Benchmark Partner, Bill Gurley: The Strategy That Makes You Stand Out in a Crowded Job Market | E150

Summary

Leap Academy Podcast with Ilana Golan

Episode 150: Benchmark Partner, Bill Gurley: The Strategy That Makes You Stand Out in a Crowded Job Market
Date: March 17, 2026
Guest: Bill Gurley (Benchmark, legendary VC; author: "Running Down A Dream—How to Thrive in a Career You Actually Love")
Host: Ilana Golan

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Overview of the Episode

In this inspiring and pragmatic episode, Ilana Golan delves deep with Bill Gurley, one of Silicon Valley’s most influential venture capitalists. They explore practical strategies to stand out in a crowded job market, the importance of continuous reinvention, how to find a career you truly love, and concrete ways to become the “candidate of one.” Bill shares personal stories, career pivots, lessons from decades in tech, and highlights from his new book. The conversation is packed with actionable insights on navigating today’s competitive, AI-driven professional landscape.

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Key Discussion Points & Insights

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Earliest Influences and Career Foundations

• Interest Sparked by Early Computers ([03:24])

  • Bill’s fascination began with a Commodore VIC 20 in high school; self-taught coding late at night from magazines.
  • Mentorship from his sister, who chose startups over safe paths, exposing him both to tech and entrepreneurial risk.

• Transition from Engineering to Business ([05:26])

  • Enjoyed early engineering roles but was prompted by boredom and curiosity—reading trade magazines and books like Peter Lynch’s “One Up on Wall Street.”
  • Annual self-reflection: “I would encourage people to at least once a year rise up and say, is this what I want to do with the rest of my life? Look forward 30 years and say, do I still want to be doing this?” ([07:15])

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Hustling into New Careers & the “Candidate of One” Concept

• Hustle and Differentiation ([08:08])

  • Broke industry norms by cold-calling influential analysts; built credibility and leveraged networking to land the right roles.
  • “How do you make yourself a candidate of one?” ([08:28])
  • Emphasizes the inefficiency of traditional application pipelines; real roles are rarely found on job boards, especially for mid/late-career shifts.
  • Leveraged unique background in tech, sports, and business to stand out—eventually landing a sell-side analyst job without conventional qualifications ([11:27]).

• On Taking Unconventional Shots

  • Wrote a spontaneous 20-page report to claim an open analyst position ([12:27]).
  • The “bedrock of best practices” came from voracious reading of business and personal development books.

“You develop frameworks and confidence of mindset about what you should be doing or what you could be doing... I’ve always had a soft spot in my heart for the entire category of books because of that.”
—Bill Gurley ([13:25])

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Lessons from Silicon Valley & the Dot-Com Era

• Reflection/Awareness in Career Moves ([14:32], [17:30])

  • Repeatedly reassessed if he was on the right path; found it essential for effective, fulfilling pivots.
  • Received pivotal career break from Frank Quattrone, who helped him move to Silicon Valley and meet every VC in tech.
  • Willingness to take risks: switched industry coverage, embraced the emerging “internet” vertical before it exploded.

• Learning Through Experimentation

  • Advocates for frequent, intentional experimentation and openness to “side hustles”—both for exposure and optionality ([32:29]).

“It’s all good… it’s never been easier to experiment. It’s never been easier to learn.”
—Bill Gurley ([34:15])

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Deep Dive: Standing Out in a Noisy, AI-Driven Job Market

• AI as Differentiator ([00:31], [34:53])

  • “If you want to protect yourself against AI, run at it. Know exactly what AI can achieve in your field and be on the edge and the forefront of playing with it, and you will be remarkably differentiated.”
  • Cautions against blending into “the people pile” — average is now easy to achieve, so the exceptional stands out more than ever.

• The Two “Barbells” of Differentiation ([34:54])

  • Study the history of your field deeply—know the pioneers, foundational stories, and classic innovations.
    • Examples: Magnus Carlsen (chess), John Lasseter (Pixar).
    • “If the notion of studying the history of the field is off putting to you, yeah, this ain’t your field.”
  • Equally, master the cutting-edge—the “edge” tools, trends, and tech (e.g., AI, TikTok in marketing).
    • Young professionals can rapidly specialize in new, under-mastered niches.

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Continuous Learning and Reinvention

• Never Stop Learning ([31:02])

  • Professional success comes from relentless curiosity, not static qualifications.
  • Encourages measuring whether a job is truly a “dream job” by asking: “Would you learn more about this for fun, in your free time—even over a show like Breaking Bad?” ([31:16])

• Permission to Pivot

  • Calls for normalization of continuous career change, side steps, and combining multiple interests (“portfolio careers”) ([46:32], [48:20]).
  • “Have the belief that you can actually do whatever you want… it’s never been easier to learn enough to do it.” ([47:10])

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The Importance of Location: “Go Where the Action Is” ([39:15])

• Dispels the myth of “bigger fish in a smaller pond”:
  • “If you’re where it’s all happening, the number of fortunate opportunities is a lot higher than if you’re not.” ([00:00], [39:15])
  • Emphasizes the density of peer/mentor networks, optionality, and serendipity found in industry hubs (Hollywood for acting, Nashville for songwriting, Silicon Valley for tech/VC).
  • “Your odds of success are so much higher if you’re in it.”

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Notable Pillars from Bill Gurley’s Book (“Running Down A Dream”)

• Six Pillars for Career Success:
  (Touched on throughout the episode; not exhaustively listed, but key elements recur—experimentation, history/edge mastery, relentless learning, differentiation, location, and following curiosity.)

• Powerful Permission to Leap ([42:33])

  • Shared moving stories: Matthew McConaughey’s father granting him full encouragement to abandon law for film (“Well, don’t half ass it”) ([42:33]), Jerry Seinfeld inspired by a single book, etc.
  • Gurley’s intent: “What I really hope the book does…the most is give as many people that experience that Matthew had as possible—give them permission.” ([45:04])

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Real Examples of “Candidate of One” Careers

• From core tech to creative industries, horticulture to esports, and beyond—spotlights people who carved unique paths by combining deep passion with practical mastery ([46:44]).

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Concluding Career Experimentation Strategies (The Leap Academy 5-5-5 Rule)

• Ilana’s “5-5-5” Experimentation Framework: ([49:57])
  • 5 days: Deep learning on a new option.
  • 5 weeks: Begin branding yourself around it; test resonance and early moves.
  • 5 months: Full leap/immersion if previous steps validate the fit.
  • Emphasize reframing the career as a series of experiments, not a lifetime binary commitment.

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Notable Quotes & Memorable Moments

• “If you want to protect yourself against AI, run at it… you will be remarkably differentiated.”
  —Bill Gurley ([00:31], [34:53])

• “How do you make yourself a candidate of one?”
  —Bill Gurley ([08:28])

• “Is this what I want to do with the rest of my life?”
  —Bill Gurley on annual self-reflection ([07:15])

• “There’s never ever been more information available for someone that’s proactive and wants to learn and wants to move.”
  —Bill Gurley ([31:02], [34:15])

• “Have the belief that you can actually do whatever you want.”
  —Bill Gurley ([47:10])

• “Go where the action is… the number of fortunate opportunities, if you’re where it’s all happening, is a lot higher than if you’re not.”
  —Bill Gurley ([00:00], [39:15])

• “Permission. It’s okay to go do these things.”
  —Bill Gurley ([45:04])

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Important Timestamps

| Segment | Topic | |-----------|----------------------------------------------------| | 00:00 | “Go where the action is” – importance of location | | 03:24 | Early influences: computers, startups, curiosity | | 05:26 | Pivoting due to boredom, curiosity, and learning | | 08:28 | The “candidate of one” approach | | 11:27 | Breaking into sell-side analyst, personal branding | | 14:13 | Book recommendations for mindset and action | | 17:30 | Silicon Valley move, VC ambitions, career pivots | | 26:24 | How to get into venture capital—differentiation | | 31:02 | Continuous learning, staying relevant | | 34:54 | Deep learning both history and cutting-edge trends | | 39:15 | Go where the action is—industry hubs matter | | 42:33 | Granting permission to leap (McConaughey story) | | 46:44 | Real-world examples of non-traditional careers | | 48:20 | Rise of portfolio careers—multiple streams | | 49:57 | Ilana’s “5-5-5” career experiment rule |

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Final Takeaways

• The most impactful careers are crafted—not found on job boards—and require both continuing to learn and stepping into new arenas.
• Stand out by combining deep knowledge of your field’s history with mastery of emerging trends.
• Go “where the action is”—location and community matter for serendipity and mentorship.
• Career is an ongoing experiment; permission to pivot breeds fulfillment and distinction.
• Strategic experiments (learning, branding, immersion) offer a low-risk path to major leaps.

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Further Resources

• Bill Gurley’s Book: "Running Down A Dream—How to Thrive in a Career You Actually Love"
• Micro-grants for career changers: rdad.org (upcoming)
• Leap Academy—career resources, training & coaching: leapacademy.com/training

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(Want to go deeper? Check out the full episode for all of Bill’s stories, frameworks, and Ilana’s hands-on advice!)

Transcript

[Bill Gurley]

I think a lot of people fool themselves with this little mental trick, which is, I'd rather be a bigger fish in a smaller pond. I'm going to do that in this city where not that many other people are doing it. The number of fortunate opportunities, if you're where it's all happening, is a lot higher than if you're not.

[Ilana Golan]

So today we're joined by one of the most influential venture capitalists in tech, Bill Gurley. He has invested and served in boards of major companies including Nextdoor and OpenTable and Uber and Zillow.

[Bill Gurley]

If you want to protect yourself against AI, run at it. Know exactly what AI can achieve in your field and be on the edge and the forefront of playing with it, and you will be remarkably differentiated. There's never ever been more information available for someone that's proactive and wants to learn and wants to move.

[Ilana Golan]

How do you find a career you love, right? Not necessarily what you thought you were supposed to do or your society expected you to do.

[Bill Gurley]

Have the belief that you can actually do whatever you want and

[Ilana Golan]

welcome to the Leap Academy with Ilana Golan show. I'm so glad you're here. In the Leap Academy podcast, I get to speak to the biggest leaders of our time about their career, how they got where they are today, the challenges, the failures, and countless lessons. So lean in. This episode is going to be amazing. I'm on a mission to help millions reinvent their career and leap into their full potential land, their dream roles, fast track to leadership, jump to entrepreneurship, or build portfolio careers. This is what we do in our Leap Academy programs for individuals and teams. And with this podcast, we can give this career blueprint for free to tens of millions. So please help my mission by sharing this with every single person you know, because this show has the power to change countless of lives. Deal. Okay, so let's dive in foreign. So today we're joined by one of the most influential venture capitalists in tech, Bill Gurley. From his legendary early bet on Uber to his role in general partner at Benchmark, he has invested and served in boards of major companies including Nextdoor and OpenTable and Stitch Fix and Uber and Zillow. For more than two decades, Bill has written about technology and leadership on his blog, above the Cloud. And he is coming out with his book, running down a how to thrive in a career you actually love. And so I love this because we are all about helping professionals achieve their big life and to leap in their career. But remember that at the end of the podcast, we will answer one of Your questions from your comments on The Leap Academy YouTube channel. In our case, we chose a beautiful question of how do you choose career direction and how do I experiment with my career? So stay tuned until the end. Bill, so great to have you here.

[Bill Gurley]

Thanks for having me.

[Ilana Golan]

It's so cool because I looked at your background and you started in engineering, but I want to take you back in time. Do you remember specific things in your childhood or teenhood that built you to who you are today?

[Bill Gurley]

Like many people you read about that made a career in Silicon Valley, I was influenced by computers early in my life. I had stumbled upon having a Commodore VIC 20, which was this keyboard thing that attached to your TV when I was a sophomore in high school and would stay up late at night entering programs in that thing from magazines and learn to code that way. And I don't know how that happened per se, like, what it was that caused me to want to do that, but that certainly is the experience that led me towards a computer engineering degree when I went to college. Another super important and influential thing which I was very fortunate about. My sister is four years older than I am, and she was a double E at Rice. And her first job, rather than going a safe route to a big company, she went to this startup in Houston called Compaq Computer Corporation, which at the time was nascent but became quite large. But that gave me exposure to more computers, but also exposure to the notion of a startup, which I might not have had had she not taken that direction.

[Ilana Golan]

But I love that you said that, by the way. And it's so fun to ask these things because I could already see the seeds that we're going to talk about curiosity later on. So something made you curious, learning these computers. But you went to engineering school and you started basically in an engineering role.

[Bill Gurley]

Yeah, I ended up working at Compaq as well. So I interviewed with IBM and a few other places. But Compaq was a super fun company at the time, and cost of living was low and outside of Houston. And so, yeah, I jumped back and went to work with her. And one thing that I think is important is even though I would transition away from that at the time, you know, when I went in, I loved it. Like, it was fun. I loved what I was doing as an engineer.

[Ilana Golan]

And why did you decide to leave to the sales side analyst portion of it?

[Bill Gurley]

What happened was, as I've written the book, when I wrote the book, just to be fair, it wasn't my own journey that inspired the book. It was some biographies that I'VE read and I've reevaluated my career path in the frame of the book after the fact that. So I do think that's important to understand. But two things happened. One, we started the third project when I was there and at the time a computer company would release usually around related to Intel's product cycles. You'd have a new processor, you'd build a new computer. And we started the third project while I was there and it looked a lot like the second one and it looked like a lot like the first one, which put the notion of boredom in my head. But the other thing that happened, and I think this is important to pay attention to what you're doing in your spare time. I had started reading the trade magazines, so I was learning more broadly about tech and that there were other things, software companies, whatnot. And I read this book, One up on Wall street by Peter lynch, and started trading stocks actively. And once again, that's in my spare time. You know, I'm not doing it while I'm at work, but now I'm at home and I've got this other activity that's drawing my curiosity. And both of those things convinced me. But I'd say more specifically the boredom notion. And I don't mean to suggest that everybody who's an engineer would find that to be true, but for me, the question that I asked myself, and I don't know that I wrote this specifically in the book, but as I've been talking about the book, it's come to my mind I would encourage people to at least once a year rise up and say is this what I want to do with the rest of my Life? Look forward 30 years and say do I still want to be doing this? Because that was very clear to me at that moment that that wasn't true. And so I went to business school. I thought about going to business school before I learned a whole bunch about finance and business that I'd never known. I developed a love for reading at business school, which I didn't have before, which I think was super influential. And I learned about the not of being a venture capitalist. I explored it briefly. It did not seem achievable even to get an entry level at that point. And so I put that on the back burner. It was sitting there in my brain. And I chased what seemed to be an exciting opportunity to be a sell side analyst on Wall Street. And I did this classic thing you'll often hear about related to Wall Street. I flew to New York and knocked on Doors. There's a little more to it than that. Today it'd be easier because of digital commun, but I literally begged to talk to people.

[Ilana Golan]

So you needed to hustle your way in.

[Bill Gurley]

Oh yeah, there was no listing for a job.

[Ilana Golan]

This is actually a really important bill because I think the most incredible jobs or opportunities are actually not on the hiring boards, especially not mid to late stage careers. So how did you land the first role?

[Bill Gurley]

To echo what you said, we use a phrase in the book, candidate of one. How do you make yourself a candidate of one? And I think when I came up with that phrase, I remember very vividly all the way back to undergrad when I went into the career office and took one of these interviews where you go in one of these interview rooms and you know there's 20 other people doing it and just thinking to myself, this has got to be the worst possible way to get a job, you know. And then I did a couple of them in business school the same way. And part of the inspiration for the book was a reaction to that idea. That can't possibly be the best way to differentiate yourself or to find your dream job. Why in the world would your dream job happen to be interviewing at the college you happen to go to? The odds would really be below 1% that that just happened to be true. And so I really hated that. And by the way, immense respect and gratefulness to all the people in those roles. I know they're trying to get a whole bunch of people hired and there's no way they can do a bespoke search for every single individual student. It wouldn't work. But I do think it falls then on the individual to go out and craft their own differentiation and their own process. So with that said, what happened was when I got to business school, I started reading business magazines, newspapers, started reading the journal, Fortune, Forbes, and everybody likes to pretend they're an executive. In business school and in the tech field, which I was enamored with, there was a group of sell side analysts at Goldman that were just dominant. And as a result, every time these newspapers or magazines wanted to ask someone about the industry, they would always ask these guys from Goldman. And so I would see their names over and over and over again. So one of the people that I cold called was that team and went and visited them and I didn't end up getting to work with them, I became friends with them. I saw one of them a few weeks ago, but I used that to get the other interviews. And when I'm in the other Interviews, I was like, yeah, yesterday I was meeting with Dan Benton and Rick Sherlin at Goldman to get credibility. And so they were super helpful in me going where I wanted to go. And I'm thrilled that they took that meeting with this kid from the University of Texas.

[Ilana Golan]

And I do want to hear how you differentiate yourself and how you do become candidate of one. Right. We call it the hidden market. But I think there's a lot of similarities of especially now we're going to talk about it. How do you rise above the noise? Because there is a lot of noise. There's a huge people pile, especially now with AI so we're going to talk about that. But tell me a little bit for a second. So you're in the sell side analyst. First of all, how do you get the job because you've never done it before? And then what are some learning that you take with you to the venture world?

[Bill Gurley]

A couple things happened that were super fortunate. The gentleman that ended up giving me a job is a guy named Al Jackson who ran the research department at Credit Suisse First Boston. And I think Al was just in intrigued by how different I was. I had worked in tech. I came from Texas. Almost every kid that gets these jobs comes from one of the Ivy League schools or Wharton or Columbia. There's a prototype that comes in. I didn't mention this earlier, but in undergrad I rode the bench at the University of Florida on the basketball team. And Al had this favoritism for athletes. He thought it was a critical thing and so he gave me a flyer. And the other thing that happened, once I arrived about two or three weeks in, they hadn't assigned me an industry yet. The gentleman that covered the PC industry, which included Compaq, where I worked, announced that he was going to transition into a mentorship role in the research department. And so this opportunity was going to be open. And despite only having been in New York for three weeks and only been associated with an investment bank for three weeks, I went back to my brownstone apartment and spent the entire weekend writing a 20 page report to go in and tell the gentleman, stepping aside and Al Jackson, you guys should give me this category. One of the things that I benefited from at business school, I told you, I developed this affection for reading. And I read a number of books. I started reading both personal development books and business books. And you read about people that have taken shots like that. You read about salesmanship, listening to your customer. Like if you read like 20 of those, these nuggets, these best practices, build up in your brain. And I've told this story recently about writing that 20 pager and everything. Wow, that's a lot of gumption. But it didn't feel odd to me at the time. And I credit that kind of bedrock of best practices from those types of books. And as I've studied for my own book, a lot of people that have been successful, I see that moment. There's a moment where they start to get a little bit of success and they, you know, they go read, you know, a Tony Robbins book or Seven Habits of High. And there's not one specific thing in them in those books that then, oh, I'll do X to Y to Z. But you do develop frameworks and confidence of mindset about what you should be doing or what you could be doing. I think it also helps your kind of gumption. But I've always had a soft spot in my heart for the entire category of books because of that.

[Ilana Golan]

And I'll just say that we'll give them a sneak peek that at the end of your book, you also mention some books.

[Bill Gurley]

I have a list. I need to add it up. I think it's about 50 books, but that is incredible.

[Ilana Golan]

So you were in the tech world when the whole dot com crash came about. Tell us a little bit.

[Bill Gurley]

That's a little ways off. So I'm covering the PC industry. It's the 93 to 96 timeframe, and I have the exact same experience. So first of all, I adored being a sell side analyst. It gave me access to people I never would have thought I'd meet. You're interviewing CEOs and CFOs when you're in your late 20s, you're in Wall street, you're in New York, you're in Manhattan. There's just a whole bunch of exciting things happening. But about three years in, I had the exact same question pop in my head. When I was at Compaq as an engineer one night, and we worked long hours, it was like 10pm And I was walking around the building and I was thinking to myself, do I want to be doing this 30 years from now? And there are a few senior people in the building that had the corner offices that had done it their whole lives. And I walked into each of their offices, just kind of peeked in and used it as a moment of reflection and said, is this what I want? And after 30 minutes of that, it was no. And I was making good money. And it was exciting. But for some reason I was able to have this reflection forward 30 years and by the way, there's a very similar construct that Jeff Bezos did when he was choosing to start Amazon. Just reflecting on what am I going to regret at the end of my life. And it ties in with this Wharton study that we did. But anyway, I think this is a useful thing to once again, maybe once a year, to ask yourself, especially early in a career, is this what I want to do the rest of my life? And recognize that shifting and pivoting and I know this is something you talk a lot about is fine, it's okay, it's not failure. And a lot of people that switch gears and David Epstein hits on this really well in his book range, end up doing remarkable things because you bring a different lens to this new thing you pivot into. So I had that reflection. I then put my head up, started looking for alternative things. I ended up getting this insanely, kind of out of the blue, very fortunate phone call from a gentleman named Frank Quattrone who was leaving Morgan Stanley and was starting a new investment bank. And this will get us close to the dot com era. And he said, bill, I want you to come be a sell side analyst for me. And I said, and by the way, I had never met Frank before, but he's one of the most successful people in the entire history of tech banking. And I said, I'm sorry, Frank, I've heard amazing things about you, but I don't think I want to do this the rest of my life. And he said, what do you want to do? And I said, my dream job was always to be a venture capitalist. And he said, come to work for me as an analyst. I'll move you to Silicon Valley and introduce you to every VC that I know. Wow. And he did.

[Ilana Golan]

That's incredible.

[Bill Gurley]

I only worked for Frank for 13 months.

[Ilana Golan]

Take me there. Why do you think he approached you and why did he have so much conviction that you are the right person person for him?

[Bill Gurley]

I think he had heard about my reputation. I was doing things very differently as a sell side analyst than other people had done in the past. I had taken some risk. I had seen some other people take some risk and was mimicking some of their techniques. Through that I developed pretty good connectivity to a lot of the execs in most of the high tech businesses. And so if he had asked around, he might have heard about me. And then I think his attitude about come to work for me, even if you might transition, I mean, I remember McKinsey having that reputation a long time ago. Like, just get as many good people in as you can. If they leave, we'll have advocates out there. And to be fair, as a venture capitalist, I leaned on the services of Frank's investment bank again and again and again and again. So we ended up having a lifelong relationship as a client rather than an employee. But I think that's the mindset of why he was okay with it.

[Ilana Golan]

We need to pause for a super brief break and while we do, take a moment and share this episode with every single person who may be inspired by this. Because this information can truly change your life and theirs. Now I want to check in with you. Yes, you, are you driven, but maybe feeling stuck in your career or a fraction of who you know you could be, do you secretly feel you should have been further along in your income, influence or impact? Do you ever wonder how to create not just a paycheck, but the life you want with a paycheck? The thought leadership, the legacy, the freedom. Because that was me. And that's exactly why I created the Leap Academy program, which already changed thousands of careers and lives. Look, getting intentional and strategic with your career is now more important than ever. The skills for success have changed. Aq, adaptability, reinventing and leaping are today the most important skills for the future of work. Building portfolio careers, multiple streams of income and ventures are no longer a nice to have, it's a must have. But no one is teaching this except for us in Leap Academy. So if you want more from your career in Life, go to leapacademy.com/training. Check out this completely free training about ways to fast track your career and you'll even be able to book a completely free strategy call with my team. That's leapacademy.com training. But before you go in, like I will just say to the listeners, like I want to make sure you hear your reputation is the way to get out of the people pile is just the most incredible way to be known for something exceptional. At the era of AI when everybody can sound roughly the same, this is your only chance.

[Bill Gurley]

Yep, during those short 13 months that I worked with Frank, we won the mandate against Goldman and Morgan, which is pretty unbelievable and probably tied more to Frank's reputation than mine. But to take Amazon public, We were the firm that helped Amazon go public and I met Jeff Bezos at that moment in time. And so this is 97, and that's the beginning of the dot com boom. And when I transitioned to work for Frank, I actually gave up coverage of the PC industry, which was a big risk, and took up coverage of this New sector called Internet, which no one knew what was. And there weren't that many companies. The reason that appealed to me is just staying on the edge and because I wanted to get to venture, so it didn't end up popping for another two years. Two or three years.

[Ilana Golan]

And I was at that point in intel and we were starting to get the waves of Internet and this thing is happening and everybody. Yeah, so take us there. Like, what got you into venture capital?

[Bill Gurley]

Well, Frank did what he said. He introduced me to every VC that he knew. And I would routinely visit with VC firms during their Monday meeting and tell them what I was seeing out there. And one of the firms I spent a lot of time at was Benchmark. Ironically, I went to work at a different firm for a short period of time. Someone asked me to be a venture capitalist. It was Ann Winblatt, actually. And I said yes almost without thinking. And I should have checked around. I made a mistake in just being too eager and move too fast. And two weeks after that was announced, one of the Benchmark partners called me and said, why didn't you call us? What are you doing? And There was another 16 to 17 months of this kind of, oops, I made a mistake. I need to be at this other firm, which it probably would have been better had I not done that. So that was a mistake. But I ended up in the right place where I would work for 25 years and just loved every minute of it. I often said when people would interview me, when I've hung up my cleats, I'm no longer making new investments. I'm glad to talk about that as well. But when I was practicing, I would often say out loud, if we lived in a socialist society where everyone made the same amount of money, I'd still want to do this. The opposite of that thing where I said, you, you know, oh, I'm sure I don't want to do this the rest of my life. This one was, no, I do want to do this. Maybe not the rest of my life, but for a quarter century is pretty good.

[Ilana Golan]

I mean, it is a lot of time. Take us a little bit into the venture world, especially in the early days. I do want to understand some of that mindset shift of why did you decide to write a book and, you know, et cetera. So I want to hear a little bit of that.

[Bill Gurley]

I loved every minute of the venture business. It's a hustle business. It's a business where the best practitioners are very independent. Our partnership would meet together on Mondays and then the other four days of the week you're writing your own script. I mean, you are doing whatever you want to be doing. And I thrived on that. By the way, the sell side analyst job was similar in that way. Like you worked at a firm but your daily activities were up to you. I don't think I could have worked in a large org the way my brain works. I thrive in this other way. Landing at Benchmark was super fortunate also. They had developed a new way to organize a venture capital firm that was an equal partnership and everyone made the exact same amount of money. There was no CEO, there's no senior partner, which is even more reinforcing of this independent mindset. And it also created this amazingly tight culture where everyone wanted everyone to win. You know, there was no up or out, there was no like it's always going to be equal. So I'm not going to renegotiate on the next fund to try and own more than you. So if that's off the table, then if you win, I win. If I win, you win. And it just created this unbelievable team dynamic. And so in addition to loving the job, I landed at a place that I loved as well where the day to day dynamic was near perfect. And so all that was awesome. We, you know, as a firm, some of the companies you mentioned are ones I was specifically working on. But as a firm we also did Twitter and Snapchat and Instagram and ebay and a whole bunch. And so just watching my partner succeed, being a part of these early stage companies where, you know, when we meet them, it might be two people in a PowerPoint and then you see, you know, I remember being in Bali walking into a restaurant and seeing an open table device and I funded it when it was three restaurants. And I think that some people struggle with the not being the person driving the car, not being the founder. I just never had that. I got enough ego boo from association and I love the diversity of being involved in multiple projects because I probably have some form of add. You know, I just want to think about a whole bunch of things simultaneously. Anyway, that's why the job was such a great fit. It's hard to get into. It's gotten more competitive every single year, you know, and it was around for 20 or 30 years before I got into it. But it was more competitive when I left and when I started and it's way more competitive today.

[Ilana Golan]

Let's talk about it for a second. And for those who don't know, I mean you've been on the Forbes Medas list because of all your successful investment, which is such a big deal. We do get this question. I want to get into venture capital, I want to get into investment. What would you say to them?

[Bill Gurley]

Once I started being successful in venture, I would start to get the cold emails and the knock on doors that I had done at that time. I wrote a three page PDF called so youo Want to Be a vc and I would send it to them in response because I couldn't handle the inbound the other way. And this might be a good transition to talk about this differentiation element. But that was my main point to them, which is you have 20 kids at Stanford, 20 kids at Harvard, 20 kids at Wharton that are all the best resume you've ever seen that want to get in. So going in the front door by applying to something listed on a website like the odds are near zero. And so I would try and encourage them to come up with some form of differentiation that would set them apart. And the best way to do that to get into venture would be to pick a new emerging private sector. AI is kind of overwhelming, but I think in the book I use the example of esports. You know, there was a moment in time where competitive gaming was popping up. Our firm was the money behind Riot Games, League of Legends that ended up with these big competitions. And it might be hard to be the best venture capital applicant writ large, but if you found a firm who was worried that they didn't know about esports and you come in with this insane knowledge and you have that puzzle piece fit and this gets back to that candidate of one idea and I'm just using esports because it's the one I mentioned in the book, but it would be something new, you know, so that's what I said to him and just. I also made it very clear the world doesn't need another venture capitalist. So don't tilt against this. You need to care a lot.

[Ilana Golan]

Your entire book is about how do you find a career you love, right? Not necessarily what you thought you're supposed to do or your society expected you to do. And by the way, I think it's like incredibly important because one of the reasons why I had such a hard time leaving the electric engineering cloud data center environment that I was in is because I studied it. What am I gonna let it all go away? And where, you know, it's like. So I think there's a lot of fear that involved. So take us there for a second. You have beautiful lessons learned and you have six pillars that you talk about in the book. So I want to talk about that. And it's kind of all ties into the people pile. So I do want to go into that candidate of one.

[Bill Gurley]

The book's about how to find and thrive in your dream job. And there's probably more effort on the thrive side. We do spend a good amount on the find. But there's techniques for success once you make that commitment. So just to make that point clear, there's some great work done by Dave Evans. The Stanford course Designing youg Life, which is all about trying to find your place. They point out some numbers and I wish I had them in front of me, but you know, if you look five years past college, like 40% of the people something like that are not doing what their major was. And if you get 10 years out, that number's like up to 60 or something like that. So it is, I think, valuable because no one else tells you this to just know that that's true. Because I'm reacting to your point about oh, am I leaving this all behind. Like a lot of people make that type of shift. And part of the benefit of going to college and completing degree is about learning how to learn and about putting up reps and succeeding at something. And it's not simply about the knowledge ingestion. And I would even go further and say, and this ties into the second principle in the book, the very best in every field are learning continuously. Learning continuously. And so I think if you looked at the best 10 years in the percentage of what they know that they gained post college is way higher than whatever they learned when they were there. And so that's another reason not to get stuck on this. I do think society leaves you with this idea that you learn in high school, you learn for four years in college and that, oh, the learning's done, now I go work. And I think it's such a big mistake because the very best never stop learning. Never stop.

[Ilana Golan]

It's always been easy to find information and now it's been accelerate it in ways that it's hard to describe. So in fact, if you're not constantly learning right now, you're losing relevance, I think at a speed that we've never seen before.

[Bill Gurley]

I think that's exactly right. The main test that I assert in the book as to whether you're in your dream job or not is whether you would go learn about like do continuous learning for fun in your free time. And I don't think most people do or most people would. And I've said If you had five episodes of Breaking Bad left, would you do this instead? Right. As a comparative point. And if you go back to when I was an engineer, I was going home and studying stocks. So there's a clue there, right? My fascination, my curiosity had moved beyond what I was doing day to day. And I think that can be a tell.

[Ilana Golan]

And I think another thing that is important to distinguish is I think we are living in an era where people will reinvent themselves all the time. And sometimes it's a different topic altogether, but sometimes it's even different functions, different responsibilities. Even in the tech world, right? You move from engineering to product to marketing to sales, and suddenly you're the leader of leaders, right? It's like you change all the time and you reinvent yourself all the time. And I think then the question is, how do you find your place and how do you thrive and how do you do it successfully?

[Bill Gurley]

On that topic specifically, I have a chapter called chase your curiosity and what I chose to do in that case, there's. I went out and found best practice from like 10 different sources on this notion of finding what you love. And I just literally put them all in the book because I think it's really about experimentation and wandering around and getting exposed to as much stuff as you possibly can. And so there were a whole bunch of different techniques for that. I love one. The two gentlemen that founded the acquired podcast, which is just remarkably successful, they had an idea. Whenever they took a job, they would try and create what they called a side hustle. So they would ask their employer, can I do this also? It was always extra work, but it was something for the benefit of the company. And he gave these great examples of having done that in three different jobs. And he was working as a venture capitalist at Madrona, and he asked him, can I start a podcast for the company? And they said, sure. You know, it was early in the podcasting days, and that ended up being this side hustle. And they are 100% in their dream job. They're making more money than they ever imagined. They're interviewing and studying the best companies in the world. And just I saw them the other day, they're just tickled pink. They walk around kind of just giddy. But that side hustle is an example of how you can get exposure to more things. And I also think you hinted at this or you said it, but just like, it's fine to do something for a while and then raise your hand and stop and do something else. And so it's all good and I

[Ilana Golan]

think it's never been easier to experiment.

[Bill Gurley]

It's never been easier to experiment. It's never been easier to learn. If you have a notion of a job that you maybe aren't in but are curious about, you could go talk to ChatGPT for six hours and have so much knowledge so quickly that was never possible before. Or go find podcasts with three of the best people in that industry. Like, it's all out there. There's never ever been more information available for someone that's proactive and wants to learn and wants to move. Now, I want to make sure we didn't forget this one thing. We were talking about differentiation and how you make yourself a candidate of one. I love that.

[Ilana Golan]

I think it's very important.

[Bill Gurley]

I think there are two types of learning that will highly differentiate you as an employee candidate. I call it a bit of a barbell because they're at different ends of a spectrum. The first one is history. If you study the history of a field and you know it better than anybody else, which is pretty easy to do, you go back to that like career center example I gave. There's 20 kids applying for a marketing role, you know, at Kellogg's or Coke or whatever. What percentage of those could name the five pioneers of marketing? Probably not many, but if you happen to be the one that walks in and can reel those off, it really differentiates you. It gives you a bedrock, I think, of strength for thinking differently. But it shows this kind of respect, curiosity. It shows curiosity, but it also shows respect for the industry. And I have two anecdotes in the book that I'll share quickly. One, there was a chess tournament, World chess tournament, and this is very recent. They took a break and during the break they did a trivia contest on the history of chess. And guess who won? Magnus Carlsen won the trivia contest. I just think it shows you the best player had the most knowledge of history. And another one, a friend of mine, won this auction to go have dinner at John Lasseter's house. He was the creative genius behind Pixar and he served us a 10 course meal in his theater room. And with each course was one of the early cartoons that affected him the most. And so he gave us a play by of Steamboat Willie was one of them. You know, you've heard of some of these, but like the notion that he had this kind of immense understanding and respect for these early pioneers and what they meant for the industry and that he was now on top doing the most innovative things, that always stuck with me. So anyway, one side is history. History. Like, I think studying the history. And by the way, it's another great test if the notion of studying the history of the field is off putting to you, yeah, this ain't your field. Like, move on. Like, it should be interesting. And by the way, as an investor, like, that's a common thing. People the best know the classics. Like, the best know the classic. So then the other thing that as a young person especially, so know the history and then know the edge. Know what the latest and greatest stuff is. If it's AI, if it's TikTok, go back to this 20 people interviewing for this marketing job. If I walk in, I know the history and I know everything about how TikTok works. I look like that candidate of one. I look remarkably interesting. Like, if I. I have the new and the old. And so if you think about any job and the legends are the older people or the masters in the field, when these new things pop up, most of. Not all of them, but most of them are like, oh, I don't know what that is. Like, oh, that'll never matter. But most firms know when they have a shortcoming or they know that things are changing. And it's very easy for young people to play with these new tools and get to know them and so roll around in them. I had a tweet yesterday about AI. Like, if you want to protect yourself against AI, run at it. Know exactly what AI can achieve in your field and be on the edge and the forefront of playing with it, and you will be remarkably differentiated.

[Ilana Golan]

And that's so, so, so important. And again, I don't know if that's an option right now. I actually believe that, you know, it's almost mandatory right now because otherwise the average just became so easy to achieve. Everybody's average. Now. The other thing that you talk about in the book, and I would love to go there, because you also talk about go where the action is and create your own luck. And. And I do think that this is really, really important, especially when it's so noisy in the system. Like, how do you decide where to go? How do you decide what opportunities to latch onto? How do you see this?

[Bill Gurley]

Bill? The book was evolved from a presentation I gave when the idea first popped in my head at the University of Texas. And it had five tenets. And we added this sixth one as we turned it into a book working with my publisher. And there's just some amazing stories of the best and the brightest just repotting themselves in the Middle of whatever, your industry is thriving. And if you want to be an actor, it's Hollywood. If you want to be a songwriter, it's Nashville. If you want to be an investment banker, it's New York City. And I think a lot of people are either intimidated by jumping into that severe of a situation where there's so much competition, or they fool themselves with this little mental trick, which I think is absolutely wrong, which is I'd rather be a bigger fish in a smaller pond. And so I'm going to go do that in this city where not that many other people are doing it. And the thing that happens when you go to the epicenter is the people you get to know, the peers that are chasing the same thing, the mentors that are available. It's just so rich that your information flow and the amount of expertise you're hearing about every day is ten to one versus being somewhere else. And then the optionality that happens, like the random chance meetings and you walk through my career and I two or three times told you I got very fortunate with this moment. Well, the number of fortunate opportunities if you're where it's all happening is a lot higher than if you're not. And a lot of people's career paths include a few of those types of moments. And so I think that if you are convinced that this might be your dream job and you have the financial wherewithal to go jump in, I would encourage you to go jump in. The worst case is it doesn't work out and you can try something else later. But I think your odds of success are so much higher if you're in it. And having gone to Silicon Valley, I can't imagine having practiced venture capital anywhere else because it was just so nutty. There was an event I could go to every night, some like, networking event, some group event where I might meet a founder, where I might meet an executive. It was insatiable amounts of information and networking available to me there. There's a great documentary, I think, on Netflix about songwriters in Nashville. And they're just remarkably open to helping one another in a way that's endearing. I get goosebumps watching it. It is a communal place where people want to help one another. Silicon Valley, same way. I was always so surprised at how quickly people would take a 15 minute meeting in Silicon Valley compared to maybe some other places.

[Ilana Golan]

Right now, our listeners are trying to figure out what's next for me. How do I become my full potential? Except for reading the book. What would be another thing that you would say to them, this would be like, one of the key things you guys have to do right now.

[Bill Gurley]

There's a story that I stumbled upon after I wrote the book that is really endearing to me, which is in Matthew McConaughey's book, Green Lights, he had told his father his whole life that he was going to be a lawyer, and his father had told his father's friends. And so there was this weight of this notion, oh, Matthew's going to be a lawyer. And he was at the University of Texas, and he met some people that were in the film school, and they convinced him that's what he should do. And so he had to arrange this phone call with his father to tell him that he wanted to give up on this lawyer thing and go to film school. And he put it off and put it off because he was worried. His father was a tough guy. And when he called his father, finally, his father, Paul, he told him. His father paused for a minute, and then he said, well, don't half ass it. And McConaughey says that it was the last thing he expected, but probably the best thing in the world his father could have said, because it gave him permission, it gave him responsibility, it pushed him forward. It was the exact right response. And I feel like our society has evolved to a place, unfortunately, and I think it was all well intended. We're cramming these kids through this kind of conveyor belt to college, and we're, you know, starting when they're 12, we're worried about what their extracurriculars are going to look like, and do they have cello and did they volunteer enough at the rescue center? We're just pushing, pushing, pushing. And now you have to apply to a major in many schools. You used to go to school for two years before you even announced a major. Now they want you to apply to a major. You're a junior in high school, and people ask them, what do you want to do the rest of your life? And they just don't know. And equally, because it's become so competitive and there's so many people pushing them in this direction, the anxiety levels are high, so there's stress, which doesn't help. And so you get to a place where there's actually not only a lack of experimentation and exploration, but there's no time for it. Like, you're not even really encouraging it. And so there's a very long answer to your question. But I think what I really hope the book does the most is give as many people that experience that Matthew

[Ilana Golan]

had as possible give them permission.

[Bill Gurley]

Yeah, yeah, permission. It's okay to go do these things. I have a book right here. So Jerry Seinfeld stumbled upon this book when he was living in New York. It's called the Last Laugh. And there's like 14 comedians that. It tells their story and how they got into the business and how they differentiate themselves. If he had never read this, I don't know if he ever becomes Jerry Seinfeld. It was disinhibiting. It gave him permission to think about this as a career. And he talks about it. And this is my biggest hope for the book, is that it gives as many people as possible this permission to go chase what it is you love. And I was having this conversation with a career counselor about the book. Obviously, I have some opinions about that process they run, but she said to me, she said, but can you really do whatever you want? Like what if you love English poetry? And it struck me that the college institution that I think wants to believe, you know, they have all these majors, they want to believe people can go do all these things, but when it gets to the career spot, they shrink up too and start cramming people towards these safe jobs. I think it's all well intentioned. They're all worried about economics and this kind of thing. But I showed her in the book, I said, here's an example of a guy that fell in love with the Grand Canyon and ended up writing books about it. Became a podcaster. Like, he made a great.

[Ilana Golan]

So many ways to make money these days. Like, I think we need to stop channeling people into the same arenas. And by the way, the same arenas are actually the ones that are going crowded. And actually they're the ones that are

[Bill Gurley]

the ones threatened by AI.

[Ilana Golan]

It's unbelievable.

[Bill Gurley]

So there's another story I showed her of a guy that was in Houston that fell in love with Texas horticulture. I mean, of all things. And now he's written books and books and books and has a T. And when I showed her those two, she said, but I bet they had to work pretty hard. I'm like, well, you got me there. But just piling on this topic, 2 days ago I got an email from a guy. He had seen the Texas Talk and he heard I was writing a book. And he reached out. He was a real estate lawyer who loved football, and he especially loved breaking down offensive schemes. He started a company just focused on football offensive schemes. He now has 900,000 followers on Twitter. He has an application you can buy to run all these simulations, and that's all he does all day. And he created this career once again, this candidate of one. Like, he went out and created his own career rather than falling into what everybody else wants you to do. And it's just so touching to me. Anyway, that's my big, big answer to your question, which is have the belief that you can actually do whatever you want. And I think it's never been easier to learn enough to do it. It's never been easier to get a whole bunch of things accomplished on your own. And it's never been easier to break into new things, make new connections, differentiate yourself.

[Ilana Golan]

I agree with all of it. And I will also say that we are in an era that I see as a portfolio career. People will have multiple things, multiple ventures, and we see it all the time. So even once you find something, you know, like you said, like you're passionate about something great, you can add a podcast to code, you can add a book, you can add speaking, you can add a bunch of things. So that creates an incredibly exciting life. So, Bill, thank you for being on the show and just showing up.

[Bill Gurley]

Thanks for having me on. All people need to do is type dream and girly into Google or Amazon and it'll pop right up.

[Ilana Golan]

Amazing. Are we going to have the show notes and if they want to reach you or reach the book or. So you just find.

[Bill Gurley]

Bill Gurley, I should mention one other thing, especially for your listeners. Simultaneously with launching the book, we're creating a foundation, and I'm putting all my proceeds into the foundation. And we're going to take applications for micro grants for people that want to shift careers but might not have the financial wherewithal to go do it. I felt strongly, I know one pushback I would get along the way was, well, what if you just can't leap to that new city or if you just can't step away from where you are? And so I thought it'd be a really nice gesture to add on. So there's going to be a website. Rdad.org it's not up yet, but that's where we'll be running those applications.

[Ilana Golan]

That's beautiful, Bill. Thank you for giving people the chance and to an incredible life.

[Bill Gurley]

Thanks for having me on.

[Ilana Golan]

Oh, my God, what a tremendous episode. And what I love about this is how aligned this is with the Leap Academy mission, to help anyone driven go chase their dreams and figure out what's next for you and learn how to experiment with your career, how to get really clear about your story and about how to leap, whether you're trying to get to a new job, switch an industry fast, act to leadership, start a business, or create an incredible portfolio career. So I love how aligned this was. So I do hope that this is helping you get that courage to go chase your dream, create a life of possibility, design not just a paycheck, but the life that you want with a paycheck. So somebody in your life needs to hear this. Do share that with them. Let's go change some lives. We are on a mission to change 10 million lives so that every single person can be not displaced by AI, but win in the era of AI. So do share it and if you did love it, please give us a like, subscribe and a five star review. These mean the world and it helps us bring incredible guests. What I do want to do now is we looked at our YouTube, there was an incredible question from Josh and Josh asked about experimenting in your career. So the question is, how do I decide what sucks for me and how do I experiment with my career? And what's beautiful is how aligned this is all with this episode and previous episode. We talked about your must haves, we talked about your zone of genius. And what I want to talk about now is how do you basically experiment with your career? Right? And what I like to do is the five, five, five rule. Five days, five weeks, five months. So let's go over it. So let's assume that out of all the possibilities, if you kind of look at your must have, you look at the zone of genius, you look at what you're passionate about, what are the things that people are intrigued by you and the things that you like to tinker with. And you look at those three to five options and what you're going to do now is five days, five weeks, five months, experiments. And when you start looking at your career as an experiment and not as something that you need to decide for 40 years, it's going to change everything for you. So for the first five days, all you're going to do is learn as much as possible about these options. So let's assume you have three options. You're not sure which one. Pick one that is either the most likely or you're most excited about. And for the next five days, just learn as much as possible about it. What are people doing before and after? How did they land these kind of opportunities? Where is this taking them? Do they seem excited? What do they write about? Right, like just learn as much as you can about it. And within those five days, the only decision that you need to make. It's not about, oh my God, I need to make a decision for 40 years. No, it's should I invest another five weeks into this experiment? That's all you need to decide. And it takes a lot of the pressure of needing to make this big mega decision. Right? So for the five days, just think like, is this worth another five weeks experiment? If the answer is no, great. Let's go back to another option. If the answer is yes, let's dive in for five weeks. For the next five week, what you're going to do is you're going to create a little bit of a branding around it. So let's assume you're trying to nail this kind of opportunity, whether it's a startup, whether it's clients, whether it's portfolio, career, whether it's like a job, whatever it is. But let's assume that this is what I'm trying to do and I want to be kind of what we just talked about, the candidate of one that rises above the people pile for this opportunity. How will I do that? And the way to do that is so you're going to learn about different people and what do they talk about, what did they post about, how do they brand themselves? You're going to look at your own story. How can I brand myself? How do I emphasize the right things? How do I adjust my LinkedIn, my resume, whatever it is, how do I adjust it? How do I emphasize it with complete integrity according to where I'm going. And you're going to still measure, is this worth a 5 months in the actual leap or do I need to go back to the drawing board? And guess what? It's a lot better to find this out in five weeks versus a whole business that you start and you see that you're not excited about. So after those five weeks, all you need to decide is this worth five months, which is the actual leap and to actually start landing opportunities and experimenting with that. So if you are going to start looking at your career as multiple experiments, it's going to lift a weight over your shoulders because you don't need to decide for something for 40 years because we all going to change every year or two. So the more you realize it, the more it creates this incredible space. So I hope this is helpful. I can't wait to see some of your questions in the YouTube channel, in other questions or other comments. And if you liked it, please let us know and please share it with people that need to hear this today. So lots of love, lots of possibilities into an incredible day ahead. Remember, this episode is not just for you and me. You never know whose life you're meant to change by sharing this episode with them. And if you love today's episode, please click the subscribe or Download button for this show and give it a five star review. This really means the world. Join me in helping tens of millions of individuals reinvent their career and leap into their full potential. Look, getting intentional and strategic with your career is now more important than ever. The skills for success have changed. Aq, adaptability, reinventing and leaping are today the most important skills for the future of work. Building portfolio careers, multiple streams of income and ventures are no longer a nice to have. It's a must have. But no one is teaching this except for us in Leap Academy. So if you want more from your career in Life, go to leapacademy.com training check out our completely free training about ways to fast track your career. You'll even be able to book a completely free career strategy call with my team. So go to leapacademy.com training.