to outside advertisers. They’re using AdSense. But when I talked to him, he didn’t seem to rule out eventually selling advertising themselves. They will also announce their first outside round of venture funding some time soon.

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