In this wide ranging interview, Bill Gurley of Benchmark Capital talks about what founders need to know about their investors, what it takes to be a venture capitalist and what are the big opportunities in today’s world.


Bill Gurley is one of the best kept secrets of Sand Hill Road. With a dozen years of venture investing under his belt, Gurley has seen it all. A big boom, a bubble, a bust, personal trials and tribulations and success. 2012 has been generous to both Gurley and his partnership, Benchmark Capital, a venture capital firm based in Menlo Park, California. Some of his investments include OpenTable, Uber, GrubHub, Zillow.com and Scale Computing.

These deals don’t really tell the story of Gurley. I first met him when he was a former Wall Street analyst and our relationship began with me questioning his analysis. He switched teams and joined Benchmark at the height of the first Internet bubble. Gurley, who in the past used to write the Above the Crowd column for C/Net, took a step out of the limelight. Of course, that is par for course, investors at white-shoe firms tend to be less public than analysts, so our interactions decreased overtime.

When I moved out to San Francisco almost a decade ago, we touched base again, and since then have made it a point to see each other at least once every quarter. He has a very unique point of view about Silicon Valley, the technology industry and the kind of companies he likes to invest in. Polite as he is, he doesn’t sugarcoat anything and has given me advice over the years that was a bitter pill to swallow at the time, but in hindsight, turned out to be exactly what I needed. The only thing we don’t agree on: his love for sports that don’t make sense to a short, somewhat rotund guy like me, basketball and college football — the American kind.

Last year Chris Albrecht and I did a lot of documentary style interviews with folks such as angel investor Chris Dixon, Square COO and angel investor, Keith Rabois and Zimbra co-founder Satish Dharmraj, but this year I took a step back, mostly because I wanted to regroup and rethink whom I wanted to interview. I wanted to bring fresh insights from people whom I respect and believe have something interesting to say. I couldn’t find anyone better than Bill Gurley to kick off this occasional series.

In this interview, Gurley talks about a whole bunch of things including the craft of being a VC, the changing VC landscape, and most importantly, his thesis around reinvention of everything local. The interview was 45 minutes, so we have made it simpler by creating six chunks for easy consumption. We will post the entire interview later. Enjoy the videos.

What it takes to be a VC.

What is the role of a VC? Questions every entrepreneur should be asking.

How network effects reshape local commerce.

What it takes to survive downturns.

Beyond the obvious: What are the opportunities in venture capital?

On Above The Crowd [Slight audio issue here.]

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  1. Thanks for the videos. Really enjoyed listening. Though the 14 second ads became a bit annoying after the third time.

  2. Great set of interviews, really enjoyed these.

    1. Thanks Matt. Glad you enjoyed this. Appreciate the words of encouragement.

  3. Jeremy J. Campbell Thursday, December 13, 2012

    Very tight to watch, loaded with excellent sound bites, thoroughly enjoyed these short interviews, amazing Om, thank you!

  4. Show My Homework Friday, December 14, 2012

    I’m really inspired by Bill. I cam across this from Fred Willson’s blog and watched all six videos a couple of times over. Mark Muster wrote a great blog post the other day about entrepreneurs not thinking enough and reading his post and watching these have made me realise I need to put the brakes on little and step back for a second. Thank you!

  5. Om,

    Awesome insights!

    I’m also a big fan of This Week in Startups (by Jason Calacanis), and they provide ITunes downloads. Is there something similar available for these interviews?

  6. This are great snippets. They codify things you think, hear, and assert, but nervier seem to get quite as clear as Bill lays them out. A clinic! Well done and thanks for the video textbook. Will look forward to the complete interview.

  7. Lasse H. Kristiansen Monday, December 17, 2012

    Seems very interesting, but Flash videos are (also) no-go on Android tablets. Suggestion: Make every video available in HTML5. It’s a really simple task.

  8. Om,
    I got directed to these video from a Fred Wilson post, I am very glad I clicked through. I watched them all – many great insights.

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