Young and Profiting with Hala Taha - Bill Gurley: Break Free From Career Regret and Design Work You Love | Career | YAPLive | E387

Starting point is 00:00:00 I feel deeply sad for a lot of founders. There is a reality where a modern venture capitalist does not want to take a meeting in anything on AI. Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor known for early investments in companies like Uber, Zillow, and Next Door. People aren't that engaged and happy in their careers. We ask a thousand people, if you could start your career over again,

Starting point is 00:00:28 would you do something different? Seven out of 10 said yes. Wow. AI is moving so fast. My advice for anyone in any field that's afraid of AI is run at it. You also started your career at the start of the dot-com bubble, and you saw that whole thing explode. How did that actually change the way you think about investing in companies,

Starting point is 00:00:51 change the way you think about sustainability? One of the things that happens anytime there's a technology wave is people get rich quick and then a whole bunch of people see people getting rich quick and they rush in. I like it when they're not around. When you're in a bubbly time, and we may be right now with AI, people do silly things. Things that don't usually work. They get very speculative. You've been ahead of the curve so many times.

Starting point is 00:01:15 Can you give us a prediction about the future of work or technology, something that we might be underestimating or unexpected? I think there will be a lot of money made in... Yeah, bam. Seven out of ten people say they'd choose a different career if they could start over. And it's not because they lack talent. It's because they chose the safe path. Today's guest has had a front row seat to what actually drives long-term success. Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor,

Starting point is 00:01:46 known for early investments in companies like Uber, Zillow, and Next Door. After decades backing billion-dollar founders, he noticed a pattern. The most successful people didn't follow the conventional route. They built careers around what genuinely fascinated them. In this episode, we unpack lessons from Bill's new book, running down a dream, including how to avoid career regret, staying relevant in the age of AI, and designing a career driven by curiosity, smart pivots, and continuous learning. Bill, welcome to Young and Profiting Podcast.

Starting point is 00:02:15 Thanks for having me on. I'm so excited for this podcast. I've heard about you for a very long time. Now we get a chance to sit down together. So you are what people have called a super investor. And now you've come out with a careers book called Running Down a Dream. Correct. And a lot of people might be thinking, like, what does a VC guy know about careers and why is he putting out a book about careers?

Starting point is 00:02:40 You could be putting out a war book on Uber or your Times at Benchmark, the VC firm, right? So why did you decide to write a book about careers? You know, as I reached the end of what was definitely my dream job, I loved being a venture capitalist, but I reached a point where I decided it was time to hang up my boots, and it was time for me to move on and leave the field for younger people to succeed. I felt a calling to write this book, and it was something that I had stumbled upon, like, eight years ago, an idea that it popped into my head. I used to write a lot of blog post, and when I would get an idea, I would scratch it down.

Starting point is 00:03:24 And sometimes it would become a post. A lot of times it just was living in a document. And this one was an idea that came to me, and I had read these three biographies and noticed that these three people had all done similar things. And I wrote down the notes. I then got invited to give a speech at the University of Texas here in Austin. and I put it together and gave that speech. And then a number of people saw that speech,

Starting point is 00:03:50 probably most notably James Clear. And people then started pushing me, you know, one day you should make that a book. And as I reached the end of my career, you know, and people had talked to me about writing a book before. You're right.

Starting point is 00:04:06 I could have written about investing. I could have written about tech. I could have written about venture capital. I could have written about Uber. and this just felt more personal to me. And now that it's done and it took a long time, I'm certain at this point that this book has a bigger chance to help more people than any of those other books.

Starting point is 00:04:26 Oh, yeah, for sure. I feel like this applies to anybody, whether they're just starting or they're, you know, 40, 50 years old and mid-career. I absolutely loved, like, some of the gems that I found in the book. So you started this project doing some surveys, And you found out that people were really unhappy with their jobs and at work. So talk to us about that.

Starting point is 00:04:45 Yeah, when we decided to make the book form, and I say we, because I worked hard with my editor and I hired a co-writer for some of it. And we did a lot of research. And one person prodded us to go look at the academic work on careers. And we talked to a lot of the best professors in the country on careers. But along the way, we had this idea to launch a survey monkey. survey and we asked a thousand people, if you could start your career over again, would you do something different? And seven out of ten said yes.

Starting point is 00:05:18 Wow. And we did it again with Wharton and did it more scientifically and it was still six out of ten. But a huge number for people to think they have career regret. And there's work that Daniel Pink has done where he talks about as you grow older, it's your regrets of inaction that weigh most on your brain like the things you didn't do. Most of us are pretty easy on ourselves when we make a mistake. We're like, oops, and we move on and you don't ruminate on it much. Yep.

Starting point is 00:05:48 But that thing you never tried just eats at you as you get older. Yeah. And so I'd like to believe, and we could talk about this as well. But I'm fairly certain that we've gotten so systematic about how we drive kids, you know, from being 12 years old into college. that we're putting blinders on them almost, and they're not having the opportunity to roam around and explore and find what they love.

Starting point is 00:06:18 And I think, I'm a parent of three, it is very, very hard for a parent to not want their child to be economically successful. And so you have this little voice in the back of your head that wants to push them towards the jobs that are considered safe, the safe jobs. Now, ironically, with AI, many of those, quote, safe jobs aren't that safe. Yeah.

Starting point is 00:06:47 But I would look back before AI and the survey work that we had done and other work gallop polls and whatnot, you know, people aren't that engaged and happy in their careers writ large. Yeah. It's a real problem. And so you're alluding to this concept you talk about in the book called the Career Conveyor Belt, right? Like we just put people on this path and, you know, you're supposedly supposed to get a really great job.

Starting point is 00:07:11 And that just doesn't really happen anymore. There's so many college students who graduate, they can't get jobs. There's so many people struggling out there. Yeah. So, talk to us about why society kind of pushes people this way. And what's the alternative? Like, what should you encourage your kid to do instead of just going to college straight away? Yeah.

Starting point is 00:07:33 I think it's well-intentioned. And I don't think it's just the parents. I think the counselors, everybody, it's, it's, it, you, you, it comes from the heart. Like, you really want them to be okay. But we've gotten into this place, Jonathan Haidt calls it the resume arms race, where, like I said, by the time you're in sixth grade, your parents are worried about whether your college application is going to be successful or not. So they're pushing you to play cello and volunteer at the thrift store. you're doing all these things.

Starting point is 00:08:07 These kids are booked solid. You know, when I was young and I've heard this from other people, my age, we'd roam around the neighborhood. No one would know where we were. But that doesn't happen anymore. They're just pressure, pressure, pressure. And I think it has the double negative consequence. One, they don't get to kind of explore and play and find what they love.

Starting point is 00:08:30 And two, they're just burn out, you know. They're just burnout. But then it even, It gets worse at college. If you go back 10 or 20 years, you would go to, everyone would go to college as a generalist, and you wouldn't declare your major until the end of your sophomore year. Nowadays, they make you apply to a major. And so you're putting the pressure on the kid to make the decision about the major

Starting point is 00:08:54 when they're a junior in high school and filling out applications. And they just don't know. Yeah. I mean, I've talked to so many of them, and I'm like, where do you want to be? I don't know. Like, they just don't know yet. And there's other data in this great book designing your life where five years after college, like 40% of people have already moved on to a career different than their major.

Starting point is 00:09:17 Oh, yeah. By 10 years, it's like 60%. And it may be important to share that information with people so they don't feel the weight. They don't feel the major doesn't become an anchor, you know, that restricts where they think they can go. Yeah, I can even think back to my journey. I went to college for organic chemistry. And then one year into it, I was like, this is not for me. I ended up dropping out of college, working at a radio station for two years.

Starting point is 00:09:45 Came back to college and was like way smarter and ready for it. Transitioned to marketing. And then here I am using those skills, you know, so many years later. I think there's a lot of data that suggest people that have roamed around and moved in different directions tend to land in a better place. one they're more passionate about. They've explored and had this time to kind of really figure it out. And then they're pressing the gas where they still have energy in the tank to go after it. Yeah.

Starting point is 00:10:17 If you find out you put in eight years grinding and find out you don't love something, I don't know if you have, you don't know how much you have left, you know, to pivot. Yeah. And as I was reading your stuff, I felt very connected to it because I do feel like I've been obsessed with podcasting and things like that. And that's why things have really worked out. So let's... You know, one thing I would say about that I think would speak especially to your audience.

Starting point is 00:10:43 Of course. You know, meeting, when you go out to promote a book, you meet a lot of publishers and you meet a lot of podcasters. And a lot of these people love what they do. And a lot of them have taken an independent path. Like, you didn't apply for a podcast degree and get in, you didn't fill out a job application to be a podcaster, right? You were crafting your own career.

Starting point is 00:11:07 There's a phrase in the book that I use called, you know, become a candidate of one. And I think a lot of people that, that are very successful in the world don't think about a career is something where I'm going to pick one off a menu and apply to it. They decide that they want to do something

Starting point is 00:11:27 and they go after it and kind of create that opportunity for themselves. and a lot of times it's acting as an entrepreneur of one. So I suspect you consider yourself in your dream job. Totally designed my dream career. Like I always tell my audience, my students, like have designed everything that I do. It never feels like work. I love what I do. I'm very, I think I'm very good at it.

Starting point is 00:11:54 And it's because I just enjoy what I'm doing. And in your book, you say, we've got to enjoy what we're doing because it's one third of our life, 80,000 hours of our life, is at work. So talk to us more about why it's so important to optimize our job and do work that we actually love. Well, the book is separated into two halves that alternate. It's stories of success, which are co-profiles and principles of success, which are the tools. And the stories are meant to inspire you and to disinhibit and make people understand and believe that they can go do this thing. And then the tools are to give people the things they need to go be successful. And the very first thing we talk about is fully understanding

Starting point is 00:12:39 what it is you're most curious about. And the reason it's so important is if you really want to differentiate yourself, you really want to be successful, you really want to dent the universe, you have to love learning about what you do. Because if you love learning about what you do, because if you love learning about what you do, and I think the ultimate test is in your spare time, instead of watching a Netflix show, you're reading about this thing that you love, you're going to out hustle everybody else. And the flip side is true. If you don't love it and you're not constantly learning, someone else is, and you're going to have a really hard time keeping up with them. Yep. And I find all too often in a lot of traditional,

Starting point is 00:13:26 jobs, people think, oh, I studied up until graduating from college, and now the learning's done, and I just go in and do the craft. And I just don't think that's how the world works, especially in this modern world where if you want to self-learn and you want to continuously learn, there's so much at your fingertips between podcast and AI and all these things. You're going to get outrun because someone's going to get out on the edge in front of you. Yeah. So the old cliche is follow your passion, but you talk more about curiosity over passion. Why didn't you say passion? The word passion has become trite and it's been said so many times. Some people attack it. And I kind of understand that. Like, you know, it's just been overused. I use the phrase, chase your curiosity. Seinfeld gave this great talk at Duke where he used the phrase fascination. That's a good word too. Fascination is. Like, it indicates something that you just can't stop learning about, right? You can't stop trying to figure out if you're fascinated with it. And the great thing is, and you're in this place, I was in that place. The learning feels free if you love it. Yep. Like you're not sitting there going, oh, my God, I got to go read this thing.

Starting point is 00:14:46 Like, you want to read this thing. And so if somehow you could measure the negative impact of having to do the work, for people that really love what they do and really are curious about it or fascinated by it, there's no, it doesn't feel like there's work effort put in to the continuous learning. But there's not going to be money in everything that we feel obsessed with or that we're curious about, right? So how do people navigate that part of it? Well, one thing, if you flip through the book, one thing you'll notice, and this is one of the reasons why from the video to the book released was six years, because I had a real bias in finding the stories

Starting point is 00:15:26 and that I mostly wanted to find people in non-traditional fields for this reason. Like I didn't want to, there's no McKinsey consultants, there's no investment bankers, there's not even really entrepreneurs. It's more, you have a restaurateur and a basketball coach and a hairstylist. And by the way, every one of those characters made a ton of money. They didn't start, every single one of them started it because they loved it. because they loved it. Yeah.

Starting point is 00:15:53 They didn't start it because they wanted to make money. But I have examples in the book of a gentleman that fell in love with the Grand Canyon and just started writing about it and was able to turn that into a career. And there's another gentleman in Houston that did that with Texas horticulture. And I, you know, so I somewhat reject the notion that you can't. I think there's plenty of studies that show rich people that aren't happy, right? And I guarantee you these people that are doing what they love every day and have an audience for it and people that reach out to them have a level of personal happiness and satisfaction that's just super high. Yeah. And when you're so obsessed with what you do, you're so good at what you do, you know the most.

Starting point is 00:16:38 And even with a small niche or small audience, there's opportunity within that. No doubt. And by the way, I think it's a fair question that you pose. And I was having a discussion with a career counselor at one of the top universities. in the country. And this topic came up. And she said, well, what if they studied English poetry or something? And I'm like, and I gave her the two examples I just gave. And I said, no, I think even there, you could probably make a career. And then she goes, but you'd have to work really hard. And I said, yes. Yes. Yeah, that's part of it. Yes. Yes. Yeah, fam, you just realized your business needs to hire somebody yesterday. How do you find great candidates fast? Easy. Use Indeed. When it comes to

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Starting point is 00:22:15 that really clicked with me is the fact that if you enjoy the preparation of your job, that's like a really good signal that you're doing something that you love, if you actually enjoy the prep work. So for people tuning in, what are some other signals or questions they can ask themselves to judge whether or not they're on the right path? Well, a couple different things. And we have a whole chapter dedicated to this topic and give, I literally went and studied all the other advice, all the greats had given and tried to, like, make it a laundry list so that you could try every one of these things.

Starting point is 00:22:48 And there's so many different fun little exercises you can do. Dave Evans and at Stanford who did Designing Your Life, he talks about create like three to five different profiles and spend a couple hours like riding out each one of them and kind of, living with it in your brain and then do it the other and then you can battle card them, which is an interesting way to really test which one you're most excited about. Your intuition when you do that will typically pick up on one of those. There's a great story in the book. There's a gentleman from here in Austin that spent the first part of his career in seismology and then he became a mortgage broker and he's watching a PBS show one night.

Starting point is 00:23:34 and they have this idea where you take a sheet of paper, you draw a line down it, you put what you love to do on one side and what you're good at on the other and try and find the middle ground. That gentleman's name is Bert Beverage and that exercise led to him starting a spirit company called Tito's Vodka.

Starting point is 00:23:52 Oh, wow. The most successful spirit business in America right now. Yeah, and the idea to do that came from that exercise. So we have a ton of those. exercises here. The other thing that Angela Duckworth talks about a lot is just don't be afraid to move around, you know, and this happened twice in my career. I was in a job. I was doing fine. I was making plenty of money. But I did this exercise in my head where I said, do I want to do this the rest of my life? Like just a moment of reflection. I said, do I want to spend 30 years doing

Starting point is 00:24:31 what I'm doing now. And in both of the first two cases, I reached a point where I was like, no, I'm pretty certain I don't want to do this for 30 years. And then I moved on. And I think having the gumption to move on and the confidence to move on is hard, but super valuable if you know you're not there. And I don't regret either of those two stopping points in my career. I built upon them and they were both relevant, and they were both helpful to what I did later. So I think, you know, one thing that's important on that point for very young people,

Starting point is 00:25:06 if you get a job and immediately build your expenses right up against that salary, then you might not have the flexibility to pivot down the road. So be careful. Yeah. You know. I want to talk about pivoting for mid-career people. I want to talk about young people.

Starting point is 00:25:26 how they should, you know, start following their dreams to your point when they have no money saved. Yeah. But first I want to spend a little bit of time on your career, too, because I want to understand how obsession played in your career. You started at Compaq, you went to Wall Street. Yeah. What did you feel like you were obsessed with that led you down VC? Okay.

Starting point is 00:25:46 It's super easy. So like many people who ended up in Silicon Valley, I had a computer early in my life. So I had a Commodore Vic 20 plugged into a TV. didn't have memory. I don't think we know what that is. Yeah, it was early, really early. But I found I liked writing programs. It was like very fulfilling.

Starting point is 00:26:05 And so when I went to the University of Florida, I got a computer engineering degree, enjoyed that process and went to work at Compact, which at the time was a very hot startup in Houston in the personal computer industry. And, yeah, so that was the first one, and that was the reason I got there. What happened was two years in, we started the third project from when I had joined, and it looked like the second project, which looked like the first, which is part of what got me wondering if I was going to grow bored doing this type of work. And then when I was at home, I had read this book, went up on Wall Street by Peter Lynch, and I had started trading stocks.

Starting point is 00:26:47 So once it gets to this test in my free time, I was playing with something else. I wasn't learning about the work. I was learning about this other thing. And so I went to business school, ended up on Wall Street. It was awesome. Being in Manhattan in your late 20s, just fantastic. Met so many great people, met so many great investors, and enjoyed reading about investing,

Starting point is 00:27:15 enjoyed being a part of Wall Street. Once again, though, three years in, I just started to think about the job. And what I was doing every day and said, do I want to do this my whole life? And came to once again to a conclusion, no, I don't. And I had along the way been building up this thought process that I wanted to be in venture capital. And the opportunity came to move to Silicon Valley. And from there, I was able to get into venture.

Starting point is 00:27:42 And three years into venture, I didn't have that, I didn't have that same discussion with myself. I knew I was in the right place. So do you think investing was really your obsession? It's a combination of things. I love technology. I loved understanding how it could be disruptive and how people could. And by the way, this is true for all entrepreneurs, how people could ride the edge of what was changing and then become successful. The book, Innovator's Dilemma, walks through exactly how that works.

Starting point is 00:28:14 And then this is a little more kind of personal. But when I was in college, we started going to Vegas and like counting cards and playing blackjack. I do think there was a little gambler mentality in there also. And those things combined. Interesting. You know, investing tech, gambling, a little bit disruption. And you put those all together and designed your dream career as a VC investor. Yeah.

Starting point is 00:28:41 It's putting all of this together. You know, I would say one, one more thing just because I know you have a lot of like founders and entrepreneurs in your in your audience. Yeah. I think there are certain people that have some form of ADD or they're just highly distracted and they get they get a lot of satisfaction out of diversity. And I'm one of those people. So whether it was working on Wall Street or as a VC, a consultant would have this. You're just looking at so many different things simultaneously and that breadth matters to me.

Starting point is 00:29:14 And one of the reasons that I left that engineering job is I felt that it didn't have that. And I was kind of, you know, down in the weeds. I've met a ton of wonderful founders who have to have their hands on the steering wheel and want to be in that position. And I think those jobs are complementary to one another. But people, if they get in touch with which one of those people they are, it may impact what career they want to go after. Totally, totally. So if somebody is young. and they want to design their dream career.

Starting point is 00:29:47 They may went to college. They're in their first job. How do you suggest that they start actually, you know, taking the steps toward independence and designing their own dream career? So we walked through a lot of it in the book, but I think it starts with learning. And once again, it's never been easier, cheaper,

Starting point is 00:30:09 more free, more accessible. Information is just, like you're so advantaged to do this today versus 10 years ago versus 20 versus 30. You'd have to what, pick up an encyclopedia to learn about something 30 or 40 years ago.

Starting point is 00:30:25 It's just insane. So start the learning process and there's so much great content out there. You know, in any industry there's typically a podcast or 10 that you can go watch and learn and listen to the best. There's

Starting point is 00:30:41 stuff on YouTube. You know, you can talk to AI until you're blue in the face. So you can just infinitely learn. One thing that I think is highly differentiating for someone is to learn the history of their field. I was going to say, you call it like the canon. Yes. And most people don't take the time to do it. But it will make you look very differentiated because it shows respect. And I also think there's a element of just bedrock knowledge that's nice to have. Yeah. There's an anecdote in the book where there's world chess tournament and they take a pause and do a trivia contest and Magnus Carlson wins the trivia contest, which I think is interesting.

Starting point is 00:31:22 Was he a good chess player? He's the best chess player in the world, but my point is he knew all the history as well. Yeah, because he was an expert in his field, so the history was a part of it. By the way, I think there's a barbell thing here. The other way to really differentiate yourself is to know the edge. And so if you, I mean, as silly as it sounds like, if you really know how TikTok works and then you want to break into sales or marketing or PR, like that's hugely differentiating. Like the people that have been in those roles for 10 or 15 years probably don't understand it at all. And so even if, you know, you're chasing a field that doesn't feel like TikTok is the main part of it, it could be highly,

Starting point is 00:32:10 relevant to what makes you look different as you apply for jobs in those areas. 100%. Especially for young people, like knowing the edge of these technologies, AI is another one, it's just a great way to separate yourself. And if you combine those two, you look really interesting. I totally agree with you on that. I can even think about from my own experience, like how I remember when I first started, I actually was in corporate for like a little bit.

Starting point is 00:32:38 When I first started corporate, I was 28 years old. Never had a corporate job before because I was in radio. I started a blog. I started all these things. I got into corporate and thought I was going to be so behind. But I actually was so much more tech savvy and knew how to hack LinkedIn and got promoted so quickly because I knew more than the other people who started at 23. About the edge. Yeah.

Starting point is 00:32:58 Yes. So it's really interesting that you say that. I love that idea of actually studying the history of a industry and also like the unsexy knowledge. Yep. which I think a lot of people miss. Like, I think of people who want to be, there's so many people who want to be podcasters, but they don't know how, like, CPMs work

Starting point is 00:33:16 and how podcasters even get paid and even really popular podcasters don't know that stuff. So talk to us about the importance of learning the unsexy stuff. You know, I had this experience in my life that was really amazing, and, you know, I was fortunate to have it

Starting point is 00:33:34 to sound like I'm name-dropping, but a partner of mine at Benchner, Mark, one at auction a dinner with John Lasseter, who was the creative genius behind Pixar. And we got invited to John's house, and he has a viewing room there, which is not that biggest surprise, but a big one. And they served us a 10-course meal, and each course had a cartoon that had, that John felt was one of the defining early cartoons in the history of cartoon. And he would, before each course, he would describe why this one mattered most to him.

Starting point is 00:34:15 And there was stuff from Japan and there was Steamboat Willie and all these things. And you're like, I mean, that's where I get back to. There's so many of these people that are at the top of their field that have this like just super respectful understanding of the history. And I have to believe that it matters. I think it matters both in terms of like a great test as to whether you should even be doing this or not. Like if that feels tedious, you know, that's not your place. Yeah. But also it's so differentiating.

Starting point is 00:34:49 I mean, just imagine yourself. And I think we could pick any field. Imagine, you know, you're in a, let's say you're interviewing for a sales job. And you have found, and you could do this with AI in five minutes, you've found the 10 like people who were the originator. in thinking about sales execution and sales techniques, and you start dropping that in the interview, like no one else is going to do that, none of the other people.

Starting point is 00:35:16 And someone's going to go like, holy crap, this person really cares. Like, you know, they really care about this field. Yeah, and it helps you, if you want to be a leader in that field field, not repeat the same mistakes. Yes, that too. You know, you're making sure that you really understand the history. And when I think about podcasting, it's pretty new.

Starting point is 00:35:37 So I guess I would study like TV and radio, right? And for AI, what would you study the internet? Well, I mean, there are some people that have been working on AI for 10 or 20 years. Yeah, AI is moving so fast. I think you should spend every last minute just using every tool you can't. You know, I've kind of separate from the. the book, but I have my advice for anyone in any field that's afraid of AI is run at it. Like, no, know what it's, what is the edge of possibility for AI in your field and, and learn

Starting point is 00:36:19 how to harness it. The same way you talked about what you knew about LinkedIn and whatnot, you have to be that with AI. Yeah. Yeah. Like the last thing you want to be as an AI skeptic who hasn't tried any of it. Totally. You're on the firing line, if that's you.

Starting point is 00:36:35 And don't stop at chatGBT. There's so many other apps out there. I know I myself, like I'm addicted to chat GBT. It's like trying to just branch out. No, try them all and ask, you can ask them this, but it's kind of circular. But what is the edge of AI usage in your field and understand what that is and play around with it there? And I meet people, especially older people. Well, I'm almost 60, so I guess I can pick on old people.

Starting point is 00:37:04 But they, like, they said, oh, AI doesn't work. I tried it. And it gave me this silly area. And they're proud that they found the error. And I'm like, have you tried it, you know, a year ago? Like, have you tried it two years ago, a year ago and today? Mm-hmm. Like, and tested whether it's still making that error.

Starting point is 00:37:21 Because it's getting better constantly, you know. And so if, if anyone's out there who's just like skeptical or naive, I, you know, I think that's really. dangerous. I totally agree. And we were just talking about how it's so important for younger, you know, people to get skills. How do you think AI is changing the way that we acquire skills and how do you think AI is changing mastery? Yeah. I think it's insane. Like, it's such an accelerant. Like, you can learn about anything. And I'm probably doing 30 searches a day on it. Oh, I'm on it. I can't do anything without it anymore. I always want to pop it. Right. It's become the number one

Starting point is 00:38:01 way you start to learn about something. Yeah, me, me too, me too. I think it's quite ironic that people feel like, oh my God, AI is coming and my job's at risk when if you're, if you have the gumption to be at the edge of your field and to be really differentiated and have this love affair with what you do, oh my God, it should allow me to separate from the field. Like, this should be my finest moment, not something to be a afraid of. Do you ever feel like AI is changing the way that your brain works? Good question. I think I'm constantly asking myself that question. And I'm skeptical, like, I don't take anything as a truism. So I try again. But it's possible. Yeah. I say that because

Starting point is 00:38:52 sometimes I'm like, I feel like in the past I would have, you know, now I'm always like, you know, bouncing back and forth between AI and my work, right? And in the past, I would have, I would have, I feel like, well, I probably would have thought of this on my own without bouncing back and forth between something. And now I feel like I always need to bounce myself. Yeah, that's a good question. Yeah, yeah. You might be limiting your own imagination by not giving yourself enough free time to ponder the possibility. I feel like there needs to be like time box, no AI, use your brain, you know.

Starting point is 00:39:25 Yeah, I think that's a good, I think that's a good call out. Okay, so let's say you're mid-career. Mm-hmm. 40 years old. Yeah. Made money, but you have responsibilities. Yeah. What do you do if you find that you are not living out, your passion?

Starting point is 00:39:41 Like, where... We have a chapter in the book called Never Too Late, where we highlight a number of people that had their defining career start after 40. I don't think it's easy for the reason you bring up, which is commitments. One of the people we profile in that chapter is Saul Kahn, who created the Kanaq. And Saul was in it. It worked at a hedge fund was doing rather well. I think fortunately his wife was working also.

Starting point is 00:40:09 And he was doing something on the side, helping a family member overseas that led to the creation of the tools that became Khan Academy. And he felt drawn to doing it as a nonprofit, which makes that math even harder. But his wife was supportive of him trying it for a year. year. They literally said, let's do it for a year. So he walked away. And once again, I think having the flexibility to do that as part of living within your means. They couldn't have done that otherwise. Yeah. But look what happened. I mean, there are very few people on this planet that

Starting point is 00:40:48 have changed the world as much as Sal Khan has. Yeah. We actually, and I interviewed him a little while ago. Wonderful guy. Yeah. One of the guys on the Acquired podcast came up with this idea, which I really loved, called side hustles. Yeah. And he says, while you're at a job, they'll probably let you do something else if you're willing to do it in your off hours or whatever. And especially it has nothing to do with the job. Yeah.

Starting point is 00:41:13 Right. And so he gives examples of three different stops in his career where he intentionally did something else on the side. One of them was at Microsoft. He started Microsoft Garage, which was this community of entrepreneurs using Microsoft projects. and that led him to a whole different set of connections and networking than if he had just sat there in the job they had defined for him. And then when he got to Medrana, he started a podcast on the side.

Starting point is 00:41:42 He said to the people at Medrona, can I do a podcast from the VC firm? They said, yeah, sure. And of course, now he's one of the most successful podcasters on the planet and loves what he's doing. But the experimentation of this side hustle gave him exposure to new things. things. And in both of those cases, in a very differentiated way. So that's another thing you could do if you're 40 and feeling trapped. You know, ask yourself, could I, would the career I'm in, the company I'm at let me go do this other thing? Totally. Well, that's what I did too. My podcast started as a side hustle while I was working at Disney. There you go. Right. And me and the acquired host, what's his name? Ben Gilbert.

Starting point is 00:42:24 Ben Gilbert. We are competing for an I-Heart podcast award for business and finance. No, it's not up to, it's up to industry panel to decide, but, you know, may the best podcaster win. There you go. One of the things that you talk about in your book is the importance of mentors. And you talk about local mentors versus aspirational mentors. What's the difference between the two? Well, I find a lot of people, I mean, a lot of people that write personal development books talk about mentors. So it's not a unique topic. But what I find happens most in the real world is people get too greedy too early. And they say, well, they either cold call someone they shouldn't. Yeah. That's out of reach. Or they get frustrated because, oh, I could never get this person to be my mentor.

Starting point is 00:43:17 So they kind of give up. And that's all because I think they stretch too far too early. So what I recommend people do is create a list of aspirational mentors. These are not people you're going to cold call tomorrow. There are people that you can watch from afar. You can study what matters to them. You can watch them on a podcast or on YouTube. And you can learn and you can follow their career.

Starting point is 00:43:42 One of my profiles is of Danny Meyer, the great restaurateur in New York. And he did this when he decided. going to be a restaurant tour. He made a list of, there's either 10 or 12 of the people that were changing the restaurant industry. And he kept a notebook of them and a profile of them, and he studied what they did. He ended up meeting every single one of them along the way. But he didn't cold call them at the beginning of the journey. And I think that's important. And if you study them the way we just described, one day when you do meet them, you know so much about it. Yeah, back to the history. That it's easy to kind of make the connection.

Starting point is 00:44:18 and you don't do it. So what I recommend is you do that kind of studying aspirational mentors. And then for your in-person mentors, you just need to be more realistic, like, about how far you reach. Yeah. And the truth of the matter is, people in the second tier get almost zero asked. So if you're more willing. Yeah, they're going to be more willing. They're going to be flattered that you ask them.

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Starting point is 00:50:03 Disclaimer, results will vary. Not all bills or subscriptions are eligible. Savings not guaranteed. Paid membership with connected payment account required. Seeexperian.com for details. You give so much great advice for people who are really just trying to, like, grow on this journey of being, like, top of their field in a career that they love. And one of the things that you mention is publicly learning, like learning in public. You did this with the blog that you started.

Starting point is 00:50:32 Yes. A lot of creator entrepreneurs nowadays who are building personal brands. They're also learning publicly. And there's so much benefit to that. Can you speak about that? Yeah. Look, I don't know if it's for everybody, and I've watched people be successful in venture capital that don't do it. But it's certainly a way to differentiate yourself is to create content on your field and to share that content publicly, as you say.

Starting point is 00:50:59 And, you know, ironically Warren Buffett has historically done this every year. There's a great bond investor named Howard Marks who writes out his thoughts. There are two benefits to it straight up. One, when you write things down and you know you're going to publish them publicly, you really test all the theories in your brain. You really work things out. You accomplish what you're afraid you're not doing by just using AI because you really don't want there to be inconsistencies. So you really think through it. And you give your brain a really good once over, I think, on the subject matter.

Starting point is 00:51:38 And then the second thing is it differentiates you. you will find people start reaching out to you, especially in a world that's so connected with LinkedIn and Twitter DM and all this stuff, you know, you start writing. You're going to create avenues for networking. Yeah. And so it's a way to differentiate yourself. I don't know if it's for everybody and I don't know if in all fields your employer will allow it. That's true.

Starting point is 00:52:04 Yeah. But I think in most cases, I think it does help. It can be very, very helpful. You also mentioned this concept of infinite games, how life is basically an infinite game and you're better off being generous than having sharp elbows. Yeah. How have you been generous in your career? Can you give us some examples or other, you know, personas and stories about people being generous? So this topic, I think, comes up in the chapter we have on peers called Embrace Your Peers.

Starting point is 00:52:34 And it's probably my favorite of the principles in the book, mainly because I don't think it's a. subject that's well, it's not well studied in the literature. Like I think I might be one of the first people really pushing on this subject. But peers can be inside your company. They can be outside. But it's, it's, think about it as a co-evolving journey. And the reason I use the, for the infinite versus finite games, so much of what we think about from a strategy perspective comes from finite games that we play that you play over and over again. And there's a winner and a loser. And in most career fields, that's just, not how it works. Like there's hundreds and hundreds of winners. And if you find a way to connect

Starting point is 00:53:17 and lock arms with your peers and share with each other, be vulnerable with each other, you just get a massive lift. And there's a, there's a great story in the book about Mr. Beast. And when he was starting his journey, which is probably similar to where you were getting into podcast. When he was getting into YouTube, there weren't, it wasn't a field yet. Yeah. Like, and he found three other people, they were on that same journey as he, and they were on 16-hour Skype calls all day long. And he very cleverly used the Malcolm Gladwell phrase 10,000 hours and said, we got 40,000 hours because we're learning together and sharing.

Starting point is 00:53:57 Yeah, that's so smart. And he also said something that I thought was really compelling. He said, if a fifth person had been on those calls, they'd have made a million dollars, like almost de facto because the stuff they were learning was so new and relevant. and executable, you know, that you could go win if you knew these things. And they were discovering them for the very first time. And the phrase sharp elbows, I have worked inside of organizations where there are people that just aren't good peers.

Starting point is 00:54:27 You know, they hog the limited equipment. They, you know, they kiss up. They, you know, you can tell who these people are. And I would just say stay far, far away from them. And then the other element of this is get over the notion that you have some kind of proprietary knowledge in your head. And this goes part and parcel with the public sharing stuff. Like, even if you have something in your head that's so compelling and so wonderful, like, it probably won't be that way 60 days from now. And I just think the benefit of open sharing far outweighs some advantage you're going to have by keeping.

Starting point is 00:55:08 knowledge proprietary to yourself. Totally. And the value of, you know, what you get in exchange for that is a personal brand. Yes. You know, which is so valuable on it. It's an asset in itself. Absolutely. The information is going to get stale, but your personal brand is just going to keep

Starting point is 00:55:24 growing, right? No doubt. The book really has two target audiences. So on one hand, it's the young person who's, or even maybe up to mid-career, who really is trying to figure out what they want to do or always wanted to chase a dream or and didn't know how and or someone who just really needs an extra push to go do that. It's for all those people for sure.

Starting point is 00:55:48 And a lot of people that have read it said, oh, I want to give it to, you know, every young adult's going to be handed this thing. I hope they take the top of treating. But the other audience is the parents, the counselors, the people that are playing a role in this shaping of these careers for other people because I do think that the now. tendency is to not kind of be supportive and give the right push at the right moment. And I know you had Matthew McConaughey on. And in his book Greenlights, he tells this story of he's going to, he's told his father's

Starting point is 00:56:26 whole life he's going to be a lawyer. And he decides that he now wants to switch to film school and he's afraid to tell his father. And it's a great scene. It really, to me, speaks to the purpose of the this. this book, when he finally gets the gumption and tells his father, his father says, well, don't half ass it. And in the book, McCona Hay says, it was the last thing he expected, but the most valuable thing his father could have said. He gave him permission, responsibility, a push, basically told him, well, if you're going to go do it, be really great at it.

Starting point is 00:57:03 And obviously, it launched an incredible career. But how do, for all that, second group, how can I help you be as good as McConaughey's dad was at that moment? And, you know, since that there's a sparkle of interest and curiosity and help it flourish. Yeah, because to your point, it's not like parents want to do, like, bad for their children, pushing them to become a doctor or something. You think you're doing good, right? So it's really important. And a lot of people, I have a lot of friends that feel very resentful of getting pushed in certain careers. So you don't want that to happen. Right. And then you, this one father who saw the original speech sent me this email, I almost started crying. And he told me a whole story about his child had been going in this direction and really wanted to go another one. And he talked about the kind of stages of himself getting comfortable with it. But he said when he finally flipped and was supportive, he saw the child's confidence rise. You know, that's just got to be such a wonderful feeling, you know.

Starting point is 00:58:07 And I have to say, like, I read two books a week, you know, because of my job, right? So I loved your book. I feel like there was so many great things in there. There's so many things that I'm going to even use. And, like, the history thing is something that really stuck with me in terms of, like, I really just need to know the history of media. Yeah. And I think that will just help me as I build this company.

Starting point is 00:58:28 So thank you for creating this book. Thanks for reading. You started in VC. You were behind so many, you know, huge companies. Zillow. Uber, Stitch Fix, so many big companies. You also started your career at the start of the dot-com bubble, and you saw that whole thing explode. Yep.

Starting point is 00:58:51 How did that actually change the way you think about investing in companies, change the way you think about sustainability for companies? Talk to us about those fundamentals. I think oddly in retrospect, it was fortunate that I, so I started my venture career in 97 and things were on fire by 99, but by 2000, they were falling apart. And that's not enough time for me to have been successful because from investment to liquidity back then was five to seven years. It's even longer now. And so there wasn't a window enough. But it also meant it wasn't a long enough window for any. to judge whether I was good at it or not.

Starting point is 00:59:36 And when the bubble burst, everything slowed down. When you're in a bubbly time, and we may be right now with AI, people do silly things. Like, they spend money in ways they shouldn't. They run TV ads and Super Bowl ads and all these things, things that don't usually work. They get very speculative. And I found the bubble part to be on. comfortable, but I found the post-crash part to be very sane and rational. And so I just thought, and it was slower, which for someone building their career,

Starting point is 01:00:15 and also the Charlottons leave town. So one of the things that happens anytime there's a technology wave is people get rich quick, and then a whole bunch of people see people getting rich quick and they rush in, fools rush in. And those people, I like it when they're not around. But they come in every wave. So it is what it is. With AI, you know, I have a lot of founder friends. And some of them say, like, you know, this year, they're only investing in AI companies.

Starting point is 01:00:49 And it's really hard for them to get funding. Even if it's a great company with great unit economics and everything like that, they can't get funding. Do you think there's a problem with the? investment in AI? And do you think that's a bubble? I think, well, there's a whole bunch in what you just said. But let me start, let me start with this high-level point that I'd like to make. This professor, Carlotta Perez, recognized something that I think is really important to understand, which is when there is a wave, there is massive wealth. There is, there's disruption,

Starting point is 01:01:27 and the deck chairs switch, and people make a lot of money. And that's already happened here because OpenAI in Anthropic are paying their employees secondary earlier than anyone ever had. So the money's being made. It's being put in people's pockets. And that's going to attract speculators. And here in Texas, we had a SPAC from the former governor, Rick Berry, or a data center. It already went up and down. So like speculators rush in.

Starting point is 01:01:53 And so bubbles and waves are actually always happening at the same time. So some people will argue, oh, if you say it's a bubble, you're anti-AI. No, I make the fact that it's real is why there's a bubble. So I think it's important to know that. There is a reality right now, and I feel deeply sad for a lot of founders. There is a reality where a modern venture capitalist does not want to take a meeting uninterested in anything on AI. And I could, if I was forced, make an argument as to why that's the exact right behavior by the venture capitalist. But I think it's unquestionably true.

Starting point is 01:02:40 Like, there's just zero interest. Yeah. And so that's a tough call for someone that's in a business that may have good unit economics that's not AI. What would my advice for them be? Make sure you understand the edge of AI in your field. like I said earlier, there may be things you could, you know, I think it's one out of five that can kind of pivot in a way that makes it really look like an AI company. So you don't want to, you don't, if it feels painted on, people will sense that. So, and then if that's not an avenue for you,

Starting point is 01:03:16 you know, try and use sweat equity to get to profitability and own way more of this thing than you would otherwise, you know. And I think one of the biggest mistakes, a lot of found make is when you take venture capital, it's usually not just the A round. There's usually a B round and a C round. And your ownership's going to get way diluted. And the number, the, the number one type of company that bigger companies would like to acquire are smaller companies that are tuck in acquisitions, $20, $30, $50 million. And the minute you take venture, that's off the table. Like, because now the venture capitalist needs a much bigger outcome.

Starting point is 01:03:55 Yeah. And so if you can scrape by, you know, and I know it's hard. Tito never took venture money. He owns 100% of this massive business. Wow. You know, and so if you can do it, you know, try and do it. And the big benefit of doing it that way is your ownership will be a lot higher. I want to do like a little mini MBA for the entrepreneurs.

Starting point is 01:04:25 a lot of people who are listening right now are like just starting as entrepreneurs or they've got like, you know, maybe a million dollar company or, you know, they're just kind of starting out. They've got a lot of potential. And so, you know, you've moved away from, or in the past, you've moved away from this like grow at all cost model and investing in companies that just want to grow. And you were looking at unit economics. So let's start there. Unit economics. How can you explain that in plain language for our listeners? Well, I suspect that the smaller entrepreneurs that are living hand to mouth on cash flow are pretty in touch with their unit economic. But they might not know what it's called. It's the guys that raise 100 million of venture capital that lose touch with unit economy. Yeah, it's just a matter of understanding what are the true variable cost associated with the product or service that you're selling. And being honest with yourself, even despite what the accounting might be that requirement, for gross margin, but what are the true variable costs? So that could include selling and customer service and all these things so that you know the marginal contribution, ideally from a cash flow

Starting point is 01:05:39 perspective, that you get with each turn of the crank. And it's basically trying to figure out, do we make money on a customer compared to how much a cost to acquire them and serve them? Like, are we actually making money on this customer? And, you know, it may be different based on on the type of customer, the size of customer, the source of the lead, like all those things might be different. You know, you may find, I've always found it to be true when you are aggressive with marketing, you have much higher churn. Like you get customer, whereas if you can earn a customer through PR or word of mouth,

Starting point is 01:06:15 they typically stay around longer. And so there, that's an even tougher mathematical problem because you're trying to calculate unit economics over the lifetime of a customer early on. Yeah. And I know you have a problem with LTV traditionally, right? I think people get into more trouble with the LTV formula than they do. Then they get success out of it. Why is that?

Starting point is 01:06:39 Well, I wrote it. It's one of my favorite blog posts I've ever written. So if someone wants to go deep, it's called the dangerous seduction of the LTV formula. And it's easy to find on Google. you know, it's not an erroneous way to measure something. It's actually a smart way to measure something, but it's not a strategy. And I think people get lost in thinking it's a strategy,

Starting point is 01:07:02 and especially if they're someone who's growing their business on a heavy marketing spin. And I just, in general, I would, you know, the blog post does all this, but I would push people, you know, really think about, Could I be winning customers with PR? Could I be winning customers with non-paid social? Could I be winning customers with product-led growth, which is a great way to think about your product, bringing you customers itself?

Starting point is 01:07:35 Like, all those things are going to create companies that are worth 10 times more than someone that's spending heavy on the marketing expense. I've never heard of product-led growth. Can you explain that? Yeah. And by the way, you could talk to AI or you could do Google searches and find people that have written extensively about product-led growth. But is there a way to build into the product the ability to find incremental customers? So could you, you know, one of the things that I've been pushing the Stitch Fix team to do that I hope will come out soon is here's your next fix. share it with your friends and let them vote on what you should keep.

Starting point is 01:08:17 Now you're exposing the company to people through the product. Yeah, you're letting the customers share it themselves. Yes, and so the product's leading to new customer introductions without these other techniques. By the way, there's plenty of people that have done that in Enterprise. You know, Slack notoriously had this way where you could invite people outside your org. So it's not just a consumer idea. Yeah, thinking of ways that your customers through the product can bring. in leads about you paying any money.

Starting point is 01:08:45 Exactly. Yes. Yes. Yes. So if, let's say you were mentoring me, my company makes $7 million a year now. Okay. What would you want to see in my dashboard in terms of metrics? Like, what kind of metrics would you want to see on a very simple dashboard baseline? One question I would ask you before I went there is, you know, and I this doesn't, I don't want to ask questions you don't want to answer, but like, do you see yourself running this company independently 30 years from now, or do you see yourself potentially selling? Selling. Yeah.

Starting point is 01:09:21 And so, because that matters a little bit because you need to think about who the natural acquires would be and how they, why they would fit it in. How do they measure their own business, you know, and so will this look appealing to them through that lens, those kind of things? You know, some of the stuff you talked about unit economics, like you want to understand, is it'd be great if the marginal customer is more profitable than the one before them. So that's a test of whether you're starting to get scale in your business, right? One exercise that I heavily encourage all founders to do,

Starting point is 01:09:58 no matter how much the size of the business is force yourself to do a three to five-year forecast. And you don't have enough information to read. do it, which is why people push back, but it forces you to ask the right question so that you can prepare. And if you, you know, if you want to grow, you know, a lot for five years, your business is going to be pretty big, you know. And so having gone to the exercise of filling out an Excel spreadsheet and thinking through what that means in terms of employees and salespeople and marketing spend, all those is a very useful exercise. And one, the, the The majority of founders do not naturally do.

Starting point is 01:10:40 Mm-hmm. Like, it's not something they want to do even, but they should do it. Is there, like, one metric that you look at that judges whether a company is healthy or not? I mean, there's so many different businesses. I think certain businesses, there's a, like in enterprise, an enterprise, that matters. Everyone agrees net dollar retention is the one that matters most. Mm-hmm.

Starting point is 01:11:00 But that doesn't apply to everything. Yeah. So it's kind of dependent on the business. So, again, you've got to learn your industry. Yeah. What matters in your industry. Okay, so let's play a game. It's called billionaire ROI ranking.

Starting point is 01:11:13 Okay. This is going to put everything that we just talked about together. I'm basically... Am I the first person to play this game? Oh, yeah. I have new games for everyone. Okay. So basically you're going to rank each thing one to ten if it's a good investment for the

Starting point is 01:11:28 entrepreneurs listen again. And it's going to be stuff that we talked about, some things we might have alluded to. And you can, you know, give some color on why you're going to. ranked it one to ten. So is it a good return on our investment? Okay. Okay. First one is reading and learning every day. Oh yeah. Nine, nine out of ten, maybe ten. And that's partially because I've always felt that way, but also the people I respect the most feel that way. I think Toby, the CEO and founder at Shopify was interviewed in the past 30 days, and this was the number one thing he said. Like, just as an example, you know, and Buffett says the same thing, you know.

Starting point is 01:12:12 Okay, moving to where the action is. Yeah. This is a, so between the talk that I gave at University Texas and the book form of the speech, we added a sixth tenant and it was moving to where the action is. I strongly believe that if you can afford it, you'd rather be an even average player where everyone's doing this thing than being the best player in a market that doesn't rank for that field. And if you're a songwriter, that means Nashville.

Starting point is 01:12:49 If you're a founder, that means Silicon Valley. If you want to work in finance, it means New York City. And the, it's, it's, the number of, what it really does is the number of chance positive things that are going to happen. I'd probably use the word optionality just goes up 20x. Like you're just going to run into so many people doing the same things. And like, and if, if you go to a job and it doesn't work out, there's so many other people hiring for that same thing. Like, it just really changes the dynamic.

Starting point is 01:13:25 And it probably is important that you're someone. that is self-motivated, but eight out of ten for most fields. There are a few fields. If you're a coach, you can't really do that. There are some fields where you can do it virtually, subreddits and things like that. Yeah, I think about, I moved to Austin a year ago as a podcaster, and there's just so much serendipity. It just things just happen naturally.

Starting point is 01:13:47 That's a great word. Yeah. Yeah. Building a personal brand. I think that that's field dependent. it's always helpful. I mean, I think there's a, I probably rank it below the others.

Starting point is 01:14:03 Let's just say six out of ten. There's always a risk that you become someone who's somewhat performant on the brand side and maybe not developing the real skills underneath it, which could have a negative ramification or someone could view you as shallow if you, you know, we're doing that. So, and not all fields. I mean, there are certain fields where I think it's harder to do. But I think if you can, it's very rewarding.

Starting point is 01:14:34 Spending heavily on ads. Well, you know, I'm somewhat negative on that. But it keeps your machine running. That would tell the truth. Yeah, I don't like it, too. Why is that? There's a great new book coming out by David Epstein. called Inside the Box where he talks about how constraints drive creativity.

Starting point is 01:15:02 And I've always felt that if you're starting a business, the easiest way you could possibly get a customer, the first way the most ignorant person would assume to go get a customer would be to run a Google ad. And I don't think people are reflective of enough to say, wow, I'm starting at the very bottom. I'm doing the simplest, that's the least creative thing I could possibly be doing. And the hardest, the most obvious. And I think if you run an exercise, which I mentioned in that blog post, where you say set to marketing budget, the advertising budget to zero, now what are you going to do?

Starting point is 01:15:45 And go run that exercise. You're going to come up with so many really creative, wonderful things that are highly differentiated. Yeah. So that's why I think. And paid ads are so, paid ads don't work also if you don't have a brand or credibility because they're going to go Google you. And there's not going to be anything there because you started with paid ads.

Starting point is 01:16:06 Okay. Networking events and conferences. I'm a big believer that it can be very, very helpful to you. I think it can help you with both peer and mentor development. I think, you know, there's probably a limit if you're known as the person that's always out at the conferences, you know, then they could. But some amount of that, there's a great, one of my favorite stories in the book is about the athletic director here at the University of Texas, Chris Delcante. And when he was very early working in athletic departments, he went to a conference and met four or five other young people that were at the exact same. station. And this is one of those fields where if you're in the epicenter, it may not matter as much.

Starting point is 01:16:57 But he was in a field where everyone's distributed. And this was the only opportunity for those chance moments. So it's like going to the action, but for a point of time. Yeah, yeah. And that group of friends stayed in touch, started a text group, started sharing ideas. And they expanded a little bit over time. But they're now all D1 athletic directors. All rows to the top. So it's seven or an eight? Yeah, yeah. Seven or an eight?

Starting point is 01:17:25 But field, you know, field dependent. Yeah, yeah. Raising as much money as possible. Well, I've historically been very negative on this. So I will put a three on it just to be consistent. We, the venture industry has evolved. And I don't think this affects the vast majority of founders, but the ones at the top. The industry has evolved to where most of the rounds.

Starting point is 01:17:50 are preemptive and proactive, which means you didn't start a fundraising process. Someone thinks you're doing well and knocked on the door and is force feeding you money. And that is currently the way things happen. And you end up with these situations where each competitor is armed with $400, $500, $600 million, maybe more. And it's not, you know, it's like I say, it's not your father's venture capital. This is a sport of kings world we've evolved into. And it's fight to the death. I live through it with the Uber Lyft situation, but it, I wouldn't wish it on anybody,

Starting point is 01:18:34 but it's the reality right now. And if you sit back and say, well, I'm not going to be, I'm not going to raise as much money. I'm going to be, you know, discipline. Well, if you're the discipline one and there's six players with $500 million each hiring salespeople, you're not going to matter. So the game on the field is kind of forced people to do this thing I don't love. Yeah. Okay. Next one.

Starting point is 01:18:58 Getting an MBA. Yeah. I'll say seven. But part of it's me reacting to the fact that so many people in the entrepreneur world make fun of it. There's a lot of people that shit on MBAs in the founder world. And the problem is some of them, I think, take that to the level of dismissing the notion of business learning, which I think is really dangerous. You know, if you don't know how to do a forecast on Excel spreadsheet, that could be a real problem. And so I just worry that the vilification of it is not good for the founders themselves because there are resources they need to understand.

Starting point is 01:19:39 It doesn't mean they have to go get an MBA, but they should read, Michael Porter's competitive strategy. They should read Innovators' Dilemma. They should read Crossing the Casm. They should know how to organize a sales team. There's just all this stuff. You need to know that one place you can get it is at a business school. But if you don't want to go to one, that's great.

Starting point is 01:19:59 But don't dismiss all of the learning as you crap on the notion of an MBA. A lot of people don't align to it. Well, now you can just learn everything online to your point. You might not need to go. The subject matter is important. Totally. Yeah. So let's move on to leadership.

Starting point is 01:20:20 I had Kevin O'Leary on the show. Yeah. And he's another billionaire, I think. I don't know, but I'll take you work for it. Just about a billionaire. And he told me how emotions are, you know, no place for emotions in business. He said, if you need to fire your mother, you fire your mother. Yeah.

Starting point is 01:20:39 And it reminded me when I was really, reading and learning about what happened at Uber with the founder and yourself and how, you know, he kind of started as a mentee and then, you know, over time, you had to make a really tough decision. Take us back to those moments, what was happening, and how are you able to kind of take a motion out of it and just be the best member of the board that you could be for Uber? One of the things that I would push back on with what Kevin said is the best. CEOs that I've talked to very much lead with the heart and have a, I'd say a passion for

Starting point is 01:21:21 leadership that includes feeling like a shepherd of the flock. And so I push back on that a little bit, like broadly against business. The situation that we got into at Uber, there was a asset, the company that, that was shared by many constituents, you know, the employees, the investors, everybody. And we, because of several things that had happened, things were in a bit of a free fall. And we had five state attorney generals after us.

Starting point is 01:21:58 We had this situation in London that was on fire. We were losing market share to lift, especially in metropolitan areas very quickly because of brand erosion. And by the way, it wasn't, I think history in the press has made it out to be me. There were five investors that worked together and signed this letter. So it wasn't just me. But I think that there were a number of people that were concerned that a change was definitely going to happen.

Starting point is 01:22:34 But if you let it happen through the legal world or the government, making a change, it was going to be six months to 12 months later, and the erosion was going to be even more. And there were a lot of constituents in this thing. You know, a lot of our investors, this was such a big number. They had already, you know, it was already moving the needle for several universities and foundations. And if it went away, you know, they have paper marks. They were going to have to mark it down. And that weight on me, that felt like a lot of responsibility.

Starting point is 01:23:12 So I've said publicly before, you know, if a venture capitalist does their job the right way, you don't get to that point. So, you know, the thing that I wish I had been able to accomplish was through leadership, preventing us from getting to the place where that hard decision has to be made. And, you know, if I could play it again, I would spend more time on that than trying to, you know, play the eventual thing that happened any differently. I think we did the best we could do at that moment and knew there would be consequences. And there were, like, our competitors use it against us constantly. But anyway, that's how I would summarize the whole thing. Do you feel like you made the right decision? Based on where we were at that point in time, yes.

Starting point is 01:24:00 Yeah. And Dara's done an amazing job. I mean, to take it from there to $200 billion public company, over $10 billion a year in free cash flow, like from where we were. Yeah, unbelievable. How do you think about reputation in your career? Like, how important is reputation to you? I think it's really important. In the venture area, it's probably a nine. I don't know that it's that high in every other field. I don't know that I'd have a good field for. In venture, your ability to compete for the next deal is everything. And that's either enhanced or hurt by what the world thinks of you. And in venture, that personal brand can shine brighter than even the corporate brand a lot of times.

Starting point is 01:24:58 And so you just have to worry about it if you want to be competitive. You've had like a really rare chance of being close to so many like extraordinary founders who built really successful companies. Yeah. What are some of the patterns you see with these founders? And I think a lot of it actually ties back to what you wrote in your book probably. Yeah, there's a couple things. They are continuous learners because they're tilting at some new problem on the edge of their field. And there's no way that could be something they learned in school five years ago because, you know, it's like AI right now.

Starting point is 01:25:36 Everything's changing so fast. Bezos has said that for his angel investments, he wants to feel like this person's going to do this no matter what. That there's this drive and commitment to attacking the problem that you just can't take them off of. So that's kind of an interesting notion. I think salesmanship is a requirement that people don't talk about enough. You're going to raise money. You're going to recruit people. You're going to lead your team through bad times.

Starting point is 01:26:11 You can't do that stuff without being able to sell in some way, shape, or form. People do it in a variety of different ways. There's people that are rah, rah, there are people that are quietly. But you have to be able to convince people to follow. you. And then lastly, I would say many, many startups have some kind of go-to-market advantage, which usually isn't advertising. So they've figured out some bespoke differentiated way to gain new customers aggressively. So good. You've been ahead of the curve so many times. Can you give us a prediction about the future of work or technology, something that we might be

Starting point is 01:26:54 underestimating or unexpected. It's so hard right now. I mean, I love the notion of contrarian investing. And when we're in one of these big waves, it's kind of off the table because everybody's doing the exact same thing. And, you know, I think there will be a lot of money made in verticals, like people who figure out how AI applies to something that's very specific to their world. And at this point in time,

Starting point is 01:27:24 coding and legal and probably medical or overfunded by the venture capitalist. So there's not much oxygen in those areas. But if you can figure out what it means for all the other fields that are out there, I think there's quite a bit of opportunity. So the intersection of AI and your field. Yes. And knowing what's possible and what that means. Bill, this has been such an awesome interview.

Starting point is 01:27:51 I end my show with two questions that I ask all my guests. All right. So the first one is what is one actionable thing our young improfitors can do today to become more profitable tomorrow. I'm going to be redundant with what we talked about. But I just think it's like continuous learning. And like just setting aside time, especially if you're a founder and entrepreneur who's hustling all the time, you may feel like you have no time. But setting aside some time during the week to learn something new. And what is your secret to profiting in life?

Starting point is 01:28:31 You know, I would say, you know, you asked me a question about why I wrote this book instead of doing a book about venture or whatever. And there's this great quote that life begins where your comfort zone ends. And I think numerous times in my life I've been willing to kind of try some. something different or on the edge or a little bit risky. And many times those have paid off. And so I'm not a kind of a conformist. Like I like attacking things in new ways. I like learning new things.

Starting point is 01:29:09 And so I'd probably say that. And would you say some of that is like gut intuition? Is that what you're alluding to? I think I use my gut to make the leap and to make the decision to push myself. but the willingness to move outside the box to walk away from something to like try something new, you know, to not be afraid to evolve past whatever the current thinking is, is something I've always done. And I'm thinking numerous examples in my history where that paid off.

Starting point is 01:29:43 And where can everybody learn more about you and everything that you do? Well, you can follow me on X. That's where I have most of my content. There's websites now for the book. We're launching a foundation alongside the book I should mention. For those people that want to chase their dreams and might not have the financial wherewithal to do it, we're going to do grants. We're going to have an application process.

Starting point is 01:30:07 Oh, very cool. And do that annually to try and help give them that extra little amount. Let me know when it launches. I'll do some free commercials for you guys and support. That's awesome. Yeah. Awesome. Well, thank you, Bill. Thank you so much for your time.

Starting point is 01:30:19 Thanks for having me. Young improfitors, sitting down with Bill Gurley was truly a special treat. He spent decades studying world-class performers and what he shared today challenges so much of the traditional career advice that we've all been given. One of the biggest takeaways from this episode is that the most fulfilled and successful people don't chase job titles or prestige. They chase curiosity. Bill made it clear that fascination is the real competitive advantage. When you genuinely love learning about something, the effort feels free and overtime, that obsession compounds into mastery, opportunity, and impact. Another lesson that really stood out is the importance of becoming a candidate of one.

Starting point is 01:31:01 Instead of picking a role off a menu, Bill encourages us to design careers intentionally and stand out. That means deeply understanding the history of your field while also running towards the edge of what's new, whether that's AI, emerging platforms, or a new way of thinking. That combination of respect for the past and fluency in the future is what makes people impossible to replace. And finally, Bill reminded us that great careers are built through exploration and smart pivots. Most people who end up loving their work didn't get there in a straight line. They experimented, reflected honestly, and had courage to move on when something no longer

Starting point is 01:31:37 fit. Progress comes from momentum, not from perfection. If this episode resonated with you and gave you something you can apply to your life or business, please share it with somebody who's rethinking their path right now. And if you haven't already, we'd be so grateful if you dropped us a five-star review on Apple, Spotify, or CastBox. This year, I'll be doing more in-person interviews, so keep an eye out for those on YouTube and Spotify video. And while you're there, make sure you subscribe and drop us a comment to let us know what resonated with you. If you want a more behind the scenes, look at my life and more personal stuff,

Starting point is 01:32:08 you can connect with me on Instagram at Yap With Hala or LinkedIn by searching my name. It's Hala Taha. Huge shout out to my incredible Yap team. As always, this is your host, Halitaha, aka the podcast Princess, signing off.

Young and Profiting with Hala Taha - Bill Gurley: Break Free From Career Regret and Design Work You Love | Career | YAPLive | E387

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