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

Career regret is more common than most professionals admit. In Bill Gurley’s survey, 7 out of 10 people said they would restart their careers if given the chance, revealing widespread dissatisfaction with their chosen paths. After decades of working alongside successful founders, Bill distilled what actually leads to meaningful, energizing work into his book Running Down a Dream, offering a clear path to designing a career you don’t want to escape from. In this episode, Bill reveals how to build your dream job and shares what top professionals do differently to create careers that bring both success and fulfillment. In this episode, Hala and Bill will discuss: (00:00) Introduction (02:17) The Career Regret Crisis (06:57) Designing Your Own Career Path (12:53) How Curiosity Over Passion Drives Success (22:10) Bill’s Journey From Engineering to Venture Capital (28:45) Mastering Career Fundamentals for Growth (41:34) The Power of Mentors and Peers in Career Development (52:10) Dot-Com Crash Lessons and the AI Wave (54:20) Unit Economics and Business Fundamentals (1:06:39) Smart ROI Decisions for Entrepreneurs (1:16:47) Making Tough Calls in Leadership (1:21:34) Traits of Extraordinary Founders Bill Gurley is a renowned Silicon Valley venture capitalist and general partner at Benchmark, known for early, pivotal investments in companies like Uber, Zillow, and Grubhub. With over 20 years at Benchmark, he is recognized as a top tech investor and the author of the influential blog Above the Crowd. In his new book, Running Down a Dream, Bill breaks down the components of balancing joy with success and identifies the key principles of career fulfillment. Sponsored By: Indeed - Get a $75 sponsored job credit to boost your job's visibility at⁠ Indeed.com/profiting⁠ Shopify - Start your $1/month trial at⁠ Shopify.com/profiting⁠. Spectrum Business - Keep your business connected seamlessly. Visit ⁠https://spectrum.com/Business⁠ to learn more. Northwest Registered Agent - Build your brand and get your complete business identity at⁠ northwestregisteredagent.com/paidyap⁠ Framer - Publish beautiful and production-ready websites. Go to⁠ Framer.com/profiting⁠ and get 30% off their Framer Pro annual plan. Quo - Run your business communications the smart way. Try Quo for free, plus get 20% off your first 6 months when you go to⁠ quo.com/profiting⁠ Working Genius - Discover your natural gifts and thrive at work. Go to⁠ workinggenius.com⁠ and get 20% off with code PROFITING Experian - Manage and cancel your unwanted subscriptions and reduce your bills. See ⁠experian.com⁠ for details. Huel -  Get all the daily nutrients you need with Huel. Grab Huel today and get 15% OFF with my code PROFITING at⁠ huel.com/PROFITING⁠. Resources Mentioned: Bill’s Book, Running Down A Dream: ⁠bit.ly/BGDream⁠ Bill’s X (Twitter): ⁠x.com/bgurley⁠ Bill’s Website: ⁠abovethecrowd.com⁠ Designing Your Life by Bill Burnett: ⁠bit.ly/BB-DYL⁠ One Up On Wall Street by Peter Lynch: ⁠bit.ly/PL-OUOWS⁠ Innovator's Dilemma by Clayton Christensen: ⁠bit.ly/CC-ID⁠ Greenlights by Matthew McConaughey: ⁠bit.ly/MM-GL⁠ Active Deals -⁠ youngandprofiting.com/deals⁠ Key YAP Links Reviews -⁠ ratethispodcast.com/yap⁠ YouTube -⁠ youtube.com/c/YoungandProfiting⁠ Newsletter - ⁠youngandprofiting.co/newsletter⁠ LinkedIn -⁠ linkedin.com/in/htaha/⁠ Instagram -⁠ instagram.com/yapwithhala/⁠ Social + Podcast Services:⁠ yapmedia.com⁠ Transcripts -⁠ youngandprofiting.com/episodes-new⁠ Entrepreneurship, Entrepreneurship Podcast, Business, Business Podcast, Self Improvement, Self-Improvement, Personal Development, Starting a Business, Strategy, Investing, Sales, Selling, Psychology, Productivity, Entrepreneurs, AI, Artificial Intelligence, Marketing, Negotiation, Side Hustle, Startup, Mental Health, Career, Leadership, Mindset, Growth Mindset, Business Ideas, Growth Hacks, Workplace, Career Podcast

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Hala Taha?

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• 0:45Hala Taha?

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• 1:08Speaker 01

  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.

• 1:20Hala Taha?

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

• 1:29Speaker 01

  People aren't that engaged and happy in their careers. We asked 1,000 people, if you could start your career over again, would you do something different? Seven out of 10 said yes.

• 1:39Hala Taha?

  Wow.

• 1:41Speaker 01

  AI is moving so fast. My advice for anyone in any field that's afraid of AI is run at it.

• 1:48Hala Taha?

  You also started your career at the start of the dot-com bubble, and you saw that whole thing explode. How did that actually change the way you think about investing in companies? Changed the way you think about sustainability?

• 2:02Speaker 01

  One of the things that happens anytime there's a technology wave is people get rich quick, and then a whole bunch of people see people getting rich quick, and they rush in. I like it when they're not around. When you're in a bubbly time, and we may be right now with AI, people do silly things, things that don't usually work. They get very speculative.

• 2:21Hala 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.

• 2:31Speaker 01

  I think there will be a lot of money made in.

• 2:36Hala Taha?

  Yep, 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. 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. The most successful people didn't follow the conventional route. They built careers around what genuinely fascinated them. In this episode, we unpack lessons from Bill's new book, Running Down a Dream, including how to avoid career regret, staying relevant in the age of AI,

• 3:17Hala Taha?

  and designing a career driven by curiosity, smart pivots, and continuous learning. Bill, welcome to Young and Profiting Podcast.

• 3:24Speaker 01

  Thanks for having me on.

• 3:25Hala 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 what people have called a super investor. And now you've come out with a careers book called Running Down a Dream.

• 3:42Speaker 01

  Correct.

• 3:42Hala 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, the VC firm, right? So why did you decide to write a book about careers?

• 3:58Speaker 01

  You know, as I, as I reached the end of what was definitely my dream job, I loved being a venture capitalist. But I reached a point where I decided it was time to hang up my boots and it was time for me to move on and, and leave the field for younger people to succeed.

• 4:17Speaker 01

  I felt a calling to write this book and it was 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 of blog posts 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 and I had read these three biographies and noticed that these three people had all done similar things. And I wrote down the notes. I then got invited to give a speech at the University of Texas here in Austin and I I put it together and gave that speech and then a number of people saw that speech, probably most notably James Clear. And

• 5:03Speaker 01

  people then started pushing me, you know, one day you should make that a book. And as I reached the end of my career, you know, and 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. And um this was this just felt more personal to me. And now that it's done and it took a long time,

• 5:29Speaker 01

  I'm certain at this point that this book has a bigger chance to help more people than any of those other books.

• 5:35Hala Taha?

  Oh, yeah, for sure. I feel like this applies to anybody, whether they're just starting or they're, you know, forty, fifty years old and mid-career. 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.

• 5:54Speaker 01

  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. And um we did a lot of research and one person prodded us to 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? And Out of ten said yes.

• 6:27Hala Taha?

  Wow.

• 6:27Speaker 01

  And we did it again with Wharton and did it more scientifically and it was still six out of ten. 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, 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.

• 6:57Hala Taha?

  Yep.

• 6:57Speaker 01

  But that thing you never tried just eats at you as you get older.

• 7:01Hala Taha?

  Yeah.

• 7:02Speaker 01

  And so I I'd like to believe, and we could talk about this as well. But I I'm fairly certain that we've gotten so systematic about how we drive kids, you know, from being twelve years old into college that we're putting blinders on them almost and they're not having the opportunity to roam around and explore and find what they love. And I think, I'm a parent of three. It is very, very hard for a parent to not want their child to be economically successful. And so you you have this this little voice in the back of your head that wants to push them towards

• 7:47Speaker 01

  the jobs that are considered safe, the safe jobs. Now ironically, with AI, many of those quote safe jobs aren't that safe.

• 7:55Hala Taha?

  Yeah.

• 7:55Speaker 01

  But I would look back before AI and the survey work that we had done and other work, Gallup polls and whatnot. You know, people aren't that engaged and happy in their careers writ large.

• 8:08Hala 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? 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. There's so many college students who graduate, they can't get jobs. There's so many people struggling out there.

• 8:27Speaker 01

  Yeah.

• 8:28Hala Taha?

  Um, even getting laid off, uh, even if they had a great job.

• 8:31Speaker 01

  Yeah.

• 8:31Hala Taha?

  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?

• 8:41Speaker 01

  Yeah, I I think it's well intentioned and I don't think it's just the parents. I think the counselors, everybody, it's it's uh, you you it comes from the heart, like you really want them to be okay. But we've gotten into this place, Jonathan Haidt calls it the resume arms race, where, like I said, by the time you're in sixth grade, your parents are worried about whether your college application is going to be successful or not. So they're pushing you to play cello and volunteer at the thrift store. And like, you're doing all these things. These kids are booked solid. You know, when I was young, and I've heard this from other people my age, we'd roam around the neighborhood, no one knew where we were.

• 9:25Speaker 01

  But that doesn't happen anymore. They're just pressure, pressure, pressure. And I think it has the double negative consequence. One, they don't get to kind of explore and play and find what they love. And two, they're just burnt out, you know, they're just burnt out. But then it even, it gets worse at college. If you go back 10 or 20 years, you would go to, everyone would go to college as a generalist, and you wouldn't declare your major until the end of your sophomore year. Nowadays, they make you apply to a major. And so you're putting the pressure on the kid to make the decision about the major when they're a junior in high school and filling out applications. And they just don't know.

• 10:08Speaker 01

  I mean, I've talked to so many of them, and I'm like, where do you want to be? And they're, I don't know, like, they just don't know yet. And 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.

• 10:26Hala Taha?

  Oh, yeah.

• 10:27Speaker 01

  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 major doesn't become an anchor. You know, that restricts where they think they can go.

• 10:42Hala 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.

• 10:50Speaker 01

  Yeah.

• 10:50Hala Taha?

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

• 10:54Speaker 01

  Yeah.

• 10:54Hala Taha?

  Came back to college and was like, way smarter and ready for it. Transitioned to marketing, and then here I am, using those skills, you know.

• 11:02Speaker 01

  I think there's a lot of data that suggests people that have roamed around and moved in different directions.

• 11:10Speaker 01

  Tend to land in a better place, one they're more passionate about. They've explored and had, you know, this time to kind of really figure it out. And then they're pressing the gas where they still have energy in the tank.

• 11:24Hala Taha?

  Yep.

• 11:24Speaker 01

  To go after it.

• 11:25Hala Taha?

  Yeah.

• 11:26Speaker 01

  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, you don't know how much you have left, you know?

• 11:36Hala Taha?

  Totally.

• 11:36Speaker 01

  To pivot.

• 11:37Hala Taha?

  Yeah. And as I was reading your stuff, I felt very connected to it because I do feel like I've been obsessed with podcasting and things like that. And that's why things have really worked out. So let's.

• 11:48Speaker 01

  You know, one thing I would say about that, that I think would speak especially to your audience.

• 11:51Hala Taha?

  Of course.

• 11:53Speaker 01

  You know, meeting, when you go out to promote a book, you, you meet a lot of publishers and you meet a lot of podcasters. And a lot of these people love what they do and a lot of them have taken an independent path. Like you didn't apply for a podcast degree and, and get in, you didn't fill out a job application to be a podcaster, right? You were crafting your own career. There's a phrase in the book that I use called, you know, become a candidate of one. And I think a lot of people that, that are very successful in the world don't think about a career as something where I'm going to pick one off a menu and apply to it.

• 12:32Speaker 01

  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. So I, and, and I suspect you consider yourself in your dream job.

• 12:50Hala 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.

• 13:20Speaker 01

  Well, the, the, 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. 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. And the reason it's so important is if you really wanna differentiate yourself, you really wanna be successful, you really wanna dent the universe. You have to love learning about what you do.

• 14:03Speaker 01

  Because if you love learning about what you do, and, and I think the ultimate test is in your spare time, instead of watching a Netflix show, you're reading about the, this thing that you love. You're gonna out hustle everybody else. And the flip side is true. If you don't love it and you're not constantly learning, someone else is. And you're gonna have a really hard time keeping up with them.

• 14:29Hala Taha?

  Yep.

• 14:30Speaker 01

  And 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. 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 podcasts and AI and all these things. You're gonna get outrun because someone's gonna, someone's gonna get out on the edge in front of you.

• 15:04Hala 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?

• 15:12Speaker 01

  The, the word passion has become trite and it's been said so many times, some people attack it. And I kinda understand that, like, you know, it's just been overused. I 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.

• 15:50Hala Taha?

  Yep.

• 15:50Speaker 01

  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. 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 it or fascinated by it, there's no, it doesn't feel like there's work effort put in to the continuous learning.

• 16:14Hala 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?

• 16:21Speaker 01

  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, because 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. And by the way, every one of those characters made a ton of money. They didn't start, they all, every single one of them started it because they loved it.

• 17:01Hala Taha?

  Yep.

• 17:02Speaker 01

  They didn't start it because they want 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 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.

• 17:41Hala 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

• 17:50Speaker 01

  No doubt. And by the way, I think it's a fair question that you posed. 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, I know, 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.

• 18:19Hala Taha?

  Yeah, that's part of it.

• 18:20Speaker 01

  Yes, you would. Yes.

• 18:22Hala Taha?

  Yeah.

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• 21:39Speaker 01

  Writing programs, it was like very fulfilling. So when I went to 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.

• 22:03Speaker 01

  Two years in, we started the third project from when I had joined and it looked like the second project, which looked like the first, which is part of what. Got me wondering if I was going to grow bored doing this type of work. And then. When I was at home, I had read this book, One Up on Wall Street by Peter Lynch, and I had started trading stocks. So. Then 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. And so I went to business school, ended up on Wall Street. Had it. It was awesome. Being in Manhattan in your late twenties, just fantastic. Met so many great people, met so many great investors.

• 22:48Speaker 01

  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? 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.

• 23:17Speaker 01

  Yeah, from there I was able to get into venture.

• 23:19Hala Taha?

  Yeah.

• 23:19Speaker 01

  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.

• 23:26Hala Taha?

  So do you think investing was really your obsession?

• 23:30Speaker 01

  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, the, the book. Innovator's Dilemma walks through exactly how that works. And then this is, 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, I do think there was a little gambler. Little gambler mentality in there also. Those things combined.

• 24:09Hala Taha?

  Interesting.

• 24:10Speaker 01

  Investing tech, gambling a little bit, disruption.

• 24:13Hala Taha?

  And you put those all together and designed your dream career as a VC investor. Yeah, it's putting, it's putting all of this together.

• 24:20Speaker 01

  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.

• 24:25Hala Taha?

  Yeah.

• 24:27Speaker 01

  I think there are certain people that have some form of ADD or they're just highly distracted and they get, they get a lot of satisfaction out of diversity. And I'm one of those people. So whether it was working on Wall Street or as a VC, a consultant would have this. You're just looking at so many different things simultaneously and that breadth matters to me. 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 ton of wonderful founders who have to have their hands on the steering wheel and want to be in that position.

• 25:07Speaker 01

  And I think those jobs are complimentary 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.

• 25:17Hala 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, and designing their own dream career?

• 25:37Speaker 01

  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. It's just 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? 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, and listen to the best. There's stuff on YouTube, you know, you can talk to AI until you're blue in the face.

• 26:22Speaker 01

  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.

• 26:31Hala Taha?

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

• 26:33Speaker 01

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

• 26:47Hala Taha?

  Yeah.

• 26:48Speaker 01

  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.

• 26:58Hala Taha?

  Was he a good chess player?

• 27:00Speaker 01

  He, he's the best chess player in the world, but, but my, my point is, he, he knew, he knew all the history as well.

• 27:06Hala Taha?

  Yeah, because he's, because he was an expert in his field. So the history was a part of it.

• 27:10Speaker 01

  The other, by the way, I think that 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, 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. Like the people that have been in those roles for 10 or 15 years probably don't understand it at all.

• 27:39Hala Taha?

  Mm hmm.

• 27:39Speaker 01

  And so 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.

• 27:52Hala Taha?

  100%.

• 27:53Speaker 01

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

• 28:04Hala 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, 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, and got promoted so quickly because I knew more than the other people who started at 23.

• 28:33Speaker 01

  About the edge.

• 28:34Hala Taha?

  Yeah. So it's really interesting that you say that. I love that idea of actually studying the history of a industry and also like the unsexy knowledge.

• 28:44Speaker 01

  Yeah.

• 28:45Hala Taha?

  Um, 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.

• 28:59Speaker 01

  Yeah.

• 28:59Hala Taha?

  So, talk to us about the importance of learning the unsexy stuff.

• 29:04Speaker 01

  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, uh, won at auction a dinner with John Lasseter, who was the creative genius behind Pixar.

• 29:21Hala Taha?

  Hmm.

• 29:22Speaker 01

  Um, and we went to, we got invited to John's house and he has a viewing room there, which was 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 was one of the defining early cartoons in the history of cartoons.

• 29:45Hala Taha?

  Hmm.

• 29:45Speaker 01

  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, there's so many of these people that are, that are at the top of their field that have this, like, just super respectful understanding of the history.

• 30:09Hala Taha?

  Mm-hmm.

• 30:09Speaker 01

  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.

• 30:22Hala Taha?

  Yeah.

• 30:23Speaker 01

  But also, the, it's so differentiating. 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.

• 30:34Hala Taha?

  Mm-hmm.

• 30:35Speaker 01

  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. Sales techniques and you start dropping that, you know, in the interview like no one else is gonna do that. None of the other people and someone's gonna go like, holy crap, this person really cares. Like, you know, they really care about this field.

• 31:00Hala Taha?

  Yeah, and it helps you if you want to be a leader in that field field, not repeat the same mistakes.

• 31:05Speaker 01

  Yes.

• 31:06Hala Taha?

  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? If and for AI, what would you study? The internet?

• 31:23Speaker 01

  Well, I mean, there are some people that have been working on AI for ten or twenty years. Yeah, AI is moving so fast. I think you should spend every last minute just using.

• 31:34Hala Taha?

  Just using.

• 31:35Speaker 01

  Every, every tool you can, I, you know, I, I've kind of separate from the book, but I've. I have my, my advice for anyone in any field that's afraid of AI is run at it. Like, know, know what it's, what is the edge of possibility for AI in your field? And, 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.

• 32:03Hala Taha?

  Yeah.

• 32:04Speaker 01

  Like, the last thing you want to be is an AI skeptic who hasn't tried any of it.

• 32:08Hala Taha?

  Totally.

• 32:09Speaker 01

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

• 32:12Hala Taha?

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

• 32:21Speaker 01

  No, try them all and, and, and ask, you can ask them this, but it's kind of circular. But, but what is the edge of AI usage in your field? And understand what that is and play around with it there. And I, I meet people, especially older people, I'm almost sixty, so I can, 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 air because it's getting better constantly.

• 33:00Speaker 01

  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.

• 33:08Hala Taha?

  I totally agree. And 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?

• 33:22Speaker 01

  Yeah, um, I think it's insane. Like, it's such an accelerant. Like, you can learn about anything. And I'm probably doing thirty searches a day on.

• 33:31Hala Taha?

  Oh, I'm on it. I can't do anything without it anymore. I always wanna.

• 33:35Speaker 01

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

• 34:08Hala Taha?

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

• 34:13Speaker 01

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

• 34:27Hala Taha?

  Yeah, I I say that because sometimes I'm like, I feel like in the past I would have, uh, you know, now I'm always like, you know, bouncing back and forth between AI and my work, right? And in the past, I would have, I 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. You know what I'm saying?

• 34:47Speaker 01

  Yeah, yeah, you might be, um, limiting your own imagination by not giving yourself enough free time to ponder the possibilities.

• 34:57Hala Taha?

  To be like time box, no, no AI, use your brain, you know?

• 35:01Speaker 01

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

• 35:04Hala Taha?

  Okay, so let's say you're mid-career.

• 35:06Speaker 01

  Mm hmm.

• 35:07Hala Taha?

  Forty years old.

• 35:08Speaker 01

  Yep.

• 35:10Hala Taha?

  Made money, but you have responsibilities.

• 35:12Speaker 01

  Yeah.

• 35:13Hala Taha?

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

• 35:18Speaker 01

  We have a chapter in the book called Never Too Late, where we highlight a number of people that had their defining career start after 40. I don't think it's easy for the reason you bring up, which is commitments. One of, one of the people we profiled in that chapter is Saul Kahn, uh, who created the Kahn Academy. And Saul was in a, 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 Kahn Academy. And, um, he, he felt drawn to doing it as a nonprofit, which makes that math even harder.

• 36:04Speaker 01

  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. And once again, I think having the flexibility to do that is part of living within your means. Um, they couldn't have done that otherwise.

• 36:19Hala Taha?

  Yeah.

• 36:20Speaker 01

  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 Kahn has.

• 36:27Hala Taha?

  Yeah.

• 36:28Speaker 01

  Like.

• 36:28Hala Taha?

  We actually, and I interviewed him a little while.

• 36:31Speaker 01

  Wonderful guy.

• 36:31Hala Taha?

  Yeah.

• 36:32Speaker 01

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

• 36:38Hala Taha?

  Yeah.

• 36:38Speaker 01

  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.

• 36:47Hala Taha?

  And especially has nothing to do with the job. Yeah.

• 36:49Speaker 01

  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, of entrepreneurs using Microsoft projects. And that get, let, led him to a whole different set of connections and networking. Then 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, uh, he's one of the most successful podcasters on the planet and loves what he's doing.

• 37:30Speaker 01

  But, but the experimentation of this side hustle gave him exposure to new things. Um, and, 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, would the career I'm in, the company I'm at, let me go do this other thing?

• 37:52Hala Taha?

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

• 37:56Speaker 01

  There you go.

• 37:57Hala Taha?

  Right. And me and the acquired host, what's his name?

• 37:59Speaker 01

  Uh, Ben Gilbert.

• 38:01Hala 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, uh, you know, may the best podcaster win. 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.

• 38:24Speaker 01

  Yeah.

• 38:24Hala Taha?

  What's the difference between the two?

• 38:25Speaker 01

  Well, I find a lot of people, I mean, a lot of, a lot of, uh,

• 38:30Speaker 01

  people that write personal development books talk about mentors. So it's not a unique, uh, topic. But what I find happens most in the real world is people get too greedy too early. And they, they say, well, I, they, they either cold call someone they shouldn't.

• 38:46Hala Taha?

  Yeah.

• 38:47Speaker 01

  Um, that's, that's out of reach, or they get frustrated because, oh, I could never get this person to be my mentor. So, so they kind of give up and, um, that's all because I think they stretched 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. 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 going to be a restaurateur. He made a list of, it was either 10 or 12 of the people.

• 39:29Speaker 01

  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. Um, he, 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.

• 39:50Hala Taha?

  Back to the history, learning the history, right?

• 39:51Speaker 01

  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.

• 40:08Hala Taha?

  Yeah.

• 40:08Speaker 01

  And the truth of the matter is people in the second tier get almost zero asked.

• 40:14Hala Taha?

  Hmm. They're more willing.

• 40:16Speaker 01

  Yeah, they're going to be more willing. They're going to 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 and you're much more likely to get help.

• 40:29Hala 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 things that you mentioned is publicly learning, like learning in public. You did this with the blog that you started.

• 40:48Speaker 01

  Yes.

• 40:48Hala Taha?

  A lot of creator entrepreneurs nowadays who are building personal brands, they're also learning publicly. And there's so much benefit to that. Can you speak about that?

• 40:58Speaker 01

  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. 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, there are two benefits to it, straight up. One, when you write things down and, and you know, you're going to publish them publicly, you really test the, all the theories in your brain. You really work things out.

• 41:39Speaker 01

  You accomplish what you're afraid you're not doing by just using AI because you 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 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.

• 42:10Hala Taha?

  Yeah.

• 42:11Speaker 01

  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.

• 42:19Hala Taha?

  That's true.

• 42:20Speaker 01

  Yeah.

• 42:20Hala Taha?

  But I think in most cases, I think it it does help.

• 42:24Speaker 01

  It could be it can be very, very helpful.

• 42:27Hala 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.

• 42:36Speaker 01

  Yeah.

• 42:37Hala 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?

• 42:43Speaker 01

  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 in the literature. Like, I think I might be one of the first people really pushing on this subject. But peers can be inside your company, they can be outside. But it's it's think about it as a co-evolving journey. And the reason I use the for the 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.

• 43:24Speaker 01

  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 and share with each other, be vulnerable with each other, you just get a massive lift and. Um, there's a, there's a great story in the book about Mr. Beast. And when he was starting his journey, which is probably similar to where you were getting into podcasts. When he was getting into YouTube, there weren't, it wasn't a field yet.

• 43:54Hala Taha?

  Yeah.

• 43:55Speaker 01

  Like, 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. 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."

• 44:13Hala Taha?

  Yeah.

• 44:14Speaker 01

  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 the.

• 44:25Hala Taha?

  What's up, Yap fam? You guys know we love reading on this show, so I'm always excited when I find a book I genuinely think is worth sharing. "Life at the Speed of Play: Launch Products People Love" by Mark Pincus is one of those books. Mark is a legendary Silicon Valley entrepreneur and investor, and this fast-paced 170-page book is his playbook for testing ideas quickly, navigating uncertainty, and figuring out what's actually worth pursuing. One of my favorite concepts is what he calls "the abyss", those moments when you feel stuck or unsure of what's next. Instead of fearing uncertainty, he shows you how to use it as a tool for discovery. Right now, Mark is doing a buy one, get one offer for Yap listeners.

• 45:09Hala Taha?

  Go to GetMark'sBook.com/Yap, buy one copy for $32 and get a second copy free. So you can keep one for yourself and give the second to a friend, future co-founder, or someone who needs a little push.

• 45:25Hala Taha?

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• 46:09Hala Taha?

  go to Shopify.com/Profiting to start your free trial. That's Shopify.com/Profiting. Go to Shopify.com/Profiting today to hear your first.

• 46:24Hala Taha?

  What's up, Yap gang? I recently had Gary Vee on the podcast and he told me something that really stuck with me. If you've got sales DNA, you've got to be paying attention to live selling because it's one of the biggest opportunities right now online. And that really got me curious, so I checked out an app that he told me about called Whatnot. I jumped into a live show and I instantly got it. The seller was showing products in real time, answering questions in the chat, and building a real relationship with the buyers. It didn't feel like boring shopping. It felt like a community. Whatnot is the largest live shopping marketplace in the country. And for entrepreneurs, the results are really hard to ignore. Sellers on Whatnot can sell up to 10 times more than traditional marketplaces. And the number of sellers making over a million dollars a year on the platform has doubled.

• 47:08Hala Taha?

  So if you've got products to sell and you're looking for a new way to reach customers, search Whatnot, W-H-A-T-N-O-T, in the App Store. Download it and you can start selling right away. That's Whatnot in the App Store.

• 47:20Speaker 01

  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.

• 47:35Hala 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?

• 47:42Speaker 01

  You do.

• 47:43Hala Taha?

  So it's really important and a lot of people, I have a lot of friends that feel very resentful of getting pushed in certain careers. So you don't want that to happen.

• 47:50Speaker 01

  Right, and you, 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 it. 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.

• 48:14Hala Taha?

  Mm hmm.

• 48:15Speaker 01

  You know, that's just got to be such a wonderful feeling, you know?

• 48:19Hala Taha?

  And I have to say, like, I read two books a week, you know, because of my job.

• 48:24Speaker 01

  Yeah.

• 48:24Hala 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 gonna even use in 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 media.

• 48:36Speaker 01

  Yeah.

• 48:36Hala Taha?

  And I think that will just help me as I build this company. So thank you for creating this book.

• 48:42Speaker 01

  Thanks for reading.

• 48:42Hala Taha?

  You started in VC. You were behind so many, you know, huge companies.

• 48:47Speaker 01

  Yeah.

• 48:47Hala Taha?

  Zillow, Uber, Stitch Fix, so many big companies. Um, you also started your career at the start of the dot com bubble.

• 48:58Speaker 01

  Mm hmm.

• 48:59Hala Taha?

  And you saw that whole thing explode.

• 49:02Speaker 01

  Yep.

• 49:03Hala Taha?

  How did that actually change the way you think about, uh, investing in companies? Change the way you think about sustainability for companies?

• 49:13Speaker 01

  Yeah.

• 49:13Hala Taha?

  Um, talk to us about those fundamentals.

• 49:16Speaker 01

  If, I think oddly 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 and, um, I, 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. Um, when, when you're in a bubbly time, and we may be right now with AI, um, people do silly things.

• 50:00Speaker 01

  Like they, they, they spend money in ways they shouldn't. They run TV ads and Super Bowl ads and all these things. Things that don't usually work. Um, 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 it was, 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

• 50:45Speaker 01

  it when they're not around. But they come in every wave. So, it is what it is.

• 50:51Hala Taha?

  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, 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?

• 51:16Speaker 01

  I think, well, there's a whole bunch on what you just said, but let me start, let me start with this high-level point that I'd like to make. This Professor Carlotta Perez recognized something that I think is really important to understand, which is, when there is a wave, there is massive wealth, there is disruption, and the deckchairs 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 gonna attract speculators. And

• 51:56Speaker 01

  we, here in Texas, we had a SPAC from the former governor, Rick Barry, for a data center, 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, the fact that it's real is why there's a bubble. So, I think, 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.

• 52:41Speaker 01

  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.

• 52:54Hala Taha?

  Yeah.

• 52:54Speaker 01

  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. 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, 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 you don't want it, you know, if it feels painted on, the 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.

• 53:34Speaker 01

  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, 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 dollars. And the minute you take venture, that's off the table. Like, cause now the venture capitalist needs a much bigger outcome.

• 54:07Hala Taha?

  Yeah.

• 54:08Speaker 01

  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.

• 54:19Hala Taha?

  Wow.

• 54:20Speaker 01

  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.

• 54:31Hala Taha?

  I wanna do like a little mini MBA for the entrepreneurs tuning. 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 costs model and investing in companies that just wanna grow and you were looking at unit economics.

• 55:00Speaker 01

  Yeah.

• 55:00Hala Taha?

  So let's start there. Unit economics, how can you explain that in plain language for our listeners?

• 55:06Speaker 01

  Well, I suspect that the smaller entrepreneurs that are living hand to mouth on cash flow are pretty in touch with their unit economics.

• 55:14Hala Taha?

  But they might not know what it's called, right?

• 55:16Speaker 01

  Guys that raise a hundred million of venture capital that lose touch with unit economics. Yeah, it's just a matter of understanding what are the true variable costs associated with the product or service that you're selling?

• 55:29Hala Taha?

  Mm-hmm.

• 55:29Speaker 01

  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.

• 55:54Hala 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 customer?

• 56:02Speaker 01

  No doubt. 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.

• 56:39Hala Taha?

  Yeah. And I know you have a problem with LTV traditionally, right?

• 56:42Speaker 01

  I think people get into more trouble with the LTV formula than they do. Then they get success out of it.

• 56:49Hala Taha?

  Why is that?

• 56:50Speaker 01

  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.

• 57:02Speaker 01

  You know, it's not

• 57:05Speaker 01

  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 spend. 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 non-paid social? Could I be winning customers with product-led growth, which is a great,

• 57:41Speaker 01

  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.

• 57:53Hala Taha?

  I've never heard of product-led growth. Can you explain that?

• 57:56Speaker 01

  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 it's, 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, here's, 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.

• 58:34Hala Taha?

  Yeah, you're letting the customers share it themselves.

• 58:37Speaker 01

  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, like, so it's not just a consumer.

• 58:51Hala Taha?

  Yeah, thinking of ways that your customers through the product can bring in leads without you paying any money.

• 58:58Speaker 01

  Yes, yes.

• 58:59Hala Taha?

  So if, let's say you were mentoring me. My company makes $7 million a year now.

• 59:04Speaker 01

  Okay.

• 59:06Hala 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?

• 59:16Speaker 01

  One question I would ask you before I went there is, you know, and this doesn't, 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?

• 59:32Hala Taha?

  Selling.

• 59:33Speaker 01

  Yeah, and so, because 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, you know, and so will this look appealing to them through that lens? Those kinds of things.

• 59:51Speaker 01

  Some of the stuff you talked about, unit economics, like you want to understand, is it'd be great if the marginal customer is more profitable than the one before them. So that's a test of whether you're starting to get scale in your business, right? One exercise that I heavily encourage all founders to do, no matter how much the size of the business, is force 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 questions so that you can prepare. And if you, you know, if you want to grow, you know, a lot for five years, your business can be pretty big, you know?

• 1:00:34Speaker 01

  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 the, 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.

• 1:00:56Hala Taha?

  Is there like one metric that you look at that like judges whether a company is healthy or not?

• 1:01:01Speaker 01

  I mean, there's so many different businesses, I think certain businesses, there's a, like in

• 1:01:05Hala Taha?

  Like every business has their own metric that matters.

• 1:01:07Speaker 01

  Everyone agrees net dollar retention is the one that matters most, but that doesn't apply to everything.

• 1:01:13Hala Taha?

  Yeah.

• 1:01:14Speaker 01

  So, so it's kind of depending on the business.

• 1:01:16Hala Taha?

  So again, you got to learn your industry, what matters in your industry.

• 1:01:20Speaker 01

  Exactly.

• 1:01:21Hala Taha?

  Okay, so let's play a game, it's called billionaire ROI ranking.

• 1:01:24Speaker 01

  Okay.

• 1:01:25Hala Taha?

  Put everything that we just talked about together. I'm basically.

• 1:01:28Speaker 01

  Am I the first person to play this game?

• 1:01:30Hala 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 listening in. And it's going to be stuff that we talked about, some things we might have alluded to. And you can, you know, give some color on why you ranked it one to 10. So is it a good return on our investment?

• 1:01:52Speaker 01

  Okay.

• 1:01:52Hala Taha?

  Okay. First one is reading and learning every day.

• 1:01:57Speaker 01

  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 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?

• 1:02:24Hala Taha?

  Okay, moving to where the action is.

• 1:02:27Speaker 01

  Yeah, this is a, 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, it was moving to where the action is.

• 1:02:42Speaker 01

  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, it's, the number of, what it really does is the number of chance positive things that are going to happen. I'd probably use the word optionality, just goes up 20x. Like, you're just going to run into so many people doing the same things.

• 1:03:27Speaker 01

  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. Like, it just really changes the dynamic. And it probably is important that you're someone that is self motivated. But, but eight out of 10 for most fields, there are a few. If you're a coach, you can't really do that. There are some fields where you can do it virtually, subreddits and things like that.

• 1:03:52Hala 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 happen naturally.

• 1:03:59Speaker 01

  That's a great word.

• 1:04:00Hala Taha?

  Yeah.

• 1:04:00Speaker 01

  Yeah.

• 1:04:01Hala Taha?

  Um, building a personal brand.

• 1:04:05Speaker 01

  I think that that's field dependent.

• 1:04:10Speaker 01

  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, if 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.

• 1:04:41Speaker 01

  But I think if you can, it's very rewarding.

• 1:04:46Hala Taha?

  Spending heavily on ads.

• 1:04:49Speaker 01

  Well, um, I, you know, I, I, I'm somewhat negative on that, but, but it keeps your, your, your machine running.

• 1:04:59Speaker 01

  Yeah, I, I, I don't like it. Um, two.

• 1:05:03Hala Taha?

  Why is that?

• 1:05:04Speaker 01

  There's a great new book coming out by, um, David Epstein, 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. Like it, and, and I don't think people are reflective enough to say, 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.

• 1:05:41Hala Taha?

  And the hardest.

• 1:05:42Speaker 01

  The most obvious and, and, and I think if you had, 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. 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.

• 1:06:05Hala Taha?

  Yeah.

• 1:06:07Speaker 01

  So that's why I think.

• 1:06:08Hala Taha?

  And paid ads are so they paid ads don't work also if you don't have a brand or credibility because they're gonna go Google you and there's not gonna be anything there because you started with paid ads. Um, okay. Networking events and conferences.

• 1:06:21Speaker 01

  Um, I'm a, I'm a big believer that it can be very, very helpful to you. Um, I think it can help you with, uh, both peer and mentor development. Um, 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 Delcante. And when he was very early working in athletic departments, he went to a conference and met four or five other young people that were at the exact same

• 1:07:02Speaker 01

  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.

• 1:07:14Hala Taha?

  Hmm. So it's like going to the action, but for a point of time.

• 1:07:18Speaker 01

  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 D1 athletic directors. They all rose to the top.

• 1:07:34Hala Taha?

  So seven or an eight?

• 1:07:35Speaker 01

  Yeah. Yeah.

• 1:07:36Hala Taha?

  Seven or an eight?

• 1:07:37Speaker 01

  But field, field, you know, field dependent. Yeah. Yeah.

• 1:07:41Hala Taha?

  Raising as much money as possible.

• 1:07:43Speaker 01

  Uh, 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. And that is currently the way things happen. And, um,

• 1:08:20Speaker 01

  You end up with these situations where each competitor is armed with 400, 500, 600 million dollars, maybe more. And it's not, you know, it's, 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, I, I lived through it with the Uber Lyft situation, but it, 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, if, if you're the disciplined one and there are six players with 500 million dollars each hiring salespeople, you, you're not going to matter.

• 1:09:03Speaker 01

  So the game on the field is kind of forced people to do this thing I don't love.

• 1:09:08Hala Taha?

  Yeah. Okay, next one, getting an MBA.

• 1:09:11Speaker 01

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

• 1:09:56Speaker 01

  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.

• 1:10:19Hala Taha?

  A lot of people, a lot of people don't align to it. Well, now you can just learn everything online to your point.

• 1:10:24Speaker 01

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

• 1:10:27Hala Taha?

  Totally.

• 1:10:28Speaker 01

  Yeah.

• 1:10:29Hala Taha?

  So let's move on to leadership. I had Kevin O'Leary on the show.

• 1:10:35Speaker 01

  Yeah.

• 1:10:35Hala Taha?

  And he's another billionaire, I think.

• 1:10:37Speaker 01

  I don't know, but I'll take your word for it.

• 1:10:40Hala Taha?

  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.

• 1:10:50Speaker 01

  Yeah.

• 1:10:51Hala 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 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?

• 1:11:17Speaker 01

  What, 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,

• 1:11:27Speaker 01

  very much lead with the heart and have a, I'd say a passion for leadership that, that includes feeling like a shepherd of the flock. And so I, I push back on that a little bit, like broadly against business.

• 1:11:45Speaker 01

  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. 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 Lyft, especially in metropolitan areas very quickly because of brand erosion. And um,

• 1:12:25Speaker 01

  And by the way, it wasn't, I think, history and 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.

• 1:12:58Hala Taha?

  Hmm.

• 1:12:58Speaker 01

  And there were a lot of constituents in this thing. You know, a lot of our investors, this was such a big number, they had already, you know, it was already moving the needle for several universities and foundations. And if it went away, you know, they have paper marks, they're going to have to mark it down. And that felt, that weighed 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.

• 1:13:32Hala Taha?

  Hmm.

• 1:13:32Speaker 01

  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.

• 1:13:44Hala Taha?

  Hmm.

• 1:13:44Speaker 01

  And, you know, if I could play it again, I would spend more time on that than trying to, you know, play the eventual thing that happened any differently. I think we did the best we could do at that moment and knew there would be consequences. And there were, like, our competitors use it against us constantly. But, but anyway, that's how I would summarize the whole thing.

• 1:14:07Hala Taha?

  Do you feel like you made the right decision?

• 1:14:08Speaker 01

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

• 1:14:12Hala Taha?

  Hmm.

• 1:14:13Speaker 01

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

• 1:14:23Hala Taha?

  Mm-hmm.

• 1:14:24Speaker 01

  Yeah, unbelievable.

• 1:14:26Hala Taha?

  How do you think about reputation in your career? Like, how important is reputation to you?

• 1:14:33Speaker 01

  I think it's really important. Um. 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. 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.

• 1:15:01Hala Taha?

  Mm hmm.

• 1:15:01Speaker 01

  And in venture, that personal brand can shine brighter than even the corporate brand.

• 1:15:09Hala Taha?

  Mm hmm.

• 1:15:09Speaker 01

  A lot of times. And so you just have to worry about it. Um, if you want to be competitive.

• 1:15:16Hala Taha?

  You've had like a really rare chance of being close to so many like extraordinary founders who built really successful companies.

• 1:15:23Speaker 01

  Yeah.

• 1:15:24Hala 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.

• 1:15:30Speaker 01

  Yeah, there's a couple of things. Um, they are continuous learners because they're tilting at some new problem on the edge of their field. And there's no way, um, 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.

• 1:15:52Speaker 01

  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.

• 1:16:08Hala Taha?

  Hmm.

• 1:16:08Speaker 01

  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. 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 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.

• 1:16:46Hala Taha?

  Hmm.

• 1:16:47Speaker 01

  Which usually isn't advertising. So they've figured out some bespoke differentiated way to gain new customers aggressively.

• 1:16:57Hala Taha?

  So good.

• 1:16:59Hala 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?

• 1:17:09Speaker 01

  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, 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. 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 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.

• 1:17:53Hala Taha?

  So the intersection of AI and your field?

• 1:17:56Speaker 01

  Yes. And knowing what's possible and what that means.

• 1:18:01Hala Taha?

  Bill, this has been such an awesome interview. I end my show with two questions that I ask all my guests. So the first one is, what is one actionable thing our young improfitters can do today to become more profitable tomorrow?

• 1:18:13Speaker 01

  Um, I'm going to be redundant with what we talked about, but I just think it's like continuous learning and like, just setting aside time, especially if you're, 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.

• 1:18:37Hala Taha?

  And what is your secret to profiting in life?

• 1:18:43Speaker 01

  You know, I, I would say, you know, you asked me a question about why I wrote this book instead of doing.

• 1:18:53Speaker 01

  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 say that.

• 1:19:22Hala Taha?

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

• 1:19:27Speaker 01

  I think I use my gut to make the leap and to make the decision to push myself. But the willingness to move outside the box, to walk away from something, to like, try something new, you know, to not be afraid to, 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.

• 1:19:55Hala Taha?

  And where can everybody learn more about you and everything that you do?

• 1:19:58Speaker 01

  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, to, 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.

• 1:20:19Hala Taha?

  Oh, very cool.

• 1:20:19Speaker 01

  And do that annually, to try and help give them that extra little amount.

• 1:20:24Hala Taha?

  Let me know when it launches. I'll do some free commercials for you guys and support.

• 1:20:28Speaker 01

  That's awesome.

• 1:20:28Hala Taha?

  Yeah. Awesome. Well, thank you, Bill. Thank you so much for your time.

• 1:20:31Speaker 01

  Thanks for having me.

• 1:20:34Hala Taha?

  Young and Profiter, Sitting Down with Bill Gurley, was truly a special treat. He's spent decades studying world-class performers, and what he shared today challenges so much of the traditional career advice that we've all been given. One of the biggest takeaways from this episode is that the most fulfilled and successful people don't chase job titles or prestige. They chase curiosity. Bill made it clear that fascination is the real competitive advantage. When you genuinely love learning about something, the effort feels free, and over time, that obsession compounds into mastery, opportunity, and impact.

• 1:21:08Hala 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 intentionally and stand out. That means deeply understanding the history of your field while also running towards the edge of what's new, whether that's AI, emerging platforms, or a new way of thinking. That combination of respect for the past and fluency in the future is what makes people impossible to replace. And finally, Bill reminded us that great careers are built through exploration and smart pivots. Most people who end up loving their work didn't get there in a straight line. They experimented, reflected honestly, and had courage to move on when something no longer

• 1:21:49Hala Taha?

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