DoubleClick Co-Founder’s Lessons Learned from Three Decades in Startups


Kevin O’Connor became an entrepreneur because of two people: Steve Jobs and Bill Gates. The investor and co-founder of DoubleClick and several other companies says he always had an inventive nature, but his dream was to get his PhD and then work for Bell Labs. “I thought the only road to innovation was via a PhD,” he says. “But around this same time a couple of college drop-outs named Steve and Bill were out there changing the world with the personal computer. I knew then that a PhD wasn’t necessary – and Bell Labs ultimately went bust.” He was accepted into the PhD program, but declined to work on his own company, a software company he started in 1983.

It was while brainstorming ideas in his basement with co-founder Dwight Merriman in the mid-90′s that O’Connor stumbled upon his big Internet idea. “After narrowing in a few ideas we explored their potential.  Is there a problem and does technology solve that problem most efficiently? That’s as simple as business gets,” he says. He started reading books about advertising theory, and realized that technology could dynamically serve ads to the right user at the right time; it was no longer just a theory. “Things advertisers were dreaming of doing could be possible on the Internet.” The pair launched DoubleClick in 1995, and it became a billion-dollar company over the course of a decade. Along with CEO Kevin Ryan, now the founder of Gilt Groupe and Business Insider, O’Connor and Merriman grew the company until a private equity firm acquired the company for $1.1 billion in 2005. The company was later acquired by Google for $3.1 billion in 2007.

After being an entrepreneur for 25 years, O’Connor decided to start O’Connor Ventures so he could be on the other side of the investment table. “I love the challenge of taking on a big problem and identifying the best solution,” he says. “After 25 years of trial and error, I think I have figured out a way to create something out of nothing, creating new ideas and turning them into successful products in the market.  I wanted to help other entrepreneurs by sharing some of my processes and insights.” He says likes founders who are really passionate about what they’re doing and believe they can change the world.  He also says he prefers to invest in companies with at least one founding engineer since tech is so fundamental for the success of the company. “And finally, can the founder afford to take the risk,” he says.

O’Connor Ventures is no longer seeking investments due to O’Connor’s return to entrepreneurship. “A couple years ago, I became increasingly frustrated and disappointed with the Internet,” he says. “I could find endless amounts of information on any subject but when I had a complicated decision to make, I found myself wasting hours, or even days, compiling information I could compare.” Or he found sites offering top 10 recommendations, but discovered they were secretly getting kickbacks from the sites they were recommending. So in 2009 he with the goal of filtering excessive junk and presenting information in a simple, comparable way.

FindtheBest is an unbiased data-driven comparison engine with funding from Kleiner Perkins Caufield & Byers. ”While the Web is great at making seemingly infinite amounts of information accessible, the Internet can be a little overwhelming in that it doesn’t allow for straight up apples-to-apples comparisons, nor is it transparent enough to allow you to spot those hidden marketing schemes influencing the data you receive,” he says. He says he uses FindTheBest to plan family ski trips, while his eldest son is using FindTheBest to compare colleges. Scaling across many verticals has been challenging though. “I’ve been asked ‘are you trying to boil the ocean?’ but the more I looked at the challenge I realized it’s the same process whether you are making a decision about the best college for your kid or the best dog for the family.”

O’Connor has built companies in the ’80′s, ’90′s, and ’00′s. He says the main difference between building a company in 1995 and 2012 is the fact that the Internet is essential. “In 1998 we were just laying the foundations, building roads, laying the plumbing, many didn’t know what it was or how to use it.  Today I can go online while flying across the country and Obama has a blackberry.” He says back then it was hard to focus on your core competency as a startup because you also needed to build your own infrastructure. “Most companies were doing it all themselves, from creating the software to deliver their website to developing an ad serving system. Some of our biggest competitors at the start were publishers that had already built an ad serving system.” Today he says startup costs are lower and there are infinitely more resources. “When starting DoubleClick we couldn’t scale fast enough, at we can scale in a day.”

O’Connor says entrepreneurship is all about standing behind your convictions. “If you chose an innovative, entrepreneurial path, you must believe in your convictions so strongly that you would stand behind your opinions no matter who tries to discourage you,” he says. “A new way of thinking often attracts a lot of nay-sayers, you can’t let that discourage you.  Of course, there’s always a chance you’re delusional – sometimes tough to tell the difference.” He says the mark of a great entrepreneur is how many profitable products they invent – they’re inventing and innovating constantly. “Ideas that take off are often a numbers game where you need to come up with a lot of bad ideas before you come up with the great idea. You must be persistent; don’t give up.” He also says successful innovators get things done quickly because they know time isn’t on their side. “You might have a multi-million dollar idea, but if you don’t get it out there before someone else does, that idea will no longer be profitable to you.”

Despite his ability to capitalize on big trends – the personal computer, online advertising, the consumer Internet – O’Connor is hesitant to look to what’s next. “I never focus on what’s next because you never really know,” he says. “I’m incredibly focused on building the best tool for making decisions online and excited about building a truly great company.”


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