In conversation with Bill Gurley, Benchmark Capital [Video]

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, 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.]