The Career Advice That Ruins Lives (And What Actually Works) - Bill Gurley

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0:58Bill Gurley:Life is a use it or lose it proposition. Young people don't see the end of times, but older people really, by the time you're 40 or 50, I think it weighs on you. And so my argument is you're going to end up working 80 ,000 hours in your life. Why not do what you love? And I fear that our society has been steering people towards quote, safe jobs, which in a day of AI may not even be that safe anymore. And I would argue the safest thing you could possibly do is find a career in something that you're totally fascinated with. And the reason is all the techniques that tell you how to be the most successful thing you can possibly be, they're all 10 times easier if you're fascinated and in love with the subject matter.

1:39Bill Gurley:Everything gets easier and you get energy rather than it costing you. Welcome to Open Book. I am your host, Anthony Scaramucci. Joining us today is Bill Gurley. The book is phenomenal. Running Down a Dream, How to Thrive in a Career you actually love. Don't all of us want to do that? But Bill, I've been following your career from a distance. It's a real pleasure for me to have you on our podcast together. And I'm a big book lover, and this is going to be on my recommended list going forward for young and old people. There's so much in the book. I want to go to something that I love, which is getting a book published.

2:22Let's start right there. How does it feel to have this published now?

2:28Bill Gurley:It's a bit overwhelming. This was a passion project on the side for me, not my day job. And it was born out of a presentation I gave eight years ago at the University of Texas. And once it began to take life as a book, for reasons that we could dive into, I took it very seriously and did a ton of academic research, talked to a ton of experts. I really wanted it to be great. And so it took about five years, literally, not full time, like in the background, to get it burnt. And then the thing I had no idea, promoting the book is quite tedious. Yeah, it's hard. Now, listen, I've done a couple of books.

3:09It's hard. You've got to get out there. You've got to get your personality out there. But you're doing a hell of a job. I've seen you on a couple of different podcasts. I've listened to you. I think the story about James Clear observing you when you were at the University of Texas at the McComb.

3:24Bill Gurley:Yeah, he found the video on the YouTube and reposted it, which gave me some confidence. You know, he's perhaps the best-selling author in the self-help categories. Well, him and Mel Robbins. He's written a phenomenal book about habits. but you have recognized something through pattern recognition, but there's also something else that you're doing, which is evident in your book. You have a tremendous amount of self-awareness, which is, if you don't mind me saying this, because I've worked on Wall Street for 40 years, venture capitalists and Wall Streeters typically don't have a lot of self-awareness, Bill Gurley.

4:04So this is something that you have, which I give you an enormous amount of credit for, So tell us about your insights from your own self and tell us how you saw these patterns. And that's why the book is so good, by the way. So tell us about that.

4:20Bill Gurley:Yeah. So I was, there was a period in my life, I'm a big book fan as well, where I was reading a ton of biographies and I finished this third biography and saw a through line between it and two others in completely different fields. And these were all people that started on the very bottom rung of the ladder, but had high intent so they they wanted to be successful in the category starting at the very bottom and i noticed that they all did very similar things and some of these things are are things that aren't generally recommended to young people i think we also live in a in a world at least in north america where our path to and through college has gotten super intense and uh kids are just way overscheduled and they don't really have the opportunity and others have written about this heights written about this rick rubens talked about they're so overscheduled that they just don't have the time to find what they love and to really fall in love with something that they can turn into a career and so um i i wrote this book with just one objective in mind which is to help unlock human potential.

5:30Bill Gurley:I want people to, to believe they can go do something that maybe their parents or some advisor told them not to and have the, the motivation and the methods to go do it. You know, you're an entrepreneur. I've been an entrepreneur in my career. And so I've gotten some things right, Bill. I've gotten some things very wrong. I've had a career setbacks. I, I infamously went into politics for a little while, got my ass fired after 11 days. So I've had my my bumps and scrapes along the way uh but there's something that you write about in this book that i want you to address because i do believe this and this is something that you cite daniel pink's research in this uh yeah about the regrets of inaction so that's me i feel like uh whatever's happened has happened i'm willing to accept it primarily because i've been on the playing field throwing interceptions and a few touchdowns so talk about the regrets of inaction as you beautifully write about it.

6:29Bill Gurley:And you mentioned earlier, you know, career regret. We did a survey first on SurveyMonkey and then we did it again with Wharton People Analytics because we wanted to make sure we got it right, where we asked people that had been to college, you know, if you start your career over again, would you do it differently? And in our original SurveyMonkey, seven out of 10 said yes. With Wharton, it was six out of 10. It's still a vast majority of people. Daniel Pink, in his book, The Power of Regrets, notes that humans dwell on regrets of inaction. He calls them boldness regrets. These are things you didn't try.

7:04Bill Gurley:And the older you get, the more they weigh on you. Humans are fabulous at forgiving themselves for mistakes, kind of what you just walked through. Those are action mistakes. We're like, oh, that's all right. Water under the bridge. I learned something and you move on. But the thing you never tried is the thing that eats at you as you get old. So young people listen to this podcast and thank God for that. So I want you to grab the young men and women that listen to this God, grab them by their shirt, grab them by the collar and shake them a little right now and give me the message, Bill. Yeah. So first of all, we have a phrase in the book, life is a use it or lose a proposition.

7:46Bill Gurley:And I think young people don't see the end of times. Like it seems very far away, but older people really, it weighs, by the time you're 40 or 50, I think it weighs on you. And so my argument is you're going to end up working 80 ,000 hours in your life and why not do what you love? And I fear that our society has been steering people towards quote safe jobs, which in a day of AI may not even be that safe anymore. And I would argue the safest thing you can possibly do is find a career in something that you're totally fascinated with. And the reason is all the techniques in the book that tell you how to be the most successful thing you can possibly be, they're all 10 times easier if you're fascinated and in love with the subject matter.

8:36Bill Gurley:Like everything gets easier and you get energy rather than it costing you energy. you so um i would also tell him i would also tell him one last thing i would just tell him if you don't know what that is that's completely fine don't stress out about it just keep trying things take shots on goal um see what really interests you until you find it and the whole chapter in our book called chase your curiosity is about that journey so it doesn't presume you know this going in i mean it's a fascinating the reason why i was going to step in is related to something that you write about, which is the ethos of the reality of most people can't afford to be wrong.

9:18And again, it's something to do with their self-image, but it could also be an economic reason. Somebody like me at the early part of my career, I didn't have the guts to start my own business. In fact, I wrote down the day I graduated from law school, Bill, I said, I'm going to have my own business, but not until I pay off all this school debt. It took me seven years. And I worked at Goldman Sachs for seven years. When the debt was paid off, I left the start of my own business. And by the way, it was scary even then without that financial rock or that boulder on my shoulder. So how do you get through that?

9:53I think it's difficult.

9:55Bill Gurley:I would tell you that for your listeners, the books are divided into profiles and principles and they interleave and alternate and the profiles are stories and a couple of the stories people have zero dollars when they start certainly right the bob dylan's one of the stories when he went to new york he had ten dollars it's a great the dylan story which even though i saw the movie i didn't really see in your context we'll get they missed this part most of our coverage is pre the movie um yeah i love i love the dylan story i want to i want to get to the dylan story but weave it in with yeah but Jen Atkins, I was going to say Jen Atkins went to New York or LA with$200.

10:34Bill Gurley:Now your situation's worse because that is, is negative money, um, which is more of a handcuff. Um, and, um, I would tell, I would tell people, uh, one thing they can do and AI can be super helpful on this is you can plan and imagine without actually doing something. So, and I think the more you do of that as an exercise, the more confidence you will build that you could possibly go in that direction. Dave Evans, who wrote Designing Your Life, talks about this as a way to find which way you want to go. He says like battle card, three or four scenarios. But it sounded like you knew what you wanted to do.

11:13Bill Gurley:So literally as a hobby at home, like have AI help you build a game plan. Like what are the first five steps going to be? How can I do this with this constraint? And I'm not saying jump tomorrow, but I think the more that you visualize what's possible and think through the difficulties, the steps you would take, the more confidence you're going to have in taking that leap. Yeah, I know this. I think it's really true. And I always tell young people that it's not as scary as it looks. And that's the weird thing about it. I remember when I left Goldman, one of the old partners at Goldman, still a very close friend of mine, he's in his 80s now.

11:56He says, you know, you'll figure it out. And, you know, and you know this expression. Entrepreneurs, they jump off a cliff. They're trying to build an airplane on the way down. And but you figure it out. And I think that's something that we need to tell young people, that believe in yourself, recognize that you have levels of resourcefulness and energy for the things you're passionate about way more than the fears. You know, the energy and passion can overcome the fears. Tell us about Bob Dylan, though, sir. I thought that that was, to me, you know, when I think of your book, I'm going to think of so many great ideas and concepts, but it's really the Bob Dylan story that resonates with me the most.

12:37Tell us about Bob Dylan.

12:39Bill Gurley:So this isn't covered in the movie, and there is some detail in the Scorsese documentary. But Dylan is a, and always was, going way back to when he got started, is a historian. He liked, and he's insanely studious about music. And so when he got to got to Minneapolis, he started studying folk music. And I have a high confidence level based on what I've read that he knew more about folk music than anyone else in Minnesota when he left for New York. And the friends they talked to, he would sit in record stores that had these listening booths back then. And he just went over it and over and over it.

13:26Bill Gurley:And now, you know, obviously so successful, you can see this. He did a podcast for a while where he went through different genres of music and you can just see how much details in his brain. And then he released this book, Coffee Table book recently, about the 50 most impactful songs of all time. And you just see that I think people have a perception that he's just sitting there writing his own songs. But the guy has just studied everyone under the sun. and the second tenant in the book is hone your craft. It's all about continuous learning. And it's a vector that I see run through all the most successful people.

14:04Bill Gurley:You know, do you go home at night and study the thing you love? And does it feel like an alternative to watching Netflix? Yeah, so I mean, that's the follow-up question. Do you think the curiosity-driven path that he was on that you wonderfully describe in this book is harder in the attention economy that rewards, you know, it rewards breadth over depth, as an example. Potentially, but I would tell you that, you know, a lot of people have brought up the threat of AI recently. And I realized, I didn't, I wrote this, I started writing this book way before the AI wave, but most of the people that are just hyper curious about their field, they act like artisans or craftsmen and part of what's really cool about an artisan or a craftsman is they're really studying the nuance at the edge of the field and that's the stuff that's not in the AI model you know if you just go to school and learn all the rote stuff and you think you have a defense defensible you know differentiation because of that that's the stuff that AI can do really great and the thing that the experts do or these artisans do is really study what's on the edge and the nuance that's out there and and they they're able to use that confidence in the nuance to really differentiate themselves so i am i'm i'm certain that now there was mark cuban had a great quote the other day he said there are two types of people in the world those that use llms to learn faster and even more in those that use LLMs to avoid learning.

15:43Bill Gurley:And I thought it was pretty profound. Like if you want to be studious about something, there's never been a better time on the planet. Like these tools will allow you to learn as fast as you possibly want to go, but you have to have the interest as, as you said, if you don't, if you don't, you don't get there. But this is, this goes back to the test being, are you fascinated with this? Like, you know it's a good it's a good segue into uh what you talk about in terms of uh people wanting success or people just excited about building things right it's sort of the same sort of concept so tell us about your observation as a venture capitalist of founders that you've met you can tell early on can't you when someone's generally i mean founders founders right founders have two two things that that are first of all they just have a super high motor they're very determined at least the best one they're like hyper determined they're going to do this come hell or high water but the second thing is they are hyper curious about what they're doing and so almost the the way that a founder entrepreneur takes advantage of some new technology wave is they go understand what it's capable of more than anyone else so just as i'm talking about maybe Bob Dylan did in folk music.

17:02Bill Gurley:They're doing that with the new AI wave and they did it with the mobile wave and the internet wave. These are the people that are on that edge studying that nuance and exploiting. Yeah. I mean, see, to me, that's the real love, right? You know, I like building things and I have intellectual curiosity and, you know, don't get me wrong. I'm in it for success. I'm not saying I'm not, but I'm not, doesn't overly inspire me. What inspires me, and one of the reasons why I do this podcast is that I love talking to authors. I mean, the fact that you took the time to synthesize and put all of these thoughts down for all of us, you know, I used to tease people, Bill, you and I are roughly the same age.

17:40I used to say for$10, you can get, you can read in 10 hours, 10 years of an author's experience. Now with inflation, it's probably$30 today, but you get my point. Um, and, and it, and it's also about the peer group. You know, I always tell my kids, you're the weighted average of the five people you hang out with. You write a great, your theme about the power of peer groups and the people you surround yourself with. How much of long-term success is talent and how much of it is just getting yourself into the right space and into the right peer group to help propel yourself?

18:15Bill Gurley:Look, I mean, I think having written this book, I would hope one thing people would walk away from is the belief that the techniques that I have in here don't require some excessive amount of intellectual power or some natural talent to go do them. Most of the people in the book are hyper fascinated by their field. They study their butts off and they collaborate and connect in multiple ways with both mentors and peers. And my favorite principle in the book is this one on peers because I think a lot of people say what you just said, like being a good friend group, but I don't think they are taught to proactively create a peer group to help them along their career path.

19:00Bill Gurley:And we have some wonderful examples in the book, but I think too many people come out of the college experience sharp elbowed, mainly because it's so competitive. Like, you know, you're trying to get good grades, you're trying to get the job someone else couldn't get. But what I would tell people is the world's not zero sum. In any field that we're in, there's many, many winners, many, many great winners. And if you can find a group of people that are on the same journey you are, they're on the same rung of the ladder climbing up, and you guys can share and trust one another, it is just so wonderful.

19:40Bill Gurley:You get so much extra horsepower. You get shared learning across the group. You get to share each other's networks. You get a support group on bad days, which is, there's a lot of them. And it's just, it's fantastic. And I think this is not, once again, this is a technique that's not taught a lot. I think this is maybe the first book that's really pounding the table on. But it can be really powerful. Two other themes, if you don't mind me going to these. No, go for it. Sam Hinckley. You give a great example of him. Okay. It's a cautionary tale, but it's really about trusting the process. And let's go to McConaughey, who I think is a philosopher king, in addition to being a great looking A-list actor, his depth and his insights.

20:31And I love his writing, by the way. And so it sounds like you guys are close. And he says something which we have to say to our kids every day and even to ourselves, don't half-ass anything, right? I guess his dad said that to him. So take those two guys, tell us a little bit about those two guys and the impact that they've had on you.

20:51Bill Gurley:Yeah, so I've gotten to meet Matthew here in Austin, where I relocated a few years ago. His book, Greenlight, is oddly, I think, has a similar objective as my book, but it comes from a very different place. He uses the metaphor of a green light to be know when knowing you should put the gas pedal and and run at things um and you know I thought it's funny I got to meet Rick Rubin through this process and his book The Creative Act is very different than my book but I think it has the same the same goal which is to encourage people to get out there and do their thing you know and there's this great anecdote in Matthew's history where he told his daddy was going to be a lawyer and he was at the university of texas pre-law track and met some people at the film school and and had a change of heart he wanted to go do this thing and he was afraid to tell his father but when he did his father said famously now don't half-ass it and he said it was the last thing he expected his father to say and the best thing his father could have said because it wasn't only encouragement but it was responsibility really he called it he called it rocket fuel and that i mean that's kind of what i hope the book can do the concluding chapter of the book's titled it ain't easy and i don't i don't want anyone to think that you know you can read this book and everything just comes at you everything's hard out there but one of the reasons you want to be fascinated by what it is you're doing is so that you have the ability to go do all these pieces that bring it all together.

22:29Bill Gurley:And so, you know, I think he's a great example of someone who's risen up, but also gives back. That's another principle we have in the book. I think his writing, I think, is intended to help and motivate people. And yeah, he's a great role model for a lot of the younger adults out there. Yeah, listen, I mean, it's just such great messaging. It's a short, you know, Bill, it's a lot of dense information in a short book. I mean, this book took me a few hours to read and I was like, wow, this is great. And even you've got your book lists in the back as well, which I tell people they should look through.

23:07And I've read some of these books and now because of you, I'm going to read more of them. But if I said to you, I get a kid in front of you and I said, okay, there's one thing that I would like you to do differently tomorrow. Okay, you just finished my book. They come and sit down, they're right there in your office. And you say, okay, there's one thing I'd like you to do differently tomorrow. What is that? What would that hope be for you, for that person?

23:34Bill Gurley:For me, especially if it's a young adult, is just to start thinking about contemplating what it is that they're truly fascinated with. Like that's the lane that if they can get in, I think they're going to have just a wonderfully fulfilling life. And I'm one of the things that motivated me to write the book, Anthony, I'm fortunate enough that that people that saw this video online many years ago, some of them shifted careers and have reached out to me. And and they're paint. And like knowing that you had this chance to get people into that lane where they're just so happy and so fulfilled. A lot of the podcasters I've met are in that lane.

24:16Bill Gurley:They're thrilled to talk to people and be excited and learn all the time. And so it's doable. And there's a ton of examples in the book. I'm glad that it went fast for you, that the way the stories were written were intended to make it super consumable. It was very consumable. I think, you know, I, uh, I think of my, uh, my 26 year old son who is, uh, he's a creative guy, uh, want to be in the film industry. So, okay. He's in the film industry. He's produced two films. Um, and he got the chance yesterday to, uh, tour George Lucas's new museum, I guess, of narrative art is what it's called. And it's in LA.

25:03And, uh, he said to me, it was the greatest day of his life, Bill. How great is that? Greatest day of his life. How good is that? And I want to share that with people because he is not following me in my career, nor did I ask him to. This is something he really wants to do. And I always tell people that Mel Brooks is my spiritual advisor. I've never met Mel, but Mel Brooks at 99 has said, relax, none of us are getting out of here alive. And I think that message in this book is so vivid.

25:34Bill Gurley:And look, if a kid goes in a museum and it's the best day of their life, that is the right direction. Because most young people go in museums and don't have any positive experience whatsoever. But I mean, look, he's walking around in the museum with one of the greatest filmmakers of all time. And of course, Anthony, my son Anthony, wants to be a filmmaker. And George Lucas puts his arm around and says, you know, making films is very hard. Yes. Okay, but you know what? So is Wall Street, so is Venture Capital. But if you like it, you can take the body blows that happened. Oh, it's so great. When you're running down a dream, you're going to get your ass kicked a few times.

26:17And that's the big message of this book. And I got to tell you, I was inspired by the book. And I'm grateful to you for writing it. And thank you for coming on the show. So we're down to the five words. Okay, so if you ever listen to my podcast, my producer and I come up with this.