Legendary Investor - How To Escape a Career You Hate | Bill Gurley

Key Takeaways

Like one of the craziest things early in the book, I think did you run this survey and it said that like six or seven out of 10 people hate their job? Yeah, so I had a co-writer, co-researcher on the book and we spent a ton of time together on Zoom calls and someone encouraged us to dive into a bunch of academic literature. We came across this Gallup poll that said 53% of people aren't engaged at work. And so we had this idea to ask like a thousand people if you could start your career over again, would you do it differently? And seven out of 10 said yes. And then we we took that to to Wharton People Analytics to do the official academic version so you make sure you get all the statistical data correct. And then their number came back six out of 10. So still a really big number. And >> Crazy. There's a great book by Daniel Pink called The Power of Regrets. And he has a somewhat similar survey data of longitudinal through people's lives. And as you get older, you you regrets of inaction start to really weigh on you and ruminate in your brain. And a regret of inaction is is choosing actively not doing something versus a regret of action is I made a mistake. And humans are really good at allowing themselves to make a mistake, but the path I never traveled, the door I never opened is heavier in their mind. And it might the survey might have been getting at that. Like people thinking, "Wow, what if I had done something differently?" Well, the reason I was asking is like I kind of want this whole like I'm kind of obsessed with this idea of finding your passion not just because of your book, but like one of my favorite books is Mastery by Robert Greene. Yes. It changed my life. That changed my life. But the reason I'm I'm interested in it is because like um I previously had a company that I sold and it was like very successful in all the traditional measurements. I have a company now that's quite successful and I like what I do. But in the back of my mind, I think that it's normal and maybe you could tell me if I'm wrong that like even grown-ups like who are successful still are like do I am I am I following like the right path? Like am I following am I going to be in that six out of 10 or the four out of 10? Do you find that like even when you were when you left Compaq and then eventually got into VC, which I imagine that would be your calling, that you still questioned it? After the engineering degree, I went to Wall Street for 3 years. So I >> You were like a written research? >> in a sell-side research analyst. Yeah, so I had two stocks before I I made it to to venture. And um in both cases, I had a moment of reflection and I it's more clear to me now than it was then, but where I I asked, "Do I see myself doing this 30 years from now?" And in many businesses, there's a lifer in the room. You know, that's that's done it their whole life. And I I don't that sounds a little judgmental. I don't mean it to be. Like but it it gives you a way to reflect on whether that's the the place you want to be in Yeah. because they did it. And and the in both cases after about two or three years, I got to a no even though I was doing well in those jobs. But thinking, "Do I want to be still be doing this 30 years from now?" was was clarifying for me. But do you say something interesting? So like all right, I thought the book was amazing. The best chapter the the best part was the early part about fat finding your passion and you're like that's the hardest part. And like you said that just now you're like it didn't seem clear to me then, but it does seem clear to me now that I was questioning that. >> Well, I did do that exercise in my brain. And there's another exercise that Bezos is famous for what he calls the regret minimization framework where he said, "What would my 80-year-old self advise me to do in this situation?" Which is another way to get at what I was doing and to get at this uh this notion of you know, you only have one life. Like are you really thinking about this decision with a reflection of the whole life? And so your 80-year-old self is probably more risk-seeking than you are in that moment because he's trying to minimize that that regret. >> the exercise you did then? How old were you? I the thing I did is what I already said. I asked myself, "Do I still want to be doing this 30 years from now?" And I did it once when I was an engineer, so I was 20 23, 24. But was that voice loud? I think it was loud. I had no inhibitions whatsoever about walking away. Like it didn't bother me. And I I may have benefited in the back of my brain uh from the fact that my father went across the country. He he took a flyer on a job. He got recruited from uh Virginia to Houston to be one of the first employees at NASA. >> And and I knew he had done that. And and so I I didn't come from I think if you come from a family where multiple generations have stayed in the same town, it may feel really wild to just take flyers. I'm from Missouri. I went to school in Nashville, Tennessee. I had a hot dog stand and that's how I paid my way through college. It was called Southern Sam's wieners as big as a baby's arm. And we had a bunch of locations at these hot dog stands. It was really fun. And I was like, "This is so hard to be out in Tennessee where there's hot hot dogs." It was so hard. And so I Googled like "Where do internet companies live?" cuz I didn't even know cuz I was obsessed with the internet. And it said San Francisco. And I was like, "What internet companies are cool?" or like I don't know what like what's like the hot thing? Well, at the time it was Uber. At the time it was called UberCab still and Airbnb. And so I started looking into this thing called Airbnb. And I cold emailed this guy named Brian, the CEO. And he didn't reply to me, but then I found like another employee to email named Justin and I emailed him and I was like, "I'm going to be there on Monday. Can I interview for this company?" Obviously Airbnb was called Airbnb. And they're like, "Yeah, you live in the Bay Area?" And I was like, "Yeah, yeah, I live there." Which of course I didn't. I was in college in Tennessee. And so I flew out there the next day, got the interview, got the job, went back to Tennessee, dropped out of college, sold everything I had. But my parents are entrepreneurs in Missouri. They started their entrepreneurial career owning a fruit stand. Yep. And I remember when I told them I was like, "I'm going to leave school. I'm going to join this thing." And they're like, "What's a startup? And does it have health insurance?" I was like, "It has health insurance and it's paying like $22 an hour. I think it's going to be fine." And they're like, "Okay, cool. We'll come pack up your stuff." And I remember at that moment like that emotional support of what's is one of the biggest things that separates what allows people to win versus allow people to lose because I have met so many people. A lot of my friends are immigrants. And like the immigrant experience is interesting because a lot of the immigrants it seems like they fall into categories. One category is like they came here with nothing, so there's they have they're willing to do anything to to win and they go down one path. And then the other path is I came here to create a big life. Don't screw this up. Take the safe path. Right. And my parents were not the safe path. And that was like the most support that they could have for me. And it was so amazing. >> I'm glad I'm so glad you told that story because um even though the person this book is written towards is the the person on the career path and and I mean that we don't have a chapter on how to advise people. Like it's not written for the advisor, but I think it will be particularly interesting to parents and advisors to test whether or not they're willing to help support people in the way that your parents did. Well, I think that's a big deal because like for example, you go to the doctor to get like your basic stuff checked. I go to college I go to school to get good grades. But at no point do they ask like are you asked like are you happy Yep. doing this? And I think that that's like I think that's why I'm still up I don't think I've ever formally I don't think we've ever formally learned how do you find I call it ikigai, which I'm sure you're very familiar with. It's this Japanese term where imagine like a Venn diagram, but there's four. It's what the world wants, what the world wants to pay for, what you're good at, and what you're passionate about. The goal is to find something right in the middle. But no one teaches that, right? It's And so it's interesting the reason I like your book is because that's what it's about. And yeah, and in in the chapter titled Chase Your Curiosity, I tried to borrow as many of those type of exercises as possible. I even went out I'm surprised I didn't find that one, but I found like 10 others. And I put them all in there. Like I'm I'm trying to give people as many of those pathways as possible cuz I think the very hardest part is to figure out actually what it is that drives you in this way that's going to make it very easy for you to differentiate yourself. And it's funny, you know, you you you mentioned that one. There's a story in the book about this guy Bert Beverage in Austin, Texas who's 40 years old and he's watching a PBS show and they say to take a sheet of paper, put it horizontal, draw a line down the middle, write on the left what you love to do, and on the right what you're good at and try and find something in the middle. And through that exercise, he quit being a mortgage broker. He had been a seismologist before that and launched a vodka company called Tito's um at the age at the age of 40. I think there's this like famous Mozart quote where someone was like asking Mozart like, "How do I find my way?" or how do I like do I have what it takes to be the man?" And Mozart was like, "Dude, if you're asking that question, the answer is no >> [laughter] >> because the conquerors just conquer." And I I hated his reply to that because I'm but I'm curious. So I don't even know all of the companies you've invested in because you've been doing it for so long. You've like I don't know how how many in the cards have you invested in? >> I don't know. Dozens? Sure. A lot. >> Yeah. And you've been around all the movers and shakers whether you invested in or you passed or not. You were somehow like touched all these amazing people. Did they follow a similar path? Um for the founders, I think you'd find a lot of different stories and different pathways that got them to where they are. I mean, if you like the Zuckerberg story is pretty famous. He's at Harvard doing messing around. And and that's very different from the path say a took or even Bezos. So, I don't know that there is a pathway to that place. I'll tell you I I once asked Jeff Bezos how he could possibly be good at angel investing while he was running this company. >> What what did what did he do angel wise? Oh, he did Google, Uber. Like he he is a murderer's row. >> He was on the he was in the seed round of Google? >> Yes. Well, that's amazing. What was the evaluation then? I think that first round was a 10 poster. But but but to get to the point he said the only thing he looks for is this insane determinism. He like he wanted to believe the person was going to go do this no matter what, come hell or high water. And I think that may be a common trait of a lot of the founders. They're just really really determined and pushing against this thing. The other thing that's true of any tech founder is they're hyper curious about the edge of what the technology can do. And anytime there's a big disruption, AI being the most recent, but before that there was social media and the mobile wave and the SaaS wave and all these waves and they create opportunity because incumbents are usually slow to embrace them and so you can run at these things fast. But that requires you to be hyper curious about where the world's going and what's changing so that you can master it before anyone else does.