Bill Gurley: The Biggest Career Regret Most People Have

Summary

Afford Anything Podcast — Detailed Episode Summary

Episode Title: Bill Gurley: The Biggest Career Regret Most People Have
Host: Paula Pant
Guest: Bill Gurley, Venture Capitalist, Benchmark Capital
Release Date: March 13, 2026

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Episode Overview

This episode tackles a fundamental yet often elusive question: How do we find and build a career that's truly a great personal fit—especially if we feel stuck or uncertain midlife? Venture capitalist Bill Gurley shares hard-won insights from his nonlinear journey, research on regret and risk, and stories of renowned entrepreneurs, artists, and professionals. The emphasis is on thinking from first principles, following “fascination” rather than loaded notions of “passion,” nurturing optionality, and the lifelong practice of learning and adaptation.

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Key Discussion Points & Insights

1. The Roots of Career Regret — It’s What You Don’t Do

• Regret of Inaction: The primary career regret, as supported by Daniel Pink’s research, is not what we do and fail at, but what we never attempt (02:50, 81:23).
  • Quote:
    “The number one regret people have at the end of their life is a regret of inaction. He calls them boldness regrets. ...But the thing we never tried eats at us. And he has a study where it actually grows in your head over time.”
    — Bill Gurley, (03:25), repeated at (81:23)

2. Rethinking "Passion" — Follow Your Fascination

• Fascination vs. Passion: Jerry Seinfeld’s notion (cited by Gurley) that “fascination” or obsessive curiosity is more reliable than “passion,” which is often ambiguous or imposed too early (04:31, 82:50).
• Finding Clues: What do you choose to study in your free time? Would you do this instead of watching Netflix?
  • Quote:
    “The key to having a lifelong dream job and being really successful at it...is to be fascinated with it. ...Is there something that you find so fascinating that in your spare time you’re studying it on your own?”
    — Bill Gurley, (04:31, 82:50)

3. Careers Are Not Ladders, They're Webs

• Iteration: Most people who find their dream job have two or three career “stops” first; don’t fear exploration or pivots (06:52).
• Permission to Shift: Society pressures young adults to plan too early—it's normal to take time or pivot away from original plans (06:52, 08:46).

4. Bill Gurley’s Own Career Path

• Story: Engineer → Wall Street Analyst → Venture Capitalist (08:58–12:45).

• Key Turning Point: Periodic self-questioning: “Would I still want to be here 30 years from now?” as a critical heuristic for making change (08:46).

  • Quote:
    “Every year, take the time to sit down and ask yourself, if I look at myself 30 years from now, do I still want to be doing this?...And knowing that other people have done that and that a lot of successful people have done that is useful information...”
    — Bill Gurley, (06:52–08:46)

5. Luck and Optionality — Creating the Surface Area for Serendipity

• Increasing “Surface Area”: Not about random dabbling, but about pursuing side hustles or projects where your interest/fascination lies.

• Example: The “side hustle” story of Dan Gilbert and how being known for a project outside your core job can pivot your trajectory (13:11–14:52).

• Optionality as a Hedge: Avoid getting “stuck” financially or career-wise by controlling spending and keeping doors open for change (02:41, 13:34).

  • Quote:
    “Luck is a function of how much optionality you expose yourself to.”
    — Bill Gurley, (12:27, 84:06)

6. Navigating Fat Tail Distributions and Survivorship Bias

• Fat Tail Fields: Many creative or “star” industries (music, sports, acting) have few winners, but many adjacent and supporting roles (16:16–16:46).
• Survivorship Bias: Success is tied to continuous/lifelong learning, not just raw talent (16:46, 19:43).

7. Lifelong Learning and Adapting Across Domains

• Craftsmanship Mindset: Treat your field—regardless of what it is—as a craft to cultivate, not just a series of tasks (24:06–24:59).

• Continuous Adaptation: As you advance, the skillset and content you study changes (e.g., from technical, to business, to leadership) (22:42–23:56).

  • Quote:
    “If you think about what you do as a craft, that makes me smile even saying it. ...You have the kind of right mindset to go attack this thing.”
    — Bill Gurley, (24:06)

8. The Role of Peer Networks, Mentorship, and Community

• Learning Collectives: Peer groups exponentially accelerate learning, as in Mr. Beast with his early YouTube “study group” and D1 athletic directors (56:19, 62:05).

• Give to Receive: Value is first given to networks before it’s received. Contribute knowledge, content, or help to build relationships (63:04).

  • Quote:
    “If you start giving away first...you can build a reputation in the digital world that can turn into relationships in the physical world.”
    — Bill Gurley, (63:04–64:20)

• Physical Epicenters: If possible, be in the city or ecosystem where your industry thrives to multiply connections and serendipity (65:26–69:01).

9. Balancing Consumption vs. Creation

• Time Allocation: Don’t just study—write, teach, and do. Synthesis is as essential as analysis, especially with the dominance of AI-fueled learning (40:32–41:44).

10. Breaking & Updating Mental Models

• Personal Example: Gurley reflects on Benchmark’s missed investment in Google because of outdated “rules” (e.g., two co-CEOs, academic founders). Adaptability is essential (45:41–47:34).

11. Age, Experience, and Intelligence

• Crystallized vs. Fluid Intelligence: Both youth (for daring) and age (for pattern synthesis) have career advantages; optimal learning happens throughout life (44:45–45:41).

12. Purpose, Not Just Passion

• Impact Beyond Self: Deep fascination and mastery in any field often lead to profound purpose and influence—measured by the legacy and influence on others, not just personal fulfillment (77:55–79:47).

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Notable Quotes & Memorable Moments

• On Regret:
  “The number one regret people have at the end of their life is a regret of inaction. He calls them boldness regrets.” (03:25, 81:23)

• On Finding Your Path:
  “The key to having a lifelong dream job and being really successful at it...is to be fascinated with it.” (04:31)

• On Optionality:
  “Luck is a function of how much optionality you expose yourself to.” (12:27)

• On Peer Learning:
  “...Their learning speed was exponential versus if any one of them were working alone. ...Every one of those people ended up with over a million followers.” (56:19–57:55; Mr. Beast story)

• On Age and Change:
  “As we get older, our mental models almost get rigid and there’s too many of them. ...One of the reasons so many young people do so well...they don’t know what they don’t know, and they don’t have a fear of what’s possible or not possible.” (44:56)

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Important Segments & Timestamps

| Timestamp | Topic/Summary | |------------|---------------------------------------------------------------| | 00:00–03:25 | Regret of inaction, financial flexibility is key to change | | 04:15–06:52 | Fascination beats “passion”; system mismatch in career design | | 08:58–12:45 | Bill Gurley’s nonlinear career path and inflection points | | 13:11–14:52 | Creating “surface area” for luck via side projects | | 16:16–19:43 | Surviving fat-tail industries, survivorship bias | | 22:42–24:59 | Mindsets of craftsmanship, artisan approach | | 40:32–41:44 | The value of writing/creating to synthesize learning | | 44:45–47:34 | The Google-missed-opportunity: discarding old mental models | | 56:16–57:55 | Mr. Beast’s study group — peer acceleration | | 62:05–62:49 | Collegial networks in high-power careers (athletic directors) | | 69:00–73:38 | Physical epicenters, book writing, and following curiosity | | 75:33–77:49 | Tito’s Vodka story; late-in-life pivots | | 77:55–79:47 | Service and lasting impact: purpose emerges from fascination |

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Three Key Takeaways (From Host & Guest)

1. Regret Is Usually About What You Never Try
   Research-backed: At life’s end, people dwell on roads not taken, not paths that led to temporary failure.
   Implication: Test ideas and explore potential—avoid letting fear of failure turn into the more enduring regret of inaction.

2. Don’t Follow Abstract “Passion”—Follow Your Fascination
   Practicality: Passion is intimidating and ill-defined. Fascination is concrete—notice where your curiosity leads in your free time.
   Practical Test: If you’d stay up late to read or tinker with something, it's a clue.

3. You Make Your Own Luck by Expanding Optionality
   Actively Seek Opportunities: Take on side projects, attend events, build diverse skills, immerse yourself in industry epicenters, and nurture wide networks.
   Quote: “Luck is a function of how much optionality you expose yourself to.”

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Additional Tips & Action Steps

• Set up a “dream job” Google Doc to collect ideas, contacts, and research (52:17).
• Annually ask: Do I want to be where I am in 30 years?
• For community: Organize or join peer learning groups. Give value first—content, help, knowledge.
• Go where the action is—move to industry epicenters if possible.
• As you learn, synthesize and share via writing, podcasts, or discussions.

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Memorable Stories & Analogies

• Tito’s Vodka: A mortgage broker at 40 pivots to spirits, combining what he loves and what he’s good at—now runs the #1 spirit brand in the US (75:33–77:49).
• Mr. Beast & Peer Group: Early YouTube fascination led to 16-hour daily “study groups”—all members reached 1 million+ followers (56:16–57:55).

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Where to Find Bill Gurley

• Twitter: @bgurley – most active and open to direct messages (80:22).

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This summary distills the inspirational and practical wisdom from Paula Pant and Bill Gurley about charting your own course in work and life, offering encouragement to stay curious, try boldly, and keep learning in public for both fulfillment and impact.

Transcript

[A]

Are you feeling stuck in your career? A lot of people are not very excited about what they're gonna do five days a week. You know, you wake up at 6am or 7am and you're gonna spend the bulk of your waking hours doing this thing that isn't really that exciting. That kind of sucks. Venture capitalist Bill Gurley joins us to talk about what to do if you feel stuck in your career and you're not sure what direction you should take. Welcome to the Afford Anything podcast, the show that knows you can afford anything. Show covers five pillars, Financial, psychology, increasing your income, investing, real estate, and entrepreneurship. It's double I fire. I'm your host, Paula Pant. And today's episode covers two out of those five. We talk about increasing your income, which is the natural organic consequence of doing something that's more aligned with you, with the real you, the inner you. And then we also talk. I mean, we don't explicitly talk about the letter E, but for, for many of you, entrepreneurship might come up as the thing that's the right fit. For some of you, it's not. How do you know if a career is the right fit or not? That's what we're going to discuss today. Our guest, Bill Gurley, is a prominent and well respected venture capitalist. As a general partner at Benchmark Capital, he made early investments in companies like Uber, Zillow, Stitch Fix, Grubhub, OpenTable, Nextdoor, and many, many more. He was named VC of the Year by TechCrunch in 2016. He was on Uber's board of directors until 2017. And there was even an actor who played him on a TV show on Showtime called Super Pumped. An actor named Kyle Chandler played a fictionalized version of our guest today, Bill Gurley. He is also consistently listed on the Forbes Midas list. He shares his story about how he got to the career that he's been in. He started off as a design engineer working at Compaq. Later he worked on Wall street as a research analyst. So he shares the story of finding work that was a great fit for him and shares advice on how the rest of us can do the same. Here he is, Bill Gurley. Hi, Bill.

[B]

Hey, how are you? Thanks for having me on.

[A]

Oh, thank you for joining us.

[B]

Thanks.

[A]

Yes, you write a lot about how to discover a career that you love.

[B]

Yeah.

[A]

For the average person who is listening to this, who is thinking, I don't know what I love, and I'm in my 50s, is this possible for me, given that I don't have a clear Picture. And given that I have a limited time horizon.

[B]

Yeah, I do think it's possible. I mean, some of that's going to be heavily determinant on financial flexibility, which I know you talk to your audience about a lot. But if you're spending right up against every last cent that you have, your ability to shift might be limited. You know. And one piece of advice I would give to anybody, not just someone in their 50s, but probably more even importantly to someone who's just coming out of college, if you want to maximize optionality to be able to explore and do things and shift gears and change lanes, which I think those are things you absolutely want to be able to do, you can't get stuck financially. So you got to be careful about your spending, especially early on.

[A]

Right.

[B]

But I think it's possible. Yeah. And in fact, Daniel Pink has a great book about regrets. And one thing he highlights, and he studied this across multiple geographies, multiple different ethnicities. The number one regret people have at the end of their life is a regret of inaction. He calls them boldness regrets. We're very good at forgiving ourselves for the things we did wrong. Like, humans are very quick to move past. Lesson learned, you know, don't dwell on it. There's not a lot of rumination on the mistakes made. But the thing we never tried eats at us. And he has a study where it actually grows in your head over time. So that might be a kind of bat signal for the people that are 50 and know there's this thing they didn't try yet that's really nagging at them. Go for it.

[A]

Well, let's go through some of the principles one by one, beginning with the passion hypothesis, because you make the argument that it isn't really about following your quote unquote, passion. That's sort of an overloaded word. It is really more about following your fascination, which is synonymous with your curiosity.

[B]

Yeah. To give credit to the person that focused on fascination versus passion was Jerry Seinfeld in a graduation speech he gave at Duke. But the reason it was interesting to me that he used that word is the key to having a lifelong dream job and being really successful at it, and it not feeling like a grind and weighing on the rest of your personal life, is to be fascinated with it. And the reason that is is because the second principle, which reflects on the first one, is you have to continuously learn. Like, you have to want to continuously learn, and that has to feel free. It's interesting because it's very important that people know it's okay that a lot of people, especially young people, they don't know their passion yet, and that's particularly fine. The school system used to be built to allow that development to happen later. We used to. Not you. If you go way back, you weren't allowed to declare a major until the end of your sophomore year. They didn't let you because they wanted you to roam around and try a bunch of things. Now at many schools, you have to apply to your major as you're applying to college. So you're a junior in high school and people are like, what's your passion? What do you want to do with the rest of your life? And you have no idea. You and I were talking before the podcast about how you discovered what you're fascinated by at the end of your senior year in college. The system's not set up well for that today. So, anyway, I think a great test is, would you do this versus watching a Netflix series? Like, is there something that you find so fascinating that in your spare time you're studying it on your own? And that sounds like exactly what happened in your case. And if that's true, I would put it on your list of maybe this is something I could have a career in.

[A]

Right? And it is that obsessive interest. How do you square that with the reality that once you go towards a given domain, once you go towards a given field, the actual day to day of it often has less to do with that substance that catches your initial interest, less to do with that substance, and more to do with operations, hiring processes, building systems, setting up workflows.

[B]

You know, it's quite common for the people that are most successful to have two or three stops before they get to their dream job, and they move through things. One thing that I really try and address in that first principle is you need to take the pressure off yourself and know that that may be how this goes. Like, we've taught these young adults to grind so hard against this college process. Getting into college, stacking your resume, getting the degree, that it probably feels quite weighty to think when you get to into that, oh, I'm going to shift in a different direction. But a lot of people do. Dave Evans at Stanford, who does the Designing youg Life class and book, you know, they highlight that like four years, five years out, 40% of people are no longer doing the work that was in their major. And so just having awareness of that and taking a deep breath and recognizing that's okay, I think puts you in a better mindset for this exploration piece, you know, to go do it. I did this thing, and I don't know why I did it or where it came from, but I think it's an interesting little heuristic, which is, every year, take the time to sit down and ask yourself, if I look at myself 30 years from now, do I still want to be doing this? I think it's a really interesting way to gauge where you are. And to your point, I get into. I thought I was going to be a marketing person. I find I'm filling out forms all day or whatever, doing all this work that doesn't appeal to me. And my journey has a little bit of this in that. And then I think you just need to wake up and say to yourself, okay, maybe I need to go find something else. And knowing that other people have done that and that a lot of successful people have done that is useful information for people that are in that place. Cause it can feel like failure if you let it feel like failure.

[A]

Right.

[B]

But I would think about it more as a stepping stone.

[A]

Well, let's actually talk about your journey then. You're known as a vc. Your journey began in Florida and in Texas. You went to ut. Tell us about that.

[B]

I had two stops before I got to venture capital. The first one was a computer engineer. So like many people who made their way to Silicon Valley, I fell in love with computers at a very early age. I had a Commodore Vic 20, which dates me severely, because you'd have to go look on Wikipedia to find out even what that was. But it was a computer that came out before the Apple and the IBM PC that you plugged into a TV. I started playing with programming in 10th grade. It was very natural. It came very easy. I was fascinated that you could create things that way. And so I got a computer science degree, and I went to work at Compaq, which was this very hot computer company in Houston at the time that probably also dates me. I wasn't unhappy in that role. But what happened is we started the third project after I had been hired, and it looked a lot like the second project, and it looks like the first project, and there wasn't. It didn't look to me like there was going to be enough dynamic change to keep me interested simultaneously. Not unlike your story. When I went home at night, I found I'd gotten fascinated with buying stocks. And so I had read this book by Peter lynch, one up on Wall street, which is very popular book at the time, still probably well read. I started trading stocks on the Prodigy Network of all things. I wasn't going home at night and studying more computer science. I was going home at night and studying something different. And I asked myself that question, do I see myself doing this in 30 years? I had grown fascinated with things beyond engineering. I was reading trade magazines and trying to study the other companies. I was still fascinated with technology and disruption and all those things. And so I went to business school. I thought about venture capital. I knocked on a few doors, I learned a little bit. None of it went anywhere. I was busy reading Forbes, Fortune, Wall Street Journal, all these things. And I found out in reading those that these people that are known as sell side analysts on Wall street were often quoted when people had a question about where the industry was going or what's this company doing? And that intrigued me. And so I pulled on some threads, ended up coming here to New York and knocking on doors like you hear about in the summer, and was able to get in touch with some of these people and was able to land a job as a sell side analyst, which was equally fascinating. I loved a lot of it. You get incredible access to the best. Like you immediately start talking to CEOs, CFOs, the access is incredible. You start getting quoted in these famous periodicals. There was a night, and I remember it clear as day, where I was working late in the Park Avenue Plaza building. I walked around the office. About 10pm I walked around the office and the four corner offices were the most senior people in the department. I paused in each one of them and said, do I want to be here 30 years from now in that office? Assume I do. Great. But I've done this my whole life. And it was a quick no, like in my brain and I was doing fine, but it was just a quick no. I immediately then started thinking about what's next and through a lot of good fortune. Although I'm a big believer that luck is a function of how much optionality you expose yourself to.

[A]

Right.

[B]

I ended up in Silicon Valley and and got into venture capital and spent 25 years there and never asked myself that question again. Like I never ruminated in that way because it all was such is almost. It's like one of those flow things where, you know, once I got into it, it's like 20 years passed like that.

[A]

Right, right. And that very much is reminiscent of the start with the end in mind, as Stephen Covey talks about. Visualize your funeral even.

[B]

Yes.

[A]

And then work backwards from there.

[B]

It's kind of a career version of that.

[A]

Right. You mentioned luck is a Function of the optionality that you expose yourself to. And I know you also tell the story of the gentleman who wanted to increase his surface area. He had a great line about increasing his surface area for optionality.

[B]

This was the side hustle. Yes, it's Dan Gilbert from the acquired podcast.

[A]

Oh, the acquired podcast, that's right.

[B]

Yes.

[A]

Yeah, exactly. Which is a wonderful way to phrase it. How does one distinguish increasing their surface level for optionality from doing things that are just a little bit random and scattershot? You know, throwing darts on a dartboard. Like, how do you do it?

[B]

Well, let me explain his heuristic because I think it's quite fascinating. He. He had seen my original presentation on YouTube and is a fan of the concept. And he told me that at every job he landed at, he would create a side hustle and he would talk the employer into. He'd say, look, in my spare time, if I do this other thing, that will help the firm, but it's not what you're paying me to do. Is that okay? And they would all say yes. In almost every case, he ended up becoming known more for the side hustle than the core job. I think it was more differentiated, something he was passionate about and kind of leaning into. At Microsoft, he helped create something called Microsoft Garage, which was a way to attract founders into the Microsoft product set. It was wildly successful, but he ended up working at Madrona vc and he went to them and said, can I start a podcast? And they said, sure, that'd be helpful for the firm and that kind of thing. Well, that's what led to the acquired podcast. And so his approach allowed him to kind of Test 2 careers at once rather than one, just to speed up the learning process. But back to your original question. I don't think you should just do random things. You should test theories where the possibility of fascination is out there.

[A]

Right? That fascination, that obsessive interest that really is a major driver.

[B]

I think it's really easy to just ask yourself what you're doing in your free time. I can't tell you how many of profiles come from someone converting a hobby into a career.

[A]

Right.

[B]

And I think, unfortunately, the powers that be have taught so many young people that we really need to focus on these safe jobs. And I think it's well intended advice. They're very worried about the economic stability of the young person. And so they want them to end up in a place where they'll have a happy life, where happy is presumed to be economically stable and assured. But like anything, an effort can Go too far. And there are a number of people that have spoken out, from Jonathan Haidt to Rick Rubin and Ken Robinson, that we've lost the novelty and creativity and discovery that used to be a part of the academic process. And a lot of the people are in these types of industries and jobs that your parents might tell you not to go into.

[A]

Right.

[B]

And that was intentional. I think you might be surprised if you bring the fascination to the table and how many different areas a career is actually possible.

[A]

Right. That said, there are many careers, many lines of work that have a fat tail distribution.

[B]

Yeah.

[A]

I mean, the mathematical reality of a fat tail distribution career is that the majority of people who attempt it will not succeed. You know, that's true in stand up comedy, that's true in acting, it's true in singing, it's true in even careers that are not necessarily in the spotlight, like managing a festival or becoming a lyricist for a band. Do we risk survivorship bias when we focus on the profiles of the people who have made it?

[B]

Well, I think there's two different things to unpack in that. So let me start with what I think the first question was and then come to the survivor by ship question. So one thing that I really think is interesting is in most of these, what you call these fat tail distribution industries, there are number of jobs that aren't the talent person. And we have a profile of Lori Bartlett who became a agent in Hollywood and her fascination growing up was the movies. It became pretty clear to her by the time she's in high school, she's not an actress. And so she closed that door and went in a different direction and only later came back to start asking questions and realized, oh wait, there's. There's hundreds of jobs for every one actor job that are in this industry that supports it. And that's true. You were hinting at. We have a profile of Jay Sweet, who runs the Newport Folk Festival. He wanted to be in the music business, which in his mind meant being a band or write lyrics. And then over time he found he could be proximate to it, play a critical role in it, without being in that role. And there's the famous book about the mail room in Hollywood, because so many people who, Barry Diller, David Geffen, all these people started sorting mail in the mail room. And so I would tell anyone that's interested in industry where they feel like talent, and this is true in sports, there's jobs everywhere. If you love it, you know, find one of these support roles and you might be surprised you know how easy it is to climb the ladder. Now to the survivorship bias point. I think anybody that studies success, you could bring this kind of critical argument to the table. The thing that really triggered me to write this was noticing these patterns of behavior that are across all these different people after I uncovered them. I think there's a real absence of people actually doing those things in most jobs, in most careers. I think people finish college and they think, okay, I'm done learning and now I'm just going to go to work every day and then quit. But the people in this book that are wildly successful, that's not what they do. Danny Meyer, who I've been fortunate to know for a long time, very successful New York restaurateur. Not just him, but his whole team, they do exploratory learning constantly. Like, I talked to him in the fall, and they had just come back from Europe and they were out visiting all the great restaurants and what's new and studying. So this, this element of studying, like, I don't think most people do it. Like, I think they quit doing it when they leave college. And so my point being, I believe that anyone that adopts these principles and starts doing these things is going to increase their odds of success. Like, can I guarantee they'll end up on the top rung of the ladder? No, but I think they'll highly differentiate themselves from other people.

[A]

Right. Broadly speaking, the people who self select as people who listen to podcasts, particularly a podcast like this one, have self selected as lifelong learners.

[B]

Yeah, that's true.

[A]

They are the lifelong learning variety. What I often hear is the opposite issue, where we'll take Danny Meyer, for example, right. The skill set required to really understand the craftsmanship of a great dish, the perfect searing on a piece of fish. That is a fundamentally different, different skill set than how to scale a franchise operation like Shake Shack. Right. Franchising is a totally different skill set from the craftsmanship of the perfect fish fillet in order to succeed when you need a skill set that is so disparate.

[B]

Yeah.

[A]

How does one engage in lifelong learning when there's so much to learn?

[B]

Well, you, I mean, Danny had launched 10 very highly successful New York restaurants before the Shake Shack idea came up. And then it was originally a unit of one in Madison park, and then it took off and then he had a second one, and then the franchise. But one thing that's interesting about that, because if you read the book, we also profile this woman, Jen Atkin, who I think, oh, yeah, way I love this, I was going to ask you about so much. I mean, talker. She started on the very bottom rung. She moved to LA with two or three hundred dollars in her pocket, but she became a hairstylist. And then once she succeeded as a hairstylist, she did this other thing just like Danny succeeded a restaurateur and then built Shake Shack. I think what you've teased out in asking that question is these people that are lifetime learners, once they achieve one level of success, they can now set their eyes on, well, now what's possible. And one of the reasons I think they end up going so far is because they learn the power of continuous learning, and they don't see any problem is unsolvable. And so they get to one tier or one rung on the ladder, and they immediately start thinking about the next one, and how do I get there? And the world feels very possible to them once they start having success with this.

[A]

Yeah, you know, I was thinking about that specifically with Jen Atkins story, because as a hairstylist, I mean, the skin skill set involved in styling Gwen Stefani's hair for a magazine cover shoot, it's a skill set not just of how to style hair, but also how to deal with the many personalities and the inherent politics of dealing with celebrities and agents and PR people. And, you know, you've got to learn how to deal with that entire environment, that work environment. As I was thinking about her story, that is a wholly different, almost like a completely different line of work than, you know, she went on to create Ouai, the shampoo conditioner. For that, you would need to learn manufacturing and sourcing and inventory management.

[B]

We covered in the book. But her learning process shifted. And I've seen this with so many of the people that we've studied. Like, they'll start reading and studying about their craft. So Danny, when he had this intent, okay, I'm not gonna be a salesman anymore. I'm not gonna be a lawyer. I'm gonna go do this. First of all, he started at the bottom rung. He got a job, like, he begged for a job at one restaurant and was in the front of the. They call it the front of the house just to get exposure. Then he went on a learning journey. But later, after he had been successful, the stuff he started consuming, the reading, the continuous learning shifted to business books. And I sat down with Jen. Same exact thing happened. So for the first 10 years, she's learning to be a stylist, she's stuttering Vidal Sassoon and, like, paying attention to the best people in her studio and like really learning it at that local level. But what she read and what she consumed changed as she moved up and she one day she started reading business books. She might have been the only hairstylist reading business books, but she started reading them and exposed herself to new possibilities and then took the next step. And yeah, her story is amazing. Just amazing.

[A]

Right. Given that wide array of things that one could possibly learn, then how does one make decisions about the appropriate allocation of time, time and focus?

[B]

Well, I think you start at the beginning and when you're talking about Danny and a shift and you use the word artisan and craft. I love those words because for anyone who's truly passionate and fascinated with something, I think they think about it that way almost regardless of the industry. And I think it's a mindset that causes you to study the history of the field, to appreciate the nuance of the field, to try and tease out the nuance of the field. Because I think those are the things we associate with those words, artisan and craftsman, and they, I think they exist in all fields. It's just people don't use those words to describe them. But if you think about what you do as a craft, that makes me smile even saying it. Like, I think, you know, you have the kind of right mindset to go attack this thing.

[A]

Right. The challenge is to maintain the craftsmanship mindset that, you know, bespoke mindset, while also scaling.

[B]

Yeah. Many of these things start becoming self reinforcing. If you're doing them well, they start compounding and what you're calling scaling. I think it comes quite natural because you're building your network, you're building your peer community, you're building your learning set, and all those things make the next peer relationship, the next mentor relationship, that everything gets easier as you build this bedrock. It really does stack on top of itself.

[A]

It stacks. But also you've got a quote in there about how, what is it? Something about good experience comes from bad experience. It comes from making a lot of mistakes.

[B]

Yeah, it's a phrase we used at Benchmark, where I spent my career as venture capitalist, which is good judgment comes from experience, which comes from bad judgment.

[A]

Right, Right, exactly. Well, and I can tell you, I felt that in that the fundamental skill set of learning how to create an excellent podcast is very different from knowing how to write a good job description or when hiring, knowing even just how to be good at choosing a good candidate and then knowing how to onboard them and then establishing KPIs or establishing some kind of a scorecard so that your team knows what objectives they're trying to meet and knows the benchmarks they're going to be measured by. That's also different from the craft of creating a podcast.

[B]

But I've been super fortunate as a venture capitalist to work with a ton of great CEOs, a ton of great leaders, and for many people, and this wasn't my calling, but it's their calling. They think of leadership as a craft. Like, it gives them immense emotional satisfaction. They get energy from the notion of leading. I have the opposite reaction. Like, If I had 100 people looking at me doe eyed saying, what do we do next? I get hives. But there are people, I've met them, they're thrilled by that experience. And for them, I think all the stuff you're talking about, like, what metric gets people most motivated, how do I hire, how do I develop humans? It really matters to them, and they're in the right lane if they're doing that. I think what you're getting at is some people approach an industry or a field because they like the work product of the field, and then they get in and they're successful, and next thing you know, they're promoted and. And all of a sudden they have management responsibilities, which may not have been their passion. And I think that's important for people to get in touch with. I'm a type of person who really enjoys, and I'm interested by a breadth of experiences. And so I ended up in a service job in venture capital where I'm working with a ton of different companies. They all do different things, and that meets my mental model for what I enjoy doing. And part of why I left that engineering job is that amount of focus and detail led to boredom for me. But there are other people who love to have their hand on the dials, who want to be in the details. They want to control everything, and so they're better in those roles. And if you like the Brett stuff, there's consulting and investment banking and services jobs like legal and lawyers. And there's all kind of jobs where you get hired across multiple clients. Like, those are great for people that want the breadth. And these more operating roles are great for people who don't. And getting in touch with what drives you and what comes easy, I mean, I think what doesn't feel like work, that's a great test for whether you're doing something that is where you should be.

[A]

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[B]

Well, I think a lot of this comes down to thinking about what's going to lead to a life of fulfillment for the individual. And, you know, once again, looking at these kind of Stephen Covey, like, begin with the end of mind type things. If you get caught in the game of climbing just for the sake of climbing, you may find yourself doing a whole bunch of activities that weren't originally what you're passionate about. There's a lot of people that have done really broad based happiness studies and money alone does not. There's no data that suggests there's this high correlation between just money and happiness and not knowing the particular individual that I'm speaking to. But I would certainly, if you find yourself moving away from what you love just because that's the path to success, I would just take a pause and ask yourself the question, is this what I want to be doing 30 years from now? Is this really what I want to be doing with my life? Could I orient in a way or shift in a way that allows me to do what I love more of the day? And I would consider it. Like, I would take a pause and consider it. Nothing's easy. Like, I don't want anyone to think, oh, if you read this book, you can work, you know, 20 hours a week at what you love and everything's joyful. Like, the people that we profile work really hard. It's just the tax on them as an individual and on their loved ones is not as high because they get emotional energy from it rather than it decaying their emotional energy. So. And it's a big difference.

[A]

Oh, yeah, yeah. No, I firmly believe a big part of success is like, the capacity to work 80 hours a week comes from loving the work that you do so much that the work imbues you with energy.

[B]

Yes.

[A]

Yeah. When you're like, what else would I do? Would I go to Hawaii and sit on the beach? That actually sounds like less fun, you

[B]

know, and by the way, Gallup did a poll in 2023 where only 23% of people feel engaged at work and they qualified like 59% as quiet quitting. And so I think a lot of people are in this state working for the sake of working. And look, I'm sure there are individuals who have such a amazing life outside of work that they don't care. And I think that's fine. Like, I don't want to try and cast a shadow on them and say that. I think that's perfectly fine. If you work an 8 to 5 job and you're out of there and because you love your community, you love your church life, you love whatever, and you're thriving in that way, I think that's a fine outcome.

[A]

You mentioned the question of what do I want to be doing 30 years from now? 30 years ago was 1996. Yeah, 1996 was the risk of making an obvious statement, an utterly different time in every regard 1996, you could viably have a career in print newspapers. The world has changed so much in the last 30 years and it likely will change at an even faster rate in the next 30. And so I think where a lot of people feel challenged in even asking that question is that 30 years or even 10 years seems so unimaginable.

[B]

There's a lot of people that are asking a lot of questions, especially in the career front with the onslaught of AI and what it might mean for different roles. I recommend two things that are seemingly at odds with one another because they're so far apart. One, I think it's important to study the history of your field and to be a historian of your field. I think it's a good test of whether you're really passionate about it because I think it'll feel really boring if you're not. But two, I think it gives you some superpowers if you walk around with the knowledge and history of your field. It's very differentiating. Elders will respect it quite a bit that you took the time.

[A]

Right. There's that chess champion who is like a master of trivia.

[B]

Yeah. Magnus crossing 18 in the middle of a tournament. They did a trivia contest and he won. And I don't think he's the only one. I've uncovered a lot of people that have really differentiated themselves by knowing the history. I got invited to this incredible dinner that someone had won in a charity auction with John Lasseter, who is the creative genius behind Pixar. He served us a 10 course meal and with each course he showed a cartoon from history that he thinks was part of the building blocks and cornerstones.

[A]

Right.

[B]

And why it was important.

[A]

Right. He talked about how the 1941 Dumbo.

[B]

Yeah.

[A]

How that influenced a recent Pixar movie.

[B]

Yeah. But just the fact that he had studied them all and passionately knew about each one of them, it was really powerful to see that. And then the second thing is an imperative. So one study the history. The other imperatives are the exact opposite end of the spectrum. Know the edge of what's happening in your field. If you are the person in the shop that knows what's happening dynamically on the edge. So I'll go back to. You brought up print journalism. Part of your career is pat, how that world has navigated. If you were at a print in any organization that was in print journalism in 1996 and you're studying and paying attention, maybe doing a side hustle within the organization about what's on the edge, you're going to see all this stuff coming a lot faster and you're going to be highly valuable to the organization, right? Like even today, let's say you're applying for a marketing job out you work, you're, you're in school at the Northwestern or whatever, the best marketing school. If you really grok TikTok, of all the candidates being interviewed by Clorox or whoever at that university, you know more about TikTok and how it works than everyone else. I'm telling you, you're gonna stand out. Like you're gonna look really interesting to these people because they're afraid of the dynamic and change also. And so I really love this notion of know the history and know the edge and if you're really studious on both of those, you're gonna do well for yourself.

[A]

Given the importance of being studious and given the importance of that depth of knowledge, how much time should a person spend consuming versus creating? Because sometimes that, that study time that, you know, you can get into analysis paralysis by just reading, reading, reading, reading, reading and never acting.

[B]

When I was a sell side analyst on Wall Street, I started a weekly. It was a facts at the time. I keep saying things that people may not know what they mean. And it became a newsletter and then a blog. But I have gotten personal benefit out of writing. And Bezos talks about this a lot with the six pagers at Amazon. Buffett famously writes his annual letters. Howard Marks, who I'm a huge fan of, continuously writes out loud, if you will. And I think it's a great exercise for organizing your thoughts and holding yourself accountable. When you write stuff down, you want it to be intellectually consistent and it causes you to do these back loops in your mind where you're double checking what you think you've uncovered and what you've learned. And so I think it's a great exercise. And someone recently brought up the notion that AI may make this even worse. Right, because you can learn at jet speed. But do you ever take the time to pause and try and have novel thoughts on your own? And I think that's a good call out. I think it's something that people should think about how they allocate some time to synthesis on their own.

[A]

Right? Well, yeah. It occurs to me as you study history, analysis is to break it all apart and then synthesis is to put it together in novel ways. But it really comes down to time allocation. The time spent consuming versus the time spent creating or doing or acting. And also the time spent consuming in your direct domain. Versus in adjacent domains.

[B]

When we were talking about Danny Meyer and Jen Atkins and them moving to these other businesses. I do think the adjacent domain stuff is more of a senior level course than a freshman or sophomore level course. There are a lot of great books, probably the one that's best known as David Epstein's Range, where people learn to borrow ideas from other industries in other sectors, end up doing the most novel things.

[A]

Right. He was a guest on this podcast.

[B]

Oh yes, David. Yeah. He's wonderful. It's not obvious to everyone how they benefit from that. And it's a little more panning for gold. In other words, the nuggets. There's a lot of. When you start consuming things far away, there's a lot of. Of noise and finding the signal. And the noise is more of an advanced skill set. If you can do it, you can do some pretty amazing and breakthrough things. So I'm a huge fan of it. It's just harder to do.

[A]

Right.

[B]

And that's why I say it's a little bit later in the game. But it's really incredible. And it also reflects on this wandering or meandering career journey. A lot of the people that end up having the biggest impact in a bunch of different areas, different fields, don't start there. Like they come into it via an unusual path just because they bring new mental models to the table that you wouldn't have if you came straight up.

[A]

Right. Yeah. And to that end, I mean, you've got a stat about the number of Nobel laureates who also have some hobby.

[B]

Yeah. This was work, I think, done by Keith Holyoke at UCLA where he took Nobel Prize winners and then the next prize below that and the next prize below that. And he studied their entire profile, including like their hobbies and how many languages they spoke. And he found the Nobel laureates actually had a wider variety of hobbies and activities than the people below them. Yeah. I'm on the board of a think tank in New Mexico called the Santa Fe Institute that dedicated to this theory of complexity, which is studying systems that are very complex, like weather and finance and all this stuff. But they have multidisciplinary professors there who all collaborate. As I've getting older, I've talked to more people at the top of different prestigious universities. Almost all the universities are trying to create these cross collaborative institutes that span multiple disciplines because that's where the edge is and that's where you end up with some of the most novel work.

[A]

In that regard. Do you think age is actually an advantage because it offers that crystallized intelligence, the ability to synthesize across domains in a way that, you know when you're younger and you have more fluid intelligence

[B]

that I think on this age topic, there's benefits to both. Like, I fear as we get older, our mental models almost get rigid and there's too many of them. And it's very easy to become cynical and to get to know very fast. And one of the reasons so many young people do so well in Silicon Valley as founders is they don't know what they don't know, and they don't have a fear of what's possible or not possible. And I think an older person wouldn't even try in many cases. And they come in guns ablazing, thinking they can change the world. And that matters sometimes. So I think there's benefits to both.

[A]

What are some mental models that you've discarded or modified throughout the years?

[B]

Yeah, I mean, the biggest mistake in my career is I was early as a venture capitalist at Benchmark and I stumbled upon this new search company called Google and invited Larry and Sergey to present to our partnership. They had 25 employees at the time. To tell you how early it was they presented. And we failed to chase that. I say fail to chase because I don't want to say we passed. Saying we passed means like, oh, we were negotiating and I didn't chase it. And one of the reasons we didn't chase it is there were two PhD students who wanted to be co CEOs. And that up until that moment in venture capital was usually a red flag. Two academics who want to co CEO. Like there was no history of that being successful. In fact, quite the opposite. And so venture capital is a game. I don't know if that's a lesson people can borrow from, but venture capital is a game where you have to. One of the reasons group decision making works so well is you're going to have to break one of your rules or you're going to say no to everything. And so you got to figure out when to break the rule at the right time. And that was a massive mistake to let that thing matter that much. And of course, the missed opportunity is gargantuan. Things change. I mean, you brought up like, how fast technology changes. And if, if a mental model or a rule that you've built is no longer relevant because the field has changed so much, you got to let it go.

[A]

Right.

[B]

And it's part of one of the benefits of really focusing on the edge and studying the edge in any field is you'll realize Very quickly, what needs to change, or at least before everybody else, right?

[A]

When you're studying the edge, how do you distinguish between random outliers versus something that is actually indicative of a pattern?

[B]

I think you can pay attention to what's happening. I mean, there are false starts. Everyone got excited about chat as a medium, and that didn't really play out. People had created several companies. There are things that pop up where, oh, everyone goes and does it for a while and it fizzles out, and that's okay. I mean, it's kind of a cost of living on the edge, but I just don't see much downside in terms of knowing what's possible. In fact, like right now, a lot of people say, well, what is your advice for people if they think AI is about to take over their job? First of all, you should have known about it two years ago because you're studying the edge, right? And you see this coming. But second, ask yourself, are you the most informed in your organization about what AI is doing to your field? Because if you are, you're probably the most important employee in that company. And so just always live on the edge. We evolve with our tools. You wouldn't think about not being proficient in a spreadsheet or a word processor or email client. And this is just that there was a time where people didn't know what those things were, and they popped up and someone used them first and someone used them last. And by the way, it's funny, you were talking about age. The cynicism really drips in fast. Like, the people I know that are older, like, when I bring up AI, they're like, oh, they're like, dismissive. Like, that's the worst thing you could possibly be for career management is dismissive of new disruptive technologies. And I would find they'd be like, oh, I got. I ask a question, you got it wrong. And then they, okay, then they turn it off and they don't try again. And I'm like, well, have you tried it a year later? And then a year later, did it still get it wrong? Because, I mean, you're well aware, right? These models are getting better every day. And so as a venture capitalist, I grew very comfortable with the idea that tomorrow's going to be different. And it was my job to know what tomorrow looked like. We would always have anxiety if some new app is in the top 10 that we've never heard of, like, immediate download, like, start playing. Like, you've got to roll around in it, right? So that's kind of how I'm wired.

[A]

Right, right. Well. And I think one of the beautiful things about tech, about being a vc, about investing generally, is the embrace of what's possible. You know, the lack of tethering to what has been and the utter embrace of what could be. Yes, yeah, it's a very future oriented and therefore like necessarily optimistic.

[B]

I agree. But not everyone's prone to it. So if you're not, you do yourself a disservice.

[A]

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[A]

For people who are listening who are currently full time W2 employees. But they have a dream of one day starting their own company.

[B]

Yeah.

[A]

How do they know when they're ready?

[B]

Yeah. There was this great book I read when I was in college called Shark proof by Harvey McKay. He's famous for his sales book, but he read this book about chasing careers and he said you should have a dream job folder in your drawer. This was 30 years ago, so no one has drawers, but maybe you have a Google Doc that is your dream job and you just start putting stuff in it. Stuff you notice, people you meet that might help you in that field. When Danny decided he wanted to get into restauranting, he Made a list of the top 10 people that were changing the restaurant industry and studied each of them. So he started keeping notes on each of them. Do that. Like those kind of activities get you mentally ready for what you might go do. And you start building your network, you start building your mental models, you start building your education set, and you're going to be in a much better position to know the answer to your question. If you've got that framework kind of built on the side, then if the answer is, you know nothing about this, it's not jump right now. Like, the answer to that question is, oh, no, just boldly go jump off a cliff. Like, you can know so much. By the way, one huge asterisk I'd put on this AI thing for anyone that wants to chase your dream job. It's never been easier. Like, it's never been easier to learn. Like, podcasts, YouTube videos, talking to AI. Like, if you want to go pursue something and run with wild abandon at it, you've never had more at your fingertips. Never, ever in the history of the world have you had more at your fingertips. So if you have the passion and the fascination and the wherewithal to go be the most learned, to study the history, to study the edge, it's all right there for you. It's near free. It's unbelievable. Yeah, but you don't hear that pitch as much as it's going to take your job. It's ironic. I think it is the very best time to become a craftsman in something you love.

[A]

Right. I'm sure the cynical view of that. There would be people who say, given that this is the best time to learn anything and to dive into anything, won't that erase my unique edge?

[B]

Yeah. One thing about survivorship bias or cynicism is the counterfactual still exists. Like, okay, you can do this new thing that I'm recommending, or you still have. If you don't do it, you're still left in the old thing. So you can't compare the new path with some idealistic other path that doesn't exist. Right. You're still stuck if you don't do this. So that's what you should compare it to. I think this notion of competition causes a lot of people to turtle up and make the wrong decisions. And in many fields, in most fields, other than maybe competitive tennis or downhill ski racing, there's not only one winner.

[A]

Right?

[B]

There's lots of winners. Look at your industry. There's hundreds of amazing podcasters that are making a living, that are Thriving, that love what they do. So getting sharp elbowed and viewing everyone as a competitor, I think cuts off so many paths. Oh, yeah, there's this great book, Finite and Infinite Games. And many of our mental models come from studying finite games where there's a winner, loser, and you run and repeat all the time. Life is an infinite game. Like you're not. There's no point at which someone blows a whistle and says, it's over, you won, you lost, and there's lots of winners. And so one of the things that I recommend is rather than viewing peers as competitors, you know, view them as teammates that can help you along the journey. And I have some amazing examples of people that did that at a. At a very intense level.

[A]

Yeah.

[B]

And had wild success that came from it.

[A]

Right. Well, I mean, you tell the story of Mr. Beast.

[B]

Yes, it's such a great story. Yeah, he told it originally on a podcast, so I borrowed it. But Jimmy Donaldson, who everyone knows is Mr. Beast, when he was 17, he fell in love with YouTube and talk about a fascination and. And a fascination on the edge, which is one of the things about having a fascination about something on the edge is you become the most learned very quickly. Like the most learned in the world. Right. Because there's no history, there's nothing. There's knowing it. And he met three other people who were trying to basically debug, reverse engineer, figure out how to gamify YouTube. They ended up, he says, on Skype calls for over 16 hours a day for four years. They learn together. And so if one of them learned something either that worked or that didn't work, that knowledge is shared. And so their learning speed was exponential versus if any one of them were working alone. Probably more than exponential. I mean, because you come back and say, oh, look, I tried this and it had this success. And then they all four go try it with an additional twist.

[A]

Right.

[B]

And your ability to move up, you know, and study and learn is so accelerated.

[A]

Right.

[B]

And he claims that every one of those people ended up with over a million followers. Every one of them ended up making over a million dollars. And even says, more profoundly, if a fifth person had been on the calls, almost no matter who they were, they would have had the same success.

[A]

Well, and not just that, but they all crossed the 1 million follower mark within about a month of each other.

[B]

Yes, yes, yes. It's a great story and it's a great call out on how co evolving in a career can be really rewarding. But it takes a certain mindset and sharp Elbowed people do exist and they shouldn't be in your group.

[A]

Right, right. Well, as I was reading that story, what I was think about is one of the things that I love about online content creation, whether it's Mr. Beast on YouTube or myself in audio podcasting or prior to this it was blogging. One of the things I love about the world of online content creation specifically is that the pie is infinitely big. We are not competing over scarce resources because there is no scarcity. There are 330 million people in the United States. That is more than the number of, you know, like when it comes to growth, that growth is. There's no upper bound. That is a fundamentally very different type of industry than somebody who's bidding on a government contract. Yeah, right. Where there is an RFP and only one company can win that particular contract. What would a person in that field do?

[B]

Man, I'm aware of two companies that are building tools for companies that bid on government contracts, leveraging AI and it's unbelievable. I go back to this edge thing. They're able to use FOI requests, freedom of information requests to get the knowledge of the previous time the bid went out and everyone that applied and who won. And so they're building these cockpits that are like salesforce on steroids for anyone that. And not only how to win that one, but identifying opportunities you may not even know about. So I don't know. It's ironic that you use that example because I know these two startups but like there's an edge in everything and these tools affect everything. If you're on that edge, you'll be successful. One thing you could do is you could find peers that a lot of those kind of contracts and bidding are local, like for a local build out. Find peers in other geographies. Like you're not competing with them.

[A]

Right.

[B]

They're going through the same process that you are and you can learn from them and they can learn from you and you get to try four or eight times as many experiments and all those things. So these five young people who'd just gotten into the very once again first rung of the ladder in sports administration and they met at a conference, which is a great place to meet peers if you're in a industry that's geographically dispersed. And they became friends and they started texting and they kept a text group and they would talk about the problems they were facing, they would share ideas on what was working. That group eventually grew to about eight people. But unbelievable reality, all eight of those people are Division 1 athletic directors now on top of the biggest programs in the country. So much so that the NCAA is worried about the power they have as a collective block. I mean, talk about getting to the very top from where they started. And that shared learning, once again, it's so powerful. And that's one of the things, like going back to the survivorship bias question, that's one of those things where I just don't think people do that. I don't think the majority of people in their everyday job have found a peer network of people that are trying to succeed just like them, that they keep in touch with. And all the tools exist once again, like there's never been a better time. All the tools exist. You create a WhatsApp group, you know, it's super easy. You can share podcasts like you co learn together. You can move quickly in this world.

[A]

Right? Yeah, that was a great story. The athletic directors, because they called themselves the text group, the young 80s.

[B]

Yes.

[A]

And then they changed their name over time to the middle aged 80s.

[B]

Yes. I think they're now the old 80s.

[A]

The old 80s.

[B]

But they really looked after each other. I mean the shared learning was how it started. And it got to the point where they were meeting and running their own mini conferences. They were inviting guest speakers in to learn on their own and learn it. But then they would share recommendations on different coaches, they'd pass resumes on people that could be helpful to them. It's like it's a real unlock. I mean you share mentors. There's all kind of things that happen through that channel.

[A]

What should you do if you're in a space where you know that those groups exist but they're not inviting you in.

[B]

Yeah.

[A]

You know, or you let it be known that you would love to participate but you feel excluded from the that crowd.

[B]

Well, I mean a couple different things. One, there are events you can go to to increase your optionality of connecting with people that are in the same place in your journey and just start looking for them. They're everywhere, conferences, meetups, like there's all kind of things you can go. The second thing is, and this is why I think all these principles kind of stack and compound on one another. If you're doing the continuous learning part, especially on the edge, you have something useful to contribute. And what it may take, which I think is non instinctive and non, it goes against common intuition, is to give away first. Like you just start sharing with other people. And that's one of the reasons I think people get into blogging. Or podcasting, they may not have the relationships, but you start putting the content out there, it's flypaper, and you bring in the relationships. And you can do that, by the way, on a Reddit group or in Twitter or wherever. Like, you can start sharing, and you may be surprised. You know, you start following people that are leaders. You start sharing, you may start to get responses. You could build a reputation in the digital world that can turn into relationships in the physical world.

[A]

Right. Be so valuable that they can't ignore you.

[B]

Yes. Yeah. No, I think in these online communities, it's super powerful. I mean, our firm was fortunate enough to invest in Twitter from the very beginning. So I started playing with it quite early. But at this point, having played with it early, I have over 700,000 followers, and any one of those people, I can now direct message because of the way the system works. That's super powerful, and I use it quite frequently.

[A]

You mentioned sports as an example of an industry that's geographically dispersed.

[B]

Yes.

[A]

There are certain industries, you know, if you're in biotech and pharma, Boston, if you want to be in Hollywood, Louisiana, what should you do? If you are beyond conferences, if you are in an industry that is either geographically dispersed or that, you know, we were talking before we started recording podcasting, there are sort of pockets, but not clear pockets. Like Austin is maybe sort of a pocket. New York, I would say is sort of a pocket. Nashville is sort of a pocket.

[B]

My advice at a high level, if you're 100%. Well, let's not do 100. Let's say if you're 90 to 95% sure that you're passionate about a career where there is an epicenter and you have the financial wherewithal to go there, I would highly recommend going.

[A]

But what if there's no clear epicenter? Or what if there are multiple maybe epicenters?

[B]

Well, let's come back to the if there is, because I feel super strongly about that. If there's nothing. I think you lean on conferences and you lean on online communities and you try and build these peer networks and mentor networks fast so that you can have. Maybe we'll go to the why you go to the epicenter, and then you're trying to create the virtual benefits of what you would get. I spent 25 years as a venture capitalist in Silicon Valley. I could have fooled myself. And I went through this mental model when I was thinking about it and said, oh, I'll be the best venture capitalist in the sixth B.C. city. And I think it would have been a massive mistake. And what happens when you go to the epicenter is all the things that we've talked about speed up. And so the ability to learn, the ability to network. I know that you're a big fan of the word optionality, which I love. The optionality increases so much because the chance meetings happen all the time. And so, you know, people like to talk about luck. I love the phrase Luck is when preparation meets opportunity. Opportunity expands exponentially when you're in the epicenter. And like your ability to randomly meet somebody who might then lead to a new direction or a new opportunity or a new job, it's intensified. Like, everyone's doing the same thing. The reason that people don't do it is because they think it's back to this irrational fear of competition. They think, oh, it'll just be too hard there. And I say, no, it's going to be really too hard to do it in the other place, because you're not going to get any of the benefits that would come from being at the epicenter. And so it's mentors, networking. I mean, one of the amazing things about Silicon Valley, and I've heard this about Nashville, there's a documentary on Netflix about songwriters in Nashville. In Silicon Valley, the frequency with which you can ask someone for 15 minutes their time and get a yes is shockingly high. It's, I think, higher than in. I worked in New York on Wall street. Way higher than that. Like, way. And I don't know exactly why it may be that so many people started at the bottom and climbed their way through and benefited from it, that the. The notion of giving back is just kind of built in because there's almost this guilt you carry with you because, you know, you benefited from it so much. But it's shocking. Like, it was just amazing how easy it is to connect and learn in Silicon Valley. And that same thing was echoed in this documentary on songwriters. Like, if you show a true passion for the art and you go up to someone who may be famous but you have a legitimate question, they take the time and say, yes. Like, if you're really passionate about something and fascinated, you're going to be like a kid in a candy store.

[A]

Yeah.

[B]

To be there.

[A]

Yeah. No, I agree. Like, after I moved to New York, Moving to New York was jet fuel on this podcast. I mean, the fact that you and I are sitting here having this conversation right now.

[B]

Right. Your ability to interview important people is. In person is way higher.

[A]

Exactly.

[B]

Because they're here all the time.

[A]

Exactly. This is where finance meets book publishing, which is exactly who I interview.

[B]

Oh, there you go.

[A]

Yeah. On the topic of finance meets book publishing. And this is just something I'm personally curious about. You're well known as a vc. This is your first book.

[B]

Yes, very first book.

[A]

So how did you approach? Because this for you is a new skill set, a new endeavor, a new undertaking. How did you develop this skill set?

[B]

How did you develop that? Yeah, and also I would tell you, like when I first decided to write this book, so everyone in the world wanted me to write a book about venture capital or investing or Uber. They really wanted to tell all on Uber. I didn't feel a calling to do that. None of those felt like they'd be fun. Like, I get why people may have thought that's, oh, that's where you could opine or be an expert. This particular thing had started as just kind of something I noticed when I was reading a bunch of biographies. And then it kind of germinated and took root via this presentation at this university. But then they posted it online and like James Clear read it and James reposted it on his website. And I started getting nudges like, you should do this. And then I had a chance meeting with the famous TV series producer Brian Koppelman, who did Billions. And he has this little thing he does where he nudges people to do creative acts. It's like something he's passionate about, especially people who are in industries that most people wouldn't call creative. He's have you ever done anything? And I mentioned that I considered writing this as a book. And he's like, you have to do it, you have to do it. That kind of kicked it off a little backstory that's relevant. Some time ago, I fell in love with really amazing long form journalism, like 20 page nonfiction articles that you can't stop that, you know, just an hour passes you by.

[A]

Yeah.

[B]

There's a website called Longreads that actually aggregates these. And when I'm. When I need to shift gears or decompress, I always go there and find something. And I'm just fascinated with that art form. There's a couple books that have been written. One called the New Journalism and then one the New New Journalism, where they study the people that have brought kind of narrative energy to nonfiction writing. And of course, people like Krakauer and Michael Lewis and Gladwell are the names that come to people's mind. But there's a broader set of people that have done it that actually many of them emerged from the newsroom and decided they kind of love this even more. But when you. Because I had read those books and thought a lot about that, when I did decide to do this, I kind of committed myself to it. And I think if I hadn't reached a point where I was hanging up my boots as a vc, I think I would have done a much poor job of it. But I actually took the time to do it as well as I could possibly do it and to do it on the back of studying those other people. I also reached out to a number of different people who are kind of in this broad genre of book writing and was so lucky to be able to talk to Adam Grant and Daniel Pink and James Clear and Angela Duckworth. And so I tested my ideas against people that are at the front of the industry. And then the last piece. And I'm very fortunate to be working with a great editor at Penguin that allowed us to do something that was non standard, which is the chapters alternate between these profiles and principles. And that all was an idea that went back to the learning about these great nonfiction writers and how bringing stories to life, I think keeps the reader more engaged, but also I think makes the material more rememberable and more approachable. Hopefully we achieved what we set out to do. Hopefully the profile chapters, the stories have an element of that art form, of that great nonfiction writing that make them come alive. That was the birthing process of this thing.

[A]

So what I'm hearing actually in your answer is, is that a lot of the principles that you've written about in the book were principles that you enacted. You know, you talk about really diving into the subject matter and studying it, studying the craft, studying its history. You talk about reaching out to mentors and in your case, James Clear and Angela Duckworth and becoming a paramecium.

[B]

Yeah. And by the way, it took forever because of that, Because I had that mentality and wanted it to be special. I invested a ton of time and probably read, like, between the video version and the book version, I probably read 100 incremental biographies, searching for the things that I thought would be the best fit for what we were trying to convey.

[A]

Yeah, yeah, it was clear how many biographies you read. I could pick that up. It was when you cracked a joke about blowing my way to the top. You know, you were like, that was the most interesting title of all the biographies I read. And it was. You kind of said it was all a throwaway line, but you were like, of all the biographies I read.

[B]

Well, I didn't mean that sounds. Yeah, that sounds snooty. I didn't mean for it to read that way.

[A]

It didn't sound snooty at all when I saw that, because you said it so casually, I was like, oh, he read a lot of biographies. Yeah.

[B]

One of the people that got really excited about the video is David Sinra, who had done this founders podcast where he would read books.

[A]

Yeah, yeah.

[B]

He did a episode on Estee Lauder when he read her biography where he took the. He almost like, took the entire presentation from my Texas speech and overlaid it with what she did. He probably should get some credit, too, in terms of pushing me to go do this, because he was starting to do it kind of on his own in that case. And her story is amazing. She didn't really start believing her hobby could be a business until she was about 40.

[A]

Right.

[B]

And then she did. And the rest is history.

[A]

Right. Which goes back to the original question that kicked off this whole interview. You know, what do you do if you're in your 50s and you don't quite know what your quote unquote passion is yet?

[B]

I'll tell you, I'll steal one last story from the book. And there's a gentleman who. His undergrad degree was in seismology. He spent some time in West Texas in the oil business and sometime in South America in the oil business. That was overwhelming for him. A lot of boom bust cycles and whatnot. So he settled down and switched to being a mortgage broker, which he didn't have particular passion for, but he was okay at it. And one night he's watching a PBS special, and someone on the PBS special is giving life advice, and they say, take a blank sheet of paper, turn it horizontal, draw a line down the middle, and on the left, right, what you love to do, what are your hobbies? And on the right, right, what are you good at? He pulled out a pen and paper, did this exercise. He's 40 years old, by the way. He starts trying to draw connectors between them and circle them and all this stuff. And that exercise led Burt Beveridge, whose nickname is Tito, to launch the first spirit company in Texas, a vodka company that now is the number one selling spirit in North America. And he had no prior experience in that business. He liked making flavored vodkas as gifts for his friends. And he understood chemistry from his undergrad degree. And that's part of how he kind of connected these two. He had zero knowledge of what it took to get a liquor license in Texas, which turned out to be really hard. He had zero knowledge of how to mass produce anything, but he came at it with a unbridled passion and change the world, you know? And so when I hear stories like that and part of why working on this book was so much fun, I can't explain why I get dopamine just from even retelling the story. I just think it's so cool that we live in a world where someone can make that decision at that age and have that kind of outcome. I think it's just fascinating.

[A]

Right? Yeah, it's. What do you love to do? What are you good at? And what does the world need?

[B]

You know, by the way, it's interesting you bring that up. I've been out, done a few campus events, and I had one young woman raise her hand and say, but I care more about purpose than passion. And I don't know if she thought she had trapped me or something, but I reflected a minute on the question, and I realized, you know, the vast majority of the people that I profile in this book have massive impact on their industries.

[A]

Right.

[B]

And the number of people whose lives are positively impacted because of what they create is immense. You know, if you are in the restaurant business in almost any city in America, you know, someone who's worked in a Danny Meyer restaurant, and they talk about it and it matters to them, and they learned something from it and they're proud of it. And, like, I gotta believe that one of the things Danny's most proud of is that we did a deep dive on Bobby Knight. And regardless of what you think about him or his temper, his coaching tree, the number of people that have leadership positions in his industry, his craft area that learn from him is bigger than anyone else who's ever been through it before. And that's got to, like. I think that's the right way to measure someone's success, is kind of the legacy that they leave and how many different lives they've touched. And if you tilt it, something with this immense passion and fascination, you're going to touch others. And if you use the approaches we're talking about with mentorship and peer networks, like, you're gonna touch others. There's no doubt. So I think, ironically, doing this thing that you love is a direct avenue to having a purposeful impact on lots and lots of people.

[A]

Absolutely. You look at the impact Mr. Beast has made.

[B]

Oh, yeah.

[A]

I mean, it's enormous in so many dimensions.

[B]

I love how much he loves giving away money.

[A]

Yeah, yeah, exactly. Exactly. Like the philanthropic impact that he's made, the impact that he's made on future YouTube creators. I mean, it's incredible.

[B]

Yeah. And he brings so much. Like, talk about do what you love. Like, does anyone doubt that he loves what he's doing?

[A]

Right. Exactly. Well, thank you for spending this time with us. Where can people find you if they'd like to learn more?

[B]

Twitter's probably the best place to track me. It's bgirly B G U R L E Y. Just because I'm most active there, that'd be the best place.

[A]

Thank you to Bill Gurley. What are three key takeaways that we got from this conversation? Key takeaway number one. The biggest regrets that people tend to have are the things that they've never tried at the end of a person's life. And there's research that backs this. People rarely dwell on their mistakes because if something goes wrong, people tend to move on. They tend to process it over time. What people regret, however, are the chances that they never took. They are regrets of inaction. And that insight becomes a reminder to test your ideas, to explore, to try new things, and to avoid letting the fear of failure turn into the regret of inaction.

[B]

Daniel Pink has a great book about regrets. And one thing he highlights, and he studied this across multiple geographies, multiple different ethnicities. The number one regret people have at the end of their life is a regret of inaction. He calls them boldness regrets. We're very good at forgiving ourselves for the things we did wrong. Like, humans are very quick to move past. Lesson learned, you know, don't dwell on it. There's not a lot of rumination on the mistakes made. But the thing we never tried eats at us. And he has a study where it actually grows in your head over time.

[A]

That is the first key takeaway. Key takeaway number two. Don't follow your passion. Follow your fascination. Passion. That's a loaded term. It's big. It's abstract. Like, that's weighty. Follow your passion. Passion is a really intimidating word. What sparks your curiosity? What fascinates you? If you were to, like, stay up late learning about a thing, kind of nerding out about a thing, what is the thing that you would stay up late to nerd out about? That's how you know what fascinates you. What are the things that you study on your own, the things that you read about for no reason other than just general curiosity. Those are signals that can point you towards the work that might be right for you, the work that you can sustain for decades.

[B]

The key to having a lifelong dream job and being really successful at it and it not feeling like a grind is to be fascinated with it. And the reason that is is because you have to continuously learn. Like you have to want to continuously learn and that has to feel free. I think a great test is would you do this versus watching a Netflix series like is there something that you find so fascinating that in your spare time you're studying it on your own?

[A]

That is the second key takeaway. Finally, key takeaway number three. Your luck grows the more that you put yourself in front of new opportunities careers. You know, we call it a career ladder, which is not really a very good term for it because it's not just a straight linear path. In fact, career paths don't typically follow some straight line. They can be webs, they can have lots of twists and turns. By experimenting, more side projects, new skills, adjacent opportunities that increases the chances of something clicking and you're increasing your surface

[B]

area of luck through a lot of good fortune. Although I'm a big believer that luck is a function of how much optionality you expose yourself to, I ended up in Silicon Valley and got into venture capital and spent 25 years there and never asked myself that question again.

[A]

Those are three key takeaways from this conversation with Bill Gurley. Thank you so much for tuning in. If you enjoyed today's episode, please share this with the people in your life. Friends, family, neighbors, colleagues. Share it with old classmates, new classmates, your kids classmates, your kids, teachers. Share it with your swim coach, your Starbucks barista, your postal worker, your dog walker. Share it with all the people in your life. That's the single most important way that you spread the message and of fi I r e second subscribe to our newsletter affordanything.com Newsletter it's completely free and worth every penny. Finally, open your favorite podcast playing app. Make sure that you hit the Follow button. We've looked up the stats. 4 out of 5 of you have done this, but 1 out of 5 of you have not. So if you are the 1 out of 5 who is not following us, Open up Spotify. Open up Apple Podcasts. Hit the Follow button because that's how you make sure that you don't miss any of our amazing upcoming interviews. While you're there, please leave us up to a five star review. Thanks again for being an afforder. I'm Paula Pant. This is the Afford Anything podcast and I'll meet you in the next episode.