Silicon Valley Legend Bill Gurley on Backing Uber and Betting Big

What is discussed, and when

1. 0:00 – 5:00: New York, New York, Todd Gurley, Silicon Valley, BHC Tommy
2. 5:00 – 10:00: Silicon Valley, Twitter, GrubHub, Jeff Bezos
3. 10:00 – 15:00: Ian Brady, Daniel Pink, First Principles Thinking, Michael Jordan
4. 15:00 – 20:00: Danny Meyer, Rich Barton, University of Texas, Austin
5. 20:00 – 25:00: Uber, Network Effects, San Francisco
6. 25:00 – 30:00: Austin, Chad Gibbtes, China, Houston
7. 30:00 – 35:00: A Man's Search for Meaning, Angela Duckworth, Austin, Bert Beverage
8. 35:00 – 38:49: Austin, Madison, North America, Wisconsin

Notable quotes from "Silicon Valley Legend Bill Gurley on Backing Uber and Betting Big"

• 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.

  about Todd Gurley · at 0:15

• I'm thrilled to be here, Tommy. Thanks.

  about BHC Tommy · at 1:12

• Don't know that helping VCs be better is going to change the world all that much. one of the things you talk about is Danny Meyer, restaurant icon owner in New York, setting…

  about Danny Meyer · at 2:13

• Such an advantage because the learning's free, the practice is free, Tommy. like if you talk to the Tom Bradies or the Jordans of the world like they didn't view practice as…

  about Ian Brady · at 12:42

• Oh 100%. I mean you know this brings me to the power of regret by Daniel Pink.

  about Daniel Pink · at 14:56

• Guy that I've spent a ton of time with over the past 20 years is Rich Barton, a founder of Zillow, who also founded Expedia before that. Rich has one element that I have found rare. I'm not.

  about Rich Barton · at 17:49

• Favorite? Look, I don't think there's any way to escape the reality that the biggest outcome I was involved with is Uber. Obviously, not just because of the size of the investment return, but the impact on the planet like that it's had.

  about Uber · at 23:15

• Many parking spots as cars because of this. we designed the country for cars. the city of Austin 3 years ago wiped out all their parking attachment requirements. And so in…

  about Austin · at 26:10

Who and what is mentioned in this episode?

People

• Todd Gurley — Person · 2 mentions · first at 0:17
• BHC Tommy — Person · 1 mention · first at 1:12
• Danny Meyer — Person · 2 mentions · first at 2:17
• Rich Barton — Person · 1 mention · first at 17:52
• Ian Brady — Person · 2 mentions · first at 11:48
• Daniel Pink — Person · 2 mentions · first at 14:56
• James Clear — Person · 1 mention · first at 1:32
  Where I went and where I got an NBA. The video got posted on YouTube. It started to get noticed. People like James Clear, who wrote Atomic Habits, noticed it. And some people…
• Jeff Bezos — Person · 1 mention · first at 7:19
  Question how much they're going to leave on the field. 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…
• Michael Jordan — Person · 1 mention · first at 12:47
  Such an advantage because the learning's free, the practice is free, Tommy. like if you talk to the Tom Bradies or the Jordans of the world like they didn't view practice as…
• Bob Dylan — Person · 1 mention · first at 15:22
  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.
• Bobby Knight — Person · 1 mention · first at 15:22
  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.
• Steve Jobs — Person · 1 mention · first at 17:13
  I missed the target seven times, but the other guy didn't even load the gun. Now we're in bullse eyes every time. Steve Jobs was amazing. You talk about a guy in China who's the new Steve Jobs. I forget his name.
• Chris Delcante — Person · 1 mention · first at 19:41
  Thought of one of the one of the more interesting characters in my book is Chris Delcante, the athletic director at the University of Texas here in Austin. And I was at an…
• Chad Gibbtes — Person · 1 mention · first at 29:17
  What I'm hearing is, robotics are coming, Optimus is coming. They're going to be able to put the Grock and Chad Gibbtes of the world, Open AI, Sam Albin into the in the robots. blue collar is pretty safe for the short term, but.
• Sam Albin — Person · 1 mention · first at 29:20
  What I'm hearing is, robotics are coming, Optimus is coming. They're going to be able to put the Grock and Chad Gibbtes of the world, Open AI, Sam Albin into the in the robots. blue collar is pretty safe for the short term, but.
• Gino Wickman — Person · 1 mention · first at 31:55
  I love this. I can't say how much I love this. U you know I had a really several encounters with Gino Wickman and he's the EOS basically inventor. He wrote a book called Shine. And he said, Tommy, I sold 87 and a half% of the business.
• Victor Frankle — Person · 1 mention · first at 32:16
  Yin-yang, but I felt this great emptiness, like I lost a piece of my soul. And I just read Victor Frankle's book again, A Man's Search for Meaning.
• Angela Duckworth — Person · 1 mention · first at 33:48
  Angela Duckworth gave a graduation speech where he she talked about how parramiums move towards warmth and nutrients. Like that's their only operating function, warmth and.
• Bert Beverage — Person · 1 mention · first at 34:38
  Or not you could have a career doing that. A lot of cases, you can. There's a guy there's a guy here in Austin, Tommy named Bert Beverage, who in his spare time like to make flavored vodka and give it to his friends as gifts.
• Elon Musk — Person · 1 mention
  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.

Books & papers

• Running Down a Dream — Book · 1 mention · first at 0:53
  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 readad.
• Atomic Habits — Book · 1 mention · first at 1:34
  Where I went and where I got an NBA. The video got posted on YouTube. It started to get noticed. People like James Clear, who wrote Atomic Habits, noticed it. And some people…
• Setting the Table — Book · 1 mention · first at 2:25
  Don't know that helping VCs be better is going to change the world all that much. one of the things you talk about is Danny Meyer, restaurant icon owner in New York, setting…
• Bottoms Up and the Devil Laughs — Book · 1 mention · first at 19:17
  Nurture that you kind of get. But leadership is something that it's very difficult that I think the a good book is leaders eat last is putting people above you. And really I…
• Elevate Build a Business — Book · 1 mention · first at 19:25
  Is leaders eat last is putting people above you. And really I call them co-workers because I need them to win. I wrote a book called Elevate Build a Business where everybody…
• A Man's Search for Meaning — Book · 1 mention · first at 32:18
  Yin-yang, but I felt this great emptiness, like I lost a piece of my soul. And I just read Victor Frankle's book again, A Man's Search for Meaning.
• Shine — Book · 1 mention
  I love this. I can't say how much I love this. U you know I had a really several encounters with Gino Wickman and he's the EOS basically inventor. He wrote a book called Shine. And he said, Tommy, I sold 87 and a half% of the business.

Companies & orgs

• Uber — Company · 2 mentions · first at 23:21
• Benchmark — Company · 1 mention · first at 0:45
  Currently, he's a partner at Benchmark, one of Silicon Valley most elite VC firms, and has become frequently cited voice in unit economics, network effects, and marketplace dynamics. Bill,.
• OpenTable — Company · 2 mentions
  The one that is most intellectually interesting is probably Open Table which came before Uber and really kind of the success of that led me to Uber. But you know we funded Open Table when there.
• Twitter — Company · 2 mentions · first at 0:24
  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.
• University of Texas — Company · 2 mentions · first at 1:26
  One day, I got invited to come speak to the NBA class at the University of Texas where I went and where I got an NBA. The video got posted on YouTube. It started to get noticed. People like James Clear,.
• YouTube — Company · 2 mentions · first at 1:30
  The NBA class at the University of Texas where I went and where I got an NBA. The video got posted on YouTube. It started to get noticed. People like James Clear, who wrote…
• Shake Shack — Company · 1 mention · first at 4:31
  Differentiation. and he's gone on to be probably New York's most successful single restaurant tour and for a broader audience after that he came up with the idea for Shake…
• GrubHub — Company · 1 mention · first at 6:02
  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. look, end of the day, what do you see in people that really.
• Netflix, Inc. — Company · 1 mention · first at 14:18
  If you love this subject matter, you pick up stuff and read it like you would a you devour it like someone else might do a Netflix show.
• Zillow — Company · 1 mention · first at 17:52
  Guy that I've spent a ton of time with over the past 20 years is Rich Barton, a founder of Zillow, who also founded Expedia before that. Rich has one element that I have found rare. I'm not going to say there's no one with this.
• Expedia Inc — Company · 1 mention · first at 17:56
  Over the past 20 years is Rich Barton, a founder of Zillow, who also founded Expedia before that. Rich has one element that I have found rare. I'm not going to say there's no…
• Shopify Inc. — Company · 1 mention · first at 28:12
  Finding information that can help propel you forward and consuming it is a superpower. the Toby from Shopify who with all the stuff that you love to dig into like if your…
• OpenAI — Company · 1 mention
  What I'm hearing is, robotics are coming, Optimus is coming. They're going to be able to put the Grock and Chad Gibbtes of the world, Open AI, Sam Albin into the in the robots. blue collar is pretty safe for the short term, but.
• Xiaomi — Company · 1 mention

Products & tech

• Optimus — Product · 1 mention · first at 29:14
  Going to know a lot more than me. And what I'm hearing is, robotics are coming, Optimus is coming. They're going to be able to put the Grock and Chad Gibbtes of the world, Open AI, Sam Albin into the in the robots. blue collar is pretty.
• Grock — Product · 1 mention
  What I'm hearing is, robotics are coming, Optimus is coming. They're going to be able to put the Grock and Chad Gibbtes of the world, Open AI, Sam Albin into the in the robots. blue collar is pretty safe for the short term, but.
• Titos — Product · 1 mention

Concepts & topics

• Network Effects — Concept · 2 mentions · first at 1:03
  Success of that led me to Uber. But you know we funded Open Table when there were three restaurants and we had this idea that if you could get the network effects to work that…
• First Principles Thinking — Concept · 1 mention · first at 13:52
  I talk about in the book that's a 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.
• Moore's Law — Concept · 1 mention · first at 29:44
  And technology creates waves. We evolve with our tools. we get more productive and what has happened historically is new jobs have popped up and people go to do new things.
• Stoicism — Concept · 1 mention · first at 32:20
  And I try not to tie up the business with the meaning of life, but that's where I get a lot of my accomplishments. That's the people I hang out with. It's a lot of the people.
• Antifragility — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Cognitive Biases — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Cold Exposure — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Compound Interest — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Deep Work — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Incentive Design — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Intermittent Fasting — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Lindy Effect — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Pareto Principle — Concept · 1 mention
• Power Law — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Second-Order Thinking — Concept · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Zone 2 Training — Concept · 1 mention
  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 cuz that's a word that crosses both are you…

Places & events

• Silicon Valley — Place · 3 mentions · first at 0:22
  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.
• Austin — Place · 4 mentions · first at 19:44
• New York, New York — Place · 3 mentions · first at 1:58
  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…
• San Francisco — Place · 2 mentions · first at 24:25
  Being with my wife in Bali going into a restaurant and seeing that device on the table in Bali when we started with three restaurants in San Francisco and I'm Wow. Like it really worked like we thought it would.
• North America — Place · 2 mentions · first at 29:34
  Bit there's going to be some chaos and I'm just curious your point of view. there was a time in North America where 98% of the people were employed in agriculture and that number is less than 2% today.
• Europe — Place · 1 mention · first at 4:04
  Think, onetenth 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.
• Houston — Place · 1 mention · first at 26:07
  Controls that dictates how many parking spots you're supposed to have. And this has caused massive urban sprawl. In Houston and LA, there are four times as many parking spots…
• Manhattan — Place · 1 mention · first at 26:24
  Wiped out all their parking attachment requirements. And so in doing that, you have the potential to design more downtown areas, more like Manhattan where not everyone owns a…
• China — Place · 1 mention · first at 28:51
  I got to talk to you about this real quick because we look at China and Eastern civilization and they're very excited about AI. obviously there's some caution that goes behind that. VCs are only investing in AI. I'm.
• Madison — Place · 1 mention · first at 35:08
  Thing. 100%. my niece and nephews, I got two nephews and one niece. My niece is at Madison in Wisconsin, and I can't wait for her to read this. And I can't wait for my sister…
• Wisconsin — Place · 1 mention · first at 35:08
  Thing. 100%. my niece and nephews, I got two nephews and one niece. My niece is at Madison in Wisconsin, and I can't wait for her to read this. And I can't wait for my sister…
• 911 — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• AWS re:Invent — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Bali — Place · 1 mention
  Really never lost faith that the network effect would play out. And then it started to work. And I can remember being with my wife in Bali going into a restaurant and seeing…
• Burning Man — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Coachella — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• COVID-19 pandemic — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Los Angeles — Place · 1 mention
  Controls that dictates how many parking spots you're supposed to have. And this has caused massive urban sprawl. In Houston and LA, there are four times as many parking spots…
• Moon Landing — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• NBA — Event · 1 mention
  One day, I got invited to come speak to the NBA class at the University of Texas where I went and where I got an NBA. The video got posted on YouTube. It started to get noticed. People like James Clear,.
• Olympics — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Oscars — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Super Bowl — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Ted Talks — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• World Cup — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Y Combinator Demo Day — Event · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…

Media & podcasts

• Breaking Bad — Media · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Game of Thrones — Media · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Inception — Media · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Joe Rogan Experience — Media · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Rick and Morty — Media · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…
• Stranger Things — Media · 1 mention
  Find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best…

Full transcript with timestamps

0:00 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 not just because of the size of the investment return, but the impact on the planet.

0:15 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.

0:42 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 readad. 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 most elite VC firms, and has become 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.

1:12 I'm thrilled to be here, Tommy. Thanks. Thanks for you 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.

1:22 One day, I got invited to come speak to the NBA class at the University of Texas where I went and where I got an NBA. 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 begin to hang up uh my boots as a VC that I had the time and attention to really turn to something and 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 or Uber or some of you know the experiences that I've had.

2:09 And I was I was what I didn't really feel a calling to do that. You know, I don't know that 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 uh New York, setting the table. I think that was one of your inspirations and one of the guys you really follow.

2:30 He took a huge pay cut to follow his dreams. And I I believe it was either his uncle or it

2:35 was his uncle. You want to talk a little bit about that? This is a really important lesson, I think, for for young people. He 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 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. Um 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 I think so many of us push children towards these safe jobs versus

3:37 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, onetenth the salary of what he was making. And then he went on a 12-month learning journey. Um, which included being a stage in Europe. Um, and he did that and and and then came back with just an unbelievable amount of curiosity, information, and and and differentiation. and he's gone on to be probably New York's most successful single restaurant tour 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 you if someone

4:39 has this deep deep obsession with an industry and then they can get in and succeed, the uh the impact they have is so huge. One of the reasons I was so I don't know if this makes any sense to you at all, but 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 I get like goosebump like I get it's like watching a great movie or something. I just really love those stories.

5:15 They're fun stories, you know. I 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 uh look I love my industry. I'm super focused and I'm just curious. you got this innate ability to to see things in people. I mean, in VCs, you're taking a big gamble, but for you, it was seemed like it worked almost every time. I'm sure there was some losses, but 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

6:14 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 prog like I don't want to see your dreams." What are some of the questions you ask? How do you recognize these winners? I I just want to see how success leaves clues on this.

6:28 I'm going to answer the question as a venture capitalist, Tommy, and talk about business founders rather than rit large. um because that's the that's the the one I've had the most pattern recognition and most at bats doing. The the first thing is they need to be like doggedly determined. I think the best entrepreneurs um 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 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

7:31 the world. And he said, I I want to know that they're going to do this no matter what. Like that's the only variable he sorted on. Um, so that's one. I think salesmanship is super important. You need to be the the the the founder of a company becomes the chief sales officer of the company. They're not only selling customers, they're selling they're recruiting employees, they're retaining employees. They own the c 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 bisdev 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 um effective as a salesperson representing what you're doing. And so that's another one. That's

8:29 the one that I think most people miss um like but is so super important. You know, I I went through the first three three chapters of Michael Porter's competitive advantage and unfortunately I do have an MBA. I didn't learn much from that program. Uh but I 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. Um I I would add one thing that I'm curious about. Well, well, you could speak to that real quick. There's a there's an antiMBA meme that's that's spread quite broadly in Silicon Valley and even even Elon and others like to jump and pile on it. And I think the correlary to that is many founders have a blind spot in not understanding business strategy and that that there are people that have built different frameworks and models and those can be helpful to you. I think you

9:25 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 I think knowing if you're going to be a lowcost 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. Uh I've tried to stay humble, keep my humility no matter how much success.

9:59 I want to be the dumbest guy in the room. In my 20s, I said I could figure anything out if I study. If I and then I started saying who, not how. And how much does humility and being able to listen and being able to to be in a board and actually take advice play into the success of some of the investments you've made? I I think those are critical um characteristics for an investor because you 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 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 um might not register on the listening or humility scale. I mean, it's 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.

10:59 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.

11:04 There's two things I would say. one the similarity the real similarity and I think it's a form of humility is is how hard do you practice you know and I would say the equivalent of practice in a business context is 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 cuz 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 that is a given. Everyone accepts it. People um 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 pro that that that technique as much in business.

11:57 And if you're, you know, in your spare time working to make yourself better at what you do, which may be very maybe a very common thing for a founder or CEO, but I I I'm saying even if you're three levels down in the organ, 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 not just doing what they tell you to do. And um 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.

12:32 I just want to work. And it's a shame because and 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 like if you talk to the Tom Bradies or the Jordans of the world like they didn't view practice as ownorous. 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.

13:05 Yeah. One of the things we talk about internally here is the law of the lid. And not 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 I mean you are just you're passionate about continuous learning and improvement obviously but how do you see your schedule? How do you how do you look at learning and how do you prioritize that?

13:49 I talk about in the book that's a the first principle is to chase your curiosity. Find this this thing that you're so enamored with that 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 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 you know if if continuous learning sucks energy from you then you're not available for the family life when you're at home all this stuff cuz 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 it it I say it comes for free.

14:56 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. Uh 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 uh provoked you to write. Is it one of the three?

15:20 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 career u 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 that weigh on you as you get in the your later years are the things you didn't do. Humans are really good at forgiving themselves for mistakes, like regrets of mistakes.

16:09 We're we're really 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 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.

16:49 You know, there's this uh 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 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 bullse eyes every time. Steve Jobs was amazing. You talk about a guy in China who's the new Steve Jobs. I forget his name.

17:20 Leun. Leun. Uh yeah, he's the he's the founder and CEO of Xiai. You may have seen there were a few videos um popping around in the past month where they sent one of their cars to a US influencer and who drove them around. Who is somebody, and it doesn't need to be somebody you know personally, but you know more people and more people at the top than anybody I know. Who has been your best mentor whether you knew them or not?

17:49 Guy that I've spent a ton of time with over the past 20 years is Rich Barton, a founder of Zillow, who also founded Expedia before that. Rich has one element that I have found rare. I'm not going to say there's no one with this skill set, but it's very rare. He's really amazing at strategy and business and all of those wonderful things. And he's simultaneously kind of A++ as a leader and understanding leadership and what it takes to lead people. And I have found over the years most people tend to spike on one of those and not the other.

18:29 Like I'm more the strategy person. I I'm I'm not all that skilled at this other's softer side. And um I it's rare to see the same to see both those things in one person. Um and so he's a he's a go-to for me um on advice because of his ability to have both of those. A lot of the the biggest problems in business that a company deals with may cross both of those. like it may involve needing to to have a a good feel for both of those elements.

19:05 Yeah. No, 100%. I I think leadership you it's one of those things you're not born with it. There's certain things in school and in your past nature versus nurture that you kind of get. But leadership is something that it's very difficult that I think the a good book is leaders eat last is putting people above you. And really I call them co-workers because I need them to win. I wrote a book called Elevate Build a Business where everybody wins. But your dreams got to be big enough for the people inside your company to come true.

19:33 When you said that, I immediately thought of one of the uh one of the more interesting characters in in in my book is Chris Delcante, the athletic director at the University of Texas here in Austin. And I was at an event, I don't know if it was this past fall or the one before, but there's a there's a you know where it's part of the football stadium. There's a big event. There's a whole bunch of people in this room, several hundred. And I'm talking to Chris and he looks over and sees a piece of trash on the floor. And there's probably 15 service professionals within within 50 ft of us. And he runs over and immediately grabs a napkin and wipes it up and throws it away. And um I suspect he does that all the time, you know, like I I suspect he does that all the time. And he's he's he's showing those people that there's no task beneath him.

20:32 He's showing them that and he's showing them that he cares about every little detail and how it looks and like it's such I was so impressed when he did that and he probably thought nothing of it like cuz it's probably instinctual for him now. But I love I love stuff like that.

20:49 You probably have one of the largest appetites for risk. I mean, that's kind of the VC motto. Uh I I think that's something that a lot of people just don't have. It's like they'll bet on themselves. There's some uncertainty, but you've been pretty good at making the right assumptions. Uh is there ever a time where you were like, I don't know if this is going to work, but I feel good about it. But hindsight, it was the best decision you've ever made?

21:17 I'm certain that's happened a whole bunch. Um you you know there's this wonderful uh graph someone came up with that on the bottom axis has what you really know and on the left axis has um what you think you know and anytime you jump into a new endeavor where you're you're quite ignorant relative to everyone else. the first few first few periods of learning, it might be a month or or or weeks or whatever, it might be a year. As you start to learn, you realize what you don't know and you're what you think you know drops because you develop this insecurity like, "Oh there's so much I don't know." And and and I've been I've had that in my career a couple different times. But if you keep pushing through, you eventually reach the bottom of that U and you start going back up again. And that's that's where you really gain confidence. I was I was talking to a young adult that I that I was mentoring

22:18 about this because they jumped in a new career and the first, you know, 4 months was just overwhelming. I don't know this. I don't know this. I don't know this. And I'm like, calm down. Take a deep breath. you know, find some peers, find some mentors, tell them what you're going through. Be vulnerable. Don't ever pretend you know something you don't. If you're in that first window of learning the your best friend, anytime you hear a phrase you don't know, a concept you don't know, you say out loud, "I don't know what that is. Tell me what that is." Like, if someone asks you a question that you don't understand, say, C, can you redescribe that? I don't know what that word means. I don't know what you're trying to get at. because that is how you will learn the fastest and they won't disrespect you for it, they'll respect you for it, but your intuition might suggest the opposite.

23:10 You've been a big part of so many companies. Which one which one was your favorite? Look, I I mean, I don't think there's any way um to escape the reality that the the biggest outcome I was involved with is Uber. Obviously, you know, not not just because of the size of the of the investment return, but the impact on the planet like that it's had and how much it's touched, you know, so many different corners of the world. And so, like that that just is what it is. The the one that is most intellectually interesting is probably Open Table which came before Uber and really kind of the success of that led me to Uber. But you know we funded Open Table when there were three restaurants and we had this idea that if you could get the network effects to work that as you got bigger it would get easier. And that was a theory that we invested behind. We really never lost faith that the network effect would play out. And then it

24:17 started to work. And I can remember being with my wife in Bali going into a restaurant and seeing that device on the table in Bali when we started with three restaurants in San Francisco and I'm like, "Wow." Like it really it really worked like we thought it would.

24:34 Yeah. There's this whole framework of changing the industry and this is exactly instead of competing with with taxis, Uber changed the game. And you thought you were competing with the taxi cabs and the medallions of the world.

24:50 Yeah. Yeah. There's a there's a famous professor in at NYU that wrote this piece that said that Uber would never be worth more than four billion. Um, and he used the taxi market as his TAM. Total available market is a business word people like to throw around. And when he wrote that, I would I mean, I had a bit of an unfair advantage. I I wrote a rebuttal that that got quite a bit of press, but I had an advantage that I knew in San Francisco, we were already 20 times bigger than the taxi market. um at the time he wrote it and and um when in that in that article in my rebuttal I I gave this famous I think McKenzie analysis that the entire market for cell phones would be 900,000 units which which was off by several orders of magnitude and the more I the more I thought about it like there there was just this potential to replace car ownership and In many cities across this country, if you launch a business, there

25:57 is a database that the government controls that dictates how many parking spots you're supposed to have. And this has caused massive urban sprawl. In Houston and LA, there are four times as many parking spots as cars because of this. Like, we designed the country for cars. Um, the city of Austin 3 years ago wiped out all their parking uh attachment requirements. And so in doing that, you have the potential to design more downtown areas, more like Manhattan where not everyone owns a car. And then all of a sudden, that's why I think Uber is going to continue to see growth for like 20 or 30 years because that process will take so long to play out. This one where we build um denser downtown areas more intelligently, but I think it's going to happen.

26:50 Oh, 100%. you get all that space back, the parking garages, all those things. Yeah. By the way, I am enjoying the hell out of this. And just to get a piece of your time, I can't tell you how much it means to me and the audience. Uh what's one piece of game-changing advice that you wish you could tell yourself in your 20s?

27:06 I mean, the the thing that pops in my mind is just this this read concept. I for whatever reason was never much of a reader in high school and even in my first job as a uh engineer I didn't read much something about going to the NBA program maybe the the free time that popped up I just started reading and it once it the bit flipped for me Tommy it it was night and day I went from none to all the time and uh I don't it may be hard to just tell someone to do because if it's not something and I a lot of young people man I guess with all the social media and stuff when I mention you should read this like I see eyes glaze over so this may be like and and look you can get information from AI or podcast or YouTube it doesn't need to be a book necessarily but this this like finding information that can help propel you forward and consuming it is a is a superpower. Uh the Toby from Shopify who with all the stuff that you love to dig

28:18 into like if if your listeners ever have a chance to listen to a Toby podcast, any interview, he's so thoughtful and willing to share and so he sits down and talks. But he on a recent podcast said the same thing. He's like reading reading a book is the biggest free hack that you could possibly have. like you somebody just spent took a lifetime of learning and synthesized it in a book and you get to read it and know that immediately. He's like that's unbelievable.

28:50 You know, I got to talk to you about this real quick because we look at China and Eastern civilization and they're very excited about AI. Uh obviously there's some caution that goes behind that. VCs are only investing in AI. I'm just curious because I've had some deep conversations with people that are at a different league than I am that are going to know a lot more than me. And what I'm hearing is, you know, robotics are coming, Optimus is coming. They're going to be able to put the Grock and and Chad Gibbtes of the world, Open AI, Sam Albin into the in the robots. blue collar is pretty safe for the for the short term, but it's kind of disturbing and I'm a little bit there's going to be some chaos and I'm just curious your point of view. You know, there was a time in North America where 98% of the people were employed in agriculture and that number is less than 2% today.

29:44 And technology creates waves. We evolve with our tools. um we we get more productive and and what has happened historically is new jobs have popped up and um and people go to do new things. If you follow the traditional educational path um and get in this big machine that we've created that everyone uses which is the college university system and you get one Yeah. you get one of those safe jobs or so-called safe jobs, you know, where you're you're graduating with a hundred of people that got the exact same degree you do. You're a bit of a widget. You're a widget that became out of this massive production machine that we've created. And I suspect that if you're a widget, AI looks daunting, like it's this thing that might come and do what I do. You're a unit of one. You're this. this individual who has a destination in mind and you're doing everything you can to make yourself better. I think those

30:54 people AI is a superpower. It's like jet fuel. It's like the I as I said like if you want to self-learn, it's never been easier. This thing is your companion that will take you on that entire journey. And I just think it's like highly ironic that one group of people could sit here and say, "Oh my god, it's coming for me. I'm afraid." And another group of people are like, "Oh my god, did you see what I just did? Do you see what I just learned?" Like this thing can do things for you. It can help you start a business with fewer employees. Like it can, you know, it can do all these wonderful things. And so I think a lot of it's about mindset, man.

31:36 and uh and whether you are charting your own individual path because if you are I think it's 180° different. This is not something to be afraid of. This is something that's going to give you even more better higher chances of success.

31:53 I love this. I can't say how much I love this. U you know I had a really several encounters with Gino Wickman and he's the EOS basically inventor. He wrote a book called Shine. And he said, "Tommy, I sold 87 and a half% of the business." And I had pockets of gold everywhere. I mean, there was money coming out the yin-yang, but I felt this great emptiness, like I lost a piece of my soul. And I just read Victor Frankle's book again, A Man's Search for Meaning. And you know, I try not to tie up the business with the meaning of life, but that's where I get a lot of my accomplishments. That's the people I hang out with. It's a lot of the people I care about. And it's the pursuit of the goal. But a lot of people are just waiting for that final destination and they're saying everything's going to change. And you've been through this so many times. What's your advice to people that are trying to hit this pinnacle

32:42 from all these people that I've studied that there are people like you and me, you know, all over this planet that love every day of their career. Not every day. You have bad days, but but but that love the journey as you say, the the the middle parts. And if you are grinding your butt off because you think, "Oh, once I get this award or this place or this spot, I'm going to stop and be so happy that I achieved it that I didn't mind." I just don't think that's a reality. I think it'll when you get there it'll just appear a bit hollow and you'll just feel the need to keep climbing and you're but if you're climbing without um energy like I I don't I don't think it'll work. Um, and by energy, it was what I was referring to either that earlier that that people that are in their lane that they love, they get energy every single day. Every time they unlock something new, every time they figure something out, like it

33:46 it gives them energy. Angela Duckworth gave a graduation speech where he she talked about how parramiums move towards warmth and nutrients. Like that's their only operating function, warmth and nutrients. And she said that people should do that in their career. You know, like if there's some engagement or task in your job that when you do it, it feels good and warm and like you get energy from it, do more of that. Like head in that direction. And it may be that that's a hobby. Like so many of the people we studied turn hobbies into careers. You know, if you're at home in your spare time doing something that gives you that energy, those warmth and nutrients, you should consider whether or not you could have a career doing that. A lot of cases, you can. There's a guy there's a guy here in Austin, Tommy named Bert Beverage, who uh in his spare time like to make flavored vodka and give it to his friends as gifts.

34:49 When he was 40, after being a seismologist and a mortgage broker, he started a tiny little vodka company called Titos, which is now the number one selling beverage and company in North America. And he owns 100% of the thing. 100%. You know, my niece and nephews, I got two nephews and one niece. My niece is at Madison in Wisconsin, and I can't wait for her to read this. And I can't wait for my sister and my brother-in-law to read this book. This has been my my favorite part of the book getting into the hands of people, which is a weird experience, but but new to me, um, is so many of the people that have read the book, Tommy, come back with what you just did, which is I know four people I immediately want to be able to read it. And I love that element of it. And and it's not it it also means that the book's not just targeted at people who are experiencing their own career or working on their own

35:49 career, but the people that advise, you know, people, which includes parents and counselors and friends and and uncles and aunts. Like I I think everyone can benefit of us that are out there that can see perhaps a twinkle in someone's eye and tell them it's okay to go do that. In fact, you should go do that. Let me help you go do that. A lot of people, a lot of well-intentioned parents, very well-intentioned parents, and I' I've lived through this. you you worry so much about the economic stability, the potential economic stability of the young adult that you don't realize it, but you're you're you're telling them to go do something for the wrong reason. Bill, I'm a I'm a massive fan of you. Uh I think you're a giver. You're wellstudied. Uh you're you're the epitome of success and you're you're giving back to us and I can't wait to get my hands on the book. I'll work this out with your team, but why

36:48 don't you close us out? Uh maybe a couple more highlights from the book and anything you want to close out on for the audience.

36:54 I just want to give people the motivation and the methods to chase their dream and to really believe in it and the confidence and permission to go do it. And um I'm not I'm not going to say that the traditional uh education or career path is like 100% broken and no one should do it. I think it works for a lot of people. But if you feel like it's not working or you didn't get there or you're not finding your way, this is an alternate door that I would heavily encourage you to consider because I think it allows you to build a crafted career for you and you become this candidate of one that's really unique and stands out and has the best chance at success.

37:38 I love it, Bill. Well, listen, I'll look you up when I go to Austin and uh All right, man. I know you're a busy man, but I really appreciate the time today and I hope you have the best week ever. Thanks, Bill.

37:47 Take care. Appreciate it. Thanks so much for listening to this episode. Like always, we're going to close it out with the Tommy truth, which is a little slice of wisdom from me to you that can help guide you in whatever you're striving towards right now. If I was 20 years old again and I wanted to make a million dollars as quick as possible, here's exactly how I'd do it. The first thing is I need to get the education. I need to figure out a way to make money. So, I need to find out a trade, something I could go duplicate very, very quickly. So, what I would do is I'd probably go to an HVAC guy or a roofing guy. I get an apprenticeship.

38:18 I'm not just trying to get to my first million. I'm trying to get to my first billion. So, I need skills. And what I'd also do is get a bartending job when I'm 20. So, I'm getting a free education. I'm giving free labor away to get educated by this billionaire guy. I'm getting money, which you can make 500 bucks a night at a good bar. I'm learning about hospitality. By the time I'm 25, I've got 10 million in the bank.

38:41 And that's it, guys. We'll talk to you next week.

Questions about this episode

What is discussed in "Silicon Valley Legend Bill Gurley on Backing Uber and Betting Big"?

In order: 0:00 New York, New York, Todd Gurley, Silicon Valley, BHC Tommy; 5:00 Silicon Valley, Twitter, GrubHub, Jeff Bezos; 10:00 Ian Brady, Daniel Pink, First Principles Thinking, Michael Jordan; 15:00 Danny Meyer, Rich Barton, University of Texas, Austin; 20:00 Uber, Network Effects, San Francisco; 25:00 Austin, Chad Gibbtes, China, Houston; 30:00 A Man's Search for Meaning, Angela Duckworth, Austin, Bert Beverage; 35:00 Austin, Madison, North America, Wisconsin.

What is mentioned in this Tommy Mello episode?

92 people, works and ideas are mentioned, including Todd Gurley, BHC Tommy, Uber, Benchmark, Running Down a Dream, Danny Meyer. Each one on this page links to its own page with every episode that mentions it.

How long is "Silicon Valley Legend Bill Gurley on Backing Uber and Betting Big"?

The episode runs 39 min; the transcript is about 6,951 words in 59 timestamped sections.

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