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

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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.