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Zillow’s Rich Barton and Benchmark’s Bill Gurley at the GeekWire Summit, joined by GeekWire’s John Cook.

Rich Barton has helped build some of Seattle’s biggest tech brands, including Expedia (market value $7.6 billion) and Zillow (market value of $3.6 billion). So, what does it take to grow startups to that scale?

According to Barton, it’s a “certain amount of craziness.”

Rich Barton speaking at the GeekWire Summit. Photos: Eugene Hsu

“A big dream and a clear vision, and a little bit of nuttiness is required to take something from an idea stage all the way to creating something that is — with Expedia it is the largest seller of travel in the world. $25 billion to $30 billion of travel is sold through Expedia, and that was our dream …. right from the very start,” said Barton, speaking at the GeekWire Summit in Seattle. “Everyone thought we were crazy. We probably were crazy, but having a dream like that that resonates with people — changing the world and achieving something big — it turns out that’s what pulls you through the hard times.”

Joining Barton on stage was one of the guys who has actually bet on some of that craziness, venture capitalist Bill Gurley of the Silicon Valley firm Benchmark.

I asked Gurley, an investor in Zillow, how he works with crazy entrepreneurs like Barton.

“It’s ironically one of the challenging things when going about making an investment decision because some of the people who are purportedly crazy, are like really crazy, and you don’t want to invest in them,” he said. “So, you can’t just use that metric…. Crazy is an interesting word, and it might just be audacious, someone who is naive enough or brave enough to think that they can go do something or accomplish something that no one else thought they could.”

We kicked off the Q&A with that question, and you can watch the full discussion in the video below (right after Barton made a crack about spilling bong water on a couch in college). Later, in minute 17, Barton talks about why he thinks TechCrunch founder Michael Arrington is a “jerk.”

And in minute 18, Gurley talks about why Seattle is a special place to invest, noting that it is a great place to build a company if you “want to go for the long ball.”

Previously on GeekWireRich Barton and Bill Gurley agree: Jeff Bezos is the most respected CEO by people in Silicon Valley

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