Trouncing career regret with famed VC Bill Gurley

Danny Crichton (0:01)

Hey, it's Danny Crichton, and this is the Riskgaming Podcast by Lux Capital. We've got a special podcast episode today with one of our longtime readers, listeners, and friends. Bill Gurley is a legendary venture capitalist for more than two decades, invested at Benchmark in such defining startups as Uber and Zillow. He's just published a new book titled, Runnin Down a Dream, How to Thrive in a Career You Actually Love. It's based on his personal story of how to avoid career regret, of sticking with a job way past the point of boredom. Chatting with Bill is our very own Josh Wolfe. Your humble host got waylaid thanks to the snowstorm in New York this weekend, so this is just a conversation between the two of them, and I think you'll love it. Let's dive right in with Josh.

Josh Wolfe (0:47)

What's up, man? How you doing?

Bill Gurley (0:48)

I'm doing great, Josh. How are you?

Josh Wolfe (0:50)

Good. I know we're supposed to do this live, and we got the blizzard bonanza apocalypse of 26 But I think I'm going to see you.

Bill Gurley (0:59)

I think it's going to be okay. The sun's coming out.

Josh Wolfe (1:02)

I agree. You're actually a natural optimist. I'm generally more of a cynic or skeptic, and I admire your-

Bill Gurley (1:08)

I think if you ask around Silicon Valley, they'd put me in the Senate camp, but maybe I get a little bit of both.

Josh Wolfe (1:16)

I actually think you have more faith in people than I do. I think you-

Bill Gurley (1:19)

Okay. I am cynical of the mass freakout of the potential blizzard apocalypse, and I think I was right.

Josh Wolfe (1:29)

You were. Let's start at the beginning. I first got to know you from a distance when I was literally obsessively reading your column, which was above the crowd apropos, because I do think not only you're a towering individual, but a towering intellect who I feel grateful to call a friend and have learned so much from you. You've given me a lot of advice that I've not always followed about not fighting with people and thinking about the heroes that certain entrepreneurs and founders celebrate, but you've really surrounded yourself with just incredible operators, incredible peers, and capital allocators. Your career started and you said that you landed a job, I think, at a famous tech company after school, and you were surprisingly bored, I think was the quote you used. What was that moment of realization like?

How close did you come to just staying on that conveyor belt?

Bill Gurley (2:24)

I don't think there was much probability of that. What I would tell you is, I fell in love with computers at a young age like many people in our industry did. I had a Commodore VIC-20, that's how old I am.

Josh Wolfe (2:39)

Mine was a Commodore 64, asterisk, comma eight, comma one, but I'm with you.

Bill Gurley (2:46)

I went and got a computer science degree, and I was blown away. Writing software in college was so much fun. The fact that you could make stuff that actually would go do things was like I thought magic. I just got out and was in the world and working on product cycles, and we started our third product, which looked like the second and looked like the first. I want to add, in the meantime, I had started reading industry trade magazines. I had read one up on Wall Street by Peter Lynch, and I had opened a trading account, a prodigy, and I was trading stocks, and I'd gotten a value line thing as a hobby. I wasn't doing that as my main gig, but one of the things I talk about in the book is, maybe your hobby should be your main gig. I had these other things going on in my brain that seemed more interesting than what I was doing.

I think it's really important to highlight that engineering may be someone else's passion. It just came to a realization it wasn't mine. I did this exercise, which I only reflected on as I wrote the book. I don't know that I said, I'm doing this exercise like Bezos did when he started. But I said to myself, do I see myself doing this 30 years from now? You can look around the org and see the people that have been in that type of job that long, and look at their life and just say, is that something I would enjoy? What Bezos did was he said, what advice would my 80-year-old self give me? But I think they're going at the same thing, like is this what you want for your whole life? For me, I didn't know it was venture at that moment. I knew it wasn't what I was doing. I went to business school, which is an easy place to repot from.