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Bill Gurley
Venture capitalist Bill Gurley.

Bill Gurley, the Benchmark venture capitalist who served for 10 years on the board of directors at Zillow Group, reunited with Spencer Rascoff for the latest episode of the CEO’s podcast “Office Hours.”

Gurley, one of the top venture capitalists in Silicon Valley, left Zillow in 2015. He was an early investor in such companies as Uber, Snapchat, Instagram, Dropbox and Twitter and currently serves on the boards of Stitch Fix, OpenTable and Nextdoor.

The two covered a range of topics in the podcast released on Friday, including what Gurley looks for when assessing a person’s leadership potential. Gurley referenced “insane curiosity” and a discussion between Bill Gates and Warren Buffett in which those two billionaires said they shared that trait.

“If you’re remarkably curious, you’re constantly learning new ways you could win, and you’re also less likely to fall into the trap of thinking that yesterday’s rules are the rules you need for tomorrow.,” Gurley said. “And so that curiosity element is something we’re looking for, raw intellect.”

Gurley also said salesmanship is necessary in potential leaders.

“If you’re gonna run a company, you’ve gotta be able to sell the customer.”

Bill Gurley and Rich Barton
GeekWire’s John Cook interviews Expedia and Zillow co-founder Rich Barton, left, and Benchmark Capital’s Bill Gurley at the 2013 GeekWire Summit. (GeekWire Photo)

Rascoff also asked Gurley how he can look at an early-stage company and determine, “Is this legit? Is this the real deal? Is this gonna become a massive company?” Without much data to analyze, Gurley said he’s looking for three things.

“One, you’re looking for a — you’re looking deep into the eyes of the entrepreneur and trying to figure out just how talented they are, and that talent could be in many shapes or forms. If it’s a particular technical company, it might be their technical depth. If it’s a vertical play, it might be their knowledge of the industry. But you’re looking for some individual that stands out.

“Two, you’re looking for a point of entry into an industry or ecosystem or a marketplace. So how has the scene developed that’s gonna allow this new company to succeed? It could be a technology disruption. It could be a different approach that’s never been done before. It could be leveraging some new technology in a way that hadn’t been done before. …

“The last thing is a moat, Warren Buffett’s moat. I use the phrase “unfair competitive advantage.” But what is it that will allow you to protect that business over the long term? That could be a network effect. It could be some kind of scale advantage. But it needs to have something like that.”

Listen to the complete conversation between Rascoff and Gurley on Apple Podcasts or Google Play.

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