Leap Academy with Ilana Golan - Benchmark Partner, Bill Gurley: The Strategy That Makes You Stand Out in a Crowded Job Market | E150

Episode Date: March 17, 2026

When Bill Gurley wanted to break into Wall Street, there were no job postings waiting for him. So he flew to New York, knocked on doors, and asked strangers for meetings. That hustle launched a career that would eventually take him to Silicon Valley, where he became one of the most respected venture capitalists in tech. In this episode, Bill joins Ilana to reveal the unconventional lessons that shaped his journey. From chasing curiosity to designing your own career path, he explains how anyone can create opportunities, stand out in a crowded field, and build a career that actually excites them. Bill Gurley is a Silicon Valley venture capitalist and a longtime partner at Benchmark Capital, a Silicon Valley venture capital firm. He has invested in and served on the boards of major companies, including Uber, OpenTable, Zillow, Nextdoor, and Stitch Fix. In this episode, Ilana and Bill will discuss: (00:00) Introduction  (03:14) Where Bill Gurley’s Tech Curiosity Began (05:09) Transitioning from Engineering to Finance (08:25) Breaking Into Wall Street Without a Job Posting (14:24) The Question That Made Him Quit Wall Street (19:59) Making a Pivot to Venture Capital (24:41) The Best Way to Get Into Venture Capital (26:50) How to Know If You’re in the Right Career (30:30) The Role of Experimentation in Career Growth (33:20) How to Stand Out in a Competitive Job Market (37:29) Why Location Can Make or Break Your Career (40:50) Breaking Free From the “Safe Career” Pressure (48:30) The 5–5–5 Rule for Career Experiments Bill Gurley is a venture capitalist, technology investor, and general partner at Benchmark Capital, best known for his early investment in companies like Uber. Before venture capital, he worked as an engineer at Compaq and later as a Wall Street technology analyst. Throughout his career, Bill has been known for identifying transformative companies early and for his widely read blog Above the Cloud. His new book, Running Down a Dream, offers a practical guide to building a fulfilling career Connect with Bill: Bill’s X (Twitter): x.com/bgurley  Bill’s Website: abovethecrowd.com  Resources Mentioned: Bill’s Book, Runnin' Down a Dream: How to Thrive in a Career You Actually Love: https://www.amazon.com/dp/0593799666  One Up On Wall Street: How to Use What You Already Know to Make Money in the Market by Peter Lynch: https://www.amazon.com/dp/0743200403  Range: Why Generalists Triumph in a Specialized World by David Epstein: https://www.amazon.com/dp/0735214484  Greenlights by Matthew McConaughey: https://www.amazon.com/dp/0593139135  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

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 of 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. 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 Next Door and over. an Uber and Zillow. 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. How do you find a career you love, right? Not necessarily what you thought you're supposed to do or your society experience. you to do. Have the belief that you can actually do whatever you want. And 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 in a mission to help millions reinvent their career and leap into their full potential, land their dream roles, fast, fast, 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 countess of lives. Deal? Okay, so let's dive in. 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 Next Door and Open Table and Stitchfix 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 Dream, How to Thrive in a Career you actually love. And so I love this because we're 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. Thanks for having me. 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? 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 Compact Computer Corporation, 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.

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 about learning these computers, but you went to engineering school and you started basically in an engineering role. 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. And why did you decide to leave to the saleside analyst portion of it? What happened was, as I've written a 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. 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 process or 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 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 had thought about going to business school before. I learned a whole bunch about finance and business that I'd never known. I developed the love for reading at business school, which I didn't have before, which I think was super influential. And I learned about the notion 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 cell-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 would be easier because of digital communication, but I literally begged to talk to people. So you needed to hustle your way in. Oh, yeah, there was no listing for a job. 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 career. So how did you land the first rule? 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, 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 cell site analysts at Goldman. that were just dominant. And as a result, every time these news papers 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 use 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 and 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. And I do want to hear how you differentiate yourself and how you become candidate of one. We call it the hidden market.

But I think there's a lot of similarities of especially now, we can. 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 cell 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? A couple of things happened that were super fortunate. The gentleman that ended up giving me a job as a guy named Al Jackson, who ran the research department at Credit Suisse First Boston.

And I think Al was just 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 Warden 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 him, 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. They 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 page. And I was like, 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. And I'll just say that we'll give them a sneak peek, that at the end of your book, you also mentioned some books. I have a list. I need to add it up. I think it's about 50 books, but. That is incredible. So you are in the tech world.

When the whole dot-com crash came about? Tell us a little bit. 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 cell site 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 Compact as an engineer. One night, and we worked long hours, it was like 10 p.m. 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 were 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 peaked in and used it as a moment of reflection. It 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, you know, 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 Quattron,

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 site 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. What? And he did. And I only worked for Frank for 13 months. Take me there. Why do you think he approached you?

And why did he have so much conviction that you are the right person for him? I think he had heard about my reputation. I was doing things very differently as a cell site analyst than other. people had done in the past. I had taken some risk. I'd seen some other people take some risk and was mimicking some of their techniques. Through that, I had developed a 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.

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 in 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 slash 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 slash 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. It's 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. Yeah. 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, in because I wanted to get to venture. So it didn't end up popping for another two years, two or three years. And I was at that point in Intel, and we were starting to get the waves of Internet and this thing is happening and everything. So take us there.

Like what got you into venture capital? 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 Winblet, actually. And I said yes, almost without thinking. And I should have checked around. I made a mistake in just being too eager and moved 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? 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 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. 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. 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 cell site 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. So 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 can 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, And it was around for 20 or 30 years before I got into it. But it was more competitive when I left than when I started. And it's way more competitive today.

Let's talk about it for a second. And for those who don't know, I mean, you've been on the Forbes Meads 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? Once I started being successful in venture, I would start to get the cold email. and the knock on doors that I had done.

At that time, I wrote a three-page PDF called So You 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 e-sports. 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 e-sports 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 e-sports 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. 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 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 going to 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. 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 fine. 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 Your 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 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 numbers, 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 gain 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 in 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. It's always been easy to find information and now it's been accelerated in ways that it's hard to describe. So in fact, if you're not constantly learning right now, you're losing relevant, I think at a speed that we've never seen before. 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. 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 a 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? On that topic specifically of 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 asked 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 Medrona. And he asked him, can I start a podcast

for the company? And they said, sure. 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 imagine. 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 think it's never been easier to experiment. 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 it, you could go talk to JetGBT for six hours and have so much knowledge so quickly that was never possible before or go find podcast 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 to want. 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,

you study the history of a field and you know it better than anybody else, which is pretty easy to do you. 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 was very recent. They took a break. And during the break, they did a trip. trivia contest on the history of chess. And guess who won? Magnus Carlson 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 playby 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. 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 I have the new and the old. And so if you think about any job and the legends or the older people or the masters in the field, when these new things pop up, most of them, not all of them, but most of them are like, oh, I don't know what

that is. Like, oh, that'll never matter. Like, 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. Add 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. 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 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 on to? How do you see this 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 tenants. 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, is thriving. And if you want to be an actor at Hollywood, if you want to be a song, writer, 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 10 to 1 versus being somewhere else. And then the optionality that happens, like the random chance meetings. And you walked 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 events, 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,

people want to help on it. 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. 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? There's a story that I stumbled upon after I wrote a 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, he told him his father Pauls 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 set 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, where 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 they're 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 had as possible. Give them permission.

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 to and start cramming people towards these safe jobs. The same things. 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 career. There's 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 being eliminated. And they're the ones threatened by AI, too.

Like, it's unbelievable. 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 TV show. 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, two 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. 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 or something. 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. 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. Amazing. Are we going to have the show notes? And if they want to reach you or reach the book, so you just find 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 microgrants, 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 would be a really nice gesture to add on. So there's going to be a website, rd-a-d-d-org. It's not up yet, but that's where we'll be running those applications. That's beautiful, Bill.

Thank you for giving people the chance and to an incredible life. Thanks for having me on. Oh, my God, what a tremendous episode. And what I would love about this is how aligned this is with the Leap Academy mission to hope 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 new. job, switch in industry, fast-acted leadership, startup business, or create an incredible

preferred 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 if 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 we're going to be. 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 sex 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 5-5-5 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-a-do, 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 sinker 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 do 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 rise 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 five 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're 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. It's not just for you and me. You never know whose life you are meant to change by sharing this episode with them. And if you love today's episode,

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