Bill Gurley | Benchmark – On finding your dream job, obsessive learning, and why passion beats the resume arms race

Daniel Dart (0:03)

Hello, and welcome to The Dart Board with me, your host, Daniel Dart, founder and general partner of Rock Yard Ventures. Each episode, I sit down with some of the world's best investors, operators, and entrepreneurs to pull back the curtain on tech, venture, and business. Whether you're just getting started in your career, or you've been doing it for 30 years, we all know there's always more to learn, and I hope you get to learn some of it here. Thank you for your time, and on to the show.

SPEAKER_2 (0:33)

Daniel Dart is the founder and general partner of Rock Yard Ventures. All opinions expressed by Daniel and the podcast guests are solely their own and do not reflect the opinion of Rock Yard Ventures. This podcast is for informational purposes only, and should not be relied upon as a basis for investment decisions. Enjoy the show.

Daniel Dart (0:59)

Today, we have a super exciting guest joining us, Bill Gurley, longtime partner at Benchmark, one of the most successful investors in venture capital history, Uber, Zillow, Open Table, Stitch Fix, the list goes on. But not only that, Bill influenced an entire generation of investors and thinkers, including myself, through his blog Above the Crowd.

SPEAKER_4 (1:25)

So I was super excited to hear about his new book, Running Down a Dream, which dives into a question he's been exploring for decades, which is why do some people thrive in work and they love it? But many people, most people don't and actually wish they could start over their whole career.

Daniel Dart (1:44)

So when I heard about this, I hit him up, I knew I had to have him on the show, and we sit down and we talk about it. It's not a feel-good career advice book, it's really about digging into the patterns that Bill's seen across founders, artists, coaches, operators, and what actually separates people who found their thing from everyone else, and how you can find yours too. It was a fantastic conversation and I'm so excited to share it with all of you. So without further ado, Bill Gurley, welcome to The Dart Board.

Bill Gurley (2:17)

Thanks for having me on, Daniel.

Daniel Dart (2:19)

Super excited about this and just to set the tone of the conversation before we shift into your new book, I'm going to give a high level just about you myself. So long time GP at Benchmark, which I would say might be the most story firm in the history of Silicon Valley. Huge, massive, amazing outcomes. But also kind of like the book, you didn't have the stereotypical background. Was it an Ivy League guy, not a Harvard dude or didn't go to some famous prep school? And so we're going to talk more about that journey.

And then really started this book based on a conversation you gave at UT. Our local austenite, you're an austenite, so that was super exciting. And so I kind of want to just jump in there and talk about this initial lecture in 2018 at UT. But you said you had been working on it for 10 years. And so the first thing is, let's go back to 2008 What was the impetus to start even thinking about this?

Bill Gurley (3:21)

I was at a moment. I mean, I've always been an obsessive reader. Well, actually, since I went to business school, I've been an obsessive reader. Ironically, before that, I almost read nothing. So I had a bit flip that had a huge impact on me because I've been an obsessive reader since then. And I was in a period in my life where I was reading a lot of biographies. And I think many people go through a similar phase. And I saw something. And I've been blogging for a long time, even before it was called blogging, writing analysis, and in trying to understand how different markets work and different business models. And so I think I had trained my brain to notice patterns and to look for patterns and alignment. Because that's kind of what I do when I put together a blog post, right? Which is, oh, I think I see a pattern to how the world works. And I was finishing the third of these three biographies, and I just started to piece together things in my head. Like they all were doing the same things, and they were in radically different fields. One was a folk singer, one was a restaurateur, and one was a basketball coach. And the other thing that really spoke to me was, none of those fields are things that your parents would tell you to go chase or do, right? Like they're not industries that are kind of sought after.