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

Summary

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Young and Profiting with Hala Taha

Episode E387 – Bill Gurley: Break Free From Career Regret and Design Work You Love
Date: February 23, 2026

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Episode Overview

In this episode, Hala Taha interviews legendary Silicon Valley VC Bill Gurley, known for early bets on Uber, Zillow, and Nextdoor. Drawing from his new book Running Down a Dream, Gurley discusses career regret, why most people don’t love their jobs, how to break free of the “career conveyor belt,” and the critical importance of building a work life driven by intense curiosity and adaptability. The wide-ranging discussion features practical strategies for career pivots, lifelong learning, relevant use of AI, unit economics for entrepreneurs, and the power of public learning and peer networks.

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Key Discussion Points & Insights

1. The Crisis of Career Regret and Disengagement

• Career Dissatisfaction Stats
  • Gurley & his research team surveyed 1,000 people: “If you could start your career over again, would you do something different?”
    Result: 7 out of 10 said yes ([00:21], [04:45]).
  • Even in a more scientific survey with Wharton, 6 out of 10 would change paths ([05:19]).
  • “It’s your regrets of inaction that weigh most on your brain...that thing you never tried just eats at you as you get older.” — Bill Gurley [05:19]
• Career Conveyor Belt
  • Pressures from parents, counselors, society drive kids into “safe” jobs, often too early, leading to burnout and lack of fulfillment ([07:06]-[09:33]).
  • College system now requires too-early specialization: “They make you apply to a major when you’re a junior in high school...and they just don’t know yet.” — Bill Gurley [08:07]

2. Designing a Career Around Obsession and Curiosity

• Gurley’s Core Principle: Lead With Curiosity
  • He prefers “chase your curiosity” or “fascination” over “follow your passion.”
  • “If you really want to dent the universe, you have to love learning about what you do....And the flip side is true: If you don’t love it, you’re going to have a really hard time keeping up.” [13:20]
  • “Fascination is like...you just can’t stop learning about [the subject]. And the great thing is...the learning feels free if you love it.” [14:04]
• Signals You’re On The Right Path
  • Enjoying the preparation behind your job ([22:06])
  • In your free time, choosing to learn/read more about your field
  • Use of career-mapping exercises (listing 3-5 dream job profiles, passion/skill intersection analysis, etc.)
  • Willingness and ability to move on from jobs that don’t fit ([22:27])

3. Nonlinear Careers and the Value of Roaming

• Experimentation and Smart Pivots
  • Data shows that 40% have changed careers off their college major within 5 years, and 60% within 10 years ([08:37]).
  • Gurley points out that those who explore multiple directions then “press the gas where they still have energy in the tank” end up most fulfilled ([09:54]).
  • Personal example: Gurley changed fields repeatedly until VC “felt right” ([25:25]-[27:44]).

4. Public Learning & Building a ‘Candidate of One’ Career

• Creating Unique Paths
  • “Become a candidate of one” — design a role for yourself, don’t just pick from a menu ([10:44]).
  • Gurley and Hala emphasize the immense opportunity in self-directed, creator careers (e.g. podcasting).
• Learning in Public
  • Gurley’s blog and public writing attracted valuable networking and solidified learning ([49:25]).
  • “When you write things down and, and you know you’re going to publish them publicly, you really test all the theories in your brain...You accomplish what you’re afraid you’re not doing by just using AI.” — Bill Gurley [49:35]

5. Mastery: Knowing the History and the Frontier

• The ‘Barbell’ Advantage:
  • Know the history of your field (“the canon”) and the edge (latest technologies, practices).
  • “Most people don’t take the time to do it, but it will make you look very differentiated.” — Bill Gurley ([30:51], [33:22])
  • Example: Pixar’s John Lasseter’s deep cartoon knowledge, Magnus Carlsen’s trivia mastery in chess [33:22], [31:05]

6. The Role of AI in Career Differentiation

• AI Fluency as Table Stakes
  • Gurley repeats: “My advice for anyone in any field that’s afraid of AI is run at it.” ([00:21], [35:41])
  • Leverage AI for accelerating learning, gaining edge skills, and creating new opportunity.
  • “It should allow me to separate from the field. Like, this should be my finest moment. Not something to be afraid of.” ([37:53])
  • Don’t be a skeptic who never experiments: “You’re on the firing line if that’s you.” ([36:27])
• AI Changes Mastery
  • “It’s such an accelerant. Like, you can learn about anything. And I’m probably doing 30 searches a day...” ([37:39])

7. Tactics for Pivoting at Any Stage

• Mid-career Pivots
  • It’s “never too late”—Gurley profiles people (like Sal Khan) who started their defining careers after 40 ([39:36]).
  • “If you get a job and immediately build your expenses right up against that salary, then you might not have the flexibility to pivot down the road. So be careful.” [24:47]
  • Use the “side hustle” approach for safe experimentation ([40:56])
• Young Professionals
  • Use freely accessible resources to learn; history and frontier advantage ([29:55])
  • Build both industry knowledge and the “unsexy” fundamentals ([32:52], [33:22])

8. Mentorship & Peers

• Aspirational vs. Local Mentors
  • Don’t immediately reach for the stars with mentorship; study aspirational mentors from afar before making direct contact ([42:32]-[44:47]).
  • Get direct help from approachable mentors one or two tiers above you — “they’re going to be flattered that you ask them.” ([44:34])
• Peer Collaboration as Acceleration
  • “Embrace your peers” is Gurley’s favorite principle; Mr. Beast’s “40,000-hour” Skype group exemplifies compounding group learning ([51:21]).

9. Entrepreneurship Fundamentals: Funding, Economics & Growth

• Unit Economics over Growth-at-all-Costs
  • “A lot of founders lose touch with [unit economics] when they raise $100 million in venture capital.” ([63:41])
  • True variable costs, not just accounting “gross margin,” matter most. Push for customers via PR, product-led growth, not just paid marketing ([66:35])
• Product-Led Growth
  • Example: Stitch Fix feature to let customers share products with friends—using product as acquisition engine ([67:16])
• Advice on Raising Money
  • Be wary of taking venture capital too early; can lose control and limit exit flexibility ([62:49])
  • “If you can do it...try and do it [without VC]. ...your ownership will be a lot higher.” ([63:01])
• Marketing and ROI Ranking Game ([70:06]-[79:09])
  • Reading/Continuous Learning: 9/10 (“Toby at Shopify and Buffett agree.”)
  • Moving to Where the Action Is: 8/10 (optional serendipity, career growth)
  • Building a Personal Brand: 6/10 (valuable, but skill depth comes first)
  • Spending Heavily on Ads: 2/10 (“That’s the least creative thing I could possibly be doing.”)
  • Networking Events/Conferences: 7/10 (especially for peer + mentor development)
  • Raising As Much Money as Possible: 3/10 (trend pressures, but risky for long-term health)
  • Getting an MBA: 7/10 (not essential, but don’t ignore business learning fundamentals!)

10. Reputation, Leadership, and Decision Making

• Reputation
  • Wildly important in VC (“probably a 9” out of 10), as it’s essential for deal flow and long-term success ([83:08]).
• Leadership in Crisis (Uber example)
  • When tough decisions come, act early; don’t let situations spiral to the point of no control ([79:59]).
  • Best CEOs “lead with the heart...a passion for leadership that includes feeling like a shepherd of the flock” ([79:59]).
  • “If a venture capitalist does their job the right way, you don’t get to that point.” ([81:03])

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Notable Quotes & Memorable Moments

• “People aren’t that engaged and happy in their careers...it’s not because they lack talent. It’s because they chose the safe path.” — Bill Gurley [00:21], [04:45]
• “The most successful people didn’t follow the conventional route. They built careers around what genuinely fascinated them.” — Bill Gurley [01:28]
• “Become a candidate of one.” — Bill Gurley on unique career creation [10:44]
• “Curiosity is greater than passion.” — Bill Gurley [14:04]
• “If someone’s obsessed, they have more in the tank...they press the gas where they have energy.” — Bill Gurley [09:54]
• “If you’re afraid of AI, my advice is: run at it.” — Bill Gurley [00:21], [35:41]
• “Knowledge compounds fastest when you learn together in public.” — (Mr. Beast example) [52:51]
• “You will find people start reaching out to you, especially in a world so connected with LinkedIn and Twitter.” — Bill Gurley on public learning [49:35]
• “Great jobs are built through exploration and pivots. Progress comes from momentum, not perfection.” — Bill Gurley ([90:07] - host summary)
• “Life begins where your comfort zone ends.” — Bill Gurley [87:25]

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Timestamps for Important Segments

• [00:21] Bill on career regret, survey results
• [04:45] Unhappiness at work, parent/society pressures
• [07:06] The “career conveyor belt” problem
• [10:44] “Become a candidate of one,” creator careers
• [13:20] Why curiosity—over passion—is key
• [14:04] “Fascination,” not just “passion”
• [22:06] How to tell you’re on the right path
• [31:05] The “barbell” of history & edge knowledge
• [35:41] “Run at AI,” using AI for learning/mastery
• [39:36] Mid-career pivots, Sal Khan story, side hustles
• [42:32] Local vs. aspirational mentors
• [51:21] Power of peer learning (Mr. Beast “40,000 hours”)
• [63:41] Unit economics vs. aggressive VC growth
• [70:06]-[79:09] Billionaire ROI Ranking game on entrepreneurship tactics
• [79:59] Leadership and ethics during Uber board crisis
• [83:08] Reputation’s critical role in VC
• [84:05] Founder patterns: learning, drive, salesmanship
• [85:50] Where the next wave of innovation will be found

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Actionable Advice from Bill Gurley

What’s one actionable thing young and profiters can do today to become more profitable tomorrow?
“Continuous learning...setting aside time every week to learn something new.” [86:56]

What’s your secret to profiting in life?
“Life begins where your comfort zone ends. Numerous times I’ve been willing to try something new or risky—and many times those have paid off.” [87:25]

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Final Takeaways

• Don’t chase titles—chase curiosity and obsession.
• Reflect honestly and pivot courageously—especially before you burnout.
• Real differentiation comes from knowing both the past and the present edge.
• Public learning and peer networks are massive career multipliers.
• Run towards AI—don’t be a skeptic from the sidelines.
• Be intentional with funding and business decisions—guard your ownership and unit economics.
• Generosity and sharing pay massive long-term dividends—infinite game, not winner-takes-all.

If you’re feeling career regret or stuck, Bill Gurley’s advice is simple: start exploring today, learning voraciously, and don’t be afraid to design a work life that is truly yours—even if it means breaking every rule you were taught.

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Transcript

[Bill Gurley]

I feel deeply sad. For a lot of founders, there is a reality where a modern venture capitalist does not want to take a meeting in anything on AI.

[Podcast Narrator/Host]

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

[Bill Gurley]

People aren't that engaged and happy in their careers. We asked a thousand people, if you could start your career over again, would you do something different? 7 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.

[Hala Taha]

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

[Bill Gurley]

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

[Hala Taha]

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

[Bill Gurley]

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

[Podcast Narrator/Host]

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 ch the safe path. Today's guest has had a front row seat to what actually drives long term success. Bill Gurley is a legendary Silicon Valley venture capitalist and a super investor known for early investments in companies like Uber, Zillow and Nextdoor. After decades backing billion dollar founders, he noticed a pattern. The most successful people didn't follow the conventional route. They built careers around what genuinely fascinated them. In this episode, we unpack lessons from Bill's new book, Running Down a Dream, including how to avoid career regret, Staying relevant in the age of AI, and designing a career driven by curiosity, smart pivots, and continuous learning. Bill, welcome to Young and Profiting Podcast.

[Bill Gurley]

Thanks for having me on.

[Hala Taha]

I'm so excited for this podcast. You know, I've heard about you for a very long time. Now we get a chance to sit down together. So you are what people have called a super investor, and now you've come out with a careers book called Running down a Dream.

[Bill Gurley]

Correct.

[Hala Taha]

And a lot of people might be Thinking like, what does a VC guy know about careers? And why is he putting out a book about careers? You could be, you know, putting out a war book on Uber or your times at Benchmark, the VC firm.

[Podcast Narrator/Host]

Right.

[Hala Taha]

So why did you decide to write a book about careers?

[Bill Gurley]

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 leave the field for younger people to succeed. 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 posts, and when I would get an idea, I would scratch it down and sometimes it would become a post. A lot of times it just was living in a document. And this one was an idea that came to me. And I had read these three biographies and noticed that these three people had all done similar things. And I wrote down the notes. I then got invited to give a speech at the University of Texas here in Austin, and I put it together and gave that speech. And then a number of people saw that speech, probably most notably James Clear. And people then started pushing me, one day, you should make that a book. And as I reached the end of my career and 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, venture capital. I could have written about Uber. And this was. This just felt more personal to me. And now that it's done, and it took a long time, I'm certain at this point that this book has a bigger chance to help more people than any of those other books.

[Hala Taha]

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

[Bill Gurley]

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

[Podcast Narrator/Host]

Wow.

[Bill Gurley]

And we did it again with Wharton and did it more scientifically, and it was still 6 out of 10, but a huge number for people to think they have career regret. And there's work that Daniel Pink has done where he talks about, as you grow older, it's your regrets of inaction that weigh most on your brain, like the things you didn't do. Most of us are pretty easy on ourselves when we make a mistake, we're like, oops, and we move on. And you don't ruminate on it much.

[Hala Taha]

Yep.

[Bill Gurley]

But that thing you never tried just eats at you as you get older. 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 I'm a parent of three. It is very, very hard for a parent to not want their child to be economically successful. And so you have this little voice in the back of your head that wants to push them towards the jobs that are considered safe. The safe jobs. Now, ironically, with AI, many of those, quote, safe jobs aren't that safe. But I would look back before AI and the survey work that we had done and other work, Gallup polls and whatnot. You know, people aren't that engaged and happy in their careers writ large.

[Hala Taha]

Yeah, 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.

[Bill Gurley]

Right.

[Hala Taha]

Like, we just put people on this path and, you know, you're supposedly supposed to get a really great job, 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, even getting laid off, even if they had a great job. So talk to us about why society kind of pushes people, people this way. And what's the alternative? Like, what should you encourage your kid to do instead of just going to college straight away?

[Bill Gurley]

Yeah, I think it's well intentioned. And I don't think it's just the parents. I think the counselors, everybody, it's, it's you, you. It comes from the heart like you really want them to be. Okay. But we've gotten into this place. Jonathan Haidt calls it the resume arms race, where, like I said, by the time you're in sixth grade, your parents are worried about whether your college application is going to be successful or not. So they're pushing you to play cello and volunteer at the thrift store. And like, you're doing all these things. These kids are booked solid. You know, when I was young and I've heard this from other people my age, we'd roam around the neighborhood. No one knew where we were. 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, they're just burnout. You know, they're just burnt out. But then it even. It gets worse at college. If you go back 10 or 20 years, you would go to. Everyone would go to college as a generalist, and you wouldn't declare your major until the end of your sophomore year. Nowadays, they make you apply to a major, and so you're putting the pressure on the kid to make the decision about the major when they're a junior in high school and filling out applications and they just don't know. 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 there's other data in this great book, Designing youg Life, where that five years after college, like 40% of people have already moved on to a career different than their major. Oh, yeah. By 10 years, it's like 60%. And it may be important to share that information with people so they don't feel the weight. They don't feel that the major doesn't become an anchor. You know, that restricts where they think they can go.

[Hala Taha]

Yeah, I can even think back to my journey. I went to college for organic chemistry. And then one year into it, I was like, this is not for me. I ended up dropping out of college, working at a radio station for two 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. You know, I think there's a lot

[Bill Gurley]

of data that suggests people that have roamed around and moved in different directions tend to land in a better place, one they're more passionate about. They've explored and had, 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.

[Podcast Narrator/Host]

Yep.

[Bill Gurley]

To go after it.

[Hala Taha]

Yeah.

[Bill Gurley]

If you find out, you. You. If you. If you put in eight years grinding and find out you don't love something, I don't know if you have. You. I don't know how much you have left, you know, totally. To pivot.

[Hala Taha]

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

[Podcast Narrator/Host]

So let's.

[Bill Gurley]

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

[Hala Taha]

Of course.

[Bill Gurley]

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 in. You didn't fill out a job application to be a podcaster. Right. You were crafting your own career. There's a phrase in the book that I use called, you know, become a candidate of one. And I think a lot of people that 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.

[Hala Taha]

Yeah.

[Bill Gurley]

So I. And I suspect you consider yourself in your dream job.

[Hala Taha]

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

[Bill Gurley]

Well, the. The. The book is separated into. Into two halves that alternate it's stories of success, which are called profiles and principles of success, which are the tools. And the stories are meant to inspire you and to disinhibit and make people understand and believe that they can go do this thing. And then the tools are. Are to Give people the, the, the, the things they need to go be successful. And the very first thing we talk about is fully understanding what it is you're most curious about. And the reason it's so important is if you really want to differentiate yourself, you really want to be successful, you really want to dent the universe, you have to love learning about what you do. Because if you love learning about what you do, and I think the ultimate test is in your spare time, instead of watching a Netflix show, you're reading about this thing that you love, you're gonna out hustle everybody else. And the flip side is true. If you don't love it and you're not constantly learning, someone else is, and you're gonna have a really hard time keeping up with them.

[Hala Taha]

Yep.

[Bill Gurley]

And I, I, I find all too often in a lot of traditional jobs, people think, oh, I studied up until graduating from college and now the learning's done and I just go in and do the craft. And I just don't think that's how the world works. Especially in this modern world where if you want to self learn and you want to continuously learn, there's so much at your fingertips between podcast and AI and all these things, you're going to get outrun because someone's going to, someone's going to get out on the edge in front of you.

[Hala Taha]

Yeah.

[Podcast Narrator/Host]

So the old cliche is follow your

[Hala Taha]

passion, but you talk more about curiosity over passion. Why, why, why didn't you say passion?

[Bill Gurley]

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

[Hala Taha]

Yep.

[Bill Gurley]

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

[Hala Taha]

learning, but there's not going to be Money in everything that we feel obsessed with or that we're curious about.

[Podcast Narrator/Host]

Right.

[Hala Taha]

So how do people navigate that part of it?

[Bill Gurley]

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

[Hala Taha]

Yeah.

[Bill Gurley]

They didn't start it because they wanted to make money. But I have examples in the book of a gentleman that fell in love with the Grand Canyon and just started writing about it and was able to turn that into a career. And there's another gentleman in Houston that did that with Texas Horticulture. And I, you know, so I, 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.

[Podcast Narrator/Host]

Yeah.

[Hala Taha]

And when you're so obsessed with what

[Podcast Narrator/Host]

you do, you're so good at what

[Hala Taha]

you do, you know, the most. And even with a small niche or small audience, there's opportunity within that.

[Bill Gurley]

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

[Hala Taha]

Yeah, that's part of it.

[Bill Gurley]

Yes, you would. Yes.

[Hala Taha]

Yeah.

[Podcast Narrator/Host]

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[Podcast Narrator/Host]

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[Hala Taha]

So one of the things that I was reading in your book that I thought was really interesting that really clicked with me is the fact that if you enjoy the preparation of your job, that's like a really good signal that you're doing something that you love if you actually enjoy the prep work. So for people tuning in, what are some other signals or questions they can ask themselves to judge whether or not they're on the right path.

[Bill Gurley]

Well, a couple different things. And we have a whole chapter dedicated to this topic. And give. I literally went and studied all the other advice all the greats had given and tried to, like, make it a laundry list so that you could try every one of these things. And there's so many different fun little exercises you can do. Dave Evans and at Stanford, who did Designing youg Life, he talks about create, like, three to five different profiles and spend a couple hours, like, writing out each one of them and kind of living with it in your brain, and then do it the other. And then you can battle card them, which is an interesting way to really test which one you're most excited about. Your intuition, when you do that, will typically pick up on one of those. There's a great story in the book. There's a gentleman from here in Austin that spent the first part of his career in seismology, and then he became a mortgage broker. And he's watching a PBS show one night, 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 side and try and find the middle ground. That gentleman's name is Burt Beveridge. And that exercise led to him starting a spirit company called Tito's Vodka.

[Hala Taha]

Oh, wow.

[Bill Gurley]

The most successful spirit business in America right now. Yeah. And like, he. The idea to do that came from that exercise. So we have a ton of those exercises here. The other thing that Angela Duckworth talks about a lot is just don't be afraid to move around. You know, and this happened twice in my career. I was in a job, I was doing fine. I was making plenty of money. But I did this exercise in my head where I said, do I want to do this the rest of my life? Like, just a moment of reflection, I said, do I want to spend 30 years doing what I'm doing now? And in both of the first two cases, I reached a point where I was like, no, I'm pretty certain I don't want to do this for 30 years. 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're both helpful to what I did later. 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.

[Hala Taha]

Yeah. You know, I want to talk about pivoting for 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.

[Bill Gurley]

Yeah.

[Hala Taha]

But first I want to spend a little bit of time on your career too, because I want to understand how obsession played in your career. You started at Compaq, you went to Wall Street.

[Bill Gurley]

Yep.

[Hala Taha]

What did you feel like you were obsessed with that led you down?

[Bill Gurley]

Okay, so it's super easy. So, like many people who ended up in Silicon Valley, I had a computer early in my life. So I had a Commodore Vic 20 plugged into a TV, didn't have memory.

[Hala Taha]

I don't think we know what that is.

[Bill Gurley]

Yeah, it was early, really early, and. But I. I found I liked writing programs. It was like, very fulfilling. And so when I went to the University of Florida, I got a computer engineering degree, enjoyed that process, and went to work at Compaq, which at the time was a very hot startup in Houston in the personal computer industry. And yeah, so that was the first one, and that was the reason I got there. What happened was, two years in, we started the third project from when I had joined, and it looked like the second project, which looked like the first, which is part of what got me wondering if I was going to grow bored doing this type of work. 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 it get into this test, in my free time, I was playing with something else. I wasn't learning about the work, I was learning about this other thing. And so I went to business school, ended up on Wall Street. It was awesome being in Manhattan in your late twenties. Just fantastic. Met so many great people, met so many great investors, and enjoyed reading about investing, enjoyed being a part of Wall street once again. Though, three years in, I just started to think about the job and what I was doing every day and said, do I want to do this my whole life? And came to once again to a conclusion, no, I don't. And I had along the way, been building up this thought process that I wanted to be in venture capital. And the opportunity came to move to Silicon Valley. And from there I was able to get into venture and Three years into venture, I didn't have that. I didn't have that same discussion with myself. I was, I knew I was in the right place.

[Hala Taha]

So do you think investing was really your obsession?

[Bill Gurley]

It's a combination of things. I love technology. I loved understanding how it could be disruptive and how people could. And by the way, this is true for all entrepreneurs. How people could ride the edge of what was changing and then become successful. The, the book innovators dilemma walks through exactly how that works. And then this is, this is a little more kind of personal. But when I was in college, we started going to Vegas and like counting cards and playing blackjack. I do, I do think there was a little gambler, little gambler mentality in there also. And it was those things combined interesting. You know, investing, tech, gambling, a little bit disruption.

[Hala Taha]

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

[Bill Gurley]

You know, I would say one more thing, just because I know you have a lot of like, founders and entrepreneurs in your, in your audience. Yeah, I think there are certain people that have some form of ADD or they're just highly distracted and they get, they get a lot of satisfaction out of diversity. And I'm one of those people. So whether it was working on Wall street or as a vc, a consultant would have this. You're just looking at so many different things simultaneously. And that breadth matters to me. And one of the reasons that I left that engineering job is I felt that it didn't have that. And I was kind of, you know, down in the weeds. I've met ton of wonderful founders who have to have their hands on the steering wheel and want to be in that position. And I think those jobs are complementary to one another. But people, if they get in touch with which one of those people they are, it may impact what career they want to go after.

[Hala Taha]

Totally, Totally. So if somebody is younger and they want to design their dream career, they may went to college, they're in their first job.

[Podcast Narrator/Host]

How do you suggest that they start

[Hala Taha]

actually, you know, taking the steps toward independence and designing their own dream career?

[Bill Gurley]

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

[Hala Taha]

I was going to say you call it like the canon.

[Bill Gurley]

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

[Hala Taha]

Yeah.

[Bill Gurley]

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

[Hala Taha]

Was he a good chess player?

[Bill Gurley]

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

[Podcast Narrator/Host]

Yeah.

[Hala Taha]

Because he was an expert in his field, so the history was a part of it.

[Bill Gurley]

The other, by the way, I think there's a barbell thing here. The other way to really differentiate yourself is to know the edge. And so if you, I mean, as silly as it sounds like, if. If you really know how TikTok works and then you want to break into sales or marketing or pr, like that's hugely differentiating. Like, the people that have been in Those roles for 10 or 15 years probably don't understand it at all. And so even if you're chasing a field that doesn't feel like TikTok is the main part of it, it could be highly relevant to what makes you look different as you apply for jobs in those areas 100%, especially for young people, knowing the edge of these technolog is another one, is just a great way to separate yourself. And if you combine those two, you look really interesting.

[Hala Taha]

I totally agree with you on that. I can even think about from my own experience, like how I remember when I first started, I actually was in

[Podcast Narrator/Host]

corporate for like a little bit.

[Hala Taha]

When I first started corporate, I was 28 years old. Never had a corporate job before because I was in radio, I started a blog, I started all these things. I got into corporate and thought I was going to be so behind, but I actually was so much more tech savvy and knew how to hack LinkedIn and got promoted so quickly because I knew more than the other People who started at 25.

[Bill Gurley]

About the edge.

[Hala Taha]

Yeah.

[Bill Gurley]

Yes.

[Hala Taha]

So it's really interesting that you say that. I love that idea of actually studying the history of a industry and also like the unsexy knowledge, which I think a lot of people miss. Like, I think of people who want to be. There's so many people who want to be podcasters, but they don't know how to CPMs work and how podcasters even get paid and even really popular podcasters don't know that stuff. So talk to us about the importance of learning the unsexy stuff.

[Bill Gurley]

You know, I had this experience in my life that was really amazing and I was fortunate to have it. It's going to sound like I'm name dropping, but a partner of mine at Benchmark won at auction a dinner with John Lasseter, who was the creative genius behind Pixar. And we went to, we got invited to John's house and he has a viewing room there. It was not that big a surprise, but a big one. And they served us a 10 course meal. And each course had a, 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 are, 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.

[Hala Taha]

Yeah.

[Bill Gurley]

But also that it's so differentiating. I mean, just imagine yourself. And I think we could pick any field. Imagine, you know, you're in a, let's say you're interviewing for a sales job and you have found, and you could do this with AI in five minutes. You found the 10, like people who were the originators and 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.

[Podcast Narrator/Host]

Yeah.

[Hala Taha]

And it helps you, if you want to be a leader in that field. Field. Not repeat the same mistakes.

[Bill Gurley]

Yes, that too.

[Hala Taha]

You Know, you're making sure that you really understand the history. And when I think about podcasting, it's pretty new. So I guess I would study, like, TV and radio.

[Bill Gurley]

Right.

[Hala Taha]

And for AI, what would you study? The Internet?

[Bill Gurley]

Well, I mean, there are some people that have been working on AI for 10 or 20 years. Yeah. AI is moving so fast. I think you should spend every last minute just using, just using it, every tool you can. You know, I, I've, it's kind of separate from the book, but I've, I have 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.

[Hala Taha]

Yeah.

[Bill Gurley]

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

[Podcast Narrator/Host]

Totally.

[Bill Gurley]

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

[Hala Taha]

And don't stop at ChatGPT. There's so many other apps out there. I know. I, I myself, like, I'm addicted to ChatGPT.

[Bill Gurley]

It's like trying to just try them all and ask. You can ask them this, but it's kind of circular, but, but what is the edge of AI usage in your field and understand what that is and with it there. And 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, like, and tested whether it's still making that error? Because 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.

[Hala Taha]

I totally agree. And 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?

[Bill Gurley]

Yeah, I think it's insane. Like, it's such an accelerant. Like, you can learn about anything. And I'm probably doing 30 searches a

[Hala Taha]

day on, oh, I'm on it. I can't do anything without it anymore. I always want to.

[Bill Gurley]

Right. It's become the number one way you start to learn about something. Yeah, me too. Me too. I think it's quite ironic that people feel like, oh my God, AI is coming and my job's at risk when. If you 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. It should allow me to separate from the field. Like, this should be my finest moment. Not something to be afraid of.

[Podcast Narrator/Host]

Do you ever feel like AI is

[Hala Taha]

changing the way that your brain works?

[Bill Gurley]

It's a good question. I think I'm constantly asking myself that question and I'm skeptical. Like I don't take anything as a truism. So I try again. But it's possible.

[Hala Taha]

Yeah. I say that because sometimes I'm like, I feel like in the past I would have, you know, now I'm always like, you know, bouncing back and forth between AI and my work. Right. And in the past I would have. I feel like, well, I probably would have thought of this on my own without bouncing back and forth between something. And now I feel like I always need to bounce myself.

[Bill Gurley]

Yeah, it's a good question.

[Hala Taha]

You know what I'm saying?

[Bill Gurley]

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

[Hala Taha]

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

[Bill Gurley]

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

[Hala Taha]

Okay, so let's say you're mid career, 40 years old.

[Bill Gurley]

Yep.

[Hala Taha]

Made money.

[Podcast Narrator/Host]

But you have responsibilities.

[Bill Gurley]

Yeah.

[Hala Taha]

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

[Bill Gurley]

We have a chapter in the book called Never Too Late where we highlight a number of people that had their defining career start after 40. I don't think it's easy for the reason you bring up, which is commitments. One of, one of the people we profile in that chapter is Saul Khan, who created the Khan Academy. And Saul was in it, worked at a hedge fund, was doing rather well, I think. Fortunately, his wife was working also and, and he was doing something on the side, helping a family member overseas. That led to the creation of the tools that became Khan Academy. And he, he felt drawn to doing it as a non profit, which makes that math even harder. But his wife was supportive of him trying it for a year. They literally said, let's do it for a year. So he walked away. And once again, I Think having the flexibility to do that is part of living within your means. They couldn't have done that otherwise. Yeah, 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 Sal Khan has.

[Podcast Narrator/Host]

Yeah.

[Hala Taha]

Like, we actually. And I interviewed him a little while ago.

[Bill Gurley]

Wonderful guy.

[Hala Taha]

Yeah.

[Bill Gurley]

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

[Podcast Narrator/Host]

Yeah.

[Bill Gurley]

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

[Hala Taha]

especially has nothing to do with the job.

[Bill Gurley]

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 entrepreneurs using Microsoft projects. And that led him to a whole different set of connections and networking than if he had just sat there in the job they had defined for him. And then when he got to Madrona, he started a podcast on the side. He said to the people at Madrona, can I do a podcast from the VC firm? They said, yeah, sure. And of course, now he's one of the most successful podcasters on the planet and loves what he's doing. But experimentation of this side hustle gave him exposure to new things 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 totally 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?

[Podcast Narrator/Host]

Totally.

[Hala Taha]

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

[Bill Gurley]

There you go.

[Podcast Narrator/Host]

Right.

[Hala Taha]

And me and the acquired host.

[Podcast Narrator/Host]

What's his name?

[Bill Gurley]

Ben Gilbert.

[Hala Taha]

Ben Gilbert, we are competing for an iHeart podcast award for business and finance. No, it's not up to. It's up to industry panel to decide, but, you know, maybe the best podcaster win.

[Bill Gurley]

There you go.

[Hala Taha]

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?

[Bill Gurley]

Well, I find a lot of people. I mean, a lot of. A lot of people that write personal development books talk about mentors. So it's not a unique topic, but what I find happens most in the real world is people get too greedy too early, and they. They Say, well, I. They either cold call someone they shouldn't. Yeah, 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 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. One of my profiles is of Danny Meyer, the great restaurateur in New York. And he did this when he decided he was going to be a restaurateur. He made a list of. 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. 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 him the way we just described, one day when you do meet him, you know so much about him.

[Podcast Narrator/Host]

Back to the history.

[Bill Gurley]

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

[Hala Taha]

Yeah.

[Bill Gurley]

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

[Hala Taha]

So if they're more willing.

[Bill Gurley]

Yeah, they're going to be more willing. They're going to be flattered that you ask them. So. 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.

[Hala Taha]

Yeah.

[Podcast Narrator/Host]

Yeah. Fam 2026 is the year I'm fully focused on growing my personal brand. I'm taking it to the next level. For years, I was focused on my company. Now I'm focused on building my brand. I'm launching a book and I'm upgrading and updating my website. My website has not been top of mind for years and it drastically needs an upgrade. And when I was talking to my team about what we're going to do, they strongly recommended that we switch our platform to Framer, which they said is a modern way to build websites in 2026. That's why so many companies from leading startups like mine to Fortune 500 brands are turning to Framer. Framer is a powerful website builder and design tool that helps businesses create better websites and faster. With Framer, you can design and publish beautiful, high performing websites without ever touching code. It's a visual drag and drop builder with smart AI tools that help you create responsive layouts quickly. And these websites are beautiful and look super custom. Nobody would ever know that you used a drag and drop tool. Everything you need is built into Framer, including SEO, support, analytics and collaboration. So you're never duct taping multiple tools together. It's one of the easiest ways to launch a high performing website or landing page that looks custom, polished and professional on any device. Learn how you can get more from your.com from a framer specialist or get started building for free [e-mail] profiting for 30% off a Framer Pro annual plan. That's framer.com profiting for 30 percent off framer.com profiting rules and restrictions apply. What's Up Yap gang? When you start a business, nobody really tells you how many hats you're about to wear. One minute you're the creator, the next you're the marketer. Then you're the finance team and customer support. Before you know it, it can feel like way too much on your shoulders. But that's why I love Shopify and what it does for entrepreneurs. Shopify is an all in one commerce platform that helps you sell online. It's been a real business partner for me as I've grown yap media and launched products like my LinkedIn Secrets Masterclass and my LinkedIn Mastermind. Shopify powers millions of businesses worldwide and 10% of all e commerce in the US. Whether you're a household name or just getting started, Shopify has got you covered. What I appreciate most is how everything lives in one place on Shopify. You can design your store, market your products and track performance without juggling a dozen tools. And you definitely do not need to be tech savvy. Shopify is so easy to use and if you ever do hit a wall, Shopify's award winning 24. 7 support is there to help you think things through. You don't have to do this alone, you can do it with Shopify. Start your business today with the industry's best business partner, Shopify and start hearing. Sign up for your $1 per month trial today. @shopify.com Holla. That's H-A L A go to shopify.com Holla all lowercase again. That's shopify.com Holla young and profiters this year, I'm all about not missing opportunities. And for me, that starts with not missing any calls because a missed call is money walking out the door. Quo, spelled Q U O, is a business phone system that helps you and your team handle calls and texts from one shared number. Think of it as an email inbox. But for your phone, everything stays in one place so no conversation gets lost and no customer gets ignored. I've seen how much calmer things feel when everybody in your company can see the full thread. All the calls, texts, voicemails all together in one place. Replies are faster, customers feel heard and taken care of, and the team stays aligned. Quo even uses AI to log calls, summarize conversations, and flag next steps, which takes a lot off your team's mental load. It works right from your phone or computer, lets you keep your existing numbers and grows with your business. That kind of setup makes a real difference. Make this a year where no opportunity and no customer slips away. Try quo for free. Plus get 20% off your first six months when you go to quo.com profiting that's Q-U-O.com profiting quo. No missed calls, no missed customers.

[Hala Taha]

You give so much great advice for people who are really just trying to like, grow on this journey of being, like, top of their field in a career that they love. And one of the things that you mention is publicly learning, like learning in public. You did this with the blog that you started?

[Bill Gurley]

Yes.

[Hala Taha]

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

[Podcast Narrator/Host]

Can you speak about that?

[Bill Gurley]

Yeah. And look, I don't know if it's for everybody, and I've watched people be successful in venture capital that don't do it, but it's certainly a way to differentiate yourself, is to create content on your field and to share that content publicly, as you say. And you know, ironically, Warren Buffett has historically done this. Every year there's a great bond investor named Howard Marks who writes out his thoughts there. 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're afraid you're not doing by just using AI because you really don't want there to be inconsistencies. So you really think through it and you give your brain a really good once over, I think, on the subject matter. And then the second thing is it differentiates you. You will find people start reaching out to you, especially in a world that's so connected with LinkedIn and Twitter, DM and all this stuff. You know, you start writing, you're going to create avenues for networking.

[Hala Taha]

Yeah.

[Bill Gurley]

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

[Hala Taha]

That's true.

[Bill Gurley]

Yeah.

[Hala Taha]

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

[Bill Gurley]

It could be, it can be very, very helpful.

[Hala Taha]

You also mentioned this concept of infinite games. How life is basically an infinite game and you're better off being generous than having sharp elbows.

[Bill Gurley]

Yeah.

[Hala Taha]

How have you been generous in your career? Can you give us some examples or other, you know, Personas and stories about people being generous?

[Bill Gurley]

So this topic, I think comes up in the chapter we have on peers called embrace your peers. And it's probably my favorite of the principles in the book, mainly because I don't think it's a subject that's, well, it's not well studied in the, in the literature. Like I think I might be one of the first people really pushing on this subject. But peers can be inside your company, they can be outside. But it's, it's. Think about it as a co. Evolving journey. And the reason I use the, for the, the infinite versus finite games so many. Much of what we think about from a strategy perspective comes from finite games that we play that you play over and over again. And there's a winner and a loser. 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 there's a, there's a great story in the book about Mr. Beast and when he was starting his journey, which is probably similar to where you were getting into podcasts when he was getting into YouTube. There weren't, it wasn't a field yet. 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're Learning together and sharing.

[Hala Taha]

Yeah.

[Bill Gurley]

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. 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's so compelling and so wonderful, like, it probably won't be that way 60 days from now. And I just think the benefit of open sharing far outweighs some advantage you're going to have by keeping knowledge proprietary to yourself.

[Hala Taha]

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

[Bill Gurley]

Yes.

[Hala Taha]

You know, which is so valuable. And it's an asset in itself.

[Bill Gurley]

Absolutely.

[Hala Taha]

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

[Podcast Narrator/Host]

Right.

[Bill Gurley]

No doubt. The book really has two target audiences. So on one hand, it's the young person who's, or even maybe up to mid career who really is trying to figure out what they want to do or always wanted to chase a dream or. And didn't know how and, and, or, and are someone who just really needs an extra push to go do that. It's for all those people, for sure. And a lot of people that have read it said, oh, I want to give it to, you know, every young adult's going to be handed this thing. I hope, I hope they take the time to read it. But the other audience is the parents, the counselors, the people that are playing a role in this shaping of these careers for other people. Because I do think that the natural tendency is to not kind of be supportive and give the right push at the right moment. Yeah, I know you had Matthew McConaughey on. And in his book Green Lights, he tells this story of. He's gonna, he's told his father his whole life he's gonna be a lawyer, and he decides that he now wants to switch to film school and he's afraid to tell his father. And it's, it's a great scene. It really to me speaks to the purpose of this book. When he finally gets the gumption and tells his father, his father says, well, don't half ass it. And, and in the book, McConaughey says it was the last thing he expected, but the most valuable thing his father could have said. He gave him permission, responsibility, a push, 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 how do for all that second group had, how can I help you be as good as McConaughey's dad was at that moment and, you know, sense that there's a sparkle of interest and curiosity and help it flourish.

[Hala Taha]

Yeah, because to your point, it's not

[Podcast Narrator/Host]

like parents want to do like bad

[Hala Taha]

for their children, pushing them to become a doctor or something. You think you're doing good. Right. So it's really important. And a lot of people, I have a lot of friends that feel very resentful of getting pushed into certain careers. So you don't want that to happen.

[Bill Gurley]

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

[Hala Taha]

And I have to say, like, I read two books a week, you know,

[Podcast Narrator/Host]

because of my job.

[Bill Gurley]

Right.

[Podcast Narrator/Host]

So I loved your book.

[Hala Taha]

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

[Bill Gurley]

Thanks for reading.

[Hala Taha]

You started in vc. You were behind so many, you know, huge companies. Zillow, Uber, Stitch, fixed so many big companies. You also started your career at the start of the dot com bubble and you saw that whole thing explode.

[Bill Gurley]

Yep.

[Hala Taha]

How did that actually change the way you think about investing in companies, Change the way you think about sustainability for companies? Talk to us about those fundamentals.

[Bill Gurley]

If I think, oddly, in retrospect, it was fortunate that I, I. So I started my venture career in 97 and things were on fire by 99, but by 2000 they were falling apart. And that's not enough time for me to have been successful because from investment to liquidity back then was five to seven years. It's even longer now. And so there wasn't a window enough. But it also meant it wasn't a long enough window for anyone to judge whether I was good at it or not. And when the bubble burst, everything slowed down. When you're in a bubbly time, and we may be right now with AI, 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 work, they get very speculative. And I found the bubble part to be uncomfortable, but I found the post crash part to be very sane and rational. And so 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, but they come in every wave.

[Hala Taha]

So it is what it is with AI. You know, I have a lot of founder friends and some of them say like, you know, this year they're only investing in AI companies and it's really hard for them to get funding. Even if it's a great company with great unit economics and everything like that, they can't get funding. Do you think there's a problem with the investment in AI and do you think that's a bubble?

[Bill Gurley]

I think, well, there's a whole bunch in what you just said. But let me start with this high level point that I'd like to make. This Professor Carlotta Perez recognized something that I think is really important to understand, which is when there is a wave, there is massive wealth, there's disruption and the deck chairs switch and people make a lot of money. And that's already happened here because OpenAI and Anthropic are paying their employees secondary earlier than anyone ever had. So the money's being made, it's being put in people's pockets and that's going to attract speculators. Here in Texas we had a spacious from the former governor Rick Barry for a data center. It already went up and down. So like speculators rush in and so bubbles and waves are actually always happening at the same time. So Some people will argue, oh, if you say it's a bubble, you're anti AI. No, I make the. Say the fact that it's real is why there's a bubble. So I, I think, I think it's important to know that there is a reality right now. And I feel deeply sad for a lot of founders. There is a reality where a modern venture capitalist does not want to take a meeting uninterested in anything on AI. And I could, if I was forced make an argument as to why that's the exact right behavior by the venture capitalist. But I, I think it's unquestionably true. Like there's just zero interest.

[Hala Taha]

Yeah.

[Bill Gurley]

And so that's a tough call for someone that's in a business that may have good unit economics. That's not AI. What would my advice for them be? You know, make sure you understand the edge of AI in your field. Like I said earlier, there may be things you could, you know, I think it's one out of five that can kind of pivot in a way that makes it really look like an AI company. So you don't want it. You know, if it feels painted on, the people will sense that. So. And then if that's not an avenue for you, you know, try and use sweat equity to get to profitability and own way more of this thing than you would otherwise, you know. And I think one of the biggest mistakes a lot of founders make is when you take venture capital, it's usually not just the A round, there's usually a B round and a C round and your ownership's going to get way diluted. And the number, the, the number one type of company that bigger companies would like to acquire are smaller companies that are tuck in acquisitions. 20, 30, $50 million. And the minute you take venture, that's off the table, like, because now the venture capitalist needs a much bigger outcome.

[Hala Taha]

Yeah.

[Bill Gurley]

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

[Podcast Narrator/Host]

Wow.

[Bill Gurley]

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

[Hala Taha]

I want to do like a little mini MBA for the entrepreneurs. A lot of people who are listening right now are like just starting as entrepreneurs or they've got like, you know, maybe a million dollar company or, you know, they're just kind of starting out. They've got a lot of potential. And so, you know, you've moved Away from or in the past, you've, 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.

[Bill Gurley]

Yeah.

[Hala Taha]

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

[Bill Gurley]

Well, I suspect that the smaller entrepreneurs that are living hand to mouth on cash flow are pretty in touch with their unit economic, but they might not know it's the guys that raise 100 million of venture capital that lose touch with unit economic. Yeah, it's just a matter of understanding what are the true variable costs associated with the product or service that you're selling and being honest with yourself, even despite what the accounting might be, the requirement for gross margin. But what are the true variable costs? So that could include selling and customer service and all these things so that, you know the marginal contribution, ideally from a cash flow perspective that you get with each turn of the crank.

[Hala Taha]

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

[Bill Gurley]

No doubt. And you know, it may be different based on the type of customer, the size of customer, the source of the lead. Like all those things might be different. You know, you may find, I've always found it to be true when you are aggressive with marketing, you have much higher churn like you get customer. Whereas if you can earn a customer through PR or word of mouth, they typically stay around longer. And so they're. That's an even tougher mathematical problem because you're trying to calculate unit economics over the lifetime of a customer early on.

[Hala Taha]

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

[Podcast Narrator/Host]

Right.

[Bill Gurley]

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

[Hala Taha]

Why is that?

[Bill Gurley]

Well, I wrote, it's one of my favorite blog posts I've ever written. So if someone wants to go deep, it's called the Dangerous Seduction of the LTV formula. And it's easy to find on Google. You know, it's not an erroneous way to measure something. It's actually a smart way to measure something. But it's not a strategy. And I think people get lost in thinking it's a strategy. And, 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 non paid social. Could I be winning customers with product led growth, which is a great, 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.

[Hala Taha]

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

[Bill Gurley]

Yeah. And by the way, you could talk to AI or you could, you know, do Google searches and find people that have written extensively about product led growth. But it's. Is there a way to build into the product the ability to find incremental customers? So could you. You know, one of the things that I've been pushing the Stitch Fix team to do that I hope will come out soon is here's 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.

[Hala Taha]

Yeah. You're letting the customers share it themselves.

[Bill Gurley]

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

[Hala Taha]

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

[Bill Gurley]

Exactly. Yes. Yes.

[Hala Taha]

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

[Bill Gurley]

Okay.

[Hala Taha]

What would you want to see in my dashboard in terms of metrics? Like what kind of metrics would you want to see on a very simple dashboard? Baseline.

[Bill Gurley]

One, one question I would ask you before I, I went there is, 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 because that, that matters a little bit, because you need to think about who the natural acquirers would be and how they, why they would fit it in. How do they measure their own business? You know, and so will this look appealing to them through that lens, those kind of things. You know, some of the stuff you talked about unit economics like you want to understand is it'd be great if the marginal customer is more profitable than the one before them. So that's a test of whether you're starting to get scale in your business. Right. One exercise that I heavily encourage all founders to do no matter how much the size of the business is, force yourself to do a three, three to five year forecast, and you don't have enough information to really do it, which is why people push back. But it forces you to ask the right questions so that you can prepare. And if you, you know, if you want to grow, you know, a lot for five years, your business 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. Like, it's not something they want to do even, but they should do it.

[Hala Taha]

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

[Bill Gurley]

I mean, there's so many different business. I think certain. Certain businesses, there's a.

[Hala Taha]

Like, in, like every business that matters,

[Bill Gurley]

everyone agrees net dollar retention is the one that matters most, but that doesn't apply to everything. Yeah, so. So it's kind of dependent on the business.

[Hala Taha]

Again, you got to learn your industry. What matters in your industry.

[Bill Gurley]

Exactly.

[Hala Taha]

Okay, so let's play a game. It's called Billionaire ROI Ranking.

[Bill Gurley]

Okay.

[Hala Taha]

This is going to put everything that we just talked about together. I'm basically.

[Bill Gurley]

Am I the first person to play this game? Yeah.

[Hala Taha]

I have new games 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, and you can, you know, give some color on why you ranked it 1 to 10. So is it a good return on our investments?

[Bill Gurley]

Okay.

[Hala Taha]

Okay. First one is reading and learning every day.

[Bill Gurley]

Oh, yeah, nine. Nine out of ten, Maybe ten. And that's partially because I've always felt that way, but also the people I respect the most feel that way, I think. Toby, the CEO and founder 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.

[Hala Taha]

Okay, moving to where the action is.

[Bill Gurley]

Yeah. This is a. So between the talk that I gave at University of Texas and the book form of the speech, we added a sixth tenant, and it was. It was moving to where the action is. I strongly believe that if you can afford it, you'd rather be an even, average player where everyone's doing this thing, than Being the best player in a market that doesn't rank for that field. And if you're a songwriter, that means Nashville. If you're a founder, that means Silicon Valley. If you want to work in finance, it means New York City. And the, it's the number of, what it really does is the number of chance positive things that are going to happen. I'd probably use the word optionality just goes up 20x. Like you're just gonna run into so many people doing the same things and like, and if, if, if you go to a job and it doesn't work out, there's so many other people hiring for that same thing. Like it just really changes the dynamic and it probably is important that you're someone that is self motivated. But, but 8 out of 10 for most fields. There are a few fields. If you're a coach, you can't really do that. There are some fields where you can do it virtually subreddits and things like that.

[Hala Taha]

Yeah, I think about, I moved to Austin a year ago as a podcaster and there's just so much serendipity.

[Podcast Narrator/Host]

It just, things just happen naturally.

[Bill Gurley]

That's a great word.

[Hala Taha]

Yeah, yeah.

[Podcast Narrator/Host]

Building a personal brand.

[Bill Gurley]

I think that that's field dependent. It's always helpful. I mean I think there's a, I probably rank it below the others. Let's just say 6 out of 10. There's always a risk that you become someone who's somewhat performant on the brand side and maybe not developing the real skills underneath it which would, could have a negative ramification or someone could view you as shallow. If, if you, you know, we're doing that so, and not all fields. I mean there are certain fields where I think it's harder to do, but I think if you can, it's very rewarding

[Hala Taha]

spending heavily on ads.

[Bill Gurley]

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

[Hala Taha]

That would tell the truth.

[Bill Gurley]

Yeah, I don't like it. 2.

[Hala Taha]

Why is that?

[Bill Gurley]

There's a great new book coming out by David Epstein called Inside the Box where he talks about how constraints drive creativity. And I've always felt that if you're starting a business, the easiest way you could possibly get a customer, the first way the most ignorant person would assume to go get a customer would be to run a Google Ad like it. 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.

[Hala Taha]

Like, and the hardest, the most obvious.

[Bill Gurley]

And, and, and I think if you run an exercise, which I mentioned in that blog post, where you say set the mark, your. 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.

[Hala Taha]

Yeah.

[Bill Gurley]

So that's why I think.

[Hala Taha]

And paid ads are so paid ads don't work also if you don't have

[Podcast Narrator/Host]

a brand or credibility because they're going

[Hala Taha]

to go Google you and there's not going to be anything there because you started with paid ads.

[Podcast Narrator/Host]

Okay.

[Hala Taha]

Networking events and conferences.

[Bill Gurley]

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

[Hala Taha]

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

[Bill Gurley]

Yeah. And that group of friends stayed in touch, started a text group, started sharing ideas and they expanded a little bit over time, but they're now all D1 athletic directors. They all to the top.

[Hala Taha]

So at the 7 RNA.

[Bill Gurley]

Yeah, yeah.

[Hala Taha]

7 R&A.

[Bill Gurley]

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

[Hala Taha]

Raising as much money as possible.

[Bill Gurley]

Well, I've historically been very negative on this, so I will put a 3 on it just to be consistent. The venture industry has evolved and I don't think this affects the vast majority of founders, but the ones at the top. The industry has evolved to where most of the rounds are preemptive and proactive, which means you didn't start a fundraising process, someone thinks you're doing well and knocked on the door and is force feeding you money. And that is currently the way things happen. And you end up with these situations where each competitor is armed with 400, 500, $600 million, maybe more. And it's not, you know, it's. I say it's not your father's venture capital. This is a sport of kings world we've evolved into, and it's fight to the death. I, I live through it with the uber Lyft situation, but it, I wouldn't wish it on anybody, but it's the reality right now. And if you sit back and say, well, I'm not going to be, I'm not going to raise as much money. I'm going to be, you know, discipline. Well, if, if, if you're the discipline one, and there's six players with $500 million each higher and salespeople, you're not going to matter. So the game on the field is kind of forced people to do this thing I don't love.

[Podcast Narrator/Host]

Yeah.

[Hala Taha]

Okay, next one. Getting an mba.

[Bill Gurley]

Yeah, I'll say seven. But, but part of it's me reacting to the fact that so many people in the entrepreneurial world make fun of it. There's a lot of, 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. It doesn't mean they have to go get an mba. But they should read Michael Porter's Competitive Strategy. They should read Innovators Dilemma. They should read Crossing the 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 crap on the notion of an mba.

[Hala Taha]

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

[Bill Gurley]

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

[Hala Taha]

Totally.

[Bill Gurley]

Yeah.

[Hala Taha]

So let's move on to leadership. I had Kevin o' Leary on the show and he's another billionaire, I think.

[Bill Gurley]

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

[Hala Taha]

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

[Bill Gurley]

Yeah.

[Hala Taha]

And it reminded me when I was reading and learning about what happened at Uber with the founder and yourself and how, you know, he kind of started as a mentee and then, you know, over time, you had to make a really tough decision. Take us back to those moments, what was happening and how were you able to kind of take emotion out of it and just be the best member of the board that you could be for Uber.

[Bill Gurley]

One of the things that I would push back on with what Kevin said is the best CEOs that I've talked to very much lead with the heart and have a. I say, a passion for leadership that includes feeling like a shepherd of the flock. And so I, I push back on that a little bit, like, broadly against business. The situation that we got into at Uber, there was a asset, the company that, that was shared by many constituents, you know, the employees, the investors, everybody. And we, because of several things that had happened, things were in a bit of a freefall. 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, and by the way, it wasn't, I think history and the press has made it out to be me. There were five investors that work together and sign this letter. So it wasn't just me, but I think that there were a number of people that were concerned that a change was definitely going to happen. But if you let it happen through the legal world or the government making a change, it was going to be six months to 12 months later, and the erosion was going to be even more. And there were a lot of constituents in this thing, you know, a lot of our investors. This was such a big number. They had already, you know, it was already moving the needle for several universities and foundations. And if it went away, you know, they have paper marks, they were going to have to mark it down. And that felt that weight on me, that felt like a lot of responsibility. So I've said publicly before, you know, if, 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. 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.

[Hala Taha]

Do you feel like you made the right decision?

[Bill Gurley]

I. Based on where we were at that point in time, yes. Yeah. And Dara's done an amazing job. I mean, to take it from there to $200 billion public company, over 10 billion a year in free cash flow. Like from where we were. Yeah. Unbelievable.

[Hala Taha]

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

[Bill Gurley]

I think it's really important in the venture area, it's probably a nine. Like, I don't know that it's that high. In every other field. I don't know that I'd have a good field for inventure. Your ability to compete for the next deal is everything. And that's either enhanced or hurt by what the world thinks of you. And in venture, that personal brand can shine brighter than even the corporate brand a lot of times. And so you just have to worry about it if you want to be competitive.

[Hala Taha]

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

[Bill Gurley]

Yeah.

[Podcast Narrator/Host]

What are some of the patterns you

[Hala Taha]

see with these founders? And I think a lot of it actually ties back to what you wrote in your book.

[Bill Gurley]

Probably. Yeah. There's a couple things. They are continuous learners because they're tilting at some new problem on the edge of their field. And there's no way that could be something they learned in school five years ago because, you know, it's like AI right now, everything's changing so fast. Bezos has said that for his angel investments, he wants to feel like this person's going to do this no matter what, that there's this drive and commitment to attacking the problem that you just can't take them off of. So that's kind of an interesting notion. I think salesmanship is a requirement that people don't talk about enough. You're. You're going to raise money, you're going to recruit people, you're going to lead your team through bad times. Like, you can't do that stuff without being able to sell in some way, shape or form. People do it in a variety of different ways. There's people that are rah, rah. There are people that are quietly. But you have to be able to convince people to follow you, you. And then lastly, I would say many, many startups have some kind of go to market advantage, which usually isn't advertising. So they've figured out some bespoke, differentiated way to gain new customers aggressively.

[Hala Taha]

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

[Bill Gurley]

It's so hard right now. I mean, I love the notion of contrarian investing. And when we're in one of these big waves, it's kind of off the table because everybody's doing the exact same thing. And, you know, I. I think there will be a lot of money made in. In verticals. Like people who figure out how AI applies to something that's very specific to their world. And at this point in time, coding and legal and probably medical are overfunded by the venture capitalists, so there's not much oxygen in those areas. But if you can figure out what it means for all the other fields that are out there, I think there's quite a bit of opportunity.

[Hala Taha]

So the intersection of AI and your field.

[Bill Gurley]

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

[Hala Taha]

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

[Podcast Narrator/Host]

All right, so the first one is,

[Hala Taha]

what is one actionable thing our young and profiters can do today to become more profitable tomorrow?

[Bill Gurley]

I'm going to be redundant with what we talked about, but I just think it's like continuous learning and just setting aside time. Especially if you're a founder and entrepreneur who's hustling all the time, you may feel like you have no time, but setting aside some time during the week to learn something new.

[Hala Taha]

And what is your secret to profiting in life?

[Bill Gurley]

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

[Hala Taha]

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

[Bill Gurley]

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

[Hala Taha]

can everybody learn more about you and

[Bill Gurley]

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

[Hala Taha]

Oh very cool.

[Bill Gurley]

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

[Podcast Narrator/Host]

Let me know when it launches.

[Hala Taha]

I'll do some free commercials for you guys and support.

[Bill Gurley]

That's awesome.

[Hala Taha]

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

[Bill Gurley]

Thanks for having me.

[Podcast Narrator/Host]

Young and Profits Sitting down with Bill Gurley was truly a special treat. He spent decades studying world class performers and what he shared today challenges so much of the traditional career advice that we've all been given. 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 important 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

[Hala Taha]

edge of what's new, whether that's AI,

[Podcast Narrator/Host]

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