Bill Gurley: Break Free From Career Regret and Design Work You Love | Career | YAPLive | E387

11:23Bill Gurley: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. And I suspect you consider yourself in your dream job.

11:42Hala Taha:Totally designed my dream career. Like I always tell my audience, my students, like have designed everything that I do. It never feels like work. I love what I do. I'm very, I think I'm very good at it. And it's because I just enjoy what I'm doing. And in your book, you say, we've got to enjoy what we're doing because it's one third of our life, 80 ,000 hours of our life is at work. So talk to us more about why it's so important to optimize our job and do work that we actually love.

12:10Bill Gurley:Well, the book is separated 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. And then the tools are to give people the things they need to go be successful. and the very first thing we talk about is fully understanding what it is you're most curious about and the reason it's so important is if you really want to differentiate yourself you really want to be successful you really want to dent the universe you have to love learning about what you do because if you love learning about what you do and I think the ultimate test is in your spare time instead of watching a Netflix show, you're reading about this thing that you love, you're going to out-hustle everybody else.

13:10Bill 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 going to have a really hard time keeping up with them. And 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. And I just don't think that's how the world works, especially in this modern world where if you want to self-learn and you want to continuously learn, there's so much at your fingertips between podcast and AI and all these things. You're going to get outrun because someone's going to get out on the edge in front of you.

13:55Hala Taha:Yeah. So the old cliche is follow your passion. But you talk more about curiosity over passion. Why, why, why didn't you say passion?

14:03Bill Gurley:The word passion has become trite and it's been said so many times. Some people attack it. And I kind of understand that. Like, you know, it's just been overused. I use the phrase chase your curiosity. Seinfeld gave this great talk at Duke where he used the phrase fascination. That's a good word, too. Fascination is like it indicates something that you just can't stop learning about. Right. You can't stop trying to figure out if you're fascinated with it. And the great thing is, and you're in this place, I was in that place, the learning feels free if you love it.

14:41Hala Taha:Yep.

14:42Bill Gurley:Like you're not sitting there going, oh, my God, I got to go read this thing. Like you want to read this thing. And so if somehow you could measure the negative impact of having to do the work, for people that really love what they do and really are curious about it or fascinated by it, there's no, it doesn't feel like there's work effort put in to the continuous learning.

15:05Hala Taha:But there's not going to be money in everything that we feel obsessed with or that we're curious about, right? So how do people navigate that part of it?

15:13Bill Gurley:Well, one thing, if you flip through the book, one thing you'll notice, and this is one of the reasons why from the video to the book release was six years, because I had a real bias in finding the stories and that I mostly wanted to find people in non-traditional fields for this reason. Like I didn't want to, there's no McKinsey consultants. There's no investment bankers. There's not even really entrepreneurs. It's more, you have a restaurateur and a basketball coach and a hairstylist. And by the way, every one of those characters made a ton of money. They didn't start, every single one of them started it because they loved it.

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

16:33Hala 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 that audience.

16:42Bill Gurley:And by the way, I think it's a fair question that you pose. And I was having a discussion with a career counselor at one of the top universities in the country. And this topic came up. And she said, well, what if they studied English poetry or something? And I'm like, and I gave her the two examples I just gave. And I said, no, I think even there you could probably make a career. And then she goes, but you'd have to work really hard. And I said, yes, yes. Yeah, that's part of it. Yes, you would. Yes.

17:13Hala Taha:Yeah.

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20:40Hala Taha:Yap 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. But this year, I'm taking it to the next level and I've basically implemented a working genius across my entire company. This is not a personality test. It's an actual test that helps you understand the way that you work best. There are six types of working geniuses. Everybody has two geniuses. It's a type of work that gives them energy. Two competencies.

21:12Hala Taha:It's a type of work that you may be good at, but over time it actually drains you. And then you have two working frustrations. 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 then 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 the frustration for me, whereas my business partner has wonder as a strength. I wanted to get things done, rally the group, keep things moving.

21:53Hala Taha: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, and it helped us work better together. And it also helped me uncover gaps within my organization. Turns out that 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. So it really helped us align on gaps.

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22:57Hala Taha:So you can get your team map. And I have a code for that too. It's profiting teams. If you use the code profiting teams, you can get 20 % off all the assessments for your entire team, your entire company. Highly recommend it. Again, that's workinggenius.com. Use code profiting or profiting teams to get 20 % off. 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 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.

23:27Hala 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?

23:34Bill Gurley:Well, a couple of different things. And we have a whole chapter dedicated to this topic and give, I literally went and studied all the other advice, all the greats had given and tried to like make it a laundry list so that you could try every one of these things. And there's so many different fun little exercises you can do. Dave Evans at Stanford who did Designing Your Life, he talks about create like three to five different profiles and spend a couple hours like writing out each one of them and kind of living with it in your brain and then do with the other, and then you can battle card them, which is an interesting way to really test which one you're most excited about.

24:17Bill Gurley:Your intuition when you do that will typically pick up on one of those. There's a great story in the book. There's a gentleman from here in Austin that spent the first part of his career in seismology, and then he became a mortgage broker, and he's watching a PBS show one night. And they have this idea where you take a sheet of paper, You draw a line down it, you put what you love to do on one side and what you're good at on the other and try and find the middle ground. That gentleman's name is Burt Beveridge. And that exercise led to him starting a spirit company called Tito's Vodka. Oh, wow.

24:54Bill Gurley:The most successful spirit business in America right now. Yeah. And like he the idea to do that came from that exercise. So we have a ton of those exercises here. The other thing that Angela Duckworth talks about a lot is just don't be afraid to move around. You know, and this happened twice in my career. I was in a job. I was doing fine. I was making plenty of money. But I did this exercise in my head where I said, do I want to do this the rest of my life? Like just a moment of reflection. I said, do I want to spend 30 years doing 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.

25:40Bill Gurley:And then I moved on. And I think having the gumption to move on and the confidence to move on is hard, but super valuable if you know you're not there. And I don't regret either of those two stopping points in my career. I built upon them, and they were both relevant. They were both helpful to what I did later. Um, so I think, you know, one thing that's 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 to, to, to pivot down the road. So be careful.

26:19Hala Taha:Yeah.

26:20Bill Gurley:You know.

26:20Hala Taha:I want to talk about pivoting for, uh, mid-career people. I want to talk about young people and how they should, you know, start following their dreams to your point when they have no money saved. But first, I want to spend a little bit of time on your career, too, because I want to understand how obsession played in your career. You started at Compaq. You went to Wall Street.

26:42Bill Gurley:Yeah.

26:43Hala Taha:What did you feel like you were obsessed with that led you down VC?

26:47Bill Gurley:Okay, it's super easy. So, like many people who ended up in Silicon Valley, I had a computer early in my life. So I had a Commodore VIC-20 plugged into a TV, didn't have memory.

26:58Hala Taha:I don't think we know what that is.

26:59Bill Gurley:Yeah, it was early, really early. But I found I liked writing programs. It was, like, very fulfilling. And so when I went to the University of Florida, I got a computer engineering degree, enjoyed that process, and went to work at Compaq, which at the time was a very hot startup in Houston in the personal computer industry. And yeah, so that was the first one. And that was the reason I got there. What happened was two years in, we started the third project from when I had joined. And it looked like the second project, which looked like the first, which is part of what got me wondering if I was going to grow bored doing this type of work.

27:40Bill Gurley:And then 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 once I 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. And so I went to business school, ended up on Wall Street. It was awesome. Being in Manhattan in your late 20s, just fantastic. Met so many great people, met so many great investors, and enjoyed reading about investing, enjoyed being a part of Wall Street. Once again, though, three years in, I just started to think about the job and what I was doing every day and said, do I want to do this my whole life?

28:27Bill Gurley:And came once again to a conclusion, no, I don't. And I had along the way been building up this thought process that I wanted to be in venture capital. And the opportunity came to move to Silicon Valley. And from there, I was able to get into venture. And three years into venture, I didn't have that same discussion with myself. I knew I was in the right place.

28:51Hala Taha:So do you think investing was really your obsession?

28:55Bill 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 all entrepreneurs, how people could ride the edge of what was changing and then become successful. The book Innovator's Dilemma walks through exactly how that works. And then this is a little more kind of personal, but when I was in college, we started going to Vegas and like counting cards and playing blackjack. I do think there was a little gambler mentality in there also. And it was those things combined.

29:33Hala Taha:Interesting.

29:34Bill Gurley:You know, investing, tech, gambling, a little bit, disruption.

29:37Hala Taha:And you put those all together and designed your dream career as a VC investor. Yeah. Yeah. It's putting all of this together.

29:44Bill Gurley:You know, I would say one more thing just because I know you have a lot of, like, founders and entrepreneurs in your audience. Yeah. I think there are certain people that have some form of ADD or they're just highly distracted and they get a lot of satisfaction out of diversity.

30:02Hala Taha:Mm-hmm.

30:02Bill Gurley:And I'm one of those people. Me 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 breadth matters to me. 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 down in the weeds. I've met a ton of wonderful founders who have to have their hands on the steering wheel and want to be in that position. And I think those jobs are complementary to one another. But people, if they get in touch with which one of those people they are, it may impact what career they want to go after.

30:42Hala Taha:Totally, totally. So if somebody is younger and they want to design their dream career, they may want to college, they're in their first job. How do you suggest that they start actually, you know, taking the steps toward independence and designing their own dream career?

31:01Bill Gurley:So we walked through a lot of it in the book, but I think it starts with learning. And once again, it's never been easier, cheaper, more free, more accessible. Information is just like you're so advantaged to do this today versus 10 years ago versus 20 versus 30. Like you'd have to pick up an encyclopedia to learn about something 30 or 40 years ago. It's just insane. So start the learning process. And there's so much great content out there. You know, in any industry, there's typically a podcast or 10 that you can go watch and learn and listen to the best. There's stuff on YouTube. You know, you can talk to AI until you're blue in the face.

31:47Bill Gurley:So you can just infinitely learn. One thing that I think is highly differentiating for someone is to learn the history of their field.

31:56Hala Taha:I was going to say, you call it like the canon.

31:58Bill Gurley:Yes. And most people don't take the time to do it, but it will make you look very differentiated because it shows respect. And I also think there's an element of just bedrock knowledge that's nice to have.

32:12Hala Taha:Yeah.

32:12Bill Gurley:There's an anecdote in the book where there's this world chess tournament and they take a pause and do a trivia contest and Magnus Carlsen wins the trivia contest, which I think is interesting.

32:23Hala Taha:Was he a good chess player?

32:25Bill Gurley:He's the best chess player in the world. But my point is he knew all the history as well.

32:31Hala Taha:Yeah, because he was an expert in his field. So the history was a part of it.

32:35Bill Gurley:By the way, I think there's a barbell thing here. The other way to really differentiate yourself is to know the edge. And so if you, I mean, as silly as it sounds, like if you really know how TikTok works and then you want to break into sales or marketing or PR, like that's hugely differentiating. Like the people that have been in those roles for 10 or 15 years probably don't understand it at all. And so even if, you know, you're chasing a field that doesn't feel like TikTok is the main part of it, it could be highly relevant to what makes you look different as you apply for jobs in those areas.

33:17Hala Taha:100%.

33:17Bill Gurley:Especially for young people, like knowing the edge of these technologies, AI is another one, is just a great way to separate yourself. And if you combine those two, you look really interesting.

33:29Hala Taha:I totally agree with you on that. I can even think about from my own experience, like how I remember when I first started, I actually was in corporate for like a little bit. When I first started corporate, I was 28 years old, never had a corporate job before because I was in radio. I started a blog. I started all these things. I got into corporate and thought I was going to be so behind, but I actually was so much more tech savvy and knew how to hack LinkedIn and got promoted so quickly because I knew more than the other people who started at 23. About the edge. Yeah. Yes. So it's really interesting that you say that.

34:01Hala Taha:I love that idea of actually studying the history of an industry and also like the unsexy knowledge.

34:09Bill Gurley:Yeah.

34:09Hala Taha:Which I think a lot of people miss. Like I think of people who want to be, there's so many people who want to be podcasters, but they don't know how like CPMs work and how podcasters even get paid. And even really popular podcasters don't know that stuff. So talk to us about the importance of learning the unsexy stuff.

34:28Bill Gurley:You know, I had this experience in my life that was really amazing. And, you know, I was fortunate to have it. It doesn't sound like I'm name dropping, but a partner of mine at Benchmark won at auction a dinner with John Lasseter, who was the creative genius behind Pixar. And we went to we got invited to John's house and he has a viewing room there. It was not that big a surprise, but a big one. And they served us a 10-course meal, and each course had a cartoon that John felt was one of the defining early cartoons in the history of cartoons. And he would, before each course, he would describe why this one mattered most to him.

35:15Bill Gurley:And there was stuff from Japan, and there was Steamboat Willie, and all these things. and you're like, I mean, that's where I get back to. There's so many of these people that are at the top of their field that have this, like, just super respectful understanding of the history. And I have to believe that it matters. I think it matters both in terms of, like, a great test as to whether you should even be doing this or not. Like, if that feels tedious, you know, that's not your place.

35:47Hala Taha:Yeah.

35:47Bill Gurley:But also, it's so differentiating. I mean, just imagine yourself, and I think we could pick any field. Imagine, you know, you're in a, let's say you're interviewing for a sales job. And you have found, and you could do this with AI in five minutes, you've found the 10, like, people who were the originators in thinking about sales execution and sales techniques. And you start dropping that, you know, in the interview. Like, no one else is going to do that. None of the other people. and someone's going to go like,

36:18Hala Taha:holy crap, this person really cares.

36:21Bill Gurley:Like, you know, they really care about this field.

36:24Hala Taha:Yeah, and it helps you, if you want to be a leader in that field, not repeat the same mistakes. Yes, that too, for sure. Because, you know, you're making sure that you really understand the history. And when I think about podcasting, it's pretty new. So I guess I would study like TV and radio, right? Sure, sure. And for AI, what would you study? The internet?

36:47Bill Gurley:Well, I mean, there are some people that have been working on AI for 10 or 20 years. Yeah, AI is moving so fast. I think you should spend every last minute just using every tool you can. You know, it's kind of separate from the book, but my advice for anyone in any field that's afraid of AI is run at it. Like, know what is the edge of possibility for AI in your field and learn how to harness it. The same way you talked about what you knew about LinkedIn and whatnot. You have to be that with AI. Yeah. Like, the last thing you want to be is an AI skeptic who hasn't tried any of it. Totally. You're on the firing line, if that's you.

37:36Hala Taha:And don't stop at ChatGBT. There's so many other apps out there. I know I myself, like I'm addicted to ChatGPT. It's like trying to just branch out.

37:46Bill Gurley:No, try them all and ask. You can ask them this, but it's kind of circular. But what is the edge of AI usage in your field and understand what that is and play around with it there? And I meet people, especially older people. I'm almost 60, so I guess I can pick on old people. But they like, they say, oh, AI doesn't work. I tried it and it gave me this silly area and they're proud that they found the error. And I'm like, have you tried it, you know, a year ago? Like, have you tried it two years ago, a year ago and today? Like, and tested whether it's still making that error because it's getting better constantly, you know?

38:25Bill Gurley: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.

38:33Hala Taha:I totally agree. and we were just talking about how it's so important for younger, you know, people to get skills. How do you think AI is changing the way that we acquire skills and how do you think AI is changing mastery?

38:46Bill Gurley:Yeah, I think it's insane. Like, it's such an accelerant. Like, you can learn about anything and I'm probably doing 30 searches a day on it.

38:56Hala Taha:Oh, I'm on it. I can't do anything without it anymore. I always want to pop it in. Right, it's become the number one way you

39:02Bill Gurley:start to learn about something. Yeah, me too. I think it's quite ironic that people feel like, oh my God, AI is coming and my job's at risk. When if you have the gumption to be at the edge of your field and to be really differentiated and have this love affair with what you do, oh my God, it should allow me to separate from the field. This should be my finest moment, not something to be afraid of.

39:32Hala Taha:Do you ever feel like AI is changing the way that your brain works?

39:37Bill Gurley:Good question. I think I'm constantly asking myself that question. And I'm skeptical. Like, I don't take anything as a truism. So I try again. But it's possible.

39:51Hala Taha:Yeah. I say that because sometimes I'm like, I feel like in the past I would have, you know, now I'm always like, you know, bouncing back and forth between AI and my work, right? Yeah. And in the past, I feel like, well, I probably would have thought of this on my own without bouncing back and forth between something. And now I feel like I always need to bounce myself back. Yeah, that's a good question. You know what I'm saying? Yeah, yeah.

40:12Bill Gurley:You might be limiting your own imagination by not giving yourself enough free time to ponder the possibilities.

40:21Hala Taha:I feel like there needs to be like time box, no AI, use your brain, you know?

40:25Bill Gurley:Yeah, I think that's a good call out.

40:28Hala Taha:Okay, so let's say you're mid-career, 40 years old.

40:33Bill Gurley:Yeah. Made money, but you have responsibilities. Yeah.

40:37Hala Taha:What do you do if you find that you are not living out your passion?

40:42Bill 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 after 40. I don't think it's easy for the reason you bring up, which is commitment. One of the people we profile in that chapter is Saul Kahn, who created the Kahn Academy. And Saul worked at a hedge fund, was doing rather well. I think, fortunately, his wife was working also. And he was doing something on the side, helping a family member overseas that led to the creation of the tools that became Kahn Academy. And he felt drawn to doing it as a nonprofit, which makes that math even harder.

41:28Bill Gurley: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. And once again, I think having the flexibility to do that is part of living within your means. They couldn't have done that otherwise. But look what happened. I mean, there are very few people on this planet that have changed the world as much as Saul Khan has.

41:52Hala Taha:Yeah. We actually, and I interviewed him a little while ago.

41:55Bill Gurley:Wonderful guy.

41:56Hala Taha:Yeah.

41:56Bill Gurley:One of the guys on the Acquired podcast came up with this idea, which I really love, called side hustles.

42:02Hala Taha:Yeah.

42:03Bill Gurley:And he says, while you're at a job, they'll probably let you do something else if you're willing to do it in your off hours or whatever.

42:12Hala Taha:And especially has nothing to do with the job, yeah.

42:14Bill Gurley:Right. And so he gives examples of three different stops in his career where he intentionally did something else on the side. One of them was at Microsoft. He started Microsoft Garage, which was this community of entrepreneurs using Microsoft projects. And that led him to a whole different set of connections and networking than if he had just sat there in the job they had defined for him. And then when he got to Madrona, he started a podcast 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 one of the most successful podcasters on the planet and loves what he's doing.

42:54Bill Gurley:But the experimentation of this side hustle gave him exposure to new things. And in both of those cases, in a very differentiated way. So that's another thing you could do if you're 40 and feeling trapped. You know, ask yourself, could I, would the career I'm in, the company I'm at, let me go do this other thing?

43:16Hala Taha:Totally. Well, that's what I did, too. My podcast started as a side hustle while I was working at Disney.

43:21Bill Gurley:There you go.

43:21Hala Taha:Right? And me and the acquired host, what's his name?

43:24Bill Gurley:Ben Gilbert.

43:25Hala Taha:Ben Gilbert. We are competing for an iHeart Podcast Award for business and finance. No, it's not up to, it's up to industry panel to decide. But, you know, may the best podcaster win. There you go. One of the things that you talk about in your book is the importance of mentors. And you talk about local mentors versus aspirational mentors. What's the difference between the two? Well, I find a lot of people, I mean, a lot of people that write personal development books talk about mentors.

43:57Bill Gurley:So it's not a unique topic. But what I find happens most in the real world is people get too greedy too early. And they say, well, they either cold call someone they shouldn't that's out of reach or they get frustrated because, oh, I could never get this person to be my mentor. So they kind of give up. And that's all because I think they stretch too far too early. So what I recommend people do is create a list of aspirational mentors. These are not people you're going to cold call tomorrow. They're people that you can watch from afar. You can study what matters to them. You can watch them on a podcast or on YouTube.

44:40Bill Gurley:And you can learn and you can follow their career. One of my profiles is of Danny Meyer, the great restaurateur in New York. And he did this. When he decided he was going to be a restaurateur, he made a list of either 10 or 12 of the people that were changing the restaurant industry. And he kept a notebook of them and a profile of them. And he studied what they did. He ended up meeting every single one of them along the way, but he didn't cold call them at the beginning of the journey. And I think that's important. And if you study them the way we just described, one day when you do meet them, you know so much about them.

45:14Hala Taha:Yeah, back to the history, learning the history. Yeah, right.

45:16Bill Gurley:That it's easy to kind of make the connection and you don't do it. So what I recommend is you do that kind of studying aspirational mentors. And then for your in-person mentors, you just need to be more realistic about how far you reach. And the truth of the matter is people in the second tier get almost zero ask. They're more willing. Yeah, they're going to be more willing. They're going to be flattered that you ask them. So whoever it is you think you want, just go one or two levels down, and you'll probably find someone who's thrilled that you reached out, super honored, and you're much more likely to get help.

45:54Hala Taha:Yeah.

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50:03Hala Taha:Disclaimer, results will vary. Not all bills or subscriptions are eligible. Savings not guaranteed. Paid membership with connected payment account required. See Experian.com for details. You give so much great advice for people who are really just trying to, like, grow on this journey of being, like, top of their field in a career that they love. And one of the things that you mention is publicly learning, like learning in public. You did this with the blog that you started. Yes. A lot of creator entrepreneurs nowadays who are building personal brands, they're also learning publicly. And there's so much benefit to that.

50:41Hala Taha:Can you speak about that? Yeah.

50:43Bill Gurley:And 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. And, you know, ironically, Warren Buffett has historically done this every year. There's a great bond investor named Howard Marks who writes out his thoughts. There are two benefits to it straight up. One, when you write things down and you know you're going to publish them publicly, you really test all the theories in your brain. You really work things out.

51:23Bill Gurley:You accomplish what you're afraid you're not doing by just using AI because you really don't want there to be inconsistencies. So you really think through it and you give your brain a really good once over, I think, on the subject matter. And then the second thing is it differentiates you. You will find people start reaching out to you, especially in a world that's so connected with LinkedIn and Twitter DM and all this stuff. you know, you start writing, you're going to create avenues for networking.

51:54Hala Taha:Yeah.

51:55Bill Gurley: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.

52:02Hala Taha:That's true. Yeah. But I think in most cases, I think it does help.

52:08Bill Gurley:It can be very, very helpful.

52:11Hala 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.

52:20Bill Gurley:Yeah.

52:20Hala Taha:How have you been generous in your career? Can you give us some examples or other, you know, personas and stories about people being generous?

52:27Bill Gurley:So this topic 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, it's not well studied in the literature. Like, I think I might be one of the first people really pushing on this subject. But peers can be inside your company. They can be outside. But think about it as a co-evolving journey. And the reason I use the infinite versus finite games, so much of what we think about from a strategy perspective comes from finite games that we play, that you play over and over again, and there's a winner and a loser.

53:08Bill Gurley:And in most career fields, that's just not how it works. Like, there's hundreds and hundreds of winners. And if you find a way to connect and lock arms with your peers and share with each other, be vulnerable with each other, you just get a massive lift. And there's a great story in the book about Mr. Beast. And when he was starting his journey, which is probably similar to where you were getting into podcasts, when he was getting into YouTube, there weren't, it wasn't a field yet. Yeah. And he found three other people that were on that same journey as he, and they were on 16-hour Skype calls all day long.

53:47Bill Gurley:And he very cleverly used the Malcolm Gladwell phrase, 10 ,000 hours, and said, we got 40 ,000 hours because we're learning together and sharing. Yeah, that's so smart. And he also said something that I thought was really compelling. He said if a fifth person had been on those calls, they'd have made a million dollars, like almost de facto, because the stuff they were learning was so new and relevant and executable, you know, that you could go win if you knew these things. And they were discovering them for the very first time. And the phrase sharp elbows, I have worked inside of organizations where there are people that just aren't good peers.

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

55:11Hala Taha:Totally. And the value of, you know, what you get in exchange for that is a personal brand.

55:17Bill Gurley:Yes.

55:17Hala Taha:You know, which is so valuable and it's an asset in itself.

55:21Bill Gurley:Absolutely.

55:22Hala Taha:The information is going to get stale, but your personal brand is just going to keep growing, right?

55:25Bill Gurley:No doubt. The book really has two target audiences. So on one hand, it's the young person who's, or even maybe up to mid-career, who really is trying to figure out what they want to do or always wanted to chase a dream and didn't know how and are someone who just really needs an extra push to go do that. It's for all those people, for sure. And a lot of people that have read it said, oh, I want to give it to, you know, every young adult is going to be handed this thing. I hope they take the time to read it. 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.

56:05Bill Gurley:because I do think that the natural tendency is to not kind of be supportive and give the right push at the right moment. And I know you had Matthew McConaughey on, and in his book Greenlights, he tells this story of he's going to—he's told his father his whole life he's going to be a lawyer, and he decides that he now wants to switch to film school, and he's afraid to tell his father. And it's a great scene. It really, to me, speaks to the purpose of this book. When he finally gets the gumption and tells his father, his father says, well, don't half-ass it. And in the book, McConaughey says it was the last thing he expected, but the most valuable thing his father could have said.

56:53Bill Gurley:He gave him permission, responsibility, a push, basically told him, well, if you're going to go do it, be really great at it. And obviously it launched an incredible career. But how do, for all that second group, how can I help you be as good as McConaughey's dad was at that moment? And, you know, sense that there's a sparkle of interest and curiosity and help it flourish.

57:23Hala Taha:Yeah, because to your point, it's not like parents want to do like bad for their children, pushing them to become a doctor or something. You think you're doing good, right? You do. So it's really important. 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. Right.

57:39Bill Gurley:And this one father who saw the original speech sent me this email. I almost started crying. And he told me a whole story about his child had been going in this direction and really wanted to go another one. And he talked about the kind of stages of himself getting comfortable with it. But he said when he finally flipped and was supportive, he saw the child's confidence rise. You know?

58:04Hala Taha:Yeah.

58:04Bill Gurley:And that's just got to be such a wonderful feeling, you know? And I have to say, like, I read two books a week, you know, because of my job, right?

58:12Hala Taha:So I loved your book. I feel like there was so many great things in there. There's so many things that I'm going to even use. And, like, the history thing is something that really stuck with me in terms of, like, I really just need to know the history of media. Yeah. And I think that will just help me as I build this company. So thank you for creating this book.

58:30Bill Gurley:Thanks for reading.

58:30Hala Taha:You started in VC. You were behind so many, you know, huge companies. Zillow, Uber, Stitch Fix, so many big companies. You also started your career at the start of the dot-com bubble. And you saw that whole thing explode.

58:50Bill Gurley:Yep.

58:51Hala Taha:How did that actually change the way you think about investing in companies, change the way you think about sustainability for companies? Talk to us about those fundamentals.

59:04Bill Gurley:I think, oddly, in retrospect, it was fortunate that I—so I started my venture career in 97, and things were on fire by 99. But by 2000, they were falling apart. And that's not enough time for me to have been successful because from investment to liquidity back then was five to seven years. It's even longer now. And so there wasn't a window enough. But it also meant it wasn't a long enough window for anyone to judge whether I was good at it or not. And when the bubble burst, everything slowed down. Yeah. When you're in a bubbly time, and we may be right now with AI, people do silly things. Like they spend money in ways they shouldn't.

59:52Bill Gurley:They run TV ads and Super Bowl ads and all these things, things that don't usually work. They get very speculative. And I found the bubble part to be uncomfortable, but I found the post-crash part to be very sane and rational. And so I just thought, and it was slower, which for someone building their career. And also the charlatans leave town. So one of the things that happens anytime there's a technology wave is people get rich quick. And then a whole bunch of people see people getting rich quick and they rush in. Fools rush in. And those people, I like it when they're not around. But they come in every wave.

1:00:37Bill Gurley:So it is what it is. With AI, you know, I have a lot of founder friends and some of them say like, you know, this year they're only investing in AI companies and it's really hard for them to get funding.

1:00:52Hala Taha:Even if it's a great company with great unit economics and everything like that, they can't get funding. Do you think there's a problem with the investment in AI? And do you think that's a bubble?

1:01:04Bill Gurley:I think, well, there's a whole bunch in what you just said, but let me start with this high-level point that I'd like to make. This professor, Carlotta Perez, recognized something that I think is really important to understand, which is when there is a wave, there is massive wealth. There is disruption, and the deck chairs switch, and people make a lot of money. And that's already happened here because OpenAI and Anthropic are paying their employees secondary earlier than anyone ever had. So the money's being made. It's being put in people's pockets. And that's going to attract speculators. And here in Texas, we had a SPAC from the former governor, Rick Barry, for a data center.

1:01:50Bill Gurley:It already went up and down. So, like, speculators rush in. And so bubbles and waves are actually always happening at the same time. So some people will argue, oh, if you say it's a bubble, you're anti-AI. No, I make the fact that it's real is why there's a bubble. So I think it's important to know that. There is a reality right now, and I feel deeply sad for a lot of founders. There is a reality where a modern venture capitalist does not want to take a meeting uninterested in anything on AI. And I could, if I was forced, make an argument as to why that's the exact right behavior by the venture capitalist.

1:02:36Bill Gurley:But I think it's unquestionably true. Like, there's just zero interest.

1:02:42Hala Taha:Yeah.

1:02:42Bill Gurley:And so that's a tough call for someone that's in a business that may have good unit economics that's not AI. What would my advice for them be? Make sure you understand the edge of AI in your field. Like I said earlier, there may be things you could, you know, I think it's one out of five that can kind of pivot in a way that makes it really look like an AI company. So you don't want it, you know, if it feels painted on, people will sense that. So and then if that's not an avenue for you, you know, try and use sweat equity to get to profitability and own way more of this thing than you would otherwise.

1:03:23Bill Gurley:You know, and I think one of the 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, and your ownership's going to get way diluted. And the number one type of company that bigger companies would like to acquire are smaller companies that are tuck-in acquisitions, 20, 30,$50 million.

1:03:50Hala Taha:And the minute you take venture, that's off the table because now the venture capitalist needs a much bigger outcome. Yeah.

1:03:56Bill Gurley:And so if you can, scrape by. And I know it's hard. And Tito never took venture money. He owns 100 % of this massive business.

1:04:08Hala Taha:Wow.

1:04:08Bill Gurley:You know, and so if you can do it, you know, try and do it. And the big benefit of doing it that way is your ownership will be a lot higher.

1:04:19Hala Taha:I want to do like a little mini MBA for the entrepreneurs. A lot of people who are listening right now are like just starting as entrepreneurs or they've got like, you know, maybe a million dollar company. or, you know, they're just kind of starting out. They've got a lot of potential. And so, you know, you've moved away from, or in the past, you've moved away from this, like, grow-at-all-cost model and investing in companies that just want to grow, and you were looking at unit economics.

1:04:48Bill Gurley:Yeah.

1:04:48Hala Taha:So let's start there. Unit economics, how can you explain that in plain language for our listeners?

1:04:54Bill Gurley:Well, I suspect that the smaller entrepreneurs that are living hand-to-mouth on cash flow are pretty in touch with their unit economy.

1:05:03Hala Taha:But they might not know what it's called, right? It's the guys that raise$100 million of venture capital

1:05:06Bill Gurley:that lose touch with unit economy. Yeah, it's just a matter of understanding what are the true variable costs associated with the product or service that you're selling. And being honest with yourself, even despite what the accounting might be, the requirement for gross margin, but what are the true variable costs? So that could include selling and customer service and all these things so that you know the marginal contribution, ideally from a cash flow perspective, that you get with each turn of the crank.

1:05:42Hala 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? No doubt. Are we actually making money on this customer?

1:05:50Bill Gurley:And, you know, it may be different based on the type of customer, the size of customer, the source of the lead. Like all those things might be different. You know, you may find I've always found it to be true when you are aggressive with marketing, you have much higher churn. Like you get customer. Whereas if you can earn a customer through PR or word of mouth, they typically stay around longer. And so there, that's an even tougher mathematical problem because you're trying to calculate unit economics over the lifetime of a customer early on.

1:06:27Hala Taha:Yeah. And I know you have a problem with LTV traditionally, right?

1:06:30Bill Gurley:I think people get into more trouble with the LTV formula than they do, than they get success out of it.

1:06:37Hala Taha:Why is that?

1:06:38Bill Gurley:Well, I wrote, it's one of my favorite blog posts I've ever written. So if someone wants to go deep, it's called the dangerous seduction of the LTV formula. And it's easy to find on Google. You know, it's not an erroneous way to measure something. It's actually a smart way to measure something. But it's not a strategy. And I think people get lost in thinking it's a strategy. And especially if they're someone who's growing their business on a heavy marketing spin. And I just, in general, I would, you know, the blog post does all this. But I would push people, you know, really think about could I be winning customers with PR?

1:07:19Bill Gurley:Could I be winning customers with non-paid social? Could I be winning customers with product-led growth, which is a great way to think about your product bringing you customers itself? Like all those things are going to create companies that are worth 10 times more than someone that's spending heavy on the marketing expense.

1:07:41Hala Taha:I've never heard of product-led growth. Can you explain that?

1:07:44Bill Gurley:Yeah. And by the way, you could talk to AI or you could, you know, do Google searches and find people that have written extensively about product-led growth. But is there a way to build into the product the ability to find incremental customers? So could you, you know, one of the things that I've been pushing the Stitch Fix team to do that I hope will come out soon is here's your next fix. Share it with your friends and let them vote on what you should keep. Now you're exposing the company to people through the product.

1:08:22Hala Taha:Yeah, you're letting the customers share it themselves.

1:08:24Bill Gurley:Yes, and so the product's leading to new customer introductions without these other techniques. By the way, there's plenty of people who have done that in enterprise. You know, Slack notoriously had this way where you could invite people outside your org. Like, so it's not just a consumer idea.

1:08:40Hala Taha:Yeah, thinking of ways that your customers through the product can bring in leads. More customers. Leads. Yes. Without you paying any money. Exactly.

1:08:46Bill Gurley:Yes. Yes.

1:08:48Hala Taha:So if, let's say you were mentoring me. Okay. My company makes$7 million a year now.

1:08:53Bill Gurley:Okay.

1:08:54Hala Taha:What would you want to see in my dashboard in terms of metrics? Like what kind of metrics would you want to see on a very simple dashboard baseline?

1:09:04Bill Gurley:One question I would ask you before I went there is, you know, and 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 or do you see yourself potentially selling? Selling.

1:09:21Hala Taha:Yeah.

1:09:22Bill Gurley:And so, because that matters a little bit because you need to think about who the natural acquirers would be and why they would fit it in. How do they measure their own business? And so, will this look appealing to them through that lens? Those kind of things. you know some of the stuff you talked about unit economics like you want to understand is is it'd be great if the marginal customer is more profitable than the one before them so that's a test of whether you're starting to get scale in your business right um one exercise that i heavily encourage all founders to do no matter how much the size of the business is force yourself to do a three to five year forecast.

1:10:04Bill Gurley: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 questions so that you can prepare. And if you want to grow a lot for five years, your business is going to be pretty big. And so having gone to the exercise of filling out an Excel spreadsheet and thinking through what that means in terms of employees and salespeople and marketing spend, all those, is a very useful exercise. And one that the majority of founders do not naturally do. Like, it's not something they want to do even, but they should do.

1:10:44Hala Taha:Is there like one metric that you look at that judges whether a company is healthy or not?

1:10:49Bill Gurley:I mean, there's so many different businesses. I think certain businesses, there's a, like in -

1:10:53Hala Taha:Like every business has their own metric that matters.

1:10:55Bill Gurley:Everyone agrees net dollar retention is the one that matters most. but that doesn't apply to everything. So it's kind of dependent on the business.

1:11:05Hala Taha:So again, you got to learn your industry and what matters in your industry. Okay, so let's play a game. It's called Billionaire ROI Ranking. Okay. This is going to put everything that we just talked about together. I'm basically going -

1:11:17Bill Gurley:Am I the first person to play this game?

1:11:18Hala Taha:Oh yeah, I have new games for everyone. Okay. So basically you're going to rank each thing one to 10 if it's a good investment for the entrepreneurs. listen again. And it's going to be stuff that we talked about, some things we might have alluded to, and you can give some color on why you ranked it one to 10. So is it a good return on our investment? Okay. First one is reading and learning every day.

1:11:45Bill Gurley:Oh yeah. Nine, nine out of 10, maybe 10. And that's partially because I've always felt that way, but also the people I respect the most feel that way. 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, you know, and Buffett says the same thing, you know? Okay.

1:12:13Hala Taha:Moving to where the action is.

1:12:15Bill Gurley:Yeah. This is a, um, so between the talk that I gave at University of Texas and the book form of the speech, we added a sixth tenant and it was moving to where the action is. I strongly believe that if you can afford it, you'd rather be an even average player where everyone's doing this thing than being the best player in a market that doesn't rank for that field. And if you're a songwriter, that means Nashville. If you're a founder, that means Silicon Valley. If you want to work in finance, It means New York City. And the number of, what it really does is the number of chance positive things that are going to happen, I'd probably use the word optionality, just goes up 20x.

1:13:11Bill Gurley:Like you're just going to run into so many people doing the same things. And if you go to a job and it doesn't work out, there's so many other people hiring for that same thing. like it just really changes the dynamic and um it probably is important that you're someone that is self-motivated but but uh eight out of ten for most fields there are a few fields if you're a coach you can't really do that um there are some fields where you can do it virtually subreddits

1:13:39Hala Taha:and things like that yeah i think about i moved to austin a year ago as a podcaster and there's just so much serendipity it just things just happen naturally when that's a great word yeah

1:13:48Bill Gurley:Yeah.

1:13:50Hala Taha:Building a personal brand.

1:13:53Bill Gurley:I think that that's field dependent. It's always helpful. I mean, I think there's a, I probably rank it below the others. Let's just say six out of 10. there's always a risk that you become someone who's somewhat performant on the brand side and maybe not developing the real skills underneath it which would could have a negative ramification or someone could view you as shallow if you you know we're doing that so and not all fields I mean there are certain fields where I think it's harder to do but I think if you can it's very rewarding.

1:14:34Hala Taha:Spending heavily on ads.

1:14:37Bill Gurley:Well, I'm, you know, I'm somewhat negative on that, but it keeps your machine running.

1:14:46Hala Taha:That would sound the truth.

1:14:47Bill Gurley:Yeah, I don't like it, too.

1:14:51Hala Taha:Why is that?

1:14:52Bill Gurley:There's a great new book coming out by David Epstein 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 first way the most ignorant person would assume to go get a customer would be to run a Google ad. And I don't think people are reflective enough to say, wow, I'm starting at the very bottom. I'm doing the simplest. that's the least creative thing I could possibly be doing.

1:15:29Hala Taha:And the hardest. The most obvious.

1:15:32Bill Gurley:And I think if you run an exercise, which I mentioned in that blog post, where you say set the marketing budget, the advertising budget to zero, now what are you going to do? And go run that exercise. You're going to come up with so many really creative, wonderful things that are highly differentiated.

1:15:53Hala Taha:Yeah. Yeah.

1:15:55Bill Gurley:So that's why I think that.

1:15:56Hala Taha:And paid ads are so, paid ads don't work also if you don't have a brand or credibility because they're going to go Google you and there's not going to be anything there because you started with paid ads. Okay. Networking events and conferences.

1:16:10Bill Gurley:I'm a big believer that it can be very, very helpful to you. I think it can help you with both peer and mentor development. I think, you know, there's probably a limit if you're known as the person that's always out at the conferences, you know, then they could. But some amount of that, there's a great, one of my favorite stories in the book is about the athletic director here at the University of Texas, Chris Del Conte. And when he was very early working in athletic departments, he went to a conference and met four or five other young people that were at the exact same station. And this is one of those fields where if you're in the epicenter, it may not matter as much.

1:16:57Bill Gurley:But he was in a field where everyone's distributed. And this was the only opportunity for those chance moments.

1:17:03Hala Taha:So it's like going to the action, but for a point in time.

1:17:06Bill Gurley:Yeah, and that group of friends stayed in touch, started a text group, started sharing ideas, and they expanded a little bit over time. But they're now all D1 athletic directors. They all rose to the top. So at seven or an eight? Yeah, yeah.

1:17:24Hala Taha:Seven or an eight?

1:17:25Bill Gurley:But field dependent. Yeah, yeah.

1:17:29Hala Taha:Raising as much money as possible.

1:17:33Bill Gurley:Well, I've historically been very negative on this. So I will put a three on it just to be consistent. We, the venture industry has evolved. And I don't think this affects the vast majority of founders, but the ones at the top. The industry has evolved to where most of the rounds are preemptive and proactive, which means you didn't start a fundraising process. Someone thinks you're doing well and knocked on the door and is force feeding you money. And that is currently the way things happen. And you end up with these situations where each competitor is armed with$400,$500,$600 million, maybe more.

1:18:17Bill Gurley:And it's not, you know, I say it's not your father's venture capital. This is a sport of kings world we've evolved into. And it's fight to the death. I lived through it with the Uber Lyft situation, but I wouldn't wish it on anybody. But it's the reality right now. And if you sit back and say, well, I'm not going to be, I'm not going to raise as much money. I'm going to be, you know, disciplined. Well, if you're the disciplined one and there's six players with$500 million each hiring salespeople, you're not going to matter. So the game on the field has kind of forced people to do this thing I don't love.

1:18:57Hala Taha:Yeah. Okay, next one. Getting an MBA.

1:18:59Bill Gurley:Yeah, I'll say seven. 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 the founder world. And the problem is some of them, I think, take that to the level of dismissing the notion of business learning, which I think is really dangerous. You know, if you don't know how to do a forecast on Excel spreadsheet, that could be a real problem. And so I just worry that the vilification of it is not good for the founders themselves because there are resources they need to understand. It doesn't mean they have to go get an MBA, but they should read Michael Porter's competitive strategy.

1:19:44Bill Gurley:They should read Innovator's Dilemma. They should read Crossing the Chasm. They should know how to organize a sales team. 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.

1:20:07Hala Taha:A lot of people don't align to it. Well, now you can just learn everything online, to your point.

1:20:12Bill Gurley:You might not need to go. The subject matter is important. Totally. Yeah.

1:20:18Hala Taha:So let's move on to leadership. I had Kevin O 'Leary on the show. Yep. And he's another billionaire, I think.

1:20:25Bill Gurley:I don't know, but I'll take your word for it.

1:20:28Hala Taha:Just about a billionaire. And he told me how emotions are, you know, no place for emotions in business. He said, if you need to fire your mother, you fire your mother.

1:20:38Bill Gurley:Yeah.

1:20:39Hala 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. Take us back to those moments, what was happening, and 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?

1:21:05Bill Gurley:One of the things that I would push back on with what Kevin said is the best CEOs that I've talked to very much lead with the heart and have a, I'd say, a passion for leadership that includes feeling like a shepherd of the flock. And so I push back on that a little bit, like broadly against business. Um, the situation that we got into at Uber, there was a asset, the company that was shared by many constituents, you know, the employees, the investors, everybody. And, um, we, because of several things that had happened, things were in a bit of a freefall. And we had five state attorney generals after us.

1:21:58Bill Gurley:We had this situation in London that was on fire. We were losing market share to Lyft, especially in metropolitan areas, very quickly because of brand erosion.

1:22:12Bill Gurley:And by the way, it wasn't, I think history in the press has made it out to be me. There were five investors that worked together and signed this letter, so it wasn't just me. But I think that there were a number of people that were concerned that a change was definitely going to happen. But if you let it happen through the legal world or the government making a change, it was going to be six months to 12 months later and the erosion was going to be even more. And there were a lot of constituents in this thing. You know, a lot of our investors, this was such a big number. They had already, you know, it was already moving the needle for several universities and foundations.

1:23:02Bill Gurley:And if it went away, you know, they have paper marks. They're going to have to mark it down. And that felt that weight on me. That felt like a lot of responsibility. So I've said publicly before, you know, if a venture capitalist does their job the right way, you don't get to that point. So, you know, the thing that I wish I had been able to accomplish was through leadership preventing us from getting to the place where that hard decision has to be made. And, you know, if I could play it again, I would spend more time on that than trying to, you know, play the eventual thing that happened any differently.

1:23:42Bill Gurley:I think we did the best we could do at that moment and knew there would be consequences. And there were. like our competitors use it against us constantly but but anyway that's how i would summarize the whole thing do you feel like you made the right decision i based on where we were at that point in time yes yeah and dar has done an amazing job i mean to take it from there to 200 billion dollar public company over 10 billion a year in free cash flow like from where we were yeah unbelievable

1:24:14Hala Taha:How do you think about reputation in your career? Like, how important is reputation to you?

1:24:21Bill Gurley:I think it's really important. 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 it. In venture, your ability to compete for the next deal is everything. And that's either enhanced or hurt by what the world thinks of you. And in venture, that personal brand can shine brighter than even the corporate brand a lot of times. And so you just have to worry about it if you want to be competitive.

1:25:04Hala Taha:You've had like a really rare chance of being close to so many like extraordinary founders who built really successful companies.

1:25:12Bill Gurley:Yeah.

1:25:12Hala 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.

1:25:18Bill Gurley:Yeah, there's a couple of things. They are continuous learners because they're tilting at some new problem on the edge of their field. And there's no way that could be something they learned in school five years ago because, you know, it's like AI right now. Everything's changing so fast. um bezos has said that for his angel investments he wants to feel like this person's going to do this no matter what that there's this drive and um commitment to attacking the problem that you just can't take them off of 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 going to raise money you're going to recruit people, you're going to lead your team through bad times.

1:26:11Bill Gurley:Like, you can't do that stuff without being able to sell in some way, shape, or form. People do it in a variety of different ways. There's people that are rah-rah, there are people that are quiet, but you have to be able to convince people to follow you. And then lastly, I would say many, many startups have some kind of go-to-market advantage, which usually isn't advertising. So they've figured out some bespoke, differentiated way to gain new customers aggressively.

1:26:45Hala 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?

1:26:57Bill 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 because everybody's doing the exact same thing. And, you know, I think there will be a lot of money made in verticals, like people who figure out how AI applies to something that's very specific to their world. And at this point in time, coding and legal and probably medical are overfunded by the venture capitalists. So there's not much oxygen in those areas. But if you can figure out what it means for all the other fields that are out there, I think there's quite a bit of opportunity.

1:27:41Hala Taha:So the intersection of AI and your field. Yes.

1:27:45Bill Gurley:And knowing what's possible and what that means.

1:27:49Hala Taha:Bill, this has been such an awesome interview. I end my show with two questions that I ask all my guests.

1:27:53Bill Gurley:All right.

1:27:54Hala Taha:So the first one is what is one actionable thing our young and profiters can do today to become more profitable tomorrow?

1:28:02Bill Gurley:I'm going to be redundant with what we talked about. That's right. But I just think it's like continuous learning and like just setting aside time, especially if you're a founder and entrepreneur who's hustling all the time, you may feel like you have no time. But setting aside some time during the week to learn something new.

1:28:25Hala Taha:And what is your secret to profiting in life?

1:28:31Bill Gurley:You know, I would say, you know, you asked me a question about why I wrote this book instead of doing a book about venture or whatever. And there's this great quote that life begins where your comfort zone ends. and I think numerous times in my life I've been willing to kind of try something different or on the edge or a little bit risky and many times those have paid off and so I'm not a kind of a conformist like I like attacking things in new ways I like learning new things and so I'd probably

1:29:09Hala Taha:say that and would you say some of that is like gut intuition is that what you're alluding to

1:29:15Bill Gurley:I think I use my gut to make the leap and to make the decision to push myself, but the willingness to move outside the box, to walk away from something, to try something new, to not be afraid to evolve past whatever the current thinking is, is something I've always done. And I'm thinking numerous examples in my history where that paid off.

1:29:43Hala Taha:And where can everybody learn more about you and everything that you do?

1:29:46Bill Gurley:Well, you can follow me on X. That's where I have most of my content. There's websites now for the book. We're launching a foundation alongside the book, I should mention. For those people that want to chase their dreams and might not have the financial wherewithal to do it, we're going to do grants. We're going to have an application process.

1:30:07Hala Taha:Oh, very cool.

1:30:07Bill Gurley:And do that annually to try and help give them that extra little amount. Let me know when it launches.

1:30:13Hala Taha:I'll do some free commercials for you guys and support. That's awesome. Yeah. Awesome. Well, thank you, Bill. Thank you so much for your time. Thanks for having me. Young Improfiter sitting down with Bill Gurley was truly a special treat. He spent decades studying world-class performers and what he shared today challenges so much of the traditional career advice that we've all been given. One of the biggest takeaways from this episode is that the most fulfilled and successful people don't chase job titles or prestige. They chase curiosity. Bill made it clear that fascination is the real competitive advantage.

1:30:47Hala Taha:When you genuinely love learning about something, the effort feels free and over time, that obsession compounds into mastery, opportunity, and impact. 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 intentionally and stand out. That means deeply understanding the history of your field while also running towards the edge of what's new, whether that's AI, emerging platforms, or a new way of thinking. That combination of respect for the past and fluency in the future is what makes people impossible to replace.

1:31:23Hala Taha: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. 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.

1:31:54Hala Taha:This year, I'll be doing more in-person interviews, so keep an eye out for those on YouTube and Spotify video. And while you're there, make sure you subscribe and drop us a comment to let us know what resonated with you. If you want a more behind the scenes look at my life and more personal stuff, you can connect with me on Instagram at Yap with Hala or LinkedIn by searching my name, it's Hala Taha. Huge shout out to my incredible Yap team. As always, this is your host, Hala Taha, AKA the podcast princess, signing off.