• (Founder Stories) O’Connor On What Makes A Good Entrepreneur: “Have You Told Your Boss To Shove It?”

    Friday, August 19th, 2011

    Josh Zelman is a Video Producer for AOL Tech. Prior to joining AOL he was a producer for CNN/HLN where he produced thousands of live studio technology segments for primetime programming. He was sent on assignment to cover such high profile events as Fortune’s Global Economic Forum, the Consumer Electronics Show and the Electronic Entertainment Expo. Josh graduated from... → Learn More

    Kevin O'Connor

    Chris Dixon begins this episode of Founder Stories with DoubleClick and FindTheBest Co-founder Kevin O’Conner by telling O’Connor that “DoubleClick is probably the closest thing New York has to a PayPal.” Meaning the two companies share an aptitude for hiring employees that go on to start innovative businesses.  Just as Paypal spawned Yelp, YouTube, and LinkedIn, DoubleClick spawned dozens of startups in New York City like Right Media.

    With this in mind, Dixon asks O’Connor if he intentionally created an environment that encouraged innovation while at DoubleClick, before going on to ask O’Connor what he considers to be the defining characteristics of successful entrepreneurs.

    O’Connor describes his systemized way of spurring innovation.  He lists a few signs of a successful entrepreneur.  A desire for control and the ability to challenge authority are near top of the list. A way to detect the second trait? “Have you told your boss to shove it?”

    In the video below, O’Connor discusses his genesis of his latest startup, FindTheBest, a service that offers side-by-side comparisons of everything from cigars to business schools. At the intersection of trying to solve a “big obvious” idea and not finding a site that served his needs, O’Connor began to build what would become the company. He describes it as a “decision engine” to help you make complicated decisions where search falls flat. What dog should I buy? Where should I send my kid to summer camp? What investment adviser should I hire?

    Make sure to watch both videos for additional insights along with the first two installments of this interview (Part I and Part II), as well as past episodes of Founder Stories here.


    Kevin O’Connor is the co-founder and CEO of FindTheBest.com. Before founding FindTheBest in 2009, O’Connor started O’Connor Ventures in 2001, a company specializing in tech startups. In 1995, he co-founded DoubleClick, an Internet advertisement-technology company which was acquired by Google in April 2007. Prior to founding DoubleClick, O’Connor co-founded the Intercomputer Communications Corporation in 1983, a microcomputer to mainframe inter-connectivity company. When the ICC was acquired by DCA in 1992, O’Connor eventually became its CTO...

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    Company: FindTheBest
    Website: FindTheBest.com
    Launch Date: May 2009
    Funding: $6M

    Simplifying Life’s Big Decisions. FindTheBest, based in Santa Barbara, CA, and New York City, is an unbiased, data-driven comparison engine. We organize and present data in a consumer-friendly format so that you can make quick and informed decisions based on what’s important to you. What Kayak does for travel, FindTheBest does for the thousands of other decisions in your life. FindTheBest was founded by DoubleClick founder and CEO Kevin O’Connor and CeBotics CEO Scott Leonard and is backed by Kleiner Perkins.

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