Trouncing career regret with famed VC Bill Gurley

Mentors, obsessions, and going where the action is

An astonishing majority of Americans claim that they hate their job and wish they could do something else. Often, though, what might drive our passions is unknown. How do we find the right path in life and how do we know we are on our way?

Joining the Riskgaming podcast this week is Bill Gurley, a legendary venture capitalist who 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 own personal story of how to avoid career regret, of sticking with a job way past the point of boredom.

He’s joined in conversation by Lux’s own Josh Wolfe. The two talk about the book as well as the intersecting points of their long friendship and careers.

Josh Wolfe:

Let’s start at the beginning. You’ve said that, after school, you landed a job, I think, at a famous tech company, and you were surprisingly bored. What was that moment of realization like, and how close did you come to just staying on that conveyor belt?

Bill Gurley:

I don’t think there was much possibility of that. I fell in love with computers at a young age, like many people in our industry did. So 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 would actually go do things was, I thought, magic.

But I 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.

In the meantime, I had started reading industry trade magazines. I had read one on Wall Street by Peter Lynch, and I had opened a trading account and I was trading stocks as a hobby. I wasn’t doing it as my main gig. But one of the things I talk about in the book is that maybe your hobby should be your main gig. And so, I had these other things going on in my brain that seemed more interesting than what I was doing.

It is important to highlight that engineering may be someone else’s passion. I just came to a realization it wasn’t mine. I did this exercise, which I only reflected on as I wrote the book. I said to myself, “Do I see myself doing this 30 years from now?”

I didn’t know what I wanted to be doing, but I knew it wasn’t what I was doing. So I went to business school, which is an easy place to re-pot from. I thought about venture while I was there. I knocked on doors and it didn’t seem like there was any reasonable path to venture as a business school student. I started reading a lot of Fortune and Forbes articles about these gentlemen at Goldman Sachs — their tech team back at the time was incredible. Their sell-side analysts were being asked the questions about these industries I was most fascinated by. I loved my corporate strategy class. I thought maybe I could be one of those guys.

I went and knocked on doors here in New York City, and met the Goldman team. Even though I was a silly first year student at University of Texas, they let me in the door and I eventually got a job as a sell-side analyst.

That’s where I became even more aware of what was going on in Silicon Valley, the young companies that were disrupting things. I had that same discussion with myself as a sell-side analyst. About two, three years in, I walked around the office late one night about 10 P.M. I paused in front of each of the corner offices — the offices of people who were lifers in their role — and thought about, “Is that what I want?” And again, I got to “no” pretty quick and started moving in a different direction.

So those experiences helped paved the way for where I would spend a quarter-century.

Josh Wolfe:

Right. Your book itself was a decade-long project. You’ve said it started in part when you noticed that there was this pattern across three different biographies: of a restaurateur, a basketball coach and a folk singer. You connected these threads.

Bill Gurley:

As a blogger, one of the things I tried to do is tear apart some new thing that’s happening in venture and create a framework for understanding it. And so, when I finished that third biography, I had this aha moment. I was like, look, these people are all in very different fields. They’re all in fields your parents would probably tell you not to go into. They all started on the very bottom rung and they all did a lot of similar things. They used similar processes and principles that could be borrowed by anyone.

I got asked to speak at my MBA school and I asked, “Can I do this presentation?” They posted it on the internet. Some people noticed. One of the people who reposted was James Clear. I don’t know how he found it, but he’s probably the most successful writer in the category by far with Atomic Habits. And eventually, a couple different people really got into my head as this is what you have to do. You have to go do this. And I give them both credit.

There’s this saying that life begins where your comfort zone ends. And writing a book about venture or investing wouldn’t have pushed me to that place. This pushed me to a different place, and I approached it as a new hard project. So I hired a researcher, a co-writer. We read 100 biographies, we went through all the academic literature. We ran our own academic study with Wharton. We took it very seriously.

Josh Wolfe:

I like this point you’re making, which is that it was at the edge of your comfort zone. You’ve talked about this idea where something like 60% of adults are basically unsatisfied with what they do, so they’re not happy.

Bill Gurley:

Yes. We did a survey with Wharton and said, if you could go back and start over, would you choose a different career path? And 60% of people said yes.

Josh Wolfe:

And so, you call it career regret, right? There’s a consistent through line in Bezos’ framework of regret minimization that people choose wrong or that the systems never really let them choose or…

Bill Gurley:

I think it’s all those things, and I think it’s gotten worse. The college matriculation industrial complex has gotten very grindy. I think everyone knows it. Most would admit that people used to have way more free time when they were young to explore and learn and make mistakes and challenge themselves. Whereas today, by the time you’re in sixth grade, a parent is worried about your college application and they’re filling your schedule immensely.

And then you and I have discussed many different forms of psychological biases. One of those is sunk costs. If you grind from sixth grade to college graduation to get a degree in computer science, you feel pretty invested in it. I also meet a lot of young people who come out of college burnt out on learning. I think that’s a problem as well because the very best and the brightest, including the folk singer and the restaurateur and the basketball coach, are lifelong learners.

Josh Wolfe:

I think it’s also really important — and you highlight a few of them — but being exposed to a panoply of heroes, a pantheon of people that you can look up to and be like, “Oh, I could be like that.” My mom wanted me to be a doctor or a lawyer when I was young. And it wasn’t until I started to be exposed to these heroes that I was like, “Wait, I want to be like that. I want to do what they’re doing.” And you find this passion.

Bill Gurley:

I have a chapter on mentors. What you just described is what I call aspirational mentors. I borrowed this from Danny Meyer, the restaurateur, whose uncle convinced him to completely pivot. His salary dropped by 10x to go work in a restaurant. But he made a list of 10 people he felt were changing the restaurant industry at that point in time and started studying them.

If you are on an intentional high-agency career path, AI is a super weapon. You can find YouTube videos and podcasts with these heroes and then you can even just tell AI, pretend you’re this person and you start throwing questions at them. It’s unbelievable what you could go do and what you could go learn in this modern world.

It’s ironic. If you’re in a job you don’t like, if you feel like you’re a widget, AI is a problem. But if you’re crafting your own path, it could accelerate you. I don’t know how to get people on a high-agency path if it’s not something they’re fascinated with. It’s got to feel easy to run at it.

Josh Wolfe:

Just as people have different genetic predispositions for risk-taking — or for fitting in or for standing out — so many of the entrepreneurs that I’ve backed, you’ve backed, are very comfortable standing out. They’re very comfortable, basically failing. They’re comfortable disagreeing with the consensus. And some of that might be wired, some of it might be youth. I say “chips on shoulders put chips in pockets.”

Another of your principles is to chase your curiosity, which is different from other advice where people tell you to chase your passions. In venture, you see people who are obsessively curious, but you also see people who confuse curiosity with restlessness. How do you tell the difference between those two?

Bill Gurley:

Yes, so the first principle is to chase your curiosity. I admit that the hardest part of figuring this whole thing out is just identifying that. And a lot of people don’t get there. You have to be willing to explore and admit and test and not view that as failure. I think when you get there, you’ll know. But I like to throw out the idea of comparing it to binge-watching your favorite Netflix show. Would you go read about this instead of doing that? And I think for the people that are the most curious about certain fields, they do that constantly.

Josh Wolfe:

Would you rather? Yeah.

Bill Gurley:

There’s also a principle about owning your craft. There’s a principle on mentors and there’s a principle on peer groups. And in all of those cases, as you start to climb the ladder and get to a higher and higher rung, I think it’s a more difficult course. It’s not a 101 class, it’s more of a 400 level course, but you start to expand your learning, your peer network and your mentors outside of your field. It’s noisier. It’s harder to gather insights, but when you do, they might be more impactful.

Josh Wolfe:

I personally have such a wide range of interests that come from... It doesn’t come from a virtuous pursuit. It comes arguably from an insecurity that I want to be smarter than the next guy. Sometimes that is a liability. Sometimes I come off like a jerk or arrogant or something, but when somebody knows something I don’t know. Oh my gosh, I got to know what they know.

Bill Gurley:

One thing you said right there: there is a mindset of FOMO about knowledge. And one thing I would tell very young people is, especially when you’re on that first rung and that second rung, if someone says something you don’t understand, tell them right then. Say, “What do you mean by that?” There’s an instinct that you’re going to look like you don’t know and therefore, you’re dumb. But all the greats talk about this: Ask the question. They’re going to respect you for asking it.

Josh Wolfe:

Another of the other principles you have is to go where the action is. And some of that requires a little bit of EQ. There’s a difference between the people who really know where the action is, the A-plus-caliber people versus the transactional hucksters. But, either way, it’s arguably great and easy advice for the 22-year-old. But what do you say to the 40-year-old or the 44-year-old that...

Bill Gurley:

Well, let me make sure I ground it properly. The title of the chapter is “Go to the Epicenter.” But it basically says if you are entering a career that has an epicenter, theater in New York or movies in Hollywood or songwriters in Nashville, or advertising’s probably in New York, or Silicon Valley for high-tech, if you take yourself to that place, things don’t get easier by a little bit. They get easier by maybe 10x or more.

Many people who are wildly successful will tell you two or three stories about a chance encounter that led to something that led to something and that they wouldn’t be where they are if that didn’t happen. And some people can push back on that and say, “Well, that’s just luck.” But the number of opportunities for luck go up tremendously if you’re in the battlefield where everyone else is.

Josh Wolfe:

So you’ve seen older entrepreneurs, you’ve seen career entrepreneurs, you’ve seen young people. Do you think Gen Z is more or less equipped to follow your playbook than my generation or older folks?

Bill Gurley:

If I read what Jonathan Haidt’s written, not just in The Anxious Generation, but in The Coddling of the American Mind as well, people are not being set up for high agency (Editor’s Note: check out our interview with Haidt). And I do think the book requires a pivot towards high agency. You have to believe you can be successful. If you’re completely of a mindset of being a victim — of I can’t win, everything’s stacked against me — I don’t know that you’ll make it to the end of the book.

Josh Wolfe:

I want to talk about a few of the characters in the book, and then I want to ask a few more questions. One of the things that I thought was interesting was how you open with Danny Meyer’s visceral memory of this meal he had before the LSAT. He’s doing really well, he is making a lot of money, and then he quits to open up this restaurant, and you open the book with this anecdote. What does it tell you that people remember the moment they almost took the wrong path more vividly than the moment that they might’ve taken the right one?

Bill Gurley:

Well, when we go to bed at night, we ruminate a bit about things. When we make mistakes, we let ourselves off the hook, but when we miss out on something, it weighs on us, it weighs on us heavily.

On the Danny story: He cared about the details at a level most of us wouldn’t. And if you are obsessive about something, those details are super interesting to you. Steve Jobs, in his graduation speech at Stanford, talked about the calligraphy class he took and how much it weighed on his brain. My point is it’s possibly a sign of what you should go and do if the details of something matter to you.

Josh Wolfe:

I want to ask about not just chasing curiosity but chasing purpose. I’ve got a friend who said, for Shabbat, “we say a prayer every Friday and we wish our kids a life not of success but of meaning.” And I thought that was a really profound end goal. But I want to ask you, your parents, what did they expect of you? What did you feel they expected of you? What did you expect of your kids?

Bill Gurley:

My parents did not put overt pressure on me in any way, shape or form.

Josh Wolfe:

What did your mom and dad do?

Bill Gurley:

My mom was a substitute teacher and mostly a stay-at-home mom after that, but then really got into civics. So the last 20 years of her life, she was an alderman in the city and ran the school board and all those things.

My dad had a dream job. He fell in love with gas-powered airplanes when he was a kid. Fell in love with them and got an aeronautical engineering degree and was working in a wind tunnel in Langley Air Force Base. So he was doing it. He was doing what he loved. And then he took a flyer — a version of go to the epicenter. 50 of the people at Langley got offered a job at the beginning of NASA in Houston, and he took it.

I don’t think he ever once said to me, “Oh, go take a leap like that.” Most of my friends didn’t leave the state. And I thought nothing of it. I think if you live in a family that’s been in a place for a very long time, you probably don’t feel like you have the permission to leave, or you might be intimidated by the notion of it. And I didn’t have that. I do think that mattered.

Josh Wolfe:

And for your expectations of your kids?

Bill Gurley:

I’m trying to live the book as much as I possibly can, so we’ll see. I don’t think any of them are right on top of their dream job yet. But one of them got a MEC-E degree at Carnegie Mellon and came to us the summer before his graduation. He said he’s convinced he wants to teach, and he’s in Teach for America now.

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