Transcript

Bill Gurley: Why Your "Safe" Career Will Completely Destroy Your Future

From Young and Profiting · Episode page · Watch on YouTube

· 1 h 29 min · 16,494 words · 245 timestamped sections

This is the full, timestamped transcript of "Bill Gurley: Why Your "Safe" Career Will Completely Destroy Your Future", an episode of Young and Profiting published February 23, 2026 (1 h 29 min, about 16,494 words). It mentions 39 people, works and ideas, including Todd Gurley, Artificial Intelligence, curiosity, Running Down a Dream, Venture Capital.

What this episode is about

Bill Gurley highlights how chasing safety and conventional paths can trap talent, arguing that long-term success comes from pursuing genuine interests, embracing risk, and capitalizing on AI-driven opportunities rather than avoiding them. He reflects on market cycles, bubbly incentives, and the mindset needed to invest and build enduring, passion-driven careers.

Key takeaways

  • AI moves so fast that investors who dodge conversations risk becoming irrelevant relics in the echo chamber.
  • Career regret isn’t talent failure; it’s safe-path choices that outperform on paper but undercut long-term curiosity.
  • Bubble dynamics repeat: plentiful capital amplifies risk-taking and silliness; the antidote is disciplined selectivity, not cynicism.
  • Start-up pace mirrors academia: rapid experimentation beats perfect planning; embrace iterative pivots to stay sustainably relevant.
  • Ask not what you fear about AI, but how to choreograph your skills to co-create it—before you’re outpaced.

Who speaks in this episode?

What is discussed, and when

  1. – 10:00: Todd Gurley, Running Down a Dream, Career Regret, Uber
  2. – 20:00: Framer, curiosity
  3. – 30:00: Wall Street, Silicon Valley, Venture Capital, Designing Your Life
  4. – 40:00: Carrie Khan, Khan Academy, Artificial Intelligence, Benchmark
  5. – 50:00: Experian, Northwest Registered Agent, Side hustles, Venture Capital
  6. – 1:00:00: curiosity, Sustainability, Matthew McConaughey, Zillow
  7. – 1:10:00: Venture Capital, Silicon Valley, University of Texas, Wall Street
  8. – 1:20:00: Uber, Venture Capital, University of Texas, The Innovator's Dilemma
  9. – 1:29:00: Todd Gurley, curiosity

Notable quotes from "Bill Gurley: Why Your "Safe" Career Will Completely Destroy Your Future"

  • Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor known for early investments in companies like Uber, Zillow, and Next Door.
    about Todd Gurley · at
  • In this episode, we unpack lessons from Bill's new book, Running Down a Dream, including how to avoid career regret, staying relevant in the age of AI, and designing a career driven by curiosity,.
    about Running Down a Dream · at
  • 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 Venture Capital · at
  • 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…
    about Career Conveyor Belt · at
  • 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…
    about curiosity · at
  • Which is commitments. one of the people we profile in that chapter is Saul Khan, who created the Khan Academy. And Saul was in a worked at a hedge fund, was doing rather well.…
    about Carrie Khan · at
  • 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…
    about Side hustles · at
  • And it reminded me when I was reading and learning about what happened at Uber with the founder and yourself and how, he kind of started as a mentee and then, over time you had to make a really tough decision. take us.
    about Uber · at

Who and what is mentioned in this episode?

People

  • Todd Gurley — Person · Main guest · 5 mentions · first at
    He shares career-design principles from his book and draws on his venture investing experience (including Uber) to discuss bubbles, unit economics, and learning.
  • Carrie Khan — Person · Profiled example · 2 mentions · first at
    Used as a 'never too late' example: leaving a hedge fund and building Khan Academy via a side project, illustrating mid-career pivot risk and impact.
  • Peter Lynch — Person · Referenced author/investor · 1 mention · first at
    Mentioned because Gurley read Lynch's book and began trading stocks, influencing his pivot from engineering to investing.
    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 that once…
  • Daniel Pink — Person · Referenced expert · 1 mention · first at
    Cited for research/ideas about regret of inaction becoming more salient with age, supporting the episode's career-regret theme.
    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.
  • Jonathan Haidt — Person · Referenced expert · 1 mention · first at
    Referenced for the 'resume arms race' concept describing escalating credential pressure on children and students.
    Heart like you really want them to be okay. but we've gotten into this place, Jonathan Height calls it the resume arms race where like I said, by the time you're in sixth…
  • Bert Beverage — Person · Anecdotal example · 1 mention · first at
    Cited as an example of a career exercise leading to entrepreneurship: founding Tito's Vodka after a PBS-inspired reflection exercise.
    Good at on the other and try and find the middle ground. M that gentleman's name is Bert Beverage and that exercise led to him starting a spirit company called Titos Vodka.
  • Matthew McConaughey — Person · Referenced example · 1 mention · first at
    His story from 'Greenlights' is used to illustrate the importance of parental support in career pivots and committing fully to a chosen path.
    Speaks to the purpose of this book. when he finally gets the gumption and tells his father, his father says, Well, don't halfass it. And in the book, McConna says it was the…
  • James Clear — Person · Referenced influencer · 1 mention · first at
    Mentioned as a notable person who saw Gurley's University of Texas speech and encouraged turning it into a book.
    I put it together and gave that speech and then a number of people saw that speech probably most notably James Clear and people then started pushing me you know one day you should make that a book and as I reached the end of my career.
  • Jerry Seinfeld — Person · Referenced speaker · 1 mention
    Referenced for framing 'fascination' as a better guide than 'passion,' reinforcing the curiosity theme.
  • Meredith Marks — Person · Referenced example · 1 mention
    Used as an example of 'learning in public' through publishing investment memos, alongside Warren Buffett.
    There's a great bond investor named Howard Marx who writes out his thoughts.

Books & papers

  • Running Down a Dream — Book · Core artifact · 2 mentions · first at
    The episode is structured around lessons from this careers-focused book: curiosity-driven work, avoiding regret, learning, mentors, and pivots.
  • Designing Your Life — Book · Referenced book · 2 mentions · first at
    Cited for data about major/career mismatch and for exercises (multiple life plans) to test intuition about career direction.
    Know. like they just don't know yet. And the there's other data in this great book, Designing Your Life, where that 5 years after college, like 40% of people have already moved…
  • One Up on Wall Street — Book · Referenced book · 1 mention · first at
    A pivotal influence on Gurley: reading it sparked his interest in stock trading and helped drive his move toward investing.
    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 that once…
  • The Innovator's Dilemma — Book · Referenced book · 1 mention · first at
    Referenced as a framework for understanding disruption—central to Gurley's interest in tech investing and venture capital.
    They should read Innovator's Dilemma.

Companies & orgs

  • Uber — Company · Case study · 4 mentions · first at
    Used as a major example of venture-scale dynamics, reputation/leadership crises, and the 'sport of kings' fundraising arms race.
  • Benchmark — Company · Affiliation · 2 mentions · first at
    Gurley's venture firm is referenced as part of his background and credibility, including his proximity to major tech outcomes.
    Careers and why is he putting out a book about careers? You could be, putting out a war book on Uber or your times at Benchmark, the VC firm, right?
  • University of Texas — Organization · Event venue / referenced institution · 3 mentions · first at
    Gurley’s speech at the University of Texas helped catalyze the book project; later referenced in a networking/conference anecdote.
    These three people had all done similar things and I wrote down the notes. I then got invited to give a speech at the University of Texas here in Austin and I put it together…
  • Khan Academy — Organization · Referenced organization · 2 mentions · first at
    Presented as a high-impact outcome of a mid-career pivot and side project by Saul Khan.
    Which is commitments. one of the people we profile in that chapter is Saul Khan, who created the Khan Academy. And Saul was in a worked at a hedge fund, was doing rather well.…
  • Zillow — Company · Referenced investment example · 3 mentions · first at
    Cited as one of Gurley's notable early investments, supporting his credibility as a 'super investor.'
    Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor known for early investments in companies like Uber, Zillow, and Next Door.
  • Next Door — Company · Referenced investment example · 2 mentions · first at
    Mentioned as another early investment associated with Gurley, reinforcing his venture track record.
    Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor known for early investments in companies like Uber, Zillow, and Next Door.
  • Gallup — Organization · Referenced data source · 1 mention · first at
    Cited as supporting evidence that many people are disengaged and unhappy at work.
    Yeah. But I would look back before AI and the survey work that we had done and other work, Gallup polls and whatnot.
  • PBS — Organization · Referenced media source · 1 mention · first at
    Mentioned as the source of a career-reflection exercise that inspired Bert Beverage to found Tito's Vodka.
    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…
  • Disney — Company · Host background reference · 1 mention · first at
    The host mentions starting her podcast as a side hustle while working at Disney, reinforcing the side-hustle theme.
    Totally. Well, that's that's what I did, too. My podcast started as a side hustle while I was working at Disney.

Concepts & topics

  • Artificial Intelligence — Concept · Core topic · 2 mentions · first at
    AI is discussed as both a fast-moving technology wave affecting careers and a driver of current venture-capital hype and funding concentration.
    AI is moving so fast. My advice for anyone in any field that's afraid of AI is run at it.
  • curiosity — Concept · Core topic · 5 mentions · first at
    Gurley argues 'chase your curiosity' is a better career compass than generic 'follow your passion,' driving sustained learning and differentiation.
  • Venture Capital — Concept · Core topic · 7 mentions · first at
    Frames Gurley's career and informs advice on fundraising dilution, bubbles, and why some founders should avoid venture money.
  • Career Regret — Concept · Core topic · 2 mentions · first at
    Central problem statement: surveys show most people would choose a different career; regret of inaction is emphasized.
    People aren't that engaged and happy in their careers. We ask a thousand people, if you could start your career over again, would you do something different?
  • tech — Concept · Core topic · 1 mention · first at
    Tech is the backdrop for Gurley's career and for advice about learning the 'edge' (TikTok, AI) and understanding disruption.
    You know and 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…
  • Career Conveyor Belt — Concept · Core concept · 1 mention · first at
    Describes the standardized, risk-averse path society pushes (school→major→safe job), which Gurley argues increases regret and reduces exploration.
  • Side hustles — Concept · Tactical advice · 3 mentions · first at
    Presented as a practical method for mid-career experimentation and optionality without immediately quitting a job.
  • Infinite Games — Concept · Supporting framework · 1 mention · first at
    Used to argue careers are not zero-sum; generosity and peer collaboration create compounding benefits over time.
    Helpful You also mentioned this concept of infinite games, how life is basically an infinite game and you're better off being generous than having sharp elbows.
  • Sustainability — Concept · Supporting topic · 2 mentions · first at
    Discussed in the context of dot-com and AI bubbles: sustainable spending, rational post-crash behavior, and unit economics discipline.
    Whole thing explode. How did that actually change the way you think about investing in companies? Change the way you think about sustainability? One of the things that happens…

Places & events

  • Silicon Valley — Place · Key location / career hub · 5 mentions · first at
    Used as the archetypal 'move to where the action is' destination for founders and venture capital careers.
    Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor known for early investments in companies like Uber, Zillow, and Next Door.
  • Wall Street — Place · Career stage location · 5 mentions · first at
    Represents Gurley's investing career phase and is used as an example of 'move to where the action is' for finance careers.
    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.
  • Texas — Place · Referenced location · 1 mention · first at
    Appears as the setting for Gurley’s University of Texas speech and as a place where speculative AI/data-center activity is mentioned.
    Things and I wrote down the notes. I then got invited to give a speech at the University of Texas here in Austin and I put it together and gave that speech and then a number of…

Media & podcasts

  • Young and Profiting Podcast — Podcast · Host platform · 1 mention · first at
    The show where the interview occurs; the host welcomes Gurley and frames the episode around his book and career advice.
    Bill, welcome to Young and Profiting Podcast.

Sponsors

  • Framer — Company · Sponsor / advertised product · 3 mentions · first at
    Advertised as a website builder with AI tools; not part of the main interview content but present in the episode.
    Leading startups to mine to Fortune 500 brands are turning to Framer now that we're due for an upgrade. Framer is a powerful website builder and design tool that helps…
  • Experian — Company · Sponsor / advertised product · 3 mentions · first at
    Appears in an ad segment promoting subscription cancellation and bill negotiation features.
    Check out Experian subscription cancellation and bill negotiation. Two powerful features that can help you save with minimal effort. Experience scans the accounts that you link, finds.
  • Northwest Registered Agent — Company · Sponsor / advertised product · 3 mentions · first at
    Appears in an ad segment promoting registered agent and LLC formation services for entrepreneurs.
    That's exactly why Northregistered agent is so helpful. That's what they're built for. Northwest Registered agent is a registered agent and LLC service that helps you build…

Full transcript with timestamps

I feel deeply sad for a lot of founders. There's a reality where a modern venture capitalist does not want to take a meeting in anything on AI.

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

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

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

You also started your career at the start of the dot bubble and you saw that whole thing explode. How did that actually change the way you think about investing in companies? Change the way you think about sustainability? One of the things that happens anytime there's a technology wave is people get rich quick and then a whole bunch of people see people getting rich quick and they rush in. I like it when they're not around. When you're in a bubbly time and we may be right now with AI. People do silly things, things that don't usually work. They get very speculative.

You've been ahead of the curve so many times. Can you give us a prediction about the future of work or technology? something that we might be underestimating or unexpected.

I think there will be a lot of money made in Yap Bam. Seven out of 10 people say they'd choose a different career if they could start over. And it's not because they lack talent. It's because they chose the safe path. 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 Next Door. After decades backing billion-dollar founders, he noticed a pattern. The most successful people didn't follow the conventional route. They built careers around what genuinely fascinated them.

In this episode, we unpack lessons from Bill's new book, Running Down a Dream, including how to avoid career regret, staying relevant in the age of AI, and designing a career driven by curiosity, smart pivots, and continuous learning. Bill, welcome to Young and Profiting Podcast.

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

and now you've come out with a careers book called Running Down a Dream. Correct.

And a lot of people might be thinking like what does a VC guy know about careers and why is he putting out a book about careers? 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? 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. Um, I felt a calling to write this book and it was it was something that I had stumbled upon like eight years ago, an idea that had popped into my head. I used to write a lot of blog post and and when I would get an idea I would would scratch it down and sometimes it would become a post some 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 um I I put it together and and gave that speech and then a number of people saw that speech probably most notably James Clear and people then started pushing me you know one day you should make that a book

and as I reached the end of my career you know and 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, um I'm certain at this point that this book has a bigger chance to help more people than any of those other books.

Oh yeah, for sure. I feel like this applies to anybody whether they're just starting or they're, you know, 40, 50 years old and midcareer. Uh I absolutely loved like some of the gems that I found in the book. So you started this project uh doing some surveys and you found out that people were really unhappy with their jobs and and at work. So talk to us about that. 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 seven out of 10 said yes.

Wow. And we did it again with Wharton and did it more scientifically and it was still six out of 10, but a huge number um for people to think they have career regret. And there's work that Daniel Pink has done where he talks about as you grow older, it's your regrets of inaction that weigh most on your brain. 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.

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

and find what they love. And I think having 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 the jobs that are considered safe, the safe jobs. Now, ironically, with AI, many of those quote safe jobs aren't that safe.

Yeah. 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 at large.

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. Um, even getting laid off, uh, even if they had a great job. So, talk to us about why society kind of pushes people this way and what's the alternative? Like, what should you encourage your kid to do instead of just going to college straight away?

Yeah, I I think it's well-intentioned. And I don't think it's just the parents. I think the counselors, everybody. It it's it's uh you you it comes from the heart like you really want them to be okay. Um but we've gotten into this place, Jonathan Height 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's 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. But that doesn't happen anymore. They're just pressure, pressure, pressure. And I think it has the con double negative consequence. One, they don't get to kind of explore and play and and find what they love. And two, um they're just burned out.

You know, they're just burn out. But then it even it it gets worse at college when 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. I mean, I've talked to so many of them and I'm like, "Where do you want to be?" And I don't know. like they just don't know yet. And um the the there's other data in this great book, Designing Your Life, where that 5 years after college, like 40% of people have already moved on to a career different than their major. And by

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 that restricts where they think they can go. I can even think back to my journey. I went to college for organic chemistry and then one year into it I was like this is not for me. I ended up dropping out of college working at a radio station for 2 years.

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

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

to go after it and if you find out you you if you if you put in eight years grinding and find out you don't love something. I don't know if you have I don't know how much you have left, you know, totally to pivot.

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

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

of course. um you know meeting when you go out to promote a book you meet a lot of publishers and you meet a lot of podcasters 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 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 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. 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.

Um so I and and I suspect you consider yourself in your dream job. totally designed my dream career. Like I always tell my audience, my students like have designed everything that I do. It never feels like work. I love what I do. I'm very I think I'm very good at it. 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 cuz it's onethird of our life, 80,000 hours of our life

is at work. So talk to us uh more about why it's so important to optimize our job and do work that we actually love. Well, the the the book is separated into into two halves that alternate. It's stories of success, which I call 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 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, um 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 the this thing that you love,

you're going to out hustle everybody else. And the flip side is true. If you don't love it and you're not constantly learning, someone else is, and you're going to have a really hard time keeping up with them.

Yep. And um I I I find all too often in a lot of traditional jobs, people think, "Oh, I studied up until graduating from college and now the learning's done and I just go in and do the craft."

And I just don't think that's how the world works. Especially in this modern world where if you want to self-learn and you want to continuously learn, there's so much at your fingertips between podcast and AI and all these things. um you're going to get outrun cuz someone's going to someone's going to get out on the edge in front of you.

Yeah. So, the old cliche is follow your passion, but you talk more about curiosity over passion. Why why why didn't you say passion?

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

Yep. Like you not 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 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 it doesn't feel like there's work effort put in to the continuous learning.

But there's not going to be money in everything that we feel obsessed with or that we're curious about, right? So how do people navigate that part of it? Well, one thing if 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 that I mostly wanted to find people in non-traditional fields for this reason. Like I didn't want to there's no Mckenzie consultants, there's no investment bankers, there's not even really entrepreneurs. It's it's more you have a restaurant tour and a basketball coach and and a hair stylist and 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. Y

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 that did that with Texas horiculture. And I, you know, so I I somewhat reject the notion that that you you can't I think there's plenty of studies that show rich people that aren't happy, right? And and I guarantee you these people that are doing what they love every day and have an audience for it and people that reach out to them have a level of personal happiness and satisfaction that's just super high.

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

No doubt. And and by the way, I to I think it's a fair question that you pose and and I was having a discussion with a career counselor at one of the top universities in the country and this topic came up and she said, "Well, what if they studied English poetry or something?" 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.

Yeah, that's part of it. Yes, you would. Yes. Yeah. Yeah. Bam. 2026 is the year I'm fully focused on growing my personal brand. I just started a new brand and content team and that means I'm going to be intentional about every part of my business, especially my website, which I've been neglecting for years. And that's why so many companies from leading startups to mine to Fortune 500 brands are turning to Framer now that we're due for an upgrade. Framer is a powerful website builder and design tool that helps businesses create better websites faster. With Framer, you can design and publish a beautiful, high-erforming website without ever touching any code. It's a visual drag and drop builder with smart AI tools that help you create responsive layouts quickly. Everything you need is built in, including SEO support, analytics, and collaboration so you're not duct taping multiple tools together. It's one

of the easiest ways to launch a website or landing page that looks custom, polished, and professional on any device. Framer is the modern way to launch a website. Learn how you can get more from your.com from a framer specialist or get started building for free today at framer.com/profiting and you can get 30% off a Framer Pro annual plan. Join companies like Gap Media and switch to Framer. That's framer.com/profiting for 30% off. Framer.com/profiting. Rules and restrictions apply. Yap gang, I have become obsessed with the Working Genius Assessment. It was created by Patrick Lenion. He came on my podcast about two years ago and taught me about working genius. I took the assessment then and it was a gamecher for me individually. This year I'm taking it to the next level and I've basically implemented 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. 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 my working frustrations are enablement and wonder. So once I found this out, everything just like clicked for me. Number one, I realized why I was butting heads with my executive team because wonder is frustration for me. Whereas my business partner has wonder as a strength. I wanted to get things done, rally the group, keep things moving. He wanted to think about the big picture and if this was the right direction at all. And so

once we figured out these are our geniuses, we realized we can't build this company without each other and our strengths. And it helped us work better together. And it also helped me uncover gaps within my organization. Turns out I'm the only person who has galvanizing as a core strength. So I'm always rallying the team and sometimes that can come off as pushy or aggressive. But now that my team knows that this is a gap. We need to hire people who have more of this galvanizing strength. So it really helped us align on gaps. It'll totally change the way that you do your work. It will totally level up and your team's happiness and productivity at work. I highly recommend that you take this assessment. and it's extremely affordable. If you're ready to stop guessing and start working on your actual genius, take the working genius assessment and get 20% off with code profiting at workinggenius.com. If you

have a company, if you have a team, you get a report tells you like how to take advantage of your learnings and things like that. If you like what you saw and you want to implement it to your team, I highly recommend that as well, so you can get your team map. And I have a code for that, too. It's profiting teams. 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 prep preparation of your job, that's like a really good signal that you're doing something that you love. If you actually enjoy the prep work. So for people tuning in, what are some other signals or questions they can ask themselves to

judge whether or not they're on the right path? Well, a couple different things and and we have a whole chapter dedicated to this topic and give I I literally went and studied all the other advice all the great had given and tried to like make it a laundry list so that you could try every one of these things. Um, and there's so many different fun little exercises you can do. Um Dave Evans and at Stanford who did Designing Your Life. Um 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 it the other and then you can battle card them which is an interesting way to really test which one you're most excited about. Your intuition when you do that will typically pick up on one of those. Um, there's a great story in the book.

There's a gentleman from here in Austin that spent the first part of his career in seismology and then he became a mortgage broker and he'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. M

um that gentleman's name is Bert Beverage and that exercise led to him starting a spirit company called Titos Vodka.

Oh wow. The most successful spirit business in America right now. Um yeah, and like he he the idea to do that came from that exercise. So we have a ton of those exercises here. The other thing that um 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." 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 and I don't regret either of those two stopping points in my career. I built upon them and and they were both relevant. They both helpful to what I did later. Mhm.

Um, so it 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. Yeah. You know, 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.

Uh 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 Compact, you went to Wall Street.

Y what did you feel like you were obsessed with that led you down VC? So it's super easy. So um like many people who ended up in Silicon Valley, I had a computer early in my life. So I had a Commodore Vic 20 plugged into a TV. didn't have memory.

I don't think we know what that is. Yeah, it was it was early, really early. And um but I I found I liked writing programs. It was like very fulfilling. And so when I went to University of Florida, I got a computer engineering degree. Um enjoyed that process and went to work at Compact, which at the time was a very hot startup in Houston, uh in the personal computer industry. And um yeah, so that was the first one and that was the reason I got there. What happened was um two years in we started the third project from when I had joined and it looked like the second project which looked like the first which is part of what got me wondering if I was going to grow bored doing this type of work and then um when I was at home I had read this book one up on Wall Street by Peter Lynch and I had started trading stocks so that once it getting to this test in my free time I was playing with something else I wasn't M

learning about the work I was learning about this other thing. And so I went to business school, ended up on Wall Street. U had it. It was awesome being in Manhattan in your late 20s. Just fantastic. Um met so many great people, met so many great investors and uh enjoyed reading about investing, enjoyed being a part of Wall Street. Once again though, three years in I just started to think about the job and it what I was doing every day and said do I want to do this my whole life and came to once again to a conclusion no I don't and I had along the way been building up this thought process that I wanted to be in venture capital and the opportunity came to move to Silicon Valley and and yeah from there I was able to get into venture. Yeah.

And 3 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.

So, do you think investing was really your obsession? It's a combination of things. I love technology. I loved understanding how it could be disruptive and how people could, and by the way, this is true for all entrepreneurs, how people could ride the edge of what was changing and then become successful. the the the book um um Innovator's Dilemma walks through exactly how that works. Um and then this is this is uh a little more kind of personal, but when I was in college, we started going to Vegas and like counting cards and playing blackjack. I do I do think there was a little gambler little gambler mentality in there also.

And it was those things combined. Interesting. you know, investing, tech, gambling, a little bit, disruption,

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

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.

Um, 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. Mhm.

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 breath 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 a ton of wonderful founders who have to have their hands on the steering wheel and want to be in that position and I think those jobs are are complimentary to one another. But people if they get in touch with what which one of those people they are, it may impact what career they want to go after.

Totally. Totally. So if somebody is younger and uh they want to design their dream career, they may went to college, they're in their first job, how do you suggest that they start actually um you know taking the steps toward independence and and designing their own dream career? So, we walk through a lot of it in the book, but I think it starts with learning. And um 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 what? Pick up an encyclopedia to learn about something 30 or 40 years ago. It's just insane. So, um, start the learning process and there's so much great content out there. Um, you know, in any industry, there's typically a podcast or 10 that you can go watch and learn and and and listen to the best. Um, there's stuff on YouTube. You know, you can talk to AI until you're blew in the face. 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. I was going to say you call it like the canon.

Yes. And most people don't take the time to do it, but it will make you look very differentiated.

Um because it shows respect. And I also think there's a element of just bedrock knowledge that's nice to have.

Yeah. There's a anecdote in the book where there's this world chess tournament and they take a pause and do a trivia contest and Magnus Carlson wins the trivia contest which I think is interesting.

Was he a good chess player? Huh? He he's the best chess player in the world. But but my point is he he knew he knew all the history as well.

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

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 Tik Tok 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. Mh.

And so even if you know you're chasing a field that doesn't feel like Tik Tok 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.

100%. 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. 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 techsavvy and knew how to hack LinkedIn and and got promoted so quickly because I knew more than the other people who started at 23.

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

Yeah. Um which I think a lot of people miss. Like I think of people who want to 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 uh even really popular podcasters don't know that stuff. So talk to us about the importance of learning the unsexy stuff.

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 going to sound like I'm name dropping, but a a partner of mine at Benchmark won at auction at dinner with John Lacier, who was the creative genius behind Pixar.

Um 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 a cartoon that had that 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. And there was stuff from Japan and there was Steamboat Willie and all these these things. And you're like, I mean, that's where I get back to. There's so many of these people that they're that they're at the top of their field that have this like just super respectful understanding of the history.

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.

Yeah. 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

and you have found and you could do this with AI in 5 minutes. You 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, "Holy crap, this person really cares." Like, you know, they really care about this field.

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

Yes. You know, you're just you're making sure that you really understand the history. Um and when I think about podcasting, it's pretty new. So, I guess I would study like TV and radio, right? If if and for AI, what would you study? The internet. Well, I mean there are some people that have been working on AI for 10 or 20 years. Um, yeah, AI is moving so fast. I think you should spend every last minute just using

just using 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.

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

Totally. You're you're you're you're on the firing line if that's you. And and don't stop at Chad GBT. There's so many other apps out there. I know I I myself like I'm addicted to Chad GBT. It's like trying to just

try them all and and and ask you can ask them this but it's kind of uh 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 60 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?

Mhm. Like, and tested whether it's still making that error cuz it's getting better constantly, 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.

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

Yeah. Um I think it's insane. Like it's such an accelerant. Like you can learn about anything and I'm probably doing 30 searches a day on

Oh, I'm on it. I I can't do anything without it anymore. I always want to. Right. It's become the number one way you start to learn about something. Yeah, me too. Me too. I I think it's quite ironic that people feel like, "Oh my god, AI is coming and my job's at risk." When if you're if you have the gumption to be at the edge of your field and to be really differentiated and have this love affair with which you do, oh my god, I it should allow me to separate from the field. Like this should be my finest moment, not something to be afraid of. Do you ever feel like AI is changing the way that your brain works? It's

a good question. Um Um I think I'm constantly asking myself that question and I and I'm skept I like I don't take anything as a truism.

So I I try again. But it it's possible. 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? Yeah.

And in the past, I would 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. You know what I'm saying?

Yeah. Yeah. You might be um limiting your own imagination by not giving yourself enough free time to ponder the possibility.

I feel like there needs to be like time box, no no AI, use your brain, you know?

Yeah, I think that's a good I think that's a good call out. Okay. So, let's say you're mid-career,

40 years old. Yep. Made money, but you have responsibilities. Yeah. What do you do if you find that you are not living out your passion? Like where what what

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. Um I don't think it's easy for the reason you bring up which is commitments. Um, one of one of the people we profile in that chapter is Saul Khan, uh, who created the Khan 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 Khan Academy. and um he he felt drawn to doing it as a nonprofit, which makes that math even harder. Um but his wife was supportive of him trying it for a year. They literally said, "Let's do it for a year." So, he walked away. 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. Yeah. Um but look what happened. I mean, I'm there are very few people on this planet that have changed the world as much as as Saul Khan has.

Yeah. Like we actually and I interviewed him a little while ago. Wonderful guy.

Yeah. One of the guys on the acquired podcast came up with this idea which I really loved called side hustles.

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

And especially has nothing to do with the job. Yeah. 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 le 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 uh he's one of the most successful podcasters on the planet and loves what he's doing. But but the experimentation of this side hustle gave him exposure to new things. Um and and in in both 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?

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

There you go. Right. And me and the acquired host, what's his name? Uh, Ben Gilbert.

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. What's the difference between the two?

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

Yeah. 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 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 and you can learn and you can follow their career. And one of my profiles is of of Danny Meyer, the great restaurant tour in New York. And he did this when he decided he was going to be a restaurant tour. He made a list of it was 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. 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 him you know so much about him

back to the history learning the history. 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. And and the truth of the matter is

people in the second tier get almost zero ask. So, if they're more willing 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.

Yeah. Hey, Appam, I know a lot of you are working hard to hit new financial goals this year, but it can be tough to get ahead when subscription creep is quietly draining your bank account. I can't tell you how many times I thought I canceled something only to realize later they were still charging me. Or how many times I tried to cancel, but it was so difficult I couldn't figure it out. And if you're like me, you have way too many subscriptions and bills, and you're probably looking for a way to track and manage them all. Lucky for us, Experian handles all that heavy lifting.

Check out Experian subscription cancellation and bill negotiation. Two powerful features that can help you save with minimal effort. Experience scans the accounts that you link, finds reoccurring charges, and puts the power in your hands. You can keep the subscriptions you want, and cancel the ones that you no longer need or use. Experian can cancel over 200 eligible subscriptions from streaming services to entertainment apps and more. And it doesn't stop there. If you want to also try saving on everyday bills, experienced expert negotiators could help you by finding better rates on eligible bills you're already paying.

The best part, you get to keep 100% of your savings. Get started now with the Experian app and let your BFF big financial friend do all the work for you. 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. Yeah, fam. Starting a business is exciting, but it can also feel really overwhelming. There's so much you need to figure out from operating agreements and compliance paperwork to legal stuff and more. And I don't know about you, but I am not an expert on the legal stuff. I actually hate doing that kind of stuff. But that's exactly why Northregistered agent is so helpful. That's what they're built for. Northwest Registered agent is a registered agent and LLC service that helps you build your complete business identity in one place. They've been helping entrepreneurs for nearly 30

years, and they're the largest registered agent and LLC service in the US. When I started my company, I wish I had known about them. In fact, I'm going to be switching to Northwest Registered Agent because as your company gets bigger, your registered agent and is actually really, really important, and I actually found that out the hard way recently. What sets Northwest Registered agent apart is that they don't just help you form your business. They give you everything you need after you form it. You get access to thousands of free guides, tools, legal forms, and even creating an account. When you do sign up for free, you get a lawyer drafted operating agreement, bylaws, and meeting minutes, all at no cost. This is such a great solution for somebody who's just starting their business, who doesn't know how to start a business. And it's they make it so easy for you. And they also just make your business super

legit. You need to do this to have a legit business. So, don't wait. Protect your privacy, build your brand, and get your complete business identity in just 10 clicks and 10 minutes. Visit Northwestregistered agent.com/yapfree yapfree and start building something amazing again. Get more with northwestregistered agent at northwestregistered agent.com/yapfree. 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 uh publicly learning like learning in public. You did this with the blog that you started. Yes. A lot of creator entrepreneurs nowadays who who are building personal brands, they're also learning publicly and there's so much benefit to that. Can you speak about that?

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 Marx 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. You accomplish what you were afraid you're not doing

by just using AI because you you really don't want to there to be inconsistencies. So you really think through it and you give your brain a 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 um you're going to create avenues for networking

um and so it's a way to differentiate yourself I don't know if it's for everybody and I don't know if in all fields your employer will allow it

that's true but I think in most cases I think it it it does help it it could be it can be very very helpful You also mentioned this concept of infinite games, how life is basically an infinite game and you're better off being generous than having sharp elbows.

Yeah. How have you been generous in your career? Can you give us some examples or other uh you know personas and stories about people being generous?

So this topic um I think comes up in the chapter we have on peers called embrace your peers. And it's probably my favorite of the principles in the book. Mainly because I don't think it's a subject that's well uh it's not well studied in the in the literature. 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 f 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.

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 podcast, when he was getting into YouTube, there weren't it wasn't a field yet. Yeah. 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 were learning together and sharing. 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 and and 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. you know, they hog the limited equipment, they, you know, they kiss up, they, you know, you you can tell who these people are. And I would just say stay far, far away from 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 that that's so compelling and so wonderful like it probably won't be that way 60 days from now.

Like and I just think the benefit of open sharing um far outweighs some advantage you're going to have by keeping knowledge proprietary to yourself.

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

Yes. you know, which is so so valuable and it's an asset in itself. Absolutely.

The information is going to get stale, but your personal brand is just going to keep growing, right?

No doubt. The book really has two target audiences. So, on one hand, it's the young person who's or even maybe up to midcareer who really is trying to figure out what they want to do or always wanted to chase a dream or and didn't know how and and and or and and or 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's going to be handed this thing. I hope I hope they take the time to read it." Um but the other audience is the parents, the counselors, the people that are playing a role in this shaping of these careers for other people because

um 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 McConna on and in his book Greenlights, he tells this story of um he's gonna

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 it's a great scene. It really to me speaks to the purpose of this book. Um when he finally gets the gumption and tells his father, his father says, "Well, don't halfass it." And and and in the book, McConna says it was the last thing he expected, but the most valuable thing his father could have said. It gave him permission, responsibility, a push. Um told 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 but h how do for all that second group? How how can I help you be as good as MCA's dad was at that moment and you know sense that there's a sparkle of of interest and curiosity and help it flourish.

Yeah. Cuz 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 you think you're doing good, right? So, 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 to them,

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

Mhm. You know, and that's just got to be such a wonderful feeling, you know. Mhm. And I have to say like I read two books a week, you know, because of my job, right? So, I loved your book. I feel like there was so many great things in there. There's so many things that I'm going to even use and like the history thing is something that really stuck with me in terms of like I really just know 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.

Thanks for reading. You started in VC. You were behind so many, you know, huge companies, Zillow, uh, Uber, Stitch Fix, so many big companies. Um, you also started your career at the start of the dot bubble.

Mhm. And you saw that whole thing explode. Yep. How did that actually change the way you think about uh investing in companies change the way you think about sustainability for companies?

Um talk to us about those fundamentals. it I think it 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 5 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 and 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 like 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 postc crash part to be very sane and rational.

And so it was I just thought and it was slower, which for someone building their career and and also the charlatans leave town. So, one of the things that happens anytime there's a technology wave is 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. Um, but they come in every wave. So, it is what it is

with AI, you know, um 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 um with great unit economics and and everything like that. They can't get funding. Um do you think there's a problem with the investment in AI and do you think that's a bubble? I think well there's a whole bunch in what you just said but let le let me start let me start with this highle uh point that I'd like to make um this professor Carlaua Perez recognized something that I think is really important to understand which is when there is a wave there is massive wealth there is ma there's disruption and the deck chairs switch and people make a lot of money and that's already happened here because open AI and entropic are paying and their employees secondary earlier than anyone ever had. So the money is being made. It's being put in people's pockets

and that's going to attract speculators and and we here in Texas we had a spa 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-AII. No, I make the argu is why there's a bubble. So I I think I think it's important to know that. Um

there is a reality right now and I feel deeply sad for a lot of founders. There is a reality where a modern venture capitalist does not want to take a meeting uninterested in anything on AI. And I could, if I was forced, make an argument as to why that's the exact right behavior by the venture capitalist, but I I think it's unquestionably true. Like there's just zero interest.

Yeah. 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're, 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 you don't want it, you don't if it feels painted on that 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, 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 is 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 tuckin acquisitions. 20 30 $50 million. And the minute you take venture that's off the table

like cuz now the venture capitalist needs a much bigger outcome. Yeah. And so if you can scrape by you know and I know it's hard.

Tito never took venture money. He owns a 100% of this massive business. Wow. 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.

I want to uh 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-doll 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 move you moved away from this like grow at all cost model and investing in companies that just want to grow

and you were looking at unit economics. So, let's start there. Unit economics. How can you explain that in plain language for our listeners? Well, I suspect that the smaller entrepreneurs that are living hand-to-mouth on cash flow are pretty in touch with their unit economic. It's the but they might not guys that raise 100 million of venture capital that lose touch with unit econom. Yeah. It's just a matter of understanding what are the true variable cost associated with the product or service that you're selling and being honest with yourself even despite what the accounting might be that requirement for gross margin but what are the true variable costs. So that could include selling and customer service and all these things so that you know the the marginal uh contribution ideally from a cash flow perspective that you get with each turn of the crank.

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

No doubt. and and you know it may be different based on uh the type of customer the size of customer the source of the lead like all those things might be different 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 and 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 um unit economics over the lifetime of a customer

early on. Yeah. And I I know you have a problem with LTV traditionally, right? I think people get into more trouble with the LTV formula than they do um than they get success out of it.

Why is that? Well, I I wrote it's one of my favorite blog posts I've ever written. So, if someone wants to go deep, uh it's called the dangerous seduction of the LTV formula, and it's easy to find on Google. um you know, it's not um an erroneous way to measure something. It's actually a smart way to measure something, but it's not a strategy.

And I think people get lost in thinking it's a strategy. And and especially if they're someone who's growing their business on a heavy marketing spin. And I just in general I would, you know, the blog post does all this, but I would push people, you know, really really think about could I be winning customers with PR? Could I be winning customers with with with non-paid social? Could I be winning customers with productled growth, which is a great uh um 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 spend.

I've never heard of productled growth. Can you explain that? Yeah. Um and and by the way, you could talk to AI or you could, you know, do Google searches and find people that have written extensively about productled growth, but it's is there a way to build into the product um the ability to find incremental customers. M.

So, could you, you know, one of the things that that I've been pushing the Stitch Fix team to do that I hope will come out soon is here's here's here's your next fix. 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. Yeah. You're letting the customers share it themselves.

Yes. And so, the product's leading to new customer introductions without these other techniques. By the way, there's plenty of people that have done that in enterprise. You know, Slack notoriously had this way where you could invite people outside your or like so it's not just a consumer.

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

Exactly. Yes. Yeah. So, if uh let's say you were mentoring me, my company makes $7 million a year now.

Okay. Um what would you want to see in my uh dashboard in terms of metrics? like what kind of metrics would you want to see on a very simple dashboard baseline?

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

selling? Yeah. And so cuz that that matters a little bit because you need to think about who the natural acquirers would be and how they would why they would fit it in. How do they measure their own business, you know, and so will this look appealing to them through that lens? Those kind of things. Um,

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 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 5 years, your business is going to be pretty big, you know, and so having, having gone to the exercise of filling out an Excel spreadsheet and thinking through what that means in terms of employees and salespeople and marketing spend, all those is a very useful

exercise and one that the majority of founders do not naturally do. Mhm. Like it's not something they want to do even, but they should do.

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

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

like every business metric that matters. Everyone agrees dollar retention is the one that matters most,

but that doesn't apply to everything. Yeah. So, um, so it's kind of dependent on the business.

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

Okay. So, let's play a game. It's called Billionaire ROI Ranking. Okay. This going to put everything that we just talked about together. I'm basically

Am I the first person to play this game? Oh, yeah. I have new games for for everyone. Okay.

So, basically, you're going to rank each thing 1 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,

but and you can, you know, give some color on why you ranked it one to 10. So, is it a good return on our investment?

Okay. Okay. First one is reading and learning every day. Oh, yeah. Uh, nine nine out of 10, maybe 10. And that's partially because um I've always felt that way, but also the people I respect the most feel that way. 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 moving to where the action is. 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 a sixth tenant and it was it was moving to where the action is. Um, I strongly believe that if you can afford it, you'd rather be an even average player where everyone's doing this thing than being the best player in a market that doesn't rank for that field.

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 it's the number of what it really does is the number of chance positive things that are going to happen. I'd probably use the word optionality just goes up 20x.

Like you're just going to run into so many people doing the same things. And like and if if 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 eight out of 10 for most fields. There are a few field if you're a coach you can't really do that. Um there are some fields where you can do it virtually subreddits and things like that.

Yeah. I think about I moved to Austin a year ago as a podcaster and there's just so much serendipity. It just things just happen naturally when you

That's a great word. Yeah. Yeah. Um, building a personal brand, I think that that's field dependent. Um, 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. Um there's always a risk that you um become someone who's somewhat performant on the brand side and maybe not developing the real skills underneath it 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.

Um, but I think if you can, it's very rewarding. Spending heavily on ads. Well, I'm I you know, I I I'm somewhat negative on that, but but it keeps your your your machine running, so I don't truth.

Yeah, I would I I I don't like it. Um, too, why is that? 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." Like,

and the hardest, the most obvious and and and and I think if you run an exercise, which I mentioned in that blog post, where you say, "Set the mark, 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.

Yeah. Um, so that's why I think that and paid ads are so they paid ads don't work also if you don't have a brand or credibility cuz they're going to go Google you and there's not going to be anything there

cuz you started with paid ads. Um, okay. Networking events and conferences. 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 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.

So it's like going to the action but for a point of time. Yeah. Yeah. and and that group of friends um stayed in touch, started a text group, started sharing ideas, and they expanded a little bit over time, but they're now all D1 athletic directors. They all rose to the top.

So, seven or eight. Yeah. Yeah. Seven or an eight. But, but field field, you know, field dependent. Yeah. Yeah.

Raising as much money as possible. Well, um, I' 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 you end up with these situations where each competitor is armed with 400500 $600 million maybe more um and it's not you know it's I like to say it's not your father's venture capital this is a sport of kings world we've evolved into

and um it's fight to the death. I I' I'd live through it with the Uber Lift 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's six players with $500 million each hiring salespeople, you're you're not going to matter. Mhm.

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

Yeah. Okay. Next one. Getting an MBA. Yeah. I'll say seven. But but part of it's me reacting to the fact that so many people in the entrepreneurial world make fun of it. There's a lot of people that 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. That doesn't mean they have to go get an NBA, but they should read Michael Porter's Competitive Strategy. 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. A lot of people a lot of people don't align to it. Well, now you can just learn everything online. To your point,

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

Yeah. Um, so let's move on to leadership. I had Kevin Olirri on the show. Y and he's another billionaire, I think.

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

Yeah. 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? What one of the things that I would push back on was what Kevin said is the the best CEOs that I've talked to um very much lead with the heart and have a

I 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. Um the situation that that we got into at Uber, there was a asset the company that that was shared by many constituents, you know, the employees, the investors, everybody. And um we because of several things that had happened, things were in a bit of a freef 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 and and by the way, it wasn't I 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 um 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 6 months to 12 months later and the erosion was going to be even more.

And um there were a lot of constituents in this thing. you know, a lot of our investors, this was such a big number. They had already, you know, it was already moving the needle for several universities and foundations

and if it went away, you know, they have paper marks, they were going to have to mark it down. Um, and that felt that weighed on me. That felt like a lot of responsibility. So, I've said publicly before, you know, I if if a venture capitalist does their job the right way, you don't get to that point.

So, the, you know, the the thing that I wish I had been able to accomplish was through leadership preventing us from getting to the place where that hard decision has to be made. Mhm.

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.

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 public company over 10 billion a year in free cash flow like from where we were.

Mhm. Yeah. Unbelievable. How do you think about reputation in your career? Like how important is reputation

to you? I think it's really important. Um in in the venture area it's probably a nine. like I don't know that it's that high in every other field. I don't know that I'd have a good field for um in venture 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 and in venture that personal brand can shine brighter than the even the the corporate brand a lot of times. And so you just have to worry about it um if you want to be competitive.

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

Yeah. What are some of the patterns you see with these founders and I think a lot of it actually ties back to what you wrote in your book probably.

Yeah. There there's a couple 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 5 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 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. Like, you can't do that stuff without being able to sell in some way, shape, or form. It's people do it in a variety of different ways. There's people that are rahrh. 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,

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

So, good. You've been ahead of the curve so many times. Can you give us a prediction about the future of work or technology? Something that we might be underestimating or unexpected?

It's so hard right now. I mean, I love the notion of contrarian investing and when we're in one of these big waves, it's kind of off the table cuz everybody's doing the exact same thing. And um you know I I think there will be a lot of money made in in verticals like people who figure out how AI applies to something that's very specific to their world.

Um and and at this point in time coding and legal and probably medical are overfunded by the venture capitalist. So there's not much oxygen in those areas. But if you can figure out what it means for all the other fields that are out there, I think there's quite a bit of opportunity.

So the intersection of AI and your field. Yes. And knowing what's possible and what that means.

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

All right. So the first one is, what is one actionable thing our young and profiters can do today to become more profitable tomorrow? Um, I'm going to be redundant with what we talked about, but I just think it's like continuous learning and like, um,

just setting aside time, especially if you're if you're a founder and entrepreneur who's hustling all the time, you may feel like you have no time, but setting aside some time during the week to learn something new.

And what is your secret to profiting in life? You know, I I would say, you know, you asked me a question about why I wrote this book instead of uh doing um a book about venture or whatever. And there's this great quote that life begins where your comfort zone ends. And I think a 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, um, I'm not a kind of a conformist. Like, I like attacking things in new ways. I like learning new things. And so, I'd probably say that.

And would you say some of that is like gut intuition? Is that what you're alluding to? I think I use my gut to make the leap and to make the decision to push myself, but the willingness to move outside the box, to walk away from something, to like try something new. Um, you know, to not be afraid to to evolve past whatever the current thinking is. It's something I've always done. And I I'm thinking numerous examples in my history where that paid off. And where can everybody learn more about you and everything that you do?

Well, you can follow me on X. That's where I have most of my content. Um, there's websites now for the book. We're launching a foundation alongside the book, I should mention, um,

to for for those people that want to chase their dreams and might not have the financial wherewithal to do it, we're going to do grants. We're going to have an application process.

Oh, very cool. um and do that annually um to try and help give them that extra little amount.

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

That's awesome. Awesome. Well, thank you, Bill. Thank you so much for your time.

Thanks for having me. Young and profiters. Sitting down with Bill Gurley was truly a special treat. He spent decades studying worldclass 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. 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 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 fivestar review on Apple, Spotify, or Castbox. This year I'll be doing more Inerson 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 thescenes look at my life and more personal stuff, you can connect with me on Instagram at Yapwithala or LinkedIn by searching my name. It's Hala Taha. Huge shout out to my incredible Yap team. As always, this is your host Kala Taha aka the podcast princess signing off.

Questions about this episode

Who speaks in "Bill Gurley: Why Your "Safe" Career Will Completely Destroy Your Future"?

Bill Gurley (Guest), Hala Taha (Host).

What is "Bill Gurley: Why Your "Safe" Career Will Completely Destroy Your Future" about?

Bill Gurley highlights how chasing safety and conventional paths can trap talent, arguing that long-term success comes from pursuing genuine interests, embracing risk, and capitalizing on AI-driven opportunities rather than avoiding them. He reflects on market cycles, bubbly incentives, and the mindset needed to invest and build enduring, passion-driven careers.

What is mentioned in this Young and Profiting episode?

39 people, works and ideas are mentioned, including Todd Gurley, Artificial Intelligence, curiosity, Running Down a Dream, Venture Capital, Uber. Each one on this page links to its own page with every episode that mentions it.

How long is "Bill Gurley: Why Your "Safe" Career Will Completely Destroy Your Future"?

The episode runs 1 h 29 min; the transcript is about 16,494 words in 245 timestamped sections.

More from Young and Profiting

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated October 29, 2026.