Why You Shouldn't Chase Your Passion: Bill Gurley on the Delusional Factor Every Outlier Needs and How to Find a Mentor

Bill Gurley (0:01)

The Art of Leadership Network. I had Larry and Sergey of Google present to our partnership when there were 25 employees. So at the very beginning, and we failed to lay chase. So they presented, left, and we didn't try and close that deal. And two of the best venture capitalists in the world, John Doerr and Mike Moritz, ended up doing that deal. And I can remember at the time there were a couple of no's in our mental models. Biggest mistake of my career.

Carey Nieuwhof (0:35)

Welcome to The Carey Nieuhof Leadership Podcast. Hey, I am so excited to bring you something a little bit different today. You know, while we're focused on helping leaders in the church space, that's people who work at churches, volunteer, sit on boards, invest, that kind of thing. Today, I'm going to talk to Bill Gurley. He is the man behind Uber, Snapchat, Twitter.

What else? Open Table, Zillow. What did he do? Well, he invested in these companies when they were very, very early stage. And my goodness, this is a fascinating conversation. We talk about why you, if you're thinking about what you should do with your life, shouldn't chase your passion. You got to chase something else instead. The delusional factor every outlier needs. I find that fascinating, right? If you're a church planter or you want to reinvent a church, are you delusional? Well, maybe you need to be. And how to actually find your dream job. So welcome to the podcast. Really glad you joined us. I want this to be a very good investment of basically 90 minutes for this one. It could have gone much longer. Bill is just fascinating. He is a general partner at Benchmark, a leading venture capital firm in Silicon Valley over his investment career. He has invested in and served on the board of such companies as Nextdoor, OpenTable, Stitch, Fix, Uber and Zillow. For more than two decades, he has written about technology and other subjects on his very popular blog Above The Crowd and on his social media accounts. He is very active on X. And now I think you are going to enjoy this conversation as much as I do. My conversation with Bill Gurley. Well, Bill, I have appreciated your work as an outsider for a while now. I think I first heard about you on Tim Ferriss' show years ago. And so I'm really delighted to have this conversation with you. We're going to talk career, going to talk AI, going to talk about everything. Welcome.

Bill Gurley (2:26)

Thanks for having me on.

Carey Nieuwhof (2:27)

Yeah. So, you know, I want to go back to the genesis of your career. You played some basketball. You're a tall guy. Is it 6'9? Is the Internet correct on that?

Bill Gurley (2:37)

I'm getting older. Start going the other direction.

Carey Nieuwhof (2:41)

Was 6'9. Yeah. I'm afraid to measure myself at this stage. I was 6'2, but I don't know whether I'm still hanging in there or not.

But you started at Compaq, which is a company a lot of listeners wouldn't even really remember, but I remember it. I'm of a certain vintage. And then you moved into Wall Street research before becoming a VC. And now you're reinventing yourself again, VC, venture capitalist. A lot of people would have been very comfortable staying at Compaq. Would have been like, wow, I got a career here. And even if the company didn't survive, you can move to Intel, you can move to NVIDIA. I mean, you could be retired or CEO at this point. So what made you decide early on that you wanted to make a jump?

Bill Gurley (3:23)

Well, it's interesting in talking through this. I wrote this book, not about myself, very intentionally, which we can get to later. But when I've been talking to people about the book, this comes up a lot. And I've actually developed a bit of a heuristic on what happened in those two situations that isn't in the book. I kind of wish maybe it was. But in both cases, I was about two to three years into that part of my career. So I was an engineer, a computer science engineer at Compaq, working on products that were shipping, desktop computers. And I'll tell you about the other job in a minute. But I had this moment where I just stopped and reflected and asked myself the question, is this what I want to be doing for the next 30 years? And I don't know why I was able to ask myself that question. And but it was provocative in my mind and very clear the answer. And what happened in that case, my brain goes all the time in every direction. And people might call it ADD. I'm very curious about a broad variety of things. And when the third project I was working on started at Compec, it looked a lot like the second one and a lot like the first one. And in my brain, and maybe that's what allowed me to do the 30 year thing, it was going to be monotonous.