You've been a big part of so many companies. Which one was your favorite?
Biggest outcome I was involved with is, you know, not just because of the size of the investment return, but the impact on the planet.
You know, more people and more people at the top than anybody I know. Bill Gurley has spent nearly three decades in Silicon Valley investing in and serving on the boards of companies like Twitter and Uber. Bill has become Silicon Valley royalty, known for his razor-sharp instincts and a talent for spotting breakout companies early on. If you've ever wondered how the best investors play the game, pay attention.
All right, guys. Welcome back to the Mellow Millionaire. Today, it's an honor to have Bill Gurley on the podcast. He's a partner at Benchmark and he's coming out with a book that's a must-read, Running Down a Dream: How to Thrive in a Career That You Actually Love. Currently, he's a partner at Benchmark, one of Silicon Valley's most elite VC firms, and has become a frequently cited voice in unit economics, network effects, and marketplace dynamics. Bill, it truly is an honor to have you on today. Thank you for taking the time to do this.
I'm thrilled to be here, Tommy. Thanks. Thanks for having me on.
So, let's just start out, you know, tell us a little bit about you, your career, and what made you want to write a book.
One day, I got invited to come speak to the MBA class at the University of Texas where I went and where I got an MBA. The video got posted on YouTube. It started to get noticed. People like James Clear, who wrote Atomic Habits, noticed it. And some people started poking me to turn it into a book. It wasn't until I really began to hang up my boots as a VC that I had the time and attention to really turn to something and do the type of work I would want to do if I was going to make a book. But here's the cool thing. I got really excited about writing this book because when I went to New York and met with publishers, they all wanted me to write about investing or venture capital or Uber or some of the experiences that I've had. And I didn't really feel a calling to do that. You know, I don't know that helping VCs be better is going to change the world all that much.
You know, one of the things you talk about is Danny Meyer, restaurant icon owner in New York, Setting the Table. I think that was one of your inspirations and one of the guys you really follow.
He took a huge pay cut to follow his dreams. And I believe it was either his uncle or it was his uncle.
You want to talk a little bit about that? This is a really important lesson, I think, for young people.
He comes out of college and he's been taught to wind up and attack things. We teach these kids like, 'Oh, take this test, do this extracurricular, do this all.' And he gets a job as a salesperson. They're actually selling those devices that go on clothes when you're in the clothing store they have to remove. He was selling those things and he did a really good job at it. He was making like over 200k and this is 30 years ago. So that's a lot of money. And he's out to dinner with his uncle and his uncle says, 'What are you doing? You've wanted to be in restaurants your entire life. Why don't you go start a restaurant?' And I think many of us don't have that uncle in our lives that tell us it's okay to go do this thing. I think so many of us push children towards these safe jobs versus allowing them to do something that they're just super passionate about. So I think his uncle did something that I hope this book can do for a whole bunch of people, which is give them the permission to dream a little bit about what they really want, what they really love to do. You know, Danny from that moment, you know, took a job, as you mentioned, at a restaurant that had, I think, one-tenth the salary of what he was making. And then he went on a 12-month learning journey, which included being a stage in Europe. And he did that and then came back with just an unbelievable amount of curiosity, information, and differentiation. And he's gone on to be probably New York's most successful single restaurateur and for a broader audience after that he came up with the idea for Shake Shack and launched that as well. So, and I mean it just goes to show if someone has this deep, deep obsession with an industry and then they can get in and succeed, the impact they have is so huge. One of the reasons I was so excited about writing the book is when I find these stories of people that make that kind of pivot and then have that kind of impact, it gives me like dopamine. I get like goosebumps. It's like watching a great movie or something. I just really love those stories.
They're fun stories, you know. I took a lot of notes out of that book. I love the order of priorities he put: employees first, then guests, suppliers, and last is investors. And he said what he's learned to do, and this is such a great observation, hire for emotional intelligence. And my question for you is, look, I'm obsessed. I mean, some people call me a maniac. Some people call me, look, I love my industry. I'm super focused and I'm just curious. You got this innate ability to see things in people. I mean, in VCs, you're taking a big gamble, but for you, it seemed like it worked almost every time. I'm sure there was some losses, but you really, like, look, the resume I read off was like a tenth of what you've invested in. I think you've done GrubHub. You were a big part of Twitter. I mean, look, end of the day, what do you see in people that really gives you the ultimate advantage from your point of view? Gary Vee last week said, 'I don't want to see what your wireframes are. I need to see real-life working progress. I don't want to see your dreams.' What are some of the questions you ask? How do you recognize these winners? I just want to see how success leaves clues on this.
I'm going to answer the question as a venture capitalist, Tommy, and talk about business founders rather than writ large, because that's the one I've had the most pattern recognition and most at-bats doing. The first thing is they need to be like doggedly determined. I think the best entrepreneurs look like someone who is going to do this no matter what. Recognizes that they're in some opportunity because of the product they have, the market disruption that's happening. AI is a good example. And they're going to run at it so hard that you're never going to question how much they're going to leave on the field. You know, using a sports analogy, I once got to ask Jeff Bezos how he was able to be so successful as an angel investor while he's running, you know, one of the most successful companies in the world that was growing to be one of the largest companies in the world. And he said, I want to know that they're going to do this no matter what. Like that's the only variable he sorted on. So that's one. I think salesmanship is super important. You need to be, the founder of a company becomes the chief sales officer of the company. They're not only selling customers, they're recruiting employees, they're retaining employees. They own the responsibility for the culture of the company and they own the responsibility for marketing the company externally. That's a lot of selling. And then you have biz dev deals, incremental investors, you know, they're just selling constantly and different people sell in very different ways. There are people that can do it quietly. There are people that do it, you know, bombastically. There's all kind, but you do need to be effective as a salesperson representing what you're doing. And so that's another one. That's the one that I think most people miss but is so super important.
You know, I went through the first three chapters of Michael Porter's Competitive Advantage and unfortunately I do have an MBA. I didn't learn much from that program. But I like the idea of differentiation like in a fragmented industry. I mean, you were dead on when you said study those first three chapters. You get a lot out of that. I would add one thing that I'm curious about. Well, you could speak to that real quick.
There's an anti-MBA meme that's spread quite broadly in Silicon Valley and even Elon and others like to jump and pile on it. And I think the corollary to that is many founders have a blind spot in not understanding business strategy and that there are people that have built different frameworks and models and those can be helpful to you. I think you owe it to yourself to try and understand some of the rudimentary frameworks that people have developed and competitive strategy is one of the best ones. I think knowing if you're going to be a low-cost producer or a differentiated player is like critically important. And if you get stuck in that middle where Porter draws the U at the bottom, it's dangerous. It's a dangerous place to have your company operating.
I meet a lot of people that tell me what they're going to do and they have a very big dream and there's a little bit of ego. I've tried to stay humble, keep my humility no matter how much success. I want to be the dumbest guy in the room. In my 20s, I said I could figure anything out if I study. And then I started saying who, not how. And how much does humility and being able to listen and being able to be in a board and actually take advice play into the success of some of the investments you've made?
I think those are critical characteristics for an investor because you have limited ability to influence and you have to build the right to influence through some of the nuances you just talked about. I don't know on the founder side. I don't know if those things are a requirement. I mean, I certainly know some wildly successful founders who might not register on the listening or humility scale. I mean, it's a fine line between just pure cockiness because you see a lot of players that don't add up to anything. They don't take feedback. And I think that's one of the most important things is can you handle feedback because I'm going to pull the best out of you.
There's two things I would say. One, the real similarity, and I think it's a form of humility, is how hard do you practice? You know, and I would say the equivalent of practice in a business context is continuous learning, which is the second principle in my book and something I'm very passionate about. And if you're training, let's use that word because that's a word that crosses both, are you training to make yourself better all the time? And in sports and even in things like ballet and some of the arts, that is a given. Everyone accepts it. People are madly appreciative of someone that puts in 12 hours a day to be a great ballet dancer, right? Or Tom Brady, but we don't talk about it that much in business. And if you're, you know, in your spare time working to make yourself better at what you do, which may be a very common thing for a founder or CEO, but I'm saying even if you're three levels down in the org, you're in accounting or marketing, are you working to improve how good you are at that outside the walls of the company? Like not just doing what they tell you to do. And I think we've made college such a grind that a lot of these young adults, they get to the end and they're like, I can't wait to not study anymore. I just want to work. And it's a shame because it's one of the reasons why I think people that are able to find a lane that's really their dream job have such an advantage because the learning's free, the practice is free, Tommy. Like if you talk to the Tom Bradys or the Jordans of the world, they didn't view practice as onerous. It was something that they wanted to do, you know. I think that's the through line between kind of great athletes and great executives and business people.
Yeah. One of the things we talk about internally here is the law of the lid. And not just with me, the founder CEO, but each department has to continue to raise the bar outside of work or they're not going to have a place on the bus. I'm sorry. What got you here can't get you to the next level. You talk about build your bedrock and I was overwhelmed just researching the heck out of you and just every single interview you've done is like five books and hey I just last week I devoured this book and I'm going how in the hell am I supposed to like keep up? I mean you are just you're passionate about continuous learning and improvement obviously but how do you see your schedule? How do you look at learning and how do you prioritize that?
I talk about in the book that the first principle is to chase your curiosity. Find this thing that you're so enamored with that you think about it all the time. And then the second one is hone your craft which is this continuous learning element. And I think there's a really amazing link between the two of them, Tommy, which is if you love this subject matter, you pick up stuff and read it like you would a, you know, you devour it like someone else might do a Netflix show. And so I think for people that are obsessed with what they do, they're able to, well, first of all, it doesn't feel like work. So you know if continuous learning sucks energy from you then you're not available for the family life when you're at home all this stuff because it's more of the grind of the day and then you're worn out. If it gives you energy to learn about your field, I say it comes for free.
Oh 100%. I mean you know this brings me to The Power of Regret by Daniel Pink. Four types of regret. The biggest one is boldness regrets. I wish I had started. I should have taken that shot. Time passes, the opportunity doesn't come back. I think that was one of the other books that you really provoked you to write. Is it one of the three?
No. No. The three were biographies. It was Danny Meyer, Bobby Knight, and Bob Dylan. They came from very different fields. But as I decided to turn what was this speech into a book, I spent about 6 years working on it because I wanted it to be really great. And so I went and read probably a hundred biographies and then went and read a whole bunch of books from the academics who had studied careers the most including the Daniel Pink book. So that's how I came upon that. But yeah, Daniel highlights that in a whole bunch of different cultures and societies, the regrets that weigh on you as you get in your later years are the things you didn't do. Humans are really good at forgiving themselves for mistakes, like regrets of mistakes. We're programmed well to be like, well, you know, I learned something and it's over. You don't ruminate on it, but the thing you never did that you knew you always wanted to do weighs more and more and more. I did it a different way on my way up. I said to myself in each job I was in, I would reflect every year or so and go, is this what I want to be doing for the rest of my life for 30 years? Do I see myself, you know, still at this company and, you know, in this field 30 years from now? And am I happy? And twice the answer to that was no. And I started looking for the next thing.
You know, there's this saying eliminate, automate or delegate. And I think that's kind of what Elon does as well is remove it, make it simple. And I think the problem with most people, especially in business, is we crave perfection. It's never the right time. And sometimes you just got to fail forward and get started and go at it and figure out, hey, I missed the bullseye. I missed the target seven times, but the other guy didn't even load the gun. Now we're in bullseyes every time. Steve Jobs was amazing. You talk about a guy in China who's the new Steve Jobs. I forget his name.
