Welcome. This is so awesome to see everyone here. We're about to get started. We have an overflow room. We're going to have a really interesting night with Bill Gurley and Malcolm Gladwell. Bill Gurley spent decades at the center of technology and transformation as a venture capitalist. He has backed companies that many of you are very familiar with that reshaped entire industries. What really distinguishes him, however, is the rigor of his thinking, a relentless focus on fundamentals and building businesses that last. His new book, Running Down a Dream, reflects that discipline and the deeper question of how to build a career around work that you genuinely care about. Also, we're very happy to have Malcolm Gladwell who has long helped us understand the world and looking at it in sort of distinct ways and new ways. Many of us, you know, reference his books. Even sometimes we don't even know we're referencing his books, whether it's The Tipping Point or Blink. He's given us frameworks of thinking about how to spread ideas and how decisions get made. So, together they bring two complementary perspectives, one from inside the boardroom, the other through the lens of storytelling and analysis on judgment and risk and the long-term thinking. So, I want to thank all of you for being here and a big round of applause for Malcolm Gladwell and Bill Gurley.
Welcome to New York, Bill.
Thank you. Thanks for having me. You know, it's not always... I think we actually asked to come, so... It's not always like this. I just wanted you to know that.
Okay. Yeah, it's come... Oh, the weather. I got you. Yes, that's right.
Well, I hadn't realized it was as long as that. This was in phase job number two. Yes, as a venture... I mean as a sell-side analyst.
Yeah. We will get to that I expect. But um... So you've written a book about career regret and how to avoid it.
Yeah. And I want to start by telling you my favorite career regret story.
A very good friend of mine who grew up in Texas like you, whose father was an investment banker, said that when her father retired, he pulled her over and he said, 'You know, Sarah, I should tell you that I never really wanted to be an investment banker. I've all my life regretted that decision. I really wanted to be something else.' And she thought, 'My dad wanted to be a poet or my dad wanted to be an artist or a...' He goes, 'Sarah, I really wish I'd been a tax attorney.' I thought about that for... That story stuck in my head for many years. And my first thought was when she told it was to laugh and she told it as a joke. It's not a joke. He really wanted to be a tax attorney. And for good reason. Of all the kinds of law you could be, I mean if you had told me I had to be a lawyer I'd say I'd want to be a tax attorney. Okay. Don't you think? Well, tell me why.
Because it strikes me as presenting a series of incredibly complex problems. That require a solution. It's not deterministic. Like you can't just shrug and say I can't do it. You got to do something, right? So there's creativity involved. There's mastery involved. There's a measurable outcome.
Measurable outcome, a happy client. And incredible returns to experience.
Got you. You're a better tax attorney at 70 than you are at 30. Right? Yeah, yeah, yeah. And that to my mind that has all the ingredients of a really great career. There you go. Right? But I... So I want to circle back to this later in the conversation cuz it brings up a really really crucial point where I mildly disagree with you.
Okay, I was certain you would come at me.
No no, I'm not coming at you. But we'll get there. This book grew out of a talk you gave at the University of Texas.
About 8 years ago. And why did you give... This was a convocation talk?
No, it wasn't. It was just a... It was to an MBA group that had just arrived on campus.
And they didn't give you the topic.
No, they didn't. I asked if I could give it. Why did you want to give that specific topic?
So, I spent years in my years as both a sell-side analyst and a venture capitalist, I did a lot of writing. One of the reasons I became such a huge fan of yours. And most of that took... Well, on Wall Street, that was reports, but as a venture capitalist, mostly blogs and blog posts. And I would synthesize ideas, and I had a big digital folder, full of ideas. You probably have something similar. And when something came to me, I'd write it down. Sometimes that would take on a life of its own and grow, and sometimes it didn't. There was a period in my life about 10 years ago, I was reading a lot of biographies, and I read these three biographies of people that were in very different fields, and just... and all started with high intention at the lowest rung. And I saw a through line through them. And it caused me to write a book.
That phrase? Highest intention at the lowest rung?
No, they had high intentionality to move into a career. And they started on the lowest rung, at the very bottom. Yeah. And they were all very successful, and I was able to see some patterns between what they did, so I wrote it down. And when the dean asked me to come speak, I was like, 'Can I try this thing?' It just felt like a piece of content I had created. And those first three were Dylan, Danny Meyer, and Bobby Knight.
Bob Dylan, Danny Meyer, a famous New York restaurateur who's probably spoken here before, and Bobby Knight. That's right. Those are the three. Now, were you drawn to that notion of high intentionality at the lowest rung, beginning at the lowest rung. Did you see that reflected in your own life?
I don't know. I mean, I added my story at the end as an epilogue and I think as I developed the story, I saw some of these techniques done along the way. I didn't have the moment of intentionality as strong as those three did. They had a particularly moment in their life where they said, 'I'm going to stop doing that. I'm going to go do this and I'm going to try and be great at it.' And mine was a little more weaving along the way.
Did you... Anyone in your family have that?
Yeah. Although I don't know that I studied his journey this way, my father grew up playing with model airplanes in rural North Carolina and went and got an aeronautical engineering degree at NC State. Ended up working in a wind tunnel at Langley Air Force Base and a few years after he started, someone came along and said, 'Hey, 50 of you, would you like to go to Houston and be a part of NASA?' And he said, 'Yes.' And...
How old was he at the time?
24. 25. Pretty early age. All the people in that early NASA, they were young. Yeah. They were really young. But I got to watch that and I think it did give me permission in the back of my mind to jump across the country, which I did multiple times by the time I was 27 and I'd been to Florida and back and New York and like... and I fear... and I don't know it's not necessarily bad, but I think some people don't... are afraid to move very far geographically.
Did your father... I'm going to dwell on your father for a moment. He didn't have any career regret.
Oh, no, no, no. None of that. He loved his job. Oh my... All those people... Half the fathers on my street were NASA. Like you have no idea. Like think about the idea of falling in love with model airplanes as a kid and being in the control room when they land on the moon in 1969. He was born... he was 33. He was born in '36. I found a paper I got...
Was your dad in the control room?
There's a picture of him in the control room in NASA.
No, he wasn't that tall. But there's a great story. I didn't know we were going to go down this track. I got invited to go see the Starship launch and I live in Austin, so it's not that far and I took my dad. He's still alive. And this was the first one they caught the base unit and on the way home I'm doing a Google search. I searched for my dad's name in NASA, which I never done before and I uncover a paper he wrote talking about how when rockets hit the atmosphere they bounce and that they needed to plan for that and it's a document he had presented to Chris Kraft and I looked at the date on that document and he was 27 years old when he wrote it.
Wait, so... Which is pretty wild. Forgive me a little psychoanalytic detour. So you write a book about these three famous people who exemplify a particular trait. But you could have written about your dad.
Yeah, I could have written about a lot of people that...
No, no, no, you could have written about your dad.
So I hear. Are you scolding me? What are we doing?
No, no, I find it... No, I find it because there's clearly something powerful and I don't even want to use the word primal, but this is a story that's very important to you. That's what comes across.
Oh, yeah, no doubt. Right? So I'm trying to figure out why is it so... Why is the notion that people ought to have purpose and passion in their career and if they don't, it's tragic. Why does that matter so much to you? And I'm suggesting because you saw the best version of it in your father.
I think to suggest if you don't have it is tragic is a little loaded like... because there's no way to write... there's no way to write a book that is the solve for global prosperity or whatever. All right, it'd be nice, but it'd be very hard. I think more what fascinates me is that in these stories and in other stories that people get really emotional about, you have this kind of rags-to-riches thing. And where someone believes that they can rise from the bottom to the top. And when they do, almost every one of the characters in this... that real people, but that we profile, have massive impacts on their industry. Like they end up with, you know, these huge... I call them boat wakes of people that have worked underneath them in touch and reach. And I just think it's awesome. I think it's awesome that someone might have not known they were going to do something and then they're able to do this thing of greatness, you know? And... or the thing that I hope to unlock is maybe I could help a whole bunch of people step through that door. And I already have cuz people have reached out to me from... Talk about motivation, people have reached out to me from the video that says it changed their lives. Yeah. And they've told me the stories. So then that gives me more motivation to share the ideas. The... Sorry, I want to make one more dad comment.
Sure.
You... I'm going to walk away with a lot of guilt, though. No, no, no. No, no, no, no, no. It's the opposite. Cuz I realized in reading your book that the greatest gift my own father gave me was exactly this. That my father was someone who just loved... He wasn't a workaholic, but he just loved his work. He never stopped. Every morning was like he was delighted. I would watch him. He had a little study off our... We lived in this little tiny bungalow. He was a mathematician. He would spend the mornings at home. And he would... I would watch him. He would go take his cup of tea and go into his study, and he was the happiest man in the world. And I realized of the million wonderful memories I have of my father, like a huge percentage of them are just watching this man delight in what he was doing and finding purpose in that. And like it wasn't something he was doing with me, but it's the... It is the last thing cuz I saw that I was like, 'Oh, that's what I want.' And it's infectious. And it's like it's infectious to the people around you. The... Obviously, you already mentioned but one of the people I profiled is Danny Meyer. He was kind enough to host the book launch dinner a few nights ago. Danny carries so much happiness with him everywhere he goes and touches so many people. And I've met chefs in San Francisco who only worked in a Danny Meyer restaurant for 1 year, but when you ask them, 'Tell me about your background.' they mention that. Like it becomes... He's part of the zeitgeist of the whole industry. Yeah. And we were talking to him. This is really cool. I was talking to him at the dinner and I mention... I did a speech before I mentioned that Tony Fadell had told... He had told me to write the book and I said, 'Why?' He said, 'It's the best thing I've ever done.' Tony Fadell, you know, built the iPod, the iPhone, and Nest. But the best thing I ever done in his brain is the book. And Danny brought that up and said he felt the same way about Setting the Table. And I said, 'Why?' And he told a story about being in South Africa in a restaurant and a chef running up and wanted to show a technique that he had learned from Danny. And he talked about the reach of impact that's possible with a written book that you can't do physically. Yeah. Yeah. That's pretty powerful. It is powerful.
You begin your book. So, just to backtrack for a moment. So, you give this talk. The talk goes viral.
And you have the idea that this is... there's a book here. And you begin the book and in many ways it's the signature story of the book is the story of Danny Meyer.
And I want you to tell me a little bit about how you know Danny Meyer. How did you meet him?
He was on the board of OpenTable from the very beginning.
Right, which is a company you backed.
Yeah, this company I backed it. So, we served on board together for 14 years.
And can you remember your first meeting with him?
I don't remember my first meeting precisely, but yeah, I don't have any... But you're... Give me your initial impression. Was the thing that you... Well, first of all, like so much you've got one of the most successful restaurateurs in New York who's hyper curious about this new technology. That's non-standard. So, when new technologies come along a lot of times the incumbent is the naysayer cuz they built their world without you and so you might feel threatening to them. But Danny immediately wanted to know more. And I've never met anyone more curious in their field than Danny. If you read his book, when he launches a new concept he usually... Even for Shake Shack they traveled to 12 of the what they considered to be the 12 top burger joints around the US and they analyze them with copious notes. Like there's just... he's a learned all and always has been.
Just for those who aren't familiar with Danny Meyer, he owns and started how many of the high-end restaurants just in New York City?
Like 11 of the top restaurants in New York City. And then went on to be the person who started Shake Shack.
Right. Right. Which began as just a random idea to put in the middle of Madison Square.
Madison Square and turned into a multi-billion dollar business.
Yes. Um and he... Now, he's... So, talk a little bit about what makes Danny Meyer special. Why begin the book with him?
Well, there's a... you mentioned the curiosity. Well, there's a story in the book that I think really is emblematic of what I'm trying to help more people attempt, which is he's a very successful salesman for this silly technology they put on clothes so you can't walk out of the store. And he's told his family, you know, he's going to go be a lawyer. He's just chasing for chasing's sake, which I think a lot of young adults do. And he's out to dinner with his uncle and his uncle's like, 'Why aren't you happy?' He's like, 'I got to take the LSAT tomorrow.' And he's kind of complaining about it. And his uncle's like, 'You don't have to take the LSAT tomorrow. You're choosing to take the LSAT tomorrow.' And this evolves into a conversation where his uncle goes, 'Why don't you just go launch a restaurant like you know you've always wanted to do?' Danny had never had that discussion with himself up in his own brain. And I think it's possibly... But he was someone who to an outsider from the youngest of ages was obsessed with food and obsessed with... journal about restaurants as a hobby.
Yeah, which I've never seen anyone do.
But he would write it down. Yeah. And he would schedule his business sales trips like around being able to stop at the newest restaurants in every city that he was keeping track of. So, yeah, he was doing all that as a hobby, which is why his uncle was like, 'Stop pretending. Like, come out. You're a restaurateur.'
How could you be so... This is a very, very interesting point I thought in that story. That here's someone who it was evident to everyone who knew him that he had this grand passion. And it was always had this grand passion. But he didn't... What was he unaware of?
To him about this... and you know his parents didn't encourage that path. You know and one of... I don't know if you noticed this but almost all of the profiles in the book are in industries your parents would probably steer you away from. Yeah. I left out the venture capitalists, investment bankers, consultants, lawyers, doctors. I have zero of those in the book. Yeah. Because those are the careers people get pushed into. And these are the careers people get pushed away from. And I think he brought up his father. He said his father was discouraging of moving... His father worked in... as a tour consultant put it. Like felt it was too close to... pushed him away from doing it. But the uncle saved the day, the hero of the story.
The uncle... The uncle was a character.
Yes. Oh a little bit in the book. I learned... There's paintings all over Union Square Cafe and Danny was showing us that his uncle had done those paintings.
Yeah. Yeah. So he... And his... So his uncle says to him, 'You're crazy. It's obvious to all of us that restaurants are where your heart lies.'
Yeah. And there's no resistance once his uncle says that. It feels like an unlock. And you know we went through it Monday night. Within a week he enrolled in an entry-level restaurant management course offered in some community college here. Like he found it... He said he back... They used to have those magazine boxes on the corner of the street. Pulled that out and found it and enrolled. Yeah. Talk about starting at the bottom rung. Yeah. Walking away from a very lucrative job.
Although that did give him flexibility, but yes. Yes. Yes. So now... And then his next 12 months, and you should read the book or read his book, is so ridiculously intentional, the learning journey he goes on in the next 12 months before he opens Union Square Cafe. Like he doesn't just run out and try and open a restaurant. It's very very meticulous before he does that.
Now... Here's where my question about him was, a couple of questions. One is that how unusual is he? So we're using him, we're opening this book with the story of Danny Meyer, someone who has a kind of singular obsession that he converts spectacularly into fame and success and... And how many of us are constructed that way? Or do you think that we can construct ourselves that way?
I do think that. And what I fear is that the first step of getting the permission to do it is maybe the hardest part. There's a story in the book where Jerry Seinfeld's wandering around New York and has an inkling he wants to be a comedian but doesn't know that it's really plausible and he reads a book called The Last Laugh. And there's so many of these stories where someone read one book and then all of a sudden they now can go do this thing. And The Last Laugh profiled 14 professional comedians who had a career and is very disinhibiting to then know, 'Oh, this is possible.' One exercise Danny did early on that I think anybody can do, especially so many of these exercises are so much easier in the modern era with AI and all these tools, but Danny created a list right when he decided to go do it, of the 10 most impressive people in the restaurant industry at that moment in time from his perspective and started keeping a journal on each one of them. And studying them from afar. And anyone can do that in any field. Not many people do that in any field. And I got to believe you start to build mental models. You start to feel confidence by being able to imagine yourself in their shoes. Yeah. I remember kind of... And seeing the success of it. Did you do something like that with writing? I kept... I remember doing it through even after I was quote unquote successful, I remember reading Michael Lewis books over and over again. Cuz I realized I wanted to be... I wanted to capture character in the way that he did.
No doubt. And so it was like a course. It's like you read those books and he immerses you in the mind of some extraordinary person. I did not know how to do that and he did.
Yeah. And I'm fortunate enough to have been a fanboy of both yours and Michael's and to get to know you both. And so I hope that the writing comes anywhere close... No, it's... But there's some elements that were definitely borrowed. Yeah.
So, what is it... So, we have this curious feature that the thing that we... the course that we should take that we ought to take in our career may at first be hidden to us.
