← Success Story with Scott D. Clary
Success Story with Scott D. Clary
Bill Gurley - Benchmark Partner, Backed Uber, Zillow, Stitch Fix | The Conveyor Belt That Ruins Your Life
01:08:19
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- [00:00]
Bill Gurley
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
- [00:14]
Scott Clary
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, OpenTable and Grubhub long before they became household names.
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Bill Gurley
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, in other fields. Most people when they go home from their job, they don't study more about what's next in their job.
- [00:57]
Scott Clary
He's not driven by hype, he's driven by insight. 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.
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Bill Gurley
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.
- [01:30]
Scott Clary
Bill, so you spent 25 years investing in the best founders in the world and then you chose to wrote a book that has nothing to do with venture capital. So why?
- [01:38]
Bill Gurley
You know, it's funny, a lot of people ask me that question and, and when we went out, when I, 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, 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, or how to invest book? And I, I didn't have any motivation to do that. I, 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, 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, you know, unique and, and different in the industry they were tackling, but the process and points were very similar. And you know, 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, and I've been a writer since I was a sell side analyst. I've had a blog post for a long time. And, and I would constantly try and see patterns and then, and then bring them together and write about them. And so that process was something I had done a lot when, when, when this clicked for me. So first of all, the, the, the three people were, one was a folk singer, one was a basketball coach, and one was a restaurant tour. So they're not even, you know, they're
- [03:33]
Scott Clary
not like in the same domain category.
- [03:36]
Bill Gurley
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. Yeah. And, and, 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, 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 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, I gave the talk the University of Texas, they put that on YouTube. It got several hundred thousand views. I started to hear from, you know, people that had changed their lives. A few people who are in the personal development space, like James Clear, noticed it and you know, all, all it, it gained momentum and people said to me, you should turn it into a book. And one, 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 like pushed me. Like, like, you know, he, he does this with a lot of people. But like, so you, you started with the question, why is a venture capitalist doing this non venture capital thing? He, he, he, he like 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, that I've now spent six years working and, and studying and learning and enhancing from the presentation, working with a co writer. And, and I think it, I, I hope it's awesome. You know, I, I've gotten a lot of early validation. You know, the, 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 know, you're supposed to be doing it and, and see if they can go change the world and, 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, you know, and so it's a, it's a passion project with, with, with hopefully a very noble objective function.
- [06:08]
Scott Clary
I think, I think there is a hugely noble objective with this and I think that 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, 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 research 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?
- [06:36]
Bill Gurley
Yeah.
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Scott Clary
And I think that 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 like 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 what my parents wanted? Is it what just like pays the bills and I'm, I'm scared to do something else. So I think that's why it hits home with so many people. I, 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?
- [07:31]
Bill Gurley
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, you know, 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 you know, in my second year as an engineer, you know, we were starting the third project I had worked on and it looked like the second and it looked like the first and, and I was seeing a bigger, broader world out there. And it was like, you know, 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'. 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, I got to know and, and that, you know, 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, the, the, the data that we stirred up, but some of one of the things that's important is, 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, they, 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. Like you don't know that you have that flexibility. And so the weight of the direction you're running feels very heavy on young adult.
- [09:54]
Scott Clary
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, it, 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. That's right, ran this survey.
- [10:27]
Bill Gurley
So, and by the way, so we, we, we, we started reading much academic research. There wasn't much data on career regret. We launched a survey monkey 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 and ten. Theirs came back six and ten.
- [10:47]
Scott Clary
I mean it's still majority don't like what they do for.
- [10:50]
Bill Gurley
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, they're, they're quite quitted. They're like intentionally trying to undermine the organization. But these are, these are horrible numbers, of course, you know, but, 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, in the book Cuddling in the American Mind, Lukianoff and Hate Height call it the resume arms race. But like about 6th 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 you know people, I say when I was young but like 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 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 you know, volunteering and like all to build up that resume and, and then it Just starts compounding and going faster and faster and faster. One other thing that's happened that I think is unfortunate is the 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 to clear a major. Now you're telling a junior in high school, you know, do you know what you would want to do? Do you know what? You really don't know. And, and I've watched people ask these kids and they, they, they, they're not, they're not, they really don't know. So they just want to say, I'm sorry, I don't know. But they're not alone.
- [12:57]
Scott Clary
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- [14:43]
Bill Gurley
By the way, we, we, we, we, we, we talk about this in the book where 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, like crazy. And you don't know, you don't know what to do. There's a, there's a here, there's. 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 tame. Free throat 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. I love this and I don't think that's intentional. Like I, I, 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, you know, parents and, and career counselors as readers of the book, just to open the aperture of what's possible, you know, to start thinking about the things in a different way.
- [15:59]
Scott Clary
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?
- [16:28]
Bill Gurley
One thing I, I give a lot of credit to. My father was a. Grew up on a rural farm in North Carolina, fell in love with model airplanes. That took him to NC State where he got aeronautical 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, he's, he's still here. I, I was just with him last week. But it, 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, you know, and one that, that word to 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, and, and feels like maybe it's something they shouldn't be doing, you know.
- [17:33]
Scott Clary
Do you feel like there's, there's traits that people can borrow from successful founders in their own career?
- [17:38]
Bill Gurley
Sure. One of the things we get into a book in, in the book a lot is just how you think about learning, you know, and I've never, you know, founders live on the edge of, 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, in 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.
- [18:32]
Scott Clary
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, 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, they are self taught individuals or people that are always trying to do the next thing or, or even break what's working now. So to build something better even in their own job or in their own life, like they're very, they adopt a lot of the same traits that a successful founder would have, but they just do it in, 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.
- [19:32]
Bill Gurley
And, and, and you touch on something that I spend a lot of time on in the book, which is I, 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, 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, you know, but it's, you're not very dynamic when somebody is
- [20:31]
Scott Clary
in a career right now and they're, they're very, they're very aware that they're not happy, they're, they're unfulfilled, they're, they're in the 30, they're in the 70% or the 60% depending on which study they, they're part of. Right. What, what is the, 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? Because like the first question, oh, this is great. I'm not thriving in my career. I have a mortgage, I have a spouse, I have kids, I have, 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 pod facet. I should be learning all these new skills.
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Bill Gurley
Understood.
- [21:09]
Scott Clary
But how do I actually change my life? And I think that that's where the, the theory it at some point has to come in contact with reality.
- [21:18]
Bill Gurley
I think that, 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, so I do think it's better for young people. But I would. One, you know, 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 permission again. Yeah, you need the permission to do it and you need to think that it's possible. The, the hardest part, I think of, of all the stuff we talk about in the book, we have a chapter title, Chase your curiosity. People talk like, find your passion. I think it's the hardest part. If, if you, if you don't have a calling it, it could be forced. It's 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 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, like does learning in this field compete with entertainment for you? And if that answer is yes, I think I think you're this is your thing. Like I really think this is your thing. And 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.
- [23:12]
Scott Clary
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Bill Gurley
Is we have a section, yeah. About Jimmy Donaldson, who I know, Mr. Beast. And he, he was on a group Skype with these other four individuals and they were talking about those exact things you just described. Right?
- [26:37]
Scott Clary
Because I love it. Yeah, I love it. And I think that, I mean, if I think about where I started my career, I started my career. And 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, and just sales in general. And you know, you finish work and like I didn't feel like researching better enterprise sales technique.
- [27:01]
Bill Gurley
Yeah, but that's that. Yeah, but I, I suspect there are some people that do.
- [27:05]
Scott Clary
I'm sure they do. I'm sure they do.
- [27:07]
Bill Gurley
I'm sure they do.
- [27:08]
Scott Clary
And it's a useful skill. You can make a lot of money doing that too. But, but, but that's, that's why this
- [27:14]
Bill Gurley
is the test I love. And there's a, there's a clip you can go watch on YouTube of a graduation talk that Seinfeld gave at Duke. And he, he uses the word fascination where you use obsession. And I, I think curiosity, fascination, obsession, all those things get back to this point. Would you spend your free time learning about. More about it?
- [27:36]
Scott Clary
Yeah.
- [27:36]
Bill Gurley
And there, you know, that's a high test, that's a high bar. But I certainly did that in my field. Like.
- [27:43]
Scott Clary
Well, I was going to ask you, so, so when was your pivot into venture capital? Because there was a question that Frank Quattrone asked you about your dream job. And he basically asked like, what, 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, what was that interaction? What did that sort of trigger.
- [28:10]
Bill Gurley
Let me give you some context. Yeah. So I was, 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, 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 company firm called Capital Group and was interviewing there and I got this call out of the blue from, 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? And I said, well, I've always dreamt of being a venture capitalist. You know it. And, 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 like, 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. 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.
- [29:44]
Scott Clary
I mean like, you get these chances in life, but you got to take them.
- [29:47]
Bill Gurley
Yes. Yeah.
- [29:47]
Scott Clary
You got to be you. You have to be. You have to be able to even recognize them. That's. That's huge. Some people don't even recognize when these opportunities.
- [29:53]
Bill Gurley
It was funny. Someone sent me something the other day. This is so far away from everybody talking about but the. There's a up and coming country singer named Charlie Crockett who's starting to really bubble up. And apparently he was outside of Green hall in New Bronzeville's and handed handing out his own CD and handed one to Evan Felker of the Turnpike Troubadours. And that led to, you know, him starting to get tour dates and stuff. And people go, wow, that's super fortunate. And I'm like, you know what? Most, most people aren't handing out CDs at Greenhawk.
- [30:24]
Scott Clary
No, you got to, you got 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, what it's like, 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, a 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 in the majority 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.
- [31:07]
Bill Gurley
Listen to this. This is also from Rick Rubin's book, which if you haven't read it, it's very different. But it's, it's.
- [31:13]
Scott Clary
Well, Rick Rubin's a. It's a really interesting guy, but he
- [31:16]
Bill Gurley
said to the best of my ability to. I've followed my intuition to make career turns and been recommended against doing so every time. That's funny. Every time and, and I, you know, I, I just think that's fascinating, right? Like this, this trusting your inner, like, voice and what is telling you versus what society or these well intended, once again, well intended, you know, thing.
- [31:43]
Scott Clary
It's always, it's always like, it's always well intended or, or well intentioned or. But it's because they are speaking from their frame or their perspective. So if you had somebody in your circle, like if you, 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.
- [32:05]
Bill Gurley
He unquestionably will. And that book, yes, you know, it's, it's targeted at more creative individuals. It's, it's funny, I reread it, you know, thinking about my book. My book's more targeted at professional career, you know, type things. And he's more focused on creative individuals. But he's unquestionably urging people to, to have more permission, to take more risks, to be more of themselves.
- [32:30]
Scott Clary
But the majority, again, have never done that. So they're speaking to you and they're giving advice from their reference point.
- [32:36]
Bill Gurley
Fair enough.
- [32:36]
Scott Clary
But that's, that's the issue. So if your parents say, well, maybe don't, don't, you know, don't switch careers. You just got this new job, they mean well, they want safety and security.
- [32:47]
Bill Gurley
But there's a, there's a, there's this also famous video you can find on the Internet where Jeff Bezos talks about his career regret minimization framework. Have you heard of this?
- [33:01]
Scott Clary
Yes. Yeah.
- [33:01]
Bill Gurley
And you can go watch it. It's like five minutes. It's not long. But when he was thinking about starting Amazon, and this is exactly what we're talking about, like a hard pivot. He is working at D.E. shaw. He, David Shaw does not want him to leave. Like, he's young, highly successful, like he's walking away from a career most people would dream of having. Right. Walking away. And he said, he went and walked around Central park and he, he asked himself the question, you know, if I'm 80 and looking back, am I gonna be more upset that I left De Char, that I didn't try this thing that was tugging, you know, on my ear, telling me, you got to go do this thing. And he said that that made it simple. Like there was in his mind, it was abundantly clear. And David Pink has a book on regret and the. He says that there's tons of academic studies that boldness, regrets are the ones that weigh on people the most. And Boldness, regrets are the things you didn't do. Like in over your life, you get to the end. And boy, I wish I had done this. I wish I had asked this girl out. I wish I had change careers. I wish I had done this thing. And life is a use it or lose it proposition you go through once. And so having that mindset from these other great individuals, like, I think that can help with that question you asked a while ago about how do you get off the snide. How do you get out of this thing if you know you don't like it?
- [34:29]
Scott Clary
So you studied a few different success stories. So Bob Dylan, you mentioned Mr. Beast, Bobby Knight, Jen Atkin. And you are, you are a master of, of pattern recognition. So explain to me why you were studying these people in the first place. So how do, how does studying Mr. Beast sort of play into having.
- [34:52]
Bill Gurley
Well, some of, some of the stories were the inspiration for the book, and some of them were to fill out the book and, and, and make it even better. And so some of them we went looking for after the fact and some of them fell upon me.
- [35:07]
Scott Clary
The ones you noticed things when you started? Yes.
- [35:09]
Bill Gurley
Yeah. The ones that fell upon me were, were from reading biographies and the. It's so funny. When I was a, I had a horrible verbal SAT score. I never read. And then somehow when I got to graduate school to my MBA program, I just started reading. And I don't know what, why the bit flipped. Maybe I had free time while I was there and, and I started consuming. And I have a list of books at the back of the book of all these books I consume. But like, you know, a lot of the people that I studied, you know, along the way, picked up a lot of the, you know, personal development. Book 7 Habits of Highly Effective People. You know, the Dale Carnegie book. Like, you know, Warren Buffett says the Dale Carnegie book had more influence him on than anything. And so I think right after those type books or Tony Robbins, you know, you start to fall into the, the biographies that, and they're fun. Like you learn a lot of things reading about these other successful people and what they've done. So that's why I, that's why I got into. Then we, we started looking for stories of people who made an intentional choice to, to, to take a career change, you know, who, who had this aha moment, I'm gonna go do this and set about it intentionally, because that's the type of framework that can be helpful to someone that wants to go do this.
- [36:39]
Scott Clary
And what was it what was the thing that, that you noticed in these people like you? I mean, like, that's why I was, I mentioned pattern recognition, because you did this for, you know, 25 plus years looking at founders. So like, one skill is easily transferable. I know this for sure. So if you notice what makes a successful founder, then you start to notice what just makes a successful person. And we sort of touched on a few different points and attributes and personality traits and whatnot. But when you study, you study the most successful people in the world, the most successful people that have made career pivots, what are some of the patterns that you start to recognize?
- [37:14]
Bill Gurley
So first of all, you have to know that you're going, you have to have this intentionality. You have to know that this is something I'm excited about and determined to go. Do you know Danny Meyer, when he, he walked away from a sales job, this company that sold these devices that hook into clothes so that you can't steal them from stores, he was making over $200,000 a year. And this was 40 years ago. And so that's a lot.
- [37:43]
Scott Clary
That's a good salary for a young person.
- [37:46]
Bill Gurley
And he took a job that was less than one tenth that salary in a restaurant to start the learning process. And so, like, the level of determination you need is ultra high. But then he, he set about a learning journey. So he enrolled in a restaurant management class. He enrolled in a, in a consigliere class. He, he, he worked at this restaurant for almost nothing to get exposure. And then he went to Europe and worked for free. He set up a series of, of sessions where he could learn at different restaurants. And so this learning part is something that I see over and over and over again. And I would divine it into two components that are critical. The, the first one is learning the history. And by the way, I think this is a piece of advice that could help anybody that's trying to get hired for any job. Most people, there are a few fields like, like American literature, where you study, it's like, can you have to study the greats, but in most fields, people don't. There's no one going into an accounting job that studied the great early accountants. But if you went into an interview and there's 20 candidates and it's quite clear you know the history, you're going to be highly differentiated. So it immediately helps with peers and mentors and all these other things. If you know that history, and if it's too boring for you to go read the history, you failed test one. You go Back to go back to the start, right, and find something else. There's this thing we uncovered that we put in the book. There's this big chess tournament, global chess tournament. And during one of the, the middle of it, they did something for fun. They did a trivia contest in the middle of it for the history of chess. And Magnus Carlson won, of course he
- [39:39]
Scott Clary
did obsess with it.
- [39:40]
Bill Gurley
See, but you say that of course he did, right. And here's another like insane thing. I, I, a friend of mine won at a charity auction dinner with John Lasseter at his house, who's the creative genius behind Pixar and the, when we showed up, they put us in his screening room and served a 10 course meal to 10 of his favorite cartoons of his life. And he walked through and described why they mattered to him and how they impacted him. And most of them were from 40 years ago. And you sit there and you say holy. Like he, like the guy that's innovating on top of his field has this kind of understanding of the history of the field. So that's one the other edge where you can highly differentiate yourself is what's brand new. So a lot of people go into careers like you go into, you go in going to work in a marketing organization, you go into work at a finance organization. Most of those people don't know how social media works, how podcasts work, how like. And if you're in those orgs and have that knowledge of what's on the edge, you're once again highly differentiated. So I love learning on both sides. Like where's innovation in this area and, and understanding all of the, you know, history like of the field. Like we, we talk about a picture in the book that Picasso did when he was 14. If you go to the museum in Barcelona, you're shocked or I was shocked to find out that this, that Picasso had nailed perfect realism by like 13 or 14. He was winning really, he was winning awards for how amazing his, his pictures were. And, and so you can go find, we, we included a description of one called the Altar. But, but everyone thinks about this cubist and all this thing and oh, anyone could do that. But it came from a place of, of fully understanding the art form.
- [41:48]
Scott Clary
First it was, it was this fascination, this Seinfeld calls it fascination. I was calling it obsession or curio, whatever you call it, but because I think that when you look at somebody like a Picasso, you'd say, well he's a, he's a savant. He's like naturally he's Naturally gifted or talented. I think that that's a, I think that that actually just is almost like a compass like that. That maybe that first little bit of talent or gift points you in a direction. But then the, the obsession to use what I call it, it's what actually allows you to be successful at that thing. Like, I mean, if you look at any great. I mean it could be Picasso, could be, it could be LeBron or, or MJ or pick. Pick a great from any field, any industry. I mean even founders that I speak with and I'm sure that you recognize this as well. They know so much about what they do. It's like it's, it's disgusting the amount of knowledge they know use useless knowledge that they sometimes know about what they do for a living. Right. They just know to the intricate detail.
- [42:48]
Bill Gurley
And by the way, it's, it's. Look at the tools we have today to get knowledgeable. It's never been easier. I mean, I started writing this before LLMs took off. Like you can just sit there and talk to Open. You want to learn about the history of a field? Yeah. Just you could, you could, could spend the next two days talking to OpenAI know more than most. Like, there's no excuse to not have this bedrock level of information because it's never been easier to get Indeed is
- [43:16]
Scott Clary
a success story partner. Now, if you're hiring Indeed is all you need. Let me give you an example. If I needed to hire a new editor for this show, I'd go to Indeed and be super specific. Not just can you edit audio. I'd say I need someone who's edited a conversational podcast for at least three years, gets our style and knows our software. Someone who's done this before. And here's the thing with Indeed sponsored jobs, I'd get people who fit that description. I'm not digging through resumes from people who've edited one YouTube video. I'm getting actual podcast editors who know what they're doing. People who've worked on shows like ours and can prove it. That's what makes a difference. You get people who actually are what you're looking for. According to Indeed data, sponsored jobs posted directly on indeed are 90% more likely to report a higher than non sponsored jobs. And people are finding quality hires right now. In the minute that I've been speaking to you, companies like yours have made 27 hires on Indeed. According to Indeed Data worldwide. Spend more time interviewing candidates who check all the boxes. Less stress, less time, and more results. Now with Indeed Sponsored Jobs and listeners of this show will get a $75 sponsored job credit to help you get your job the premium status it deserves. @inn Indeed.com Clary just go to Indeed.com Clary right now and support our show by saying you heard about Indeed on this podcast. Indeed.com Clary terms and conditions apply. Hiring do it the right way with Indeed. HubSpot is a success story. Partner now if you're looking for a new podcast, one of my favorite show right now is Demand Decoded. If you're in the B2B marketing space, you need to be listening to this. It's hosted by the team at Blend. They are a demand gen agency. They know what they're doing. They're also part of the HubSpot podcast network. What I love about it is they skip all the theory and they just tell you what's actually working today. So demand gen marketing, content, LinkedIn ads, attribution, they talk about real strategies that they are using that you can use today that are working. So if you're an entrepreneur, if you're building a business, if you're really selling anything to anyone, go search Demand Decoded wherever you get your podcast past. I'm curious because obviously you've been like incredibly successful at your quote unquote career, your, your job. When you look at, when you look at some of the sort of the things that the most successful people in the world have done with their pivot and their career, have you mirrored that in your career? Like when you first started in vc, did you like study the greats? Did you go down rabbit holes? Did you learn the history? Were you just like obsessed with this thing more than anybody else?
- [45:33]
Bill Gurley
I think it was a little broader than vc. I think when I got into finance and investing, you know, I did that. So I read all the Buffett letters. You know, I read, you know, Howard Marks. I mean his stuff's fast. And I read all I possibly could. Yes. So I think if someone said, you know, compared to other venture capitalists, who knows more about investing history, I, I think I might be at the top of the list like among venture capitalists. Like I don't think most of them. And a lot of people that roll into it new almost never understand investing. They don't study investing. So yeah, I do it. I as a nod to all the people that wanted this book to be about me, I. In the epilogue, I do kind of walk through my story in the lens of the book. So that's in there.
- [46:19]
Scott Clary
Also, I'm curious why, I'm curious why people don't find value in history. Me, it's almost like they think that they're, it's like an ego thing or they think they're smarter than they are.
- [46:31]
Bill Gurley
I mean, you, you've obviously hung out with a lot of founders. I think in the, in the, in the tech community, founders view they've been taught that old companies are stodgy and bureaucratic and stupid and, and I think they put all of history in, into that, into that world, which is unfortunate. I, I understand why, like I'm once again, it's not something where I like, you know, and, and there is, there is an element of rebelness that allows a founder to be successful. And that mindset can cause you to question everything that's been done historically. Every true.
- [47:07]
Scott Clary
Which is, which is a benefit. Like, like saying, saying like, okay, we're not going to do things the way they've always been done. That's, that's what allows some people to be successful. But I was listening to your interview with Tim Ferriss where you were talking about how a lot of founders could actually benefit from an mba. And I think it's the same mindset, like whether or not you study the history of company and organization or you study, or you study sort of like, you know, a more formal business education. I think there is value in understanding history, but maybe that's not what you replicate. You just learn from it.
- [47:45]
Bill Gurley
Well, like I said earlier, like history, having understanding the bedrock, I think gives you a full mental model for knowing where you now want to innovate on top of what's been done prior. And I think the, the Picasso examples that way, you know, the one of the thing, the big unlocks on the Dylan story that like, if you watch the movie, you don't see. When he was in Minnesota, he probably listened to more folk, folk albums and studied more folk artists than anyone in Minnesota. I'd have to believe that when he left to go find what he got through, like, he knew more. Like, he just knew more. And there was. When they talked to people back then in that neighborhood, he was like, they'd be like, where'd that record go? Oh, Bob took it like, like he was just gathering. He would go back then the record stores had these listening rooms. If you couldn't afford the record, you, you know, he's just sitting in there listening to over and over and over again. And people don't think about that element of any musician. Like, how much did they study the past?
- [48:50]
Scott Clary
You know, when you do make a pivot in your life and your career, what allows you to be successful?
- [48:57]
Bill Gurley
Well, the, the you brought up earlier like this is harder if you're older. We have a chapter near the end of the book called Never Too Late where we profile several people that made post 40 changes and, and drastically impacted the world, which is kind of fun to know that it's still possible. You know, I don't know that the techniques are any different. I think the amount of gumption that's required is so much, you know, higher and harder. Society, you know, doesn't. I don't think. I think for, for whatever reason, the things that we've evolved to a place in society where if you're 40 and have three children, you don't leave your job and go chase the dream. Like, it's just. It looks reckless. Right.
- [49:47]
Scott Clary
I think that's sad though. I think it's sad because I think that that's actually when you have like the life experience where you actually could have a higher success rate than somebody who's just like a, you know, the Stanford dropout, the, the, you know, the typical entrepreneur. I think that if you are, have like, I think, I think, and I mean, like, you work with people that are probably on average, like, if you look at the companies you've invested in, they are sort of like the more typical entrepreneur, right? Sort of like the, the Hollywood version of entrepreneurship. But think about somebody who's 45 who, who's worked in a career or a business their whole life. They recognize the gaps in that industry better than anybody else. They have like the lived experience, the business acumen, and then they can either strategically pivot their career, they can go build something in that industry. At 45, like, I feel like their success rate is much higher. Yeah, I, I don't, I don't know. I'm just making these, I'm making these assumptions up, but I feel like just intuitively this person, I would assume that they would have a higher likelihood of success because of what they've gone through in life and what they know.
- [50:49]
Bill Gurley
I am, the reason I'm smiling, as you say that is like, I have a lot of ambitions for the book. It's obviously, you know, more targeted young adults in it. And, and as we talked about, the, the people that serve in like, mentor roles for that group. But I would be thrilled. Like, I would be tickled pink if, you know, store as the book launches, if I start to get inbound stories from people who, just, like you described, who. This book gives them that permission. My, my co writer uses the phrase Disinhibiting, like, and, and there we found stories like Seinfeld decided he loved stand up and wanted to give it a try, but it wasn't till he read this book. Someone wrote a book about 20 successful standup comedians and here they are and here's their profile and they all make money. And like that book gave him this disinhibiting moment where he's, oh, oh, you can act. One can do this right? One can go do this. And I, I hope, I hope, I hope I hear from a ton of the people you just described and I hope they go on to do really amazing things.
- [51:58]
Scott Clary
When you look at all the people, like, even like the, the founders that you work with, because outside of this study, you work with founders on a day to day, do you find that people that are more entrepreneurial are more in love with the work they do? Even if they're not, say they're not, say they're not like founders by name. Say they're people that work within like a, like an early stage startup and they built from scratch. Do you feel like they're, they're a little bit more in love? They're thriving more often than not in their career. Like, is there anything else that sort of is a good signal for.
- [52:29]
Bill Gurley
I would, I would say this. You're making me smile once again. Like, there are more smiles in a startup than I've ever seen in a non startup. And in that you're coming up with all these theories like, like in the, in an unknown world, like, you're, well, what if we did this? Or what if we did this? Or what if we did this product or changed this pricing? And when something works, when, and many of those theories don't, like maybe it's 1 in 5, 1 in 10, or whatever, but they keep tilting at it. But when it does work, there's this massive smile. I mean, I just look, I see founders in my brain, like they want to call you and tell you, guess what, guess what? We just like, you know, what happened, like, just, just came. So yeah, I do, I do think that, like, I do think they're constantly experimenting, constantly learning and constantly thrilled when, when something comes together.
- [53:32]
Scott Clary
So that being said, because now I'm trying to, I'm trying to really unlock why people have so much regret. And it's like it's not just one thing that leads to regret, right? It could be that the job you're working in was something that you just thought you had to do. It could be. And you've just been Doing it for forever. But I think it's also because you feel like you stopped winning in your career. Like, you stopped, you stopped doing anything interesting. It stopped taking chances, you stopped taking any kind of risk, you stopped growing, you stopped achieving anything as an individual or even as a team. And you're just in, you know, you're just in this routine, this comfort zone routine that you've been doing for X amount of years. And there's no newness. Like, at least in a startup environment, there's super high risk, but a lot of newness all the time. And I think that that can also create a lot of career satisfaction. So how do you. I mean, like the question.
- [54:24]
Bill Gurley
I think that's a great point that you're making. And look, I, I do want to acknowledge there are many people in this life that have decided that their career is their career and their, their fulfillment is outside their career and they view one as a means to an ends and they don't want to hear about it. And this book's not for them. Like, like, I'm not judging in this, this book's not for them. If you are in that situation you just talked about and feel frustrated, you know, pick up the book like this. I. This is who I want to speak to and talk to.
- [55:00]
Scott Clary
Do you. Do you have any career regret?
- [55:03]
Bill Gurley
No, but, you know, I don't. Because I fell into that spot. I had I not fallen into that spot. Yeah, I might, but. But I don't. And, and by the way, one thing I, I harp on in the book, those two jobs that I had for three years, you know, each. I don't regret those. Like, they were part of the path. They got me where I was going, you know, and, and I'm glad that I had both of those stops along the way.
- [55:32]
Scott Clary
I feel like I, I feel like people always think they have more time than they actually do. I don't know. I've noticed since. I've noticed. I actually have noticed this even more since, since, Since COVID I don't know why, but I just feel like time flies now. Like, I feel like.
- [55:46]
Bill Gurley
I think it's because you're getting older. I think time moves slow when you're young. Yeah. And gets faster when you're old.
- [55:52]
Scott Clary
But like years are flying by. Yeah, years are flying.
- [55:55]
Bill Gurley
I have this theory that it relates to your, your storage capacity in your brain when you're young. When you're young, you get to store everything so everything feels slow, but your brain fills up and then you're not storing much New.
- [56:09]
Scott Clary
No, no, it's true. Well, I think that, I think that I've actually read. I can't remember where I read this, but it's, there's this idea, a few different ideas as to why, like, time moves faster when you're, when you're older. But one of them is like, you don't experience as many new things. Kind of like what you're, you're speaking, you don't experience as many new things. There's not as much newness.
- [56:30]
Bill Gurley
Yes.
- [56:31]
Scott Clary
So routine, like life is routine. You do the same things day in, day out, day in, day out. And if you actually took time to do something new every single day, time would feel like it's moving slowly.
- [56:43]
Bill Gurley
And by the way, that ties really nicely back to this thing I, I said where if you're chasing your dream job, you learn at night as an alternative to entertainment. Like, and so the newness kind of comes with it. You know, I was talking to Danny Meyer recently and he had just come back from an yet another European learning trip with books full of notes like, like you. Yeah. Who goes on learning trips? Like, how many whippers? What percentage of people in their career go on learning trips?
- [57:17]
Scott Clary
But this is what, this is what differentiates you.
- [57:20]
Bill Gurley
You, no doubt.
- [57:20]
Scott Clary
This is what differentiates you. I think you have a Satya Nadella quote in the book. I buy more books than I can finish. I sign up for more online courses than I can complete. I fundamentally believe that if you are not learning new things, you stop being great. You stop doing great and useful things. I mean, whether or not it's learning through reading, learning through podcasts, learning through exposure of just trying something, it doesn't work out. It failed. You learned the lesson. You try something else. Like, there's not a single person who I know who's successful, happy and fulfilled, who is not constantly exploring new ideas. And there's no, like, I mean, up until the point, you know, when, when you, when you are no longer on this earth, like, there's, you are always, always learning new information.
- [58:14]
Bill Gurley
By the way, Sachs turnaround at Microsoft may be a unit of one. Like, it may be the most successful business turnaround ever from.
- [58:25]
Scott Clary
I don't think many people know that story.
- [58:27]
Bill Gurley
Yeah, and he, in that, when he was talking about that, someone asked him how he led so much change there, he intentionally took that mindset and said, this is going to be the mindset of the org. And you know, are you in or out? Like, are you going to become a self learner and be a part of the New Microsoft. And if not, you know, this probably isn't a place for you. And that's really cool and innovative and new.
- [58:56]
Scott Clary
First of all, hats off to him for accomplishing this. I feel like a lot of CEOs wish they could do that with their companies. It's not easy though. No, it's not easy because it pushes people outside your comfort zone. Yes, no doubt to become a self taught individual because then you start to realize, I think this is probably the scariest part for when somebody is not happy with their work. And I love the idea of, of agency and of internal locus of control and of taking responsibility for your own outcomes. But you start to realize that, oh, I'm not in a job I love, it is entirely my fault that I'm still in this job and, or fault or responsibility or whatever word you want to call it. And then the responsibility becomes yours to learn the skill or to do the thing or to make the move or to take the action. So then it becomes quite scary because you realize that whatever you actually want to achieve is on the other side of your action and your agency. And I think that a lot that puts a lot of people in an uncomfortable position if they are not used to adopting that mindset and that mental model. Whereas a, I think a good founder, or even, you know, forget founder, a successful executive that has worked his or her way up through the corporate ladder, they understand that the most of their success has been contingent on them and they are personally responsible for all outcomes, good and bad. And I think it's a very scary idea for people to adopt.
- [60:24]
Bill Gurley
Well, I think the book can be super helpful for people that have that feel that way. So the structure of the book I think is somewhat unique. We divide it half between what I call profiles which are stories of success and principles which are tools or methods of success. And you know, in addition to giving people permission, I want them to read about other people doing this so that they feel the possibility. And I think the stories will really help on that front and then give you very straightforward tools and processes to, to go about the journey and, and you know, once again, these aren't really mine. I've studied other people that have been wildly successful. I see some mirrors in my own success. But, but I've, I've brought them together and synthesized them in a way that I think it could give someone like you just described confidence to take the leap and, and that to have some conviction that they'll be successful as they go forward.
- [61:26]
Scott Clary
One, one last idea that I think is really important. And not to, not to throw AI into every single conversation I have. But you mentioned that AI is about to eliminate some of sort of the more safe careers.
- [61:37]
Bill Gurley
Correct.
- [61:39]
Scott Clary
So this conversation, this book, some of these ideas, you know, the need for somebody to take action in their own life is probably becoming a little bit more relevant now than it even was five years ago. Because if it's not, if it's not just, you know, we're looking at it from the angle of you are doing it for fulfillment and you're doing it so that you love your life and there's no regret. But like if you look at it from the other angle of maybe the job that you have right now is not around in five years or maybe, maybe it's downsized or the people that are doing your job are specialists in AI and they can 10x the efficiency of every single person in that business unit because they know how to use LLMs and different sort of AI tools and generative chat tools or whatever. If you don't, if you don't learn new shit, if you don't, if you don't find a way to move into a career you love, or if you don't find a way to become even, you know, significantly better and more proficient and, and forward looking in the career that you're doing right now, at some point you're going to get replaced. Which is just a hard truth. Whether or not you, you love it or not. It's, it's just the truth. So I think that the, the mindset of learning new shit, understanding that that can either be applied to make you more probably like secure your career and the job that you're doing right now and, or set you up for a potential successful pivot if you're just like again, self taught person. I think that idea is one of
- [63:10]
Bill Gurley
the most important ideas and I, I would, I'd say three things to that. One, if you are in a dream, 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 like that's, that's what you should go do if you're in your dream job. If you're not in your dream job and it's threatened by AI. Yes. Or all the more urgency to jump out. And then lastly, I would just say I think those well intentioned parents and coaches send people towards the safe jobs because they think that if you make enough money you'll be happy in life. There's all kind of of surveys that show that not to be true, that fulfillment matters way more than, than wealth. And, and so, you know, I, I didn't think it was right, but, but now that all those jobs are in question, hopefully some of these people will stop cramming the kids, you know, down these, down these conveyor belts towards COMPSAI or, or whatever. Because, because now it's not as certain.
- [64:14]
Scott Clary
No, now nothing's, now nothing is certain. Right. So the only, the only, the only thing that's certain is you have to be somebody who's adaptable, who is a self taught individual. If, if you have those skill sets and that mindset, I think then your
- [64:26]
Bill Gurley
career and you're much more likely to have that mindset if you have found something where you, that you're highly curious about. There's. I stumbled upon this podcast with Angela Duckworth, who has obviously written this famous book Grit. And she took some time to talk with us as we were writing this. And her book said there's two things that lead to success, passion and perseverance. And that's what Grit is all about. And she says if she were rewriting the book today, she'd focus way more on the passion side because what she discovered is we've taught a lot of these kids how to grind. You know, just like you teach a kid how to practice piano for four hours a day. And what ends up happening is, you know, you crush your SATs, you get into the best school possible, you get one degree, maybe two, but you run out of steam if you don't have this, this passion that drives this curiosity. You've been trained to run, you know, but eventually you run. You just run out of energy.
- [65:33]
Scott Clary
You mentioned something interesting and I just want to touch on that. You shouldn't be racing towards money, you should be racing towards fulfillment. How do you measure fulfillment? Like, how do you know if you are truly fulfilled? Is it a feeling? Is. It's like when you look at some of the people you've, you've interviewed. What's the, what's the metric?
- [65:51]
Bill Gurley
I, I have to believe that there are other academics or authors who have written books specifically on that topic.
- [65:58]
Scott Clary
Probably.
- [65:58]
Bill Gurley
I'm good. I'm gonna go talk to chat GBT after this so I can have a better answer. You know, I, I really have found that people that have this self learning element to their job are the ones that are fulfilled. And, and I, I don't know if it's for the reason you said, where there's just constant newness in their life. I I think, you know, all the people we, I mentioned this earlier, but all the people we profile end up touching a lot of other people's lives in a positive way. You know, if you become extraordinary in your field and, and at least if you're following the principles I talk about, you're, you're, you're co. Evolving with your peers. You're, you know, these kind of things. You're, you're building relationships, you're having success, you're impacting people's lives. I think those are, you know, the elements of fulfillment that matter the most.
- [66:55]
Scott Clary
So running down a dream that, that'll be available wherever you get your books and we'll put links in the show notes and everything like that. Where do you want to send people? Is there any other socials or websites that you want people to go to?
- [67:07]
Bill Gurley
There's one thing I'll mention and we're just putting it up right now. But, but I'm going to take all the, the proceeds that I would get from the book and more and launch a foundation called Running Down a Dream. And we're going to take applications for micro grants for people that are kind of stuck financially that want to go chase their dreams. And you know, we'll, we'll, we'll take those applications in and, and I'll create a committee and make some choices and we're going to hand out some grants to see if, if, you know, because some people came to me and say, well, what if someone just is too stuck financially to.
- [67:44]
Scott Clary
Which is valid.
- [67:45]
Bill Gurley
Yeah, which is valid. So hopefully we can do that and hopefully some of those people will be successful and then we'll tell those stories.
- [67:52]
Scott Clary
I love that. When someone's finished reading, what's the first thing you want them to do?
- [67:57]
Bill Gurley
There's two things that have already happened in the, in the handful of people that read the book. One. One is they immediately want three or four copies because they have a mind in their mind. Someone, they want to read this. So I think they know of a kid that's got too much pressure or hasn't really isn't happy or feels like maybe they started down the wrong major or, you know, they, they know someone, they want to hand it to that hat that's. I'm very optimistic about the fact that the book may have a viral loop built into it already from that. And then the second one I've heard
- [68:32]
Scott Clary
is like, you can't take it away.
- [68:35]
Bill Gurley
Get away from it. Yeah, whatever. It's good. You know, I've even had like a 60 year old road distance said I thought I was retired. I there's something I need to go do which is fun, like fun because that's I'll finish where we started, like unlocking human potential. Like if I can get, I mean if I could get 100 people to go be extraordinary that, that were otherwise not going to be, I'd feel like this was huge success. Hopefully it can be way more than that.