Bill Gurley: [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.

Hala Taha: Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor known for early ins in companies like Uber, Zillow, and Nextdoor.

Bill Gurley: We asked a thousand people, if you could start your career over again, would you do something different?

Bill Gurley: Seven out of 10 said yes.

Hala Taha: Wow.

Bill Gurley: People aren't that engaged and happy in their careers at large. If AI is moving so fast, my advice for anyone in any field that's afraid of AI is run at it.

Hala Taha: You also started your career at the start of the.com bubble and you saw that whole thing explode. How did that actually change the way you think about investing in companies change the way you think about sustainability.

Bill Gurley: One of the things that happens anytime there's a technology wave is people get rich quick [00:01:00] 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.

Hala Taha: 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 underestimating or unexpected?

Bill Gurley: I think there will be a lot of money made in

Hala Taha: Yap. Bam. Seven out of 10 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.

Hala Taha: 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 known for early investments in companies like Uber, Zillow, and Nextdoor. After decades backing billion dollar founders, he noticed a pattern.

Hala Taha: The most successful people didn't follow the conventional route. They built careers around what [00:02:00] genuinely fascinated them. In this episode, we unpack lessons from Bill's new book, running Down a Dream, including How to Avoid Career Regrets. Staying relevant in the age of AI and designing a career driven by Curiosity, smart Pivots and continuous learning.

Hala Taha: Bill, welcome to Young and Profiting podcast.

Bill Gurley: Thanks for having me on.

Hala Taha: I'm so excited for this podcast. You know, I've heard about you for a very long time. Now we get a chance to sit down together. So you are, uh, what people have called a super investor.

Bill Gurley: Hmm.

Hala Taha: And now you've come out with a careers book called Running Down A Dream.

Bill Gurley: Correct.

Hala Taha: 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? You could be, you know, putting out a war book on Uber or your Times at Benchmark. Yeah, the VC firm, right? Yeah. So why did you decide to write a book about careers?

Bill Gurley: You know, as I.

Bill Gurley: 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 [00:03:00] hang up my boots, and it was time for me to move on and, and leave the field for younger people to succeed. Um, I felt a calling to write this book and it was.

Bill Gurley: It was something that I'd stumbled upon like eight years ago, an idea that had popped into my head. I used to write a lot, a blog post and, and when I would get an idea, I would would scratch it down and sometimes it would become a post. A lot of times it just was living in a document. And this one, um, was an idea that came to me.

Bill Gurley: 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, um, I, I put it together and, and gave that speech. And then a number of people saw that speech.

Bill Gurley: Mm. Probably most notably James Clear. And people then started pushing me, you know, one day you should make that a book.

Hala Taha: Mm-hmm.

Bill Gurley: And [00:04:00] as I reached the end of my career. You know, and I, I, people had talked to me about writing a book before, you're right. 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.

Bill Gurley: And, um, this was, this just felt more personal to me. Mm. And now that it's done, and it took a long time, um. I am certain at this point that this book has a bigger chance to help more people than any of those other books.

Hala Taha: 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.

Hala Taha: Uh, I absolutely loved like some of the gems that I found in the book. So you started this project, uh, doing some surveys and you found out that people were really unhappy with their jobs and, and at work. So talk to us about that.

Bill Gurley: Yeah. When, when, 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.

Bill Gurley: And, um, we did a lot of research and one person prodded us to [00:05:00] go look at the academic work on, 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?

Bill Gurley: Mm. And seven out of 10 said yes.

Hala Taha: Wow.

Bill Gurley: And we did it again with Wharton and did it more scientifically. And it was still six out of 10, but a huge number, um, 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.

Bill Gurley: Mm-hmm. Like the things you didn't do. Most of us are pretty, um, easy on ourselves. When we make a mistake, we're like, oops. And we move on. And you don't ruminate on it much.

Hala Taha: Yep.

Bill Gurley: But that thing you never tried just eats at you as you get older. Yeah. And, and so I, I'd like to believe, and we could talk about this as well, but I, I, I'm [00:06:00] fairly certain that we've gotten so.

Bill Gurley: Systematic about how we drive kids, you know, from being 12 years old into college, that we're putting blinders on 'em almost, and they're not having the opportunity to roam around and explore Yeah. And find what they love. And I think having, I, I'm a parent of three, it is very, very hard for a parent to not want their child to be economically successful.

Bill Gurley: Mm-hmm. And so you, you have this, this little voice in the back of your head that wants to push 'em towards the jobs that are considered safe, the safe jobs. Now, ironically. With ai. Mm-hmm. Many of those quote, safe jobs aren't that safe.

Hala Taha: Yeah.

Bill Gurley: But I would look back before AI and the survey work that we had done in other work, Gallup polls and whatnot, you know, people aren't that engaged and happy in their careers writ large.[00:07:00]

Hala Taha: Yeah. It's a, it's a real problem. And so you're, you're alluding to this concept you talk about in the book called The Career Conveyor Belt, right? Yeah. Like we just put people on this path and, you know, you're supposedly supposed to get a really great job and, and that just doesn't really happen anymore.

Hala Taha: There's so many college students who graduate, they can't get jobs. There's so many people struggling out there.

Bill Gurley: Yeah.

Hala Taha: Um, even getting laid off, uh, even if they had a great job. 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?

Bill Gurley: Yeah. I look. I think it's well intentioned and I don't think it's just the parents, I think the counselors, everybody. Mm-hmm. It, it's, it's, uh, you, you, it comes from the heart like you really want them to be. Okay. Um, but we've gotten into this place, Jonathan, he 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 [00:08:00] application's gonna be successful or not.

Bill Gurley: So they're pushing you to play cello and volunteer at the thrift store and like you're doing all these things. These kids are booked solid.

Hala Taha: Mm-hmm.

Bill Gurley: You know, when I was young, and I've heard this from other people my age, we'd roam around the neighborhood. No one knew where we were, but that doesn't happen anymore.

Bill Gurley: They're just. Pressure, pressure, pressure. And I think it has the con double negative consequence. One, they don't get to kind of explore and play and, and find what they love. And two, um, they're just burn out. Mm.

Hala Taha: You

Bill Gurley: know, they're just burn out. But then it, even, it, 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.

Bill Gurley: Nowadays they make you apply to a major.

Hala Taha: Mm-hmm.

Bill Gurley: And so you're putting the pressure on the kid to make the decision about the major when they're a junior in high school mm-hmm. And filling out applications and they just [00:09:00] don't know.

Hala Taha: Yeah.

Bill Gurley: I mean, I've talked to so many of 'em and I'm like, where do you wanna be?

Bill Gurley: And they're, I don't know, like they just don't know yet. And, um, the, the, there's other data in this great book Designing Your Life where. That five years after college, like 40% of people have already moved on to a career different than their major. Oh,

Hala Taha: yeah. By,

Bill Gurley: 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 that the, the major doesn't become an anchor.

Bill Gurley: Mm-hmm. You know, that, that, that restricts where they think they can go.

Hala Taha: 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.

Bill Gurley: Yep.

Hala Taha: I ended up dropping out of college, working at a radio station for two years.

Bill Gurley: Yep.

Hala Taha: Came back to college and was like, way smarter and ready for it.

Hala Taha: Transition to marketing, and then here I am using those skills, uh, you know,

Bill Gurley: so many years later. I think there's a lot of data that suggests people that have roamed around and moved [00:10:00] in different directions, um, tend to land in a better place. One they're more passionate about, they've explored and had a, you know, this time to kind of really figure it out.

Bill Gurley: Mm-hmm. And then. They're pressing the gas where they still have energy in the tank

Hala Taha: Yep.

Bill Gurley: To go after it. Yeah. And if you find out, you, you, if you, if you put in eight years grinding and find out you don't love something, I don't know if you have, I don't know how much you have left, you know?

Hala Taha: Totally.

Bill Gurley: To pivot.

Hala Taha: Yeah. And as I was reading your stuff, I've 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,

Bill Gurley: you know, one thing I would say about that Yeah. That I think would speak especially to your audience,

Hala Taha: of course.

Bill Gurley: Um, you know, meeting, when you go out to promote a book, you meet a lot of publishers and you meet a lot of podcasters. Mm-hmm. And a lot of these people love what they do, and a lot of them have taken an independent path. I like you didn't apply for a [00:11:00] podcast degree and, and get in. Yeah. You didn't. Fill out a job application to be a podcaster.

Bill Gurley: Right. You were crafting your own career. Mm-hmm. We, there's a phrase in the book that I used called, you know, become a candidate of one.

Hala Taha: Mm.

Bill Gurley: And I think a lot of people that, that, that are very successful in the world, don't think about a career is something where I'm gonna pick one off a menu and apply to it.

Bill Gurley: They, they decide that they want to do something 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. Yeah. Um, so I, and, and I suspect you consider yourself in your dream job.

Hala Taha: Totally designed my dream career, right? Like, I always tell my audience, my students like.

Hala Taha: Have designed ev 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 and it's because I just enjoy what I'm doing. And in your book you say, we've gotta enjoy what we're [00:12:00] doing 'cause it's one third of our life. 80,000 hours Yeah. Of our life is at work. So talk to us, uh, more about why it's so important to optimize our job and do work that we actually love.

Bill Gurley: Well, the. The I the book is separated into, into two halves that alternate it's stories of success, which are called 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.

Bill Gurley: And then the tools are, are to give people the, the, the, the things they need to go be successful. And the very first thing we talk about is fully understanding what it is you're most curious about. Mm. And the reason it's so important is if you really want to differentiate yourself, you really wanna be successful.

Bill Gurley: You really want to dent the universe. Um, you have to love learning about what you do. Mm-hmm. Because if you love learning about what you do, and, and, and I think the ultimate [00:13:00] test is in your spare time, instead of watching a Netflix show mm-hmm. You're reading about the this thing that you love, you are gonna out hustle everybody else.

Bill Gurley: And the flip side is true. If you don't love it and you're not. Constantly learning someone else is, and you're gonna have a really hard time keeping up with them.

Hala Taha: Yep.

Bill Gurley: And um, I, I, I find all too often in a lot of traditional 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.

Hala Taha: Mm-hmm.

Bill Gurley: 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. Um, you're gonna get outrun 'cause someone's gonna, someone's gonna get out on the edge in front of you.

Hala Taha: Yeah. So the old cliche is follow your passion, [00:14:00] but you talk more about curiosity over passion. Why, why, why don't you say passion?

Bill Gurley: The, the, the word passion, um, 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. Um. I, I used the phrase, chase your curiosity.

Bill Gurley: Seinfeld gave this great talk at Duke where he used the phrase, uh, 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.

Bill Gurley: If you love it.

Hala Taha: Yep.

Bill Gurley: Like, you're not, you're not sitting there going, oh my God, I gotta go read this thing. Like, you want to read this thing. Mm-hmm. And so if, 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 or fascinated by it, [00:15:00] there's no, it, it doesn't feel like there's work effort put in to the continuous learning.

Hala Taha: There's not gonna 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?

Bill Gurley: Well, one thing if, if you flip through the book, one thing you'll notice, and I, this is one of the reasons why from the, the video to the book release was six years.

Bill Gurley: 'cause I had a real bias in finding the stories. And then 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, it's more you have a restaurateur and a basketball coach and, and a hairstylist.

Bill Gurley: And, and by the way, every one of those characters made a ton of money.

Hala Taha: Hmm.

Bill Gurley: They didn't start. W they all, every single one of 'em started it because they loved it.

Hala Taha: Yep.

Bill Gurley: They didn't start it because they wanted to make money, but I, I have examples in the book of a gentleman that fell in [00:16:00] love with the Grand Canyon and just started writing about it and was able to turn that into a career.

Bill Gurley: And there's another gentleman in Houston that did that with Texas Horticulture and I. So I, I somewhat reject the notion that, that you, you can't, I think there's plenty of studies that show rich people that aren't happy. Right? And, 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 just super high.

Hala Taha: Yeah. And when you're so obsessed with what you do, you're so good at what you do, you know the most. And even with a small niche or small audience, there's opportunity within

Bill Gurley: that audience. No doubt. And, and by the way, I to, I, I think it's a fair question that you pose and, 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?

Bill Gurley: And I'm like. [00:17:00] And I gave her the two examples I just gave and I said, I, 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.

Hala Taha: Yeah, that's part

Bill Gurley: of it. Yes, you would. Yes.

Hala Taha: Yeah. Yeah, fam 2026 is the year I'm fully focused on growing my personal brand.

Hala Taha: I just started a new brand and content team, and that means I'm going to be intentional about every part of my business, especially my website, which I've been neglecting for years, and that's why so many companies from leading startups to mine to Fortune 500 brands are turning to framer now that we're due for an upgrade.

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Hala Taha: Gang. I have become obsessed with the Working Genius Assessment. It was created by Patrick Lencioni. He came on my podcast about two years ago and taught me about working genius. I took the assessment then, and it was a game changer for me individually. This year, I'm taking it to the next level, and I've basically implemented a working genius across my entire company.

Hala Taha: So this is not a personality test. It's an actual test that helps you [00:19:00] understand the way that you work best. There are six types of working geniuses. Everybody has two geniuses. It's the type of work that gives them energy. Two competencies. It's the type of work that you may be good at, but over time it actually drains you, and then you have two working frustrations.

Hala Taha: It's the work you don't like to do and it drains your energy. I uncovered that my two geniuses are invention and galvanizing. My two competencies are discernment and tenacity, and my working frustrations are. Enablement and wonder. So once I found this out, everything just like clicked for me. Number one, I realized why I was butting heads with my executive team because wonder is frustration for me, whereas my business partner has wonder as a strength.

Hala Taha: I wanted to get things done, rally the group, keep things moving. He wanted to think about the big picture and if this was the right direction at all. And so once we figured out these are our geniuses, we realized we can't build this company without each other and our strengths, [00:20:00] and it helped us work better together.

Hala Taha: And it also helped me uncover gaps within my organization. Turns out I'm the only person who has galvanizing as a core strength. So I'm always rallying the team. And sometimes that can come off as pushy or aggressive, but now that my team knows that this is a gap, we need to hire people who have more of this galvanizing strength.

Hala Taha: So it really helped us align on gaps. It'll totally change the way that you do your work. It will totally level up and your teams. Happiness and productivity at work. I highly recommend that you take this assessment and it's extremely affordable. If you're ready to stop guessing and start working on your actual genius, take the Working Genius Assessment and get 20% off with code [email protected].

Hala Taha: If you have a company, if you have a team, you get a report, tells you like how to take advantage of your learnings and things like that. If you like what you saw and you wanna implement it to your team, I highly recommend that as well. So you can get your team map, and I have a code for that too. It's profiting teams.

Hala Taha: If you use the code profiting teams, you can get 20% off all the assessments for [00:21:00] your entire team, your entire company. Highly recommend it. Again, that's working genius.com. Use code profiting or profiting teams to get 20%. So one of the things that I was reading in your book that I thought was really interesting, that really clicked with me is the fact that if you enjoy the prep 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.

Hala Taha: 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?

Bill Gurley: Well, a couple different things and, and we have a whole chapter dedicated to this topic and give, I, I literally went and studied all the other advice every, all the greats had given and tried to like, make it a laundry list so that you could try every one of these things.

Bill Gurley: Um, and there's so many different fun little exercises you can do. Um, DD Dave Evans and at at Stanford who did designing your life. Um, he talks about create like three to five different profiles and [00:22:00] spend a couple hours like writing out each one of 'em and kind of living with it in your brain. Mm. And then do it the other, and then you can battle card 'em, which is an interesting way to really test which one you're most excited about.

Bill Gurley: Your intuition when you do that will typically pick up on one mm-hmm. Of those. Um, 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 is watching a PBS show one night, 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.

Bill Gurley: Hmm. Um, that gentleman's name is Burt Beverage. And that exercise led to him starting a spirit company called Titos Vodka. That's

Hala Taha: Oh, wow.

Bill Gurley: The most successful spirit business in America right now. Um, yeah. And like he, he, the idea to do that came from that exercise. So we have a ton of [00:23:00] those exercises here.

Bill Gurley: The other thing that, um, that Angela Duckworth talks about a lot is. Don't be afraid to move around, you know? Mm. 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?

Hala Taha: Mm.

Bill Gurley: Like just a moment of reflection. I said, do I want to spend 30 years doing 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. Mm. 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.

Bill Gurley: And, and I don't regret either of those two stopping points in my career. I built upon 'em and, and they were both relevant. They were both helpful to what I did later. Mm-hmm. Um, so it, I think, you know, one thing that's [00:24:00] important on that point for very young people, if you get a job and immediately build your expenses right up against that salary, then you might not have the flexibility mm-hmm.

Bill Gurley: To, to, to pivot down the road. So be careful.

Hala Taha: Yeah.

Bill Gurley: You know.

Hala Taha: I wanna talk about pivoting for, uh, mid-career people. I wanna talk about young people and how they should, you know, start following their dreams to your point, when they have no money saved.

Bill Gurley: Yes. Yeah.

Hala Taha: Uh, but first I wanna spend a little bit of time on your career too, because I want to understand how obsession played in your career.

Hala Taha: Okay. You started at Compact, you went to Wall Street.

Bill Gurley: Yep.

Hala Taha: What did you feel like you were obsessed with that led you down vc? Okay, so

Bill Gurley: super easy. So, um, 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,

Hala Taha: I don't think we know what that is.

Bill Gurley: Yeah, it was, it was it early, really early. And, um, but I, I found, I liked writing [00:25:00] programs. It was like very fulfilling. And so when I went to University of Florida, I got a computer engineering degree, um, enjoyed that process and went to work at Compact, which at the time was a very hot startup in Houston, uh, in the personal computer industry.

Bill Gurley: And, um, yeah, so that was the first one and that was the reason I got there. What happened was, um, 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 gonna grow bored. Hmm.

Bill Gurley: Doing this type of work. And then, um, when I was at home, I had read this book one up on Wall Street by Peter Lynch, and I had started trading stocks so that once it get into 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.

Bill Gurley: And so I went to business school, ended up on Wall Street, uh, had [00:26:00] it, it was awesome being in Manhattan in your late twenties, just fantastic. Mm-hmm. Um, met so many great people, met so many great investors, and, uh, enjoyed reading about investing. Enjoyed being a part of Wall Street once again, no three years in.

Bill Gurley: I just started to think about the job and it 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, and yeah.

Bill Gurley: From there I was able to get into venture.

Hala Taha: Yeah.

Bill Gurley: And three years into venture, I didn't have that, I didn't have that same discussion with myself. I was, I knew I was in the right place.

Hala Taha: So do you think. Investing was really your obsession.

Bill Gurley: 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 [00:27:00] all entrepreneurs, how people could ride the edge of what was changing mm-hmm.

Bill Gurley: And then become successful. The, the, the book, um, um, innovator's Dilemma walks through exactly how that works. Um, and then this is, this is, uh, 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, I do think there was a little gambler.

Bill Gurley: Little gambler mentality in there also. And it was, those things combine

Hala Taha: interesting,

Bill Gurley: you know, investing, tech, gambling, a little bit disruption.

Hala Taha: And you put those all together and designed your dream career Exactly. As a VC investor.

Bill Gurley: Yeah.

Hala Taha: Yeah. It's putting, it's putting all of this together,

Bill Gurley: you know, I would say one more thing, just because I know you have a lot of like founders and entrepreneurs in your, in your audience.

Hala Taha: Yeah.

Bill Gurley: Um, I think there are certain people that have, uh, some form of a DD or they're just highly distracted and they get, um, they get a lot of satisfaction out of diversity.

Hala Taha: Mm-hmm.

Bill Gurley: And I'm one of those people Me [00:28:00] too. 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 breath matters to me.

Bill Gurley: 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, are complimentary to one another, but people, if they get in touch with what, which one of those people they are, it may impact what career they want to go after.

Hala Taha: Totally. Totally. So if somebody is younger and, uh, they wanna design their dream career, they may went to college, they're in their first job, how do you suggest that they start actually, um, you know, taking the steps toward independence and, and designing their own dream career?

Bill Gurley: So we walked through a lot of it in the book, but I think [00:29:00] it starts with learning and, um, once again, it's never been easier, cheaper, more free, more accessible information.

Bill Gurley: It's just s like, you're so advantaged to do this today versus 10 years ago versus 20 versus 30. Like, you'd have to what? Pick up an encyclopedia to learn about something 30 or 40 years ago. Mm-hmm. It's just insane. So, um, start the learning process and there's so much great content out there. Um, you know, in any industry there's typically a podcast or 10 that you can go watch and learn and, and, and listen to the best.

Bill Gurley: Um, there's stuff on YouTube, you know, you can talk to AI until you're blue in the face. Mm-hmm. So you can just infinitely learn. One, one thing that I think is highly differentiating for someone is to learn the history of their field.

Hala Taha: I was gonna say, you call it like the canon.

Bill Gurley: Yes. And most people don't take the time to do it, but it will make you look very [00:30:00] differentiated.

Bill Gurley: Mm-hmm. Um, because it shows respect. I also think there's an element of just bedrock knowledge. That's nice to have.

Hala Taha: Yeah.

Bill Gurley: There's a anecdote in the book where there's this 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.

Hala Taha: Was he a good chess player?

Bill Gurley: Huh? He, he's the best chess player in the world, but, but I know about that. But my point is he, he knew. He knew all the history as well.

Hala Taha: Yeah. Because he is, because he was an expert in his field, so the history was a part of it.

Bill Gurley: The other, by the way, I think that there's a barbell thing here.

Bill Gurley: Mm-hmm. The other way to really differentiate yourself is to know the edge. And so if you, I mean as, as silly as it sounds like if, if you really know how TikTok works and then you want to break into sales or marketing or pr, like that's hugely differentiating. Mm-hmm. Like the people that have been in those roles for 10 or 15 years probably don't understand it at all.

Hala Taha: Mm-hmm.

Bill Gurley: And so [00:31:00] even if you know you're chasing a field that doesn't feel like TikTok is the main point, part of it, it could be highly relevant to what makes you look different as you apply for jobs in those areas.

Hala Taha: 100%.

Bill Gurley: Especially for young people, like knowing the edge of these technologies, AI is another one.

Bill Gurley: Like is just a great way to separate yourself. Yeah. And if you combine those two, you look really. Interesting.

Hala Taha: I totally agree with you on that. Um, I can even think about from my own experience, like how, um, I remember when I first started, I actually was in corporate for like a little bit when I first started corporate.

Hala Taha: 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 gonna be so behind. But I actually was so much more tech savvy and knew how to hack LinkedIn and, and Exactly. Got promoted so quickly. Right.

Hala Taha: Because I knew more than the other people who started at 23 about the edge. Yeah.

Bill Gurley: Yes.

Hala Taha: So it's really interesting that you say that. I, I love that idea of actually studying the, the [00:32:00] history of a industry and also like the unsexy knowledge.

Bill Gurley: Yeah.

Hala Taha: Um, which I think a lot of people miss. Like, I think of people who wanna be, there's so many people who wanna be podcasters, but they don't know how like CPMs work and how podcasters even get paid.

Hala Taha: And, uh, even really popular podcasters don't know that stuff. Yeah. So, talk to us about the importance of learning the unsexy stuff.

Bill Gurley: You know, I, I had this experience in my life that, that was really amazing and, and, you know, I was fortunate to have it, it's gonna sound like I'm name dropping, but a, a partner of mine at Benchmark.

Bill Gurley: Uh, one at auction, a dinner with John Lasseter, who was the creative genius behind Pixar. Hmm. Um, and we went to, we got invited to John's house and he has a viewing room there, which not that big a surprise, but a big one. And they served us a 10 course meal and each course had a, a cartoon that had that, that John felt [00:33:00] was one of the defining early cartoons in the history of cartoons.

Hala Taha: Hmm.

Bill Gurley: And he would, before each course, he would describe why this one mattered most to him. And there was stuff from Japan and there was Steamboat Willie, and all these, these things. And you're like, I mean, that's where I get back to, there's so many of these people that they're, they're that they're at the top of their field that have this like.

Bill Gurley: Just super respectful understanding of the history.

Hala Taha: Mm-hmm.

Bill Gurley: And I have to, I have to believe that it matters. I, 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.

Hala Taha: Yeah.

Bill Gurley: But also the, it, it's so differentiating.

Bill Gurley: I mean, just imagine yourself, and I think we could pick any field. Imagine, you know, you're in a, uh, let's say you're interviewing for a sales job.

Hala Taha: Mm-hmm.

Bill Gurley: And you have found, and you could do this with ai, in five minutes you've found the 10 like [00:34:00] people who were the originators and thinking about sales execution and sales techniques.

Bill Gurley: And you start dropping that. You know, in the interview, like, no one else is gonna do that. Yeah. None of the other people, and someone's gonna go like, holy crap, this person really cares. Mm-hmm. Like, you know, they really care about this field.

Hala Taha: Yeah. And it helps you if you wanna be a leader in that field field, re uh, not repeat the same mistakes.

Bill Gurley: Yes,

Hala Taha: that too. You

Bill Gurley: know,

Hala Taha: for sure. You're making sure that you really understand the history. Um, and when I think about podcasting, it's pretty new. It's, so, I guess I would study like TV and radio, right? Sure. If, if, sure. And for ai, what would you study? The internet?

Bill Gurley: Well, I mean, there are some people that have been working on AI for 10 or 20 years. Um, yeah. AI is moving so fast. I think you should spend every last minute just using,

Hala Taha: just using it

Bill Gurley: every, every tool you can. I. You know, I, I've, it is kind of separate from the [00:35:00] book, but I've, I have my, my advice for anyone in any field that's afraid of AI is run at it like, no.

Bill Gurley: Know what it's, what is the edge of possibility for AI in your field? And, and learn how to harness it. Mm-hmm. The same way you talked about what you knew about LinkedIn and whatnot. You have to be that with ai. Yeah.

Hala Taha: Yeah.

Bill Gurley: Like the last thing you want to be as an AI skeptic who hasn't tried any of it.

Hala Taha: Totally.

Bill Gurley: You're, you're, you're, you're on the firing line if that's you.

Hala Taha: And don't stop at chat. GBT. There's so many other apps out there. I know. I, I myself, like, I'm addicted to chat GBT. It's like trying to just

Bill Gurley: brain out. No. Try 'em all and, and, and ask, you can ask them this, but it is kind of, uh. Circular, but, but what is the edge of AI usage in your field?

Bill Gurley: And understand what that is and play around with it there. And I, I meet people, especially older people, I'm almost 60 so I can, I guess I can pick [00:36:00] on old people, but they like, they say, oh, AI doesn't work. I tried it and they gave me the silly area and they're proud that they found the error. And I'm like, have you tried it, you know, a year ago?

Bill Gurley: Like, have you tried it two years ago, a year ago and today?

Hala Taha: Mm-hmm.

Bill Gurley: Like, and tested whether it's still making that error. 'cause it's getting better constantly.

Hala Taha: Mm-hmm.

Bill Gurley: You know? And so if, if, if anyone's out there who's just like skeptical or naive, I, you know, I think that's really dangerous.

Hala Taha: I totally agree.

Hala Taha: And um, we were just talking about how it, 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?

Bill Gurley: Yeah. Um. 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

Hala Taha: Oh, I'm on it.

Hala Taha: Yeah. I, I can't do anything without it anymore. Right. I always wanna pop.

Bill Gurley: Right, right. It's become the number one way you start to learn about something. Mm-hmm. Yeah. [00:37:00] Me, me too, me too. I, 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 which you do, oh my God, I, it should allow me to separate from the field.

Bill Gurley: Like this should be my finest moment. Not something to be afraid of.

Hala Taha: Do you ever feel like AI is changing the way that your brain works?

Bill Gurley: Good question. Um, um. I think I'm constantly asking myself that question, and I, and I'm s like, I don't take anything as a truism. Yeah. So I, I try again, but it, it's possible.

Hala Taha: Yeah. I, I say that because sometimes I'm like, I feel like in the past I would've, uh, you know, now I'm always like, you know, bouncing back and forth between AI and my work. Right? Yeah. And in the past I would've, I feel like, well, I probably would've thought of this [00:38:00] on my own without bouncing back and forth between something.

Hala Taha: And now I feel like I always need to bounce myself better. Yeah. That's a, you know what I'm saying?

Bill Gurley: A yeah. Yeah. You might be, um, limiting your own imagination by not giving yourself enough free time to ponder the

Hala Taha: possibilities. I feel like it needs to be like, time box. No, no. Ai use your brain. You know?

Bill Gurley: Yeah. I think that's a good, I think that's a good call out.

Hala Taha: Okay. So let's say you're mid-career.

Bill Gurley: Mm-hmm.

Hala Taha: 40 years old. Yep. Made money, but you have responsibilities.

Bill Gurley: Yeah.

Hala Taha: What do you do if you find that you are not living out your passion? Like where what? What?

Bill Gurley: We have a chapter in the book called Never Too Late, where we highlight a number of people that had their defining career start.

Bill Gurley: After 40. Um, I don't think it's easy for the reason you bring up, which is commitments. Um, one of, one of the people we profile in that chapter is Sa Khan, uh, who created the Khan Academy. Yep. And Saul was in a, [00:39:00] worked at a hedge fund, was doing rather well, I think fortunately his wife was working also. And, and, um, he was doing something on the side helping a family member overseas that led to the creation of the tools that became Khan Academy.

Bill Gurley: And, um, he, he felt drawn to doing it as a nonprofit, which makes that math even harder. Um, but his wife was supportive of him trying it for a year. They literally said, let's do it for a year. So he walked away. Mm-hmm. And once again, I think having the flexibility to do that as part of living within your means, um, they couldn't have done that otherwise.

Bill Gurley: Yeah. Um, but look what happened. I mean. I'm, there are very few people on this planet that have changed the world as much as, as Saul Khan has.

Hala Taha: Yeah.

Bill Gurley: Like

Hala Taha: we actually, and I interviewed him a a little while ago.

Bill Gurley: Wonderful guy.

Hala Taha: Yeah.

Bill Gurley: One of the guys on the acquired podcast came up with this idea, which I really love, called Side Hustles.

Hala Taha: Yeah.

Bill Gurley: And he says, while [00:40:00] 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.

Hala Taha: Mm-hmm. And especially has nothing to do with the job. Yeah.

Bill Gurley: Right. And so he gives examples of three different stops in his career where he intentionally did something else on the side.

Bill Gurley: One of 'em was at Microsoft. He started Microsoft Garage, which was this community of, of entrepreneurs using Microsoft projects. And that G let 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.

Hala Taha: Mm-hmm.

Bill Gurley: And then when he got to Madrona.

Bill Gurley: He started a podcast.

Hala Taha: Mm-hmm.

Bill Gurley: On the side, he said to the people at Madrona, can I do a podcast from the VC firm? They said, yeah, sure. And of course now he's, uh, he's one of the most successful podcasters on the planet and loves what he's doing. But, but the experimentation of this side hustle gave him exposure to new things.

Bill Gurley: Um, and, and in, in both of those cases in a very [00:41:00] differentiated way. So that's another thing you could do if you're 40 Totally. And feeling trapped. You know, ask yourself, could I, would the, would the career? I'm in the company I'm at, let me go do this other thing.

Hala Taha: Totally. Well that's, that's what I did too.

Hala Taha: My podcast started as a side hustle while I was working at Disney.

Bill Gurley: There you go.

Hala Taha: Right. And me and, uh, the acquired host, what's his name?

Bill Gurley: Uh, Ben Gilbert.

Hala Taha: Ben Gilbert. We are competing for an iHeart podcast. Oh, no. Award for business and finance. No, it's not up to, it's up to industry panel to decide, but yeah.

Hala Taha: Uh, you know, be 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. Yeah. What's the difference between the two?

Bill Gurley: Well, I find a lot of people, I mean a lot of, a lot of, uh. Uh, people that write personal development books talk about mentors.

Bill Gurley: Mm-hmm. So it's not a unique, uh, topic, but what I find happens most in the real world is people get too [00:42:00] greedy too early and they, they say, well, I, they, they either cold call someone they shouldn't.

Hala Taha: Yeah.

Bill Gurley: Um, that's, that's out of reach. Or they get frustrated because, oh, I could never get this person to be my mentor.

Bill Gurley: So, so they kind of give up and, um, 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 gonna cold call tomorrow. There are people that you can watch from afar. Mm-hmm. You can study what matters to them.

Bill Gurley: You can watch 'em on a podcast or on YouTube, and you can learn and you can follow their career. Now one of my profiles is of, of Danny Meyer, the great restaurateur in New York. And he did this when he decided he was gonna be a restaurateur, he made a list of, it was either 10 or 12 of the people that were changing the restaurant industry.

Bill Gurley: And he kept a notebook of 'em and a profile of 'em, and he studied what they did. Um, he, he ended up meeting every single one of 'em along the way, but he didn't [00:43:00] cold call 'em at the beginning of the journey. And I think that's important. And if you study 'em the way we just described one day, when you do meet him, you know so much about

Hala Taha: him.

Hala Taha: Yeah. Back to the history then. The history.

Bill Gurley: Yeah. Right. That it's easy to, to kind of make the connection, like, and you don't do it. So what I recommend is you do that kind of studying aspirational mentors, and then for your, for your in-person mentors, you just need to be more realistic, like about how far you reach.

Bill Gurley: Yeah. And, and the truth of the matter is. People in the second tier get almost zero ask. Mm. So if

Hala Taha: you They're more willing.

Bill Gurley: Yeah. They're gonna be more willing, they're gonna be flattered that you ask them. So you know, whoever it is you think you want, like just go one or two levels down and you'll probably find someone who's thrilled that you reached out, super honored.

Bill Gurley: Mm-hmm. And you're much more likely to get help.

Hala Taha: Yeah. 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 [00:44:00] things that you mention is, uh, publicly learning. Like learning in public. You did this with the blog that you started.

Hala Taha: Yes. A lot of creator entrepreneurs nowadays. Yeah. Who are building personal brands, they're also learning publicly and there's so much benefit to that. Can you speak about that?

Bill Gurley: Yeah, and I, 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.

Bill Gurley: And you know. Ironically, Warren Buffet has historically done this every year. Mm-hmm. There's a great bond investor named Howard Marks who writes out his thoughts. There. There are two benefits to it, straight up. One, when you write things down and, and you know you're gonna publish 'em publicly, you really test the, all the theories in your brain.

Bill Gurley: You really work things out. You [00:45:00] accomplish what you are afraid you're not doing.

Hala Taha: Mm-hmm.

Bill Gurley: By just using AI because you, you really don't want to there to be inconsistencies. So you really think through it and you give your brain a a really good once over, I think. Mm-hmm. On the subject matter. And then the second thing is it differentiates you.

Bill Gurley: You, you'll 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, um, you're gonna create avenues. For networking.

Hala Taha: Yeah.

Bill Gurley: Um, 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.

Hala Taha: That's true.

Bill Gurley: Yeah.

Hala Taha: But I think in most cases, I think it, it, it does help.

Bill Gurley: It, it could be, it can be very, very helpful.

Hala Taha: 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.

Bill Gurley: Yeah.

Hala Taha: How have you been generous in your career?

Hala Taha: Can you give us some examples or [00:46:00] other, uh, you know, personas and stories about people being generous?

Bill Gurley: So this topic. Um, I think comes up in the chapter we have on peers called Embrace Your Peers. 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, uh, it's not well studied in the, in the literature.

Bill Gurley: 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, the infinite versus finite games, so many, 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.

Bill Gurley: And in most career fields, that's just not how it works. Mm-hmm. Like there's hundreds and hundreds of winners and if you find a way to connect and lock arms with your peers and, and share with each other, be vulnerable with each other, you just get [00:47:00] a massive lift. Mm-hmm. And. Um, there's a, there's a great story in the book about Mr.

Bill Gurley: Beast and when he was starting his journey, which is probably similar to where you were getting into podcasts, when he was getting into YouTube, there weren't, it wasn't a field yet.

Hala Taha: Yeah.

Bill Gurley: Like, and he found three other people that were on that same journey, you see. And they were on 16 hour Skype calls all day long.

Bill Gurley: And he, he, 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.

Hala Taha: Yeah.

Bill Gurley: 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.

Hala Taha: Mm-hmm.

Bill Gurley: Like almost defacto because the stuff they were learning was so new and relevant and, and, and, and executable, you know, that you could go win if you knew these things. And they were discovering 'em for the very first time. And I, the phrase sharp elbows, I have worked inside of organizations where there are [00:48:00] people.

Bill Gurley: That just aren't good peers. Mm-hmm. You know, they hog the limited equipment. They, you know, they kiss up, they, you know, you, you can tell who these people are. And I would just say stay far, far away from 'em. And then the other element of this is get over the notion that you have some kind of proprietary knowledge in your head.

Bill Gurley: And this goes part and parcel with the public sharing stuff. Like even if you have something in your head that's, that, that's so compelling and so wonderful, like it probably won't be that way 60 days from now.

Hala Taha: Mm-hmm. Like,

Bill Gurley: and I just think the benefit of open sharing. Um, far outweighs some advantage you're gonna have by keeping knowledge proprietary to yourself.

Hala Taha: Totally. And the value of, uh, you know, what you get in exchange for that is a personal brand.

Bill Gurley: Yes.

Hala Taha: You know, which is so valuable and it's, it's an asset in itself.

Bill Gurley: Absolutely.

Hala Taha: The information's gonna get stale, but your personal brand is just [00:49:00] gonna keep growing. Right.

Bill Gurley: No doubt. The book really has two target audiences.

Bill Gurley: Mm-hmm. 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 wanna do, or always wanted to chase a dream or, and didn't know how and, and, or, and, and or someone who just really needs a extra push to go do that. It's for all those people.

Bill Gurley: For sure. 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, I hope they take the time to read it. Um, 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 mm-hmm.

Bill Gurley: Um, I do think that the natural tendency is to not kind of be supportive and give the right push at the right moment. Yeah. And I know you had, uh, Matthew McConaughey on. Mm-hmm. And in his book, green Lights, he tells this story of, um, he's gonna, [00:50:00] he's told his father his whole life, he's gonna be a lawyer, and he decides that he now wants to switch to film school and he's afraid to tell his father.

Bill Gurley: And it's a, it's a great scene. It really. To me speaks to the purpose of this book. Um, when he finally gets to the gumption and tells his father, his father says, well, don't half as it. And, and, and in the book, McConaughey says, it was the last thing he expected, but the most valuable thing his father could have said.

Hala Taha: Mm-hmm.

Bill Gurley: And gave him permission, responsibility, a push, um, told, basically told him, well, if you're gonna go do it, be really great at it. Mm-hmm. And obviously it launched an incredible career, but, but h how do. For all that second group, how, how can I help you be as good as McConaughey's dad was at that moment?

Bill Gurley: And, you know, sense that there's a sparkle of, of interest mm-hmm. And curiosity and help it flourish.

Hala Taha: Yeah. 'cause to your point, [00:51:00] it's not like parents wanna do like bad for their children, pushing them to become a doctor or something. You're, you think you're doing good. Right. You do. So, so it's really important.

Hala Taha: And a lot of people, I have a lot of friends that feel very resentful of getting pushed into certain careers. So you don't want that to happen down online.

Bill Gurley: Right. And, and you, I, this one father who saw the original speech, sent me this email. I almost started crying and he, he told me a whole story about his child had been going in this direction and really wanted to go another one.

Bill Gurley: And the, 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.

Hala Taha: Mm-hmm.

Bill Gurley: You know. Yeah. And that, that's just gotta be such a wonderful feeling, you know?

Hala Taha: Mm-hmm. And I have to say, like, I read two books a week, you know, because of my job.

Hala Taha: Right? Yeah. So I loved your book. I feel like there, thank you

Bill Gurley: so

Hala Taha: much. 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 know, need to know the history of [00:52:00] media. Yeah.

Hala Taha: And I think that will just help me as I build this company. No doubt. No doubt. So thank you for Yeah. Creating this book.

Bill Gurley: Thanks for reading.

Hala Taha: You started in vc. Mm-hmm. You were behind so many, you know, huge companies. Yeah. Zillow, uh, Uber, stitch Fix, so many big companies. Um, you also started your career at the start of the.com bubble.

Bill Gurley: Mm-hmm.

Hala Taha: And you saw that whole thing. Explode.

Bill Gurley: Yep.

Hala Taha: How did that actually change the way you think about, uh, investing in companies change the way you think about sustainability for companies? Yeah. Um, talk to us about those fundamentals.

Bill Gurley: It, I think it, oddly in, in retrospect, it was fortunate that I, I, so I started my venture career in 97 and things were on fire by 99, but by 2000 they were falling apart.

Bill Gurley: Mm-hmm. And, um, I, that's not enough time for me to have been successful because from [00:53:00] 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 anyone to judge whether I was good at it or not.

Bill Gurley: And when the bubble burst, everything slowed down. Um, when, when you're in a bubbly time, and we may be right now with ai, um, people do silly things. Like they, they, they spend money in ways they shouldn't. They run TV ads and Super Bowl ads mm-hmm. And all these things, things that don't usually work. Um, they get very speculative.

Bill Gurley: And I found the bubble part to be uncomfortable. Mm. But I found the post crash part to be very sane and rational. And so it was, I just thought, and it was slower, which for someone building their career and, and also the charlatans leave town. So one of the things that happens anytime there's a technology wave is it, [00:54:00] it people get rich quick and then a whole bunch of people see people getting rich quick and they rush in.

Hala Taha: Mm.

Bill Gurley: Fools rush in. And those people, I like it when they're not around. Um, but they come in every wave. So it is what it is.

Hala Taha: With ai, you know, um, I have a lot of founder friends. Yeah. And some of them say like, you know, this year they're only investing in AI companies. Yeah. And it's really hard for them to get funding, even if it's a great company, um, with great unit economics.

Hala Taha: Yeah. And, and everything like that. They can't get funding. Um, do you think there's a problem with the investment in AI and do you think that's a bubble?

Bill Gurley: I think well, uh, there's a whole bunch in what you just said, but let, let, let, let me start, let me start with this high level, uh, point that I'd like to make.

Bill Gurley: Um, this professor Carlotta Perez. Uh, recognize something that I think is really important to understand, which is when there is a wave, there is [00:55:00] massive wealth. There is ma, there's disruption and the deck chair switch and people make a lot of money. And that's already happened here. 'cause OpenAI and Anthropic are paying their employees secondary earlier than anyone ever had.

Bill Gurley: Mm-hmm. So the money's being made, it's being put in people's pockets and that's gonna attract speculators. And, and we had here in Texas, we had a SPAC from the former governor, Rick Berry or a data center had already went up and down, so

Hala Taha: mm-hmm.

Bill Gurley: Like speculators rush in. And so bubbles and. Waves are actually always happening at the same time.

Bill Gurley: So some people will argue, oh, if you say it's a bubble, you're anti ai. No, I make the argument say, uh, the fact that it's real is why there's a bubble. So I, I think, I think it's important to know that. Mm-hmm. Um, 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 [00:56:00] want to take a meeting uninterested in anything on ai.

Bill Gurley: 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, I think it's unquestionably true. Like, there's just zero interest.

Hala Taha: Yeah.

Bill Gurley: And so, um, that's a tough call for someone that's in a business that may have good unit economics, that's not ai.

Bill Gurley: Um, what would my advice for them be? Um, you know, make sure you understand the edge of AI in your field. Like I said earlier, there may be things you could, you know, that I, 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 mm-hmm. You, you don't want to, you don't, if it feels painted on, the people will sense that, so.

Hala Taha: Mm-hmm.

Bill Gurley: And then if that's not an avenue for you, you know, try and new sweat equity to get to profitability and own way more of this thing than you would otherwise.

Hala Taha: Mm-hmm.

Bill Gurley: You know, and I think one of the [00:57:00] biggest mistakes a lot of founders 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.

Hala Taha: Mm-hmm.

Bill Gurley: And your ownership's gonna get way diluted. And the number, the, the, the number one type of company that, 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. Mm-hmm. Like, 'cause now the venture capitalist needs a much bigger outcome.

Hala Taha: Yeah.

Bill Gurley: And so if you can. Scrape by, you know, and I know it's hard. Tito never took venture money. He owns a hundred percent of this massive business.

Hala Taha: Wow.

Bill Gurley: You know, and so, uh, if you can do it, you know, try and do it. And, and the, the, the big benefit of doing it that way is your ownership will be a lot higher.

Hala Taha: Hmm. I wanna, uh, do like a little mini MBA [00:58:00] for Okay. The entrepreneurs tuning. A lot of people who are listening right now are like, just starting as entrepreneurs. Yeah. Or they've got like, you know, maybe a million dollar company. Yeah. Or, you know, they're just kind of starting out. They've got a lot of potential.

Hala Taha: And so, you know, you've moved away from, or in the past, you've mo you moved away from this like grow at all cost model and investing in companies that just wanna grow. And you were looking at unit economics. Yeah. So let's start there. Unit economics, how can you explain that in plain language for our listeners?

Bill Gurley: Well, I suspect that the smaller entrepreneurs that are living hand to mouth on cash flow are pretty in touch with their unit economic, it's the, but

Hala Taha: they might not know

Bill Gurley: what it's the called the guys that raise a hundred million of venture capital that lose touch with unit economic. Yeah. It's just a matter of understanding what are the true variable costs associated with the product or service that you're selling.

Hala Taha: Mm-hmm.

Bill Gurley: And being honest with yourself. Even despite what the accounting might be, the [00:59:00] requirement for gross margin, but what are the true variable costs? So that could include selling and customer service and all these things. Mm-hmm. So that, you know, the, the marginal, uh, contribution, ideally from a cash flow perspective that you get with each turn of the crank.

Hala Taha: And it's basically trying to figure out do we make money on a customer compared to how much it costs to acquire them and serve them? Like, are we actually making money on this

Bill Gurley: customer? No, no doubt. And, and, and you know, it may be different based on, uh. The type of customer, the size of customer, the source of the lead, like all those things might be different.

Bill Gurley: Mm-hmm. You know, you may find, I've always found it to be true. When you are aggressive with marketing, you have much higher churn. Mm-hmm. Like, you get customer. And whereas if you can earn a customer through PR or word of mouth, they typically stay around longer. And so they're, that's an even tougher mathematical problem.

Bill Gurley: 'cause you're trying to calculate, um, unit economics over the [01:00:00] lifetime of a customer.

Hala Taha: Mm-hmm.

Bill Gurley: Early on. Yeah. And

Hala Taha: I, I know you have a problem with LTV traditionally, right?

Bill Gurley: I think people get into more trouble with the LTV formula than they do, um, then they get success out of it.

Hala Taha: Why is that?

Bill Gurley: Well, I, I wrote it is one of my favorite blog posts I've ever written.

Bill Gurley: So if someone wants to go deep, uh, it's called the Dangerous Seduction of the LTV formula and it's easy to find on Google. Um, you know, it's not, um. An erroneous way to measure something. It's actually a smart way to measure something, but it's not a strategy.

Hala Taha: Mm.

Bill Gurley: And I think people get lost in thinking it's a strategy and, and especially if they're someone who's growing their business on a heavy marketing spin.

Hala Taha: Mm.

Bill Gurley: And I just in general, I would, you know, the blog post does all this, but I would push people, you know, really, really think about could I be winning customers with pr? Could I be winning customers with, with, with non-paid social? Could I be winning customers [01:01:00] with product-led growth? Which is a great, uh, um, uh.

Bill Gurley: A great way to think about your product bringing you customers itself. Like all those things are gonna create companies that are worth 10 times more than someone that's spending heavy on the marketing spend.

Hala Taha: I've never heard of product led growth. Can you explain that?

Bill Gurley: Yeah. Um, and, and by the way, you could talk to AI or you could, you know, do Google searches and find people that have written.

Bill Gurley: Extensively about product-led growth, but it's, is there a way to build into the product, um, the ability to find incremental customers? So could you, you know, one of the things that, that I've been pushing the Stitch Fix team to do that I hope will come out soon is here's, here's, here's your next fix.

Bill Gurley: Share it with your friends and let 'em vote on what you should keep.

Hala Taha: Mm.

Bill Gurley: Now you're exposing the company to people through the product.

Hala Taha: Yeah. You're letting the customers share it [01:02:00] themselves.

Bill Gurley: 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.

Bill Gurley: Mm-hmm. Like so. It's not just a consumer idea.

Hala Taha: Yeah.

Bill Gurley: Thinking

Hala Taha: of ways that your customers through the product can bring in leads, customers, lead leads.

Bill Gurley: Yes.

Hala Taha: Without you paying any

Bill Gurley: money. Exactly. Yes, yes, yes.

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Hala Taha: Free. So if, uh, let's say you were mentoring me, okay. My company makes $7 million a year now.

Bill Gurley: Okay.

Hala Taha: Um, what would you wanna see in my, uh, dashboard in terms of metrics? Like what kind of metrics would you wanna see on a very simple dashboard baseline?

Bill Gurley: One, one question I would ask you before I, I went there is, um, you know, and, and I, this doesn't, I, I don't want to ask you questions you don't want to answer, but like, do you see yourself running this company independently 30 years from now?

Bill Gurley: Or do you see yourself potentially selling and

Hala Taha: selling?

Bill Gurley: Yeah. [01:06:00] And so, 'cause that, that matters a little bit because you need to think about who the natural acquirers would be and how they, why they would fit it in. How do they measure their own business? Mm. You know? And so will this look appealing to them through that lens?

Bill Gurley: Those kind of things. Um. You know, some of the stuff you talked about, unit economics, like you wanna understand is, is it'd be great if the marginal customer is more profitable than the one before 'em. So that's a test of whether you're starting to get scale in your business, right? Um, one exercise that I heavily encourage all founders to do, no matter how much the size of the business has forced yourself to do a three, three to five year forecast, and you don't have enough information to really do it, which is why people push back, but it forces you to ask the right question so that you can prepare.

Bill Gurley: And if you, you know, if you want to grow, you know, a lot for five years, your business can be pretty big, [01:07:00] you know, and so having, 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.

Bill Gurley: That the majority of founders do not naturally do.

Hala Taha: Mm-hmm.

Bill Gurley: Like, it's not something they want to do even, but they should do.

Hala Taha: Is there like one metric that you look at that's like, judges, whether a company's healthy or not?

Bill Gurley: I mean, there's so many different business. I think certain businesses, there's a, like in,

Hala Taha: like every business

Bill Gurley: has their own, own me

Hala Taha: that matters.

Bill Gurley: Everyone agrees. Net dollar retention is the one that matters most.

Hala Taha: Mm-hmm.

Bill Gurley: But that doesn't apply to everything.

Hala Taha: Yeah.

Bill Gurley: So, um, so it's kind of dependent on the

Hala Taha: business. So again, you gotta learn your industry. Yeah. And what matters in your industry. Exactly. Okay. So let's play a game. It's called billionaire, ROI Ranking.

Hala Taha: Okay. This is gonna put everything that we just talked about together. I'm basically, am

Bill Gurley: I the first person to play this game, or

Hala Taha: a lot? Oh yeah, I have new games for, okay. For everyone. Okay. [01:08:00] So basically you're gonna rank. Each thing one to 10, if it's a good investment for the entrepreneurs. Listen again.

Hala Taha: Okay. And it's gonna be stuff that we talked about. Yeah. Some things we might have alluded to. And you can, you know, give some color on why you ranked it one to 10. So is it a good return on our investment? Okay. Okay. First one is reading and learning every day.

Bill Gurley: Oh, yeah. Uh, nine. Nine out of 10, maybe 10. And that's partially because, um, I've always felt that way, but also the people I respect the most feel that way.

Bill Gurley: I think. Um, Toby, the CEO and founder of Shopify was interviewed in the past 30 days. And this was the number one thing he said, like, just as an example. Hmm. You know, and Buffet says the same thing, you know.

Hala Taha: Okay. Moving to where the action is.

Bill Gurley: Yeah. This is a, um, so between the talk that I gave at University of Texas and the book [01:09:00] form of the speech, we added a, a sixth tenant and it was, it was moving to where the action is.

Bill Gurley: Um, 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.

Hala Taha: Mm-hmm.

Bill Gurley: And if you're a songwriter, that means Nashville. If you're a founder, that means Silicon Valley. If you wanna work in finance, it means New York City.

Bill Gurley: And the, it, it's the number of what it really does is the number of chance. Positive things that are gonna happen, I'd probably use the word optionality, just goes up 20 x. Hmm. Like, you're just gonna run into so many people doing the same things. And like, and if, if, if you go to a job and it doesn't work out, there's so many other people hiring for that same thing.[01:10:00]

Bill Gurley: Like it just really changes the dynamic. Mm-hmm. And, um, it probably is important that you're someone that is self-motivated, but, but, uh, eight outta 10 for most fields. There are a few field, if you're a coach, you can't really do that. Mm-hmm. Um, there are some fields where you can do it virtually subreddits and things like that.

Hala Taha: 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 happened naturally when you,

Bill Gurley: that's a great word.

Hala Taha: Yeah.

Bill Gurley: Yeah.

Hala Taha: Um, building a personal brand,

Bill Gurley: I think that that's field dependent. Um. I, it's always helpful. I mean, I think there's a, I, I'd probably rank it below the others, let's just say six out of 10.

Bill Gurley: Um, there's always a risk that you, um, become someone who's somewhat performant on the brand side and maybe not developing the real skills underneath it. Mm. Which would, could have a negative ramification or someone could view you as shallow if, if [01:11:00] you, you know, were doing that. So, um, and not all fields. I mean, there are certain fields where I think it's harder to do.

Bill Gurley: Um, but I think if you can, it's very rewarding.

Hala Taha: Hmm. Spending heavily on ads.

Bill Gurley: Well, I'm, I, you know, I, I, I'm somewhat negative on that, but, but I, it keeps your, your, your machine running, so I,

Hala Taha: that's not the truth.

Bill Gurley: Yeah, I would, I, I I don't like it. Um, two,

Hala Taha: why is that?

Bill Gurley: There's a great new book coming out by, um, David Epstein.

Bill Gurley: Um. Called Inside the Box where he talks about how constraints drive creativity. And I've always felt that if you're starting a business, the easiest way you could possibly get a customer, the, the first way the most ignorant person would assume to go get a customer would be to run a Google ad.

Hala Taha: Mm-hmm.

Bill Gurley: Like it. And, and I don't think people are reflective of enough to say, [01:12:00] wow, I'm starting at the very bottom. Like, I'm doing the simplest, that's the least creative thing I could possibly be doing. Mm-hmm.

Hala Taha: And the hardest,

Bill Gurley: the most, most obvious. Mm-hmm. And, and I think if you ha run an exercise, which I mentioned in that blog post where you say, set the market, set the marketing budget, the advertising budget to zero.

Bill Gurley: Now what are you gonna do? Mm. And go run that exercise. You're gonna come up with so many really creative, wonderful things that are highly differentiated.

Hala Taha: Yeah.

Bill Gurley: Um. So that's why I think that

Hala Taha: and paid ads are so they paid ads don't work also if you don't have a brand or credibility. Yeah. Because they're gonna go Google you.

Hala Taha: Yeah. And there's not gonna be anything there because you started with paid ads. Um, okay. Networking events and conferences.

Bill Gurley: Um, I'm a, I'm a big believer that it can be very, very helpful to you. Mm-hmm. Um, I think it can help you with, uh, both peer and mentor development. Um, [01:13:00] 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, 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 Del Conte.

Bill Gurley: 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, and this is one of those fields. Where if you're in the epicenter, it may not matter as much, but he was in a field where everyone's distributed and this was the only opportunity for those chance moments.

Hala Taha: Mm-hmm. So it's like going to the action, but for a point of time.

Bill Gurley: Yeah. Yeah. And, and that group of friends, um, stayed in touch, started a text group, started sharing ideas, and they expanded a little bit over time, but they're now all D one athletic directors. Amazing. They all rose to the top. [01:14:00]

Hala Taha: So at seven R eight?

Bill Gurley: Yeah. Yeah. Seven

Hala Taha: R

Bill Gurley: eight, but, but field, field de, you know, field dependent. Yeah. Yeah.

Hala Taha: Raising as much money as possible.

Bill Gurley: Well, um, I've, I've historically been very negative on this, so I, 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 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, um, money.

Bill Gurley: Mm-hmm. And that is currently the way things happen. And, um, you end up with these situations where each competitor is armed with 400, 500, $600 million maybe more. Um, and. It's not, you know, it's, I, like I say, it's not your father's venture [01:15:00] capital. This is a sport of king's world we've evolved into, and, um, it's fight to the death.

Bill Gurley: I, I, I live through it with the Uber Lyft situation, but it, I wouldn't wish it on anybody, but it is the reality right now. And if you sit back and say, well, I'm not gonna be, I'm not gonna raise as much money. I'm gonna be, you know, disciplined. Well, if, if, if you're the disciplined one and there's six players with $500 million each hiring salespeople, you're, you're not gonna matter.

Bill Gurley: Mm. So the game on the field has kind of forced people to do this thing. I don't love.

Hala Taha: Yeah. Okay. Next one. Getting an BA.

Bill Gurley: Yeah. I'll say seven, but, but part of it's me reacting to the fact that so many people in the entrepreneurial world make fun of it. There's a lot of people that shit on MBAs in, 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.

Hala Taha: Mm-hmm.

Bill Gurley: Which I think is really [01:16:00] dangerous. You know, if you don't know how to do a forecast on Excel spreadsheet, that could be a real problem. Hmm. And so I just worry that the vilification of it. Is is not good for the founders themselves because there are resources they need to understand. Mm-hmm. It doesn't mean they have to go get an MBA, but they should read Michael Porter's competitive strategy.

Bill Gurley: They should read Innovator's Dilemma. They should read Crossing the Chasm. They should know how to organize a sales team. They should like, 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, but don't dismiss all of the learning as you, you know, crap on the notion of an MBA.

Hala Taha: Mm-hmm. A lot of people, a lot of people don't align to it. Well, now you can just learn everything online. To your point. That's true.

Bill Gurley: You might not, you might not need to go. The subject matter is important.

Hala Taha: Totally.

Bill Gurley: Yeah.

Hala Taha: Um, so let's move on to leadership. I had Kevin O'Leary [01:17:00] on Okay. The show.

Bill Gurley: Yep.

Hala Taha: And he's another billionaire.

Hala Taha: I think.

Bill Gurley: I, I, I don't know,

Hala Taha: but I'll take you work for it. Just about, just about a billionaire. Um, 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.

Bill Gurley: Yeah.

Hala Taha: And it reminded me when I was 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.

Hala Taha: Yeah. Take us back to those moments, to what was happening and, um, how were you able to kind of take emotion out of it and just be the best member of the board that you could be for Uber?

Bill Gurley: One, one of the things that I would push back on with what Kevin said is the, the, the best CEOs that I've talked to, um.

Bill Gurley: Very much a lead with the heart and have a, I say a passion for leadership, that [01:18:00] that includes feeling like a shepherd of the flock. And so I, I push back on that a little bit, like broadly against business. Um, the situation that, 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.

Bill Gurley: And, um, 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. 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, um.

Bill Gurley: And by the way, it wasn't, I, I think history in the press has made it out to be me. There were five investors that worked together and signed this [01:19:00] letter. So it wasn't just me, but, um, I think that there were a number of people that were concerned that a change was definitely gonna happen, but if you let it happen through the legal world or the government making a change, it was gonna be six months to 12 months later and the erosion was gonna be even more.

Hala Taha: Mm.

Bill Gurley: And um, 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.

Hala Taha: Mm-hmm.

Bill Gurley: And if it went away, you know, they have paper marks, they were gonna have to mark it down.

Bill Gurley: Um, and now felt that weight on me that felt like a lot of responsibility. So I've said publicly before, you know it, if, if a venture capitalist does their job the right way, you don't get to that point. Hmm. So the, you know, [01:20:00] the, 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.

Hala Taha: Mm-hmm.

Bill Gurley: 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, yeah. Like our competitors use it against us constantly, but, but.

Bill Gurley: Anyway, that's how I would summarize the whole

Hala Taha: thing. Do you feel like you made the right decision?

Bill Gurley: I, based on where we were at that point in time, yes.

Hala Taha: Mm.

Bill Gurley: Yeah. And Dora's done an amazing job. I mean, to take it from there to $200 billion public company over 10 billion a year, and free cash flow, like from where we were.

Hala Taha: Mm-hmm.

Bill Gurley: Yeah. Unbelievable.

Hala Taha: How do you think about reputation in your career? Like how important is reputation to you?

Bill Gurley: [01:21:00] I think it's really important. Um, in, in, in the venture area, it's probably a nine. Like, 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, um, in venture.

Bill Gurley: Your ability to. Compete for the next deal is everything. And that's either enhanced or hurt by what the world thinks of you.

Hala Taha: Mm-hmm.

Bill Gurley: And, and in venture, that personal brand can shine brighter than the even the, the corporate brand. Mm-hmm. A lot of times. And so you just have to worry about it. Um, if you want to be competitive,

Hala Taha: you've had like a really rare chance of being close to so many, like extraordinary founders mm-hmm.

Hala Taha: Who built really successful companies.

Bill Gurley: Yeah.

Hala Taha: 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,

Bill Gurley: yeah. There's, there's a couple things. Um. They, they [01:22:00] are continuous learners because they're tilting at some new problem on the edge of their field.

Bill Gurley: And there's no way, um, that could be something they learned in school five years ago because, you know, it is like AI right now. Everything's changing so fast. Um. Bezos has said that for his angel investments, he wants to feel like this person's gonna do this no matter what. That there's this drive and, um, commitment to attacking the problem that you, you just can't take 'em off of.

Bill Gurley: Hmm. So that's kind of an interesting notion. Um, I think salesmanship is a requirement that people don't talk about enough. You're, you're gonna raise money, you're gonna recruit people, you're gonna lead your team through bad times. Like you can't do that stuff without being able to sell in some way, shape, or formance.

Bill Gurley: People do it in a variety of different ways. There's people that are rah rah, there are [01:23:00] people that are quietly, but you have to be able to convince people to follow you. Um, and then lastly, I would say many, many startups have some kind of go to market advantage.

Hala Taha: Mm-hmm.

Bill Gurley: Which usually isn't advertising. So they, they've figured out some.

Bill Gurley: Bespoke differentiated way to gain new customers aggressively.

Hala Taha: 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 underestimating or unexpected?

Bill Gurley: 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 'cause everybody's doing the exact same thing.

Bill Gurley: And um, you know, I I think there will be a lot of money made in, in verticals like people who figure out how AI applies to something that's very specific to their world.

Hala Taha: Mm. [01:24:00]

Bill Gurley: Um, and, and at this point in time, coding and legal and probably medical are overfunded by the venture capitalists. So there's not much oxygen in those areas, but.

Bill Gurley: If you can figure out what it means for all the other fields mm-hmm. That are out there, I think there's quite a bit of opportunity.

Hala Taha: So the intersection of AI and your field.

Bill Gurley: Yes.

Hala Taha: Hmm.

Bill Gurley: And knowing what's possible and what that means.

Hala Taha: Bill, this has been such an awesome interview. I end my show with two questions that I ask all my guests.

Hala Taha: Okay.

Bill Gurley: Alright.

Hala Taha: So the first one is, what is one actionable thing our young and profits can do today to become more profitable tomorrow?

Bill Gurley: Um, I'm gonna be redundant with what we talked about. That, that's fine. But I just think it's like continuous learning. Mm-hmm. And like, um, just setting aside time, especially if you're, 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 [01:25:00] to learn something new.

Hala Taha: Mm. And what is your secret to profiting in life?

Bill Gurley: Uh. You know, I, I would say, you know, you asked me a question about why I wrote this book instead of, uh, doing, um, a book about venture or whatever, and there's this great quote that life begins where your comfort zone ends. And I think a new, numerous times in my life, I've been willing to kind of try something different or on the edge or a little bit risky.

Bill Gurley: And many times those have paid off. And so, um. I'm not a kind of a conformist. Like, I like attacking things in new ways. I like learning new things. And so I'd probably say that.

Hala Taha: Hmm. And would you say some of that is like gut intuition? Is that what you're alluding to?

Bill Gurley: I think I use my gut to make the leap and to make the decision to push myself, but the willingness [01:26:00] to move outside the box, to walk away from something, to like try something new.

Bill Gurley: Um, you know, to not be afraid to, to evolve past whatever the current thinking is, is something I've always done. And I, I'm thinking numerous examples in my history where that paid off

Hala Taha: and where can everybody learn more about you and everything that you do.

Bill Gurley: Well, uh, you can follow me on X. That's where I have most of my content.

Bill Gurley: Um, there's websites now for the book. We're launching a foundation alongside the book, I should mention, um, to, for, for those people that want to chase their dreams and might not have the financial wherewithal to do it, we're gonna do grants. We're have an application process.

Hala Taha: Oh, very

Bill Gurley: cool. Um, and do that annually, um, to try and help give 'em that extra little amount that

Hala Taha: you let me know when it launches.

Hala Taha: I'll do some free commercials for you guys. Okay. That's awesome. Some support.

Bill Gurley: That's awesome. Yeah. Yeah.

Hala Taha: Awesome. Well, thank you Bill. Thank you so much for your time. Thanks for

Bill Gurley: having me. [01:27:00]

Hala Taha: Young and profits. 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.

Hala Taha: 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 over time, that obsession compounds into mastery, opportunity and impact.

Hala Taha: Another lesson that really stood out is the importance of becoming a candidate of one. Instead of picking a role off a menu, bill encourages us to design careers and 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.

Hala Taha: That combination of respect for the past and fluency in the future is what makes people [01:28:00] 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 fit.

Hala Taha: 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.

Hala Taha: 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 wanna more behind the scenes, look at my life and more personal stuff, you can connect with me on Instagram at YAP with Hala or LinkedIn by searching my name.

Hala Taha: It's Hala Taha. Huge shout out to my incredible yap team. As always, this is your host, Kala Taha, AKA, the podcast princess signing off.