I was an engineer. I had an engineering degree in undergrad. In my second year, we were starting the third project I had worked on and this probably isn't what I want to do. After a couple years, I thought to myself, is this what I want to do my whole life? I got to know.
What does it take to spot the next big thing before anyone else does? Bill Gurley is the venture capitalist whose intuition has shaped the modern tech landscape. As a general partner at Benchmark, he backed companies like Uber, Open Table, and Grubhub long before they became household names.
58% of people say they're not engaged at work. 15 of those 58 say they're quiet quitting. These are horrible numbers. Founders live on the edge of a new technological shift constantly and they can't not know what's happening next. It requires a level of studying that is foreign in other industries and other fields. Most people when they go home from their job, they don't study more about what's next in their job.
He's not driven by hype. He's driven by insight, discipline, and a deep understanding of how markets evolve. His career is proof that great investing isn't luck. It's vision sharpened by rigor.
If you're in your dream job already, embrace AI. You want to become the superhuman. That is what's new on the edge. You should be self-learning. If you're not in your dream job and it's threatened by AI, all the more urgency to jump out.
Bill, so you spent 25 years investing in the best founders in the world and then you chose to write a book that has nothing to do with venture capital. So why?
You know, it's funny. A lot of people ask me that question and when I decided to write the book and I went out and talked to agents and publishers, I'd say 80, 90% of them ended up in a non-connection because they would constantly steer back towards don't you want to write a venture capital or a tell-all or how to invest book. And I didn't have any motivation to do that. I can't explain why, but I didn't have any motivation to do that.
This started about 10 years ago. I was at a moment in my life where I was consuming tons of biographies, which I think lots of people have that thing where they read a great biography and they want more and more and more of them. And I was reading a biography and noticed certain patterns about this individual's process and how they went about learning and how they went about connecting and how they went about executing their career. And I noticed similarities between three backgrounds that were very unique and different in the industry they were tackling, but the process and points were very similar.
And in venture capital is a game of pattern recognition. So, you're constantly out there trying to look at how the new world's evolving and what the key patterns are. And I've been a writer since I was a sell-side analyst. I've had a blog post for a long time and I would constantly try and see patterns and then bring them together and write about them. And so that process was something I had done a lot when this clicked for me.
So, first of all, the three people were one was a folk singer, one was a basketball coach, and one was a restaurateur. So, they're not even, you know, they're not like in the same domain category.
They're not in the same domain.
And they're all in domains where your parents would tell you not to pursue this job. And they're all in domains where people would tell you you can't make money.
And yet these people went on to exceptional greatness. Wealth became a part of it. I don't think any of them started for wealth in those areas. And it touched me in a way where I was like, 'Wow, that's a cool unlock like that there might be some things these people are doing that other people aren't doing and that haven't been written down.'
And so I initially thought this would be a great presentation to give to someone maybe at like an MBA class because that's a point in your life where people that go to MBA school have a very unique opportunity to shift careers if they wanted to. So anyway, I gave the talk at the University of Texas. They put that on YouTube. It got several hundred thousand views. I started to hear from people that had changed their lives. A few people who are in the personal development space like James Clear noticed it and it gained momentum and people said to me, 'You should turn it into a book.'
And one person in particular who is very outspoken about trying to encourage people to do creative things. When he heard I had this kind of in the can, he pushed me. He does this with a lot of people but so you started with the question why is a venture capitalist doing this non-venture capital thing. He really kind of shoved me in the back and said no this will be good for you to go do this non-venture capital thing.
So, it's a passion project. It's something that I've now spent six years working and studying and learning and enhancing from the presentation, working with a co-writer, and I think I hope it's awesome. You know, I've gotten a lot of early validation. The goal, the sole goal of it is to unlock human potential, like to get people who maybe didn't have the gumption to go do this thing, particularly if it's in a field that doesn't feel like you're supposed to be doing it, and see if they can go change the world. And not only change the world, but I think all the stories we have in the book are of people who once they're successful have huge impact on others. And so it's a passion project with hopefully a very noble objective function.
Well, I think there is a hugely noble objective with this and I think that's also why it resonates with so many people because the question that you asked me like do you enjoy what you're doing for a living? And the question of like do you like your job? Do you like your career? You did research on this and 70% of people that you researched in this 10,000 person study that you did for this book did not say that they enjoyed what they were doing. That they wanted to sort of like if they could sort of restart, right?
Yep. And I think I'm very fortunate because I said like, 'Yes, I do enjoy what I'm doing,' but that's obviously not the majority. So, this is why this idea resonates with so many people because I think a lot of people, I've thought about this a lot. I feel like people start in a career and time just flies. Like time really just flies. And then they look up and they're 40, 50 plus sometimes and they're like, 'Where did my life go? What am I actually doing with my life? Is a career that I'm in even something I want to do or is it what I was pushed into after college or university? Is it what my parents wanted? Is it what just pays the bills and I'm scared to do something else?' So, I think that's why it hits home with so many people.
I have to ask you like was there a point in your life where you were in a career that you absolutely hated that was that like did any of writing this book like take you back to a point in your life?
Yeah, there I think there was an undertone. First of all, my career as a venture capitalist, I adored and I'm still kind of at the tail end of it, but I loved every minute of it. And I would often say in interviews, you know, if we lived in a socialist world where everyone got paid the same for a job, I would still want this one, because I had so much fun doing it. And I had two jobs before that. I wouldn't say I hated them, but I was an engineer. I had an engineering degree in undergrad. And in my second year as an engineer we were starting the third project I had worked on and it looked like the second and it looked like the first and I was seeing a bigger broader world out there and was like this probably isn't what I want to do.
And so I went to MBA at University of Texas. Thought about venture a little bit while I was there, but it looked very hard to break into. And I went to Wall Street and I was a Wall Street analyst on the sell side. I had a great time. Met a lot of amazing people. A sell-side analyst gets connected immediately to CEOs and CFOs, which is insanity. You're 27 like there shouldn't. But after a couple years, I walked around the office and I thought to myself, is this what I want to do my whole life? And I got to know. And that eventually led to me getting into venture.
So I do think one of the things that's important and I want to come back to some of the data that we stirred up but one of the things that's important is letting young adults know that it's okay to try a career and stop. You know and Dave Evans who wrote Designing Your Life talks about this a lot. They have data in that book where like I won't get it exactly right but like five years post college 40% of people are no longer in the career that their major was and then 10 years after it's like 60%. And no one tells you that when you start and it all feels like you're on this kind of treadmill and we call it a conveyor belt and you don't know that you have that flexibility and so the weight of the direction you're running feels very heavy on young adults.
Mhm. And then I think that also there's all these expectations that they feel they have to live up to and they don't know where those maybe they do know where those expectations are coming from. Maybe like I mentioned it is your parents or your peers or your guidance counselor or your professors or whatever but you have all these expectations and then you actually start running a race that isn't even your own. And that's what I think a lot of I think if we talk about the data like it's like it's the data is shocking but also kind of sad and I think that you probably felt the same way because you ran this survey twice because you didn't believe the data when you first ran this survey. So,
And by the way, so we started reading much academic research. There wasn't much data on career regret. We launched a SurveyMonkey survey of a thousand, but eventually to make sure it was hardened, you know, great academic work, we partnered with Wharton and did a much broader one. Ours was seven in 10, theirs came back six in 10. I mean, it's still majority don't like what they do for a living.
Well, the question was, if you could start over, would you do something different?
The Gallup poll does an employee engagement survey every year. Those numbers are at 15-year lows right now. There's this whole phrase quiet quitting. You may have heard about which they say like 58% of people say they're not engaged at work and 15 of those 58 say they're quiet quitting. They're like intentionally trying to undermine the organization. But these are horrible numbers of course, you know.
But I do think part of the problem is the very well-intentioned people that want the child to be as successful as they can possibly be. And in the book Coddling of the American Mind, Lukianoff and Haidt call it the resume arms race. But like about sixth grade, parents take on an enormous amount of anxiety about their college application and whether it's going to be full or not. And so when people were younger, you know, they came home and they left the house and they went and ran around the neighborhood and nobody said the these kids today have their life scheduled from when they wake up to when they go to bed. And it's lacrosse and it's cello lessons and it's the foreign language and it's volunteering and all to build up that resume and then it just starts compounding and going faster and faster.
One other thing that's happened that I think is unfortunate is that many universities now require you to apply to a major as part of your application. So, you used to go take core classes for two years and then at the end of your sophomore year declare a major. Now, you're telling a junior in high school, do you know what you would want to do? Do you know what you love? Like they really don't know. And I've watched people ask these kids and they really don't know. So, they just want to say, 'I'm sorry, I don't know.' But they're not allowed to have that answer.
You get thrown into these situations where first of all it's very expensive and there's a lot of pressure and again your whole circle and peer group is saying this is what you have to do. Like in my family the expectation was just get a degree, it doesn't really matter what you do but then that shapes it when you just get a degree that does shape to an extent where you're going to end up in your career and there's so much pressure early on and you're trying to navigate it. Your parents come from a different generation where there wasn't the same kind of pressure like now I feel there's so much pressure to pursue higher education and there's not just pressure but there's so many different choices too in career right so there's pressure with choices and it just makes for like a really I think for a young kid like a very stressful environment.
By the way we talk about this in the book where you up through like 10th grade, 11th grade, you don't make a lot of choices and then all of a sudden there's 2,000 colleges to choose from in all these majors. Like it just opens up like crazy and you don't know what to do. There's a there's a I found this great quote from Rick Rubin's book, but he says as children few of us are taught to understand and prioritize our feelings. For the most part, the education system doesn't ask us to access our sensitivity, but to be obedient, to do what it's expected. Our natural independent spirit is tamed. Free thought is constrained. There's a set of rules and expectations put upon us that are not about exploring who we are or what we're capable of.
And I don't think that's intentional. Like I'm not mad at the parents or at the college counselors or any of that. I just think it's a big system that has evolved to this place. And I'm hopeful that we can get a few parents and career counselors as readers of the book just to open the aperture of what's possible, to start thinking about the things in a different way.
If you look at was it a personality trait? Was it exposure to people? Was it this inflection point in your life where you had the courage to pivot careers and to make different choices because you were on a path and then you pivoted and then you pivoted. So I mean why did you do this? Why did for example even I do this when so many people stay stuck in one thing far after it's sort of expired?
One thing I give a lot of credit to my father was grew up on a rural farm in North Carolina. Fell in love with model airplanes. That took him to NC State where he got a nautical engineering degree and he was working at Langley Air Force Base and he got invited to move to Houston and help be a part of the launch of NASA and he took the leap and he's still here. I was just with him last week, but that knowing that he did that and knowing the outcome from it and how it shaped his whole life and our community. I mean, just so much came from that. I think it just gave me permission. I want that that word's a word I use a lot talking about the book like I want to give people permission to do something that feels a little bit risky, that feels a little bit ambitious and feels like maybe it's something they shouldn't be doing, you know?
Do you feel like there's traits that people can borrow from successful founders in their own career?
Sure. One of the things we get into in the book a lot is just how you think about learning. And I've never, you know, founders live on the edge of a new technological shift constantly and they can't not know what's happening next. And it requires a level of studying that is foreign in other industries and other fields. Not to the people we profile, but to most people. Like most people when they go home from their job, they don't study more about what's next in their job. Like it's just not what they do. It's not a common trait. All the people in this book and all founders have to live in constant fear that there's something new on the edge that they don't know.
One thing that I've always this is like a working thesis and you work with a lot more founders than me, so bear with me if you agree with this or not, but I've always thought that the best employees could be founders in another life for whatever reason. That's just not the season of the life that they're in right now. So when you hire somebody, the people that are going to kill it in their career, they are ambitious. They are curious. They are self-taught individuals. They're people that are always trying to do the next thing or even break what's working now so to build something better even in their own job or in their own life. Like they adopt a lot of the same traits that a successful founder would have, but they just do it in a work environment because that's the place they want to play in right now. So I think that like when I think about the most successful people who have had the careers that are fulfilling that they actually enjoy, they act like founders even if they don't have the title.
And you touch on something that I spend a lot of time on in the book, which is I think that in order to be great, you want to learn all the bedrock principles you possibly can, but then once you know those, have the independence of thought and the confidence to innovate on top of those principles. So it's not ignorance of the past. It's full understanding of the past with an appreciation, the self-learning and the ability to do something different. One of the things that I think would make many employees bad choices of founders is if they get the first level rote knowledge and then they just apply it all the time and they don't have curiosity and they don't evolve that. But I see a lot of people execute that way in life and you can get through, but you're not very dynamic.
When somebody is in a career right now and they're very aware that they're not happy. They're unfulfilled. They're in the 70% or the 60% depending on which study they're part of, right? What is the new mental model they have to adopt or how do they change the way they view the world? Like what's the action step they got to take cuz like the first question be oh this is great I'm not thriving in my career I have a mortgage I have a spouse I have kids I have all these payments I have been doing only the one thing for the past 30 years it's great to like pontificate on a podcast that I should be learning all these new skills but how do I actually change my life and I think that's where the theory at some point has to come in contact with reality.
I that it's obviously easier for people younger in their career and that's the same for starting a company like the more you get locked into obligations like you described you do start to reduce your own flexibility although I want to come back to that. So I do think it's better for young people but one three or four things I would say one recognize that lots of people lots of successful people start in one place and move to another this is the stuff that Dave Evans talks a lot about like it's okay to change because you need the permission to do it and you need to think that it's possible.
The hardest part I think of all the stuff we talk about in the book we have a chapter titled Chase Your Curiosity. People talk like find your passion I think it's the hardest part if you don't have a calling it could be forced like there's some entrepreneurs I'm going to start a company and they just kind of force start a company versus like really having an aha moment. And I think you need the aha moment. But I have a test that I think is the right test for whether something is the type of passion where the tools in this book could help you be successful. And that is simply would you spend time outside of work learning about this topic? Like would you pick up a new paper on this topic and not watch Breaking Bad? Like does learning in this field compete with entertainment for you? And if that answer is yes, I think this is your thing. Like I really think this is your thing. And I think if you're in a field where you have that level of curiosity, you're going to do extremely well almost whatever the field is.
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I like to talk about obsession a lot because obsession for me is such a fun idea in a good way. Like a good obsession. It's like, okay, so if I'm running a podcast, like I'm up until 3:00 or 4 in the morning like researching how to ask the best question. What does the setup look like? What are the clips with the hook the first 3 seconds of a clip and how does that perform on social media so I can market the show better, right? Like I just get obsessed with it. So I know that I'm doing my thing. I know that I hopefully am thriving in a
The reason I'm smiling is we have a section in the book about Jimmy Donaldson who's MrBeast and he was on a group Skype with these other four individuals and they were talking about those exact things you just described, right?
Yeah, I love it. And I think that if I think about where I started my career, I started my career in it's so funny that you clocked I don't know if you looked into what I did for a living, but I was in when I first started like B2B enterprise SaaS sales and just sales in general. And you know, you finish work and I didn't feel like researching better enterprise sales technique.
But that's that. Yeah. But I suspect there are some people that do.
I'm sure they do. I'm sure they do. I'm sure they do. And it's a useful skill. You can make a lot of money doing that, too. But but that's why this is the test I love. And there's a clip you can go watch on YouTube of a graduation talk that Seinfeld gave at Duke and he uses the word fascination where you use obsession and I think curiosity, fascination, obsession, all those things get back to this point. Would you spend your free time learning more about it?
Yeah. And there, you know, that's a high test. That's a high bar.
But I certainly did that in my field like
Well, I was going to ask you so when was your pivot into venture capital? Because there was a question that Frank Quattrone asked you about your dream job.
Yes. And he basically asked like what was it? And then you answered, I've always dreamed of being a venture capitalist. And then Frank said he'd make it happen. Then within 13 months, you were a VC. So what was that interaction? What did that sort of trigger?
Let me give you some context on that. So I was in my third year as a sell-side analyst in New York and Frank Quattrone who's a very famous investment banker in high-tech world left Morgan Stanley and was starting a new investment bank. I knew I didn't want to be a sell-side analyst anymore. I had been approached to be a buy-side investor at a really great firm called Capital Group and was interviewing there and I got this call out of the blue from Frank and I talked to someone who knew him well and he says you have to take the meeting. This other individual said you have to take the meeting. So I took the meeting and he asked that question. He said what's your dream job? I said well I've always dreamt of being a venture capitalist. And that goes back to I worked at Compaq which was venture-backed as I studied companies on Wall Street I could see the young up-and-coming disruptions interesting to me I've always been fascinated with gambling and edge and those notions and so I was going to go on the buy side but that's what I wanted and he said come work for me because I told him I didn't want to do the job he wanted to hire me for and he said come work for me and I'll introduce you to every venture capitalist I know which was a very fortunate moment and that word fortune comes up a lot when you study great people but I do believe that what's the famous saying that's where preparation meets opportunity.
I mean like you get these chances in life but you got to take them.
You got to be you have to be able to even recognize them that's huge some people don't even recognize when these opportunities
It was funny someone sent me something the other day this is so far away from everybody we're talking about but there's an up-and-coming country singer named Charley Crockett who's starting to really bubble up and apparently he was outside of Gruene Hall in New Braunfels and handing out his own CD and handed one to Evan Felker of the Turnpike Troubadours and that led to him starting to get tour dates and stuff and people go wow that's super fortunate and I'm like you know what most people aren't handing out CDs at Gruene Hall. No, you got to to a degree you got to make your own luck in life. Like you do got to make your own luck in life. And that's like this is listen if it's career, if it's entrepreneurship, if you take enough shots and if you take enough action, I think you do start to actually create your own luck just through like pure volume of things done, something's going to work out in your favor. I think that the people that are again in the minority of being unfulfilled in their career and saying I would start over if I could. It's because for a period of time for like 5, 10, 15 years they haven't really taken any ambitious shots that could lead to the result they want there.
Listen to this. This is also from Rick Rubin's book, which if you haven't read, it's very different, but it's
Well, Rick Rubin's a really interesting guy,
But he said, 'To the best of my ability, I've followed my intuition to make career turns and been recommended against doing so every time.' Every time. And I just think that's fascinating, right? Like this trusting your inner voice and what it's telling you versus what society or these well-intended once again well-intended you know
That's the thing it's always well-intended or well-intentioned but it's because they are speaking from their frame or their perspective so if you had somebody in your circle like if you were speaking to Rick Rubin about career change. Rick Rubin's going to tell you, 'Go take the career change. Go do the crazy thing.'
He unquestionably will. And that book, you know, it's targeted at more creative individuals. It's funny. I reread it, you know, thinking about my book. My book's more targeted at professional career type things. And he's more focused on creative individuals. But he's unquestionably urging people to have more permission to take more risks to be more of themselves.
But the majority again have never done that. So they're speaking to you and they're giving advice from their reference point.
