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Rich Barton (left) and Bill Gurley speak with GeekWire's John Cook at the 2013 GeekWire Summit.
Rich Barton (left) and Bill Gurley speak with GeekWire’s John Cook at the 2013 GeekWire Summit.

I had a blast interviewing Zillow co-founder Rich Barton and Benchmark’s Bill Gurley on stage at the GeekWire Summit last week. After all, it’s not everyday that you get entrepreneur and venture capitalist on the same couch, trading war stories.

We talked about a wide variety of topics during the 50-minute discussion, starting with what it takes to build big companies — a certain amount of “craziness” in the words of Barton — to their thoughts on mobile to the parallels betweens sports and startups.

My only regret is that I wish I could have convinced Gurley to somehow give us the scoop on Twitter’s IPO filing, which was announced about an hour after he left the stage. You can hear the discussion around Twitter, as well as Gurley’s comments on Uber and other companies in the full video below.

Video Markers:

Minute 5:00 on the next big opportunities for disruption in the tech industry, including Gurley’s thoughts on why mobile is so exciting right now and why Barton doesn’t even consider entrepreneurs

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Rich Barton at the GeekWire Summit

Minute 10:00 on the early days of Zillow.

Minute 16:00 on why it is important to build companies without a marketing budget.

Minute 17:00 Zillow’s Rich Barton on why TechCrunch founder Michael Arrington is a “jerk.” Gurley thinks there is “something in the water in Seattle that allows companies to grow big and strong and long.”

Minute 22:00 Gurley on the emergence of Amazon.com as a tech powerhouse. “Having that kind of ambition to launch (Amazon Web Services), it is like nearly heroic that someone would think that up,” said Gurley. “99 out of 100 boards would have probably tried to shut it down as an idea.”

Minute 23:00 “(Jeff Bezos) has shown an ability not just to dig a wide moat around his castles, but to like scorch the Earth for a mile around the moat,” said Barton.

Minute 27:00 On Webvan, the online grocery service that Benchmark invested in before it imploded during the dot-com bust. “I would say it was a good idea, and I think it was something we’d do it again at that moment in time. I think it was well executed on the product side, less so on the business side,” said Gurley.

Minute 31:00 On incubators and whether they are good for the tech ecosystem.

Minute 33:30 Gurley avoids my question on the Twitter IPO, and then shares his thoughts on why it is such an amazing platform. “Twitter has a lot of elements of optionality,” says Gurley, meaning it can get “bigger than we ever expected.”

Minute 35:30 On private driving service Uber.

Minute 38:30 On the next CEO of Microsoft. “I found out over the years that I give direction, better than I take it,” said Barton, who successfully spun off Expedia from Microsoft in 1990s. “And, I think the next CEO is going to have to be able to do both.”

Minute 42:30 On the tough economics in venture capital and why it is tough to measure venture capital performance.

Minute 46:00 On changes to the automobile industry and the rise of Tesla.

Previously on GeekWireRich Barton and Bill Gurley agree: Jeff Bezos is the most respected CEO by people in Silicon ValleyZillow’s Rich Barton on building big companies: It takes a little bit of ‘craziness’

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