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Find your work.
I'm Bill Allred, and this is Craftsmith, a podcast about people doing work they love so you can too. This episode is a Craftsmith Letter to Bill Gurley. About eight years ago, Bill stood up at his alma mater, the University of Texas, and gave a talk called running down a dream. In it, he shared six principles for finding and thriving in a career that you love. The author James Clear founded on YouTube, tweeted that everyone should watch it, and millions of people did.
Speaker 1:That this year, Bill turned that talk into a book. In a conversation with Rick Rubin, he described why. The main purpose of me wanting to launch this book into the world is to give people the permission to go chase something that they want to do. I perked up at that word permission. I've gotta say, Bill's work did exactly that for me.
Speaker 1:I watched that talk years ago, and it was one of the things that gave me permission to build what you're listening to right now, which makes this letter somewhat recursive. The thing Bill Gurley's work gave me permission to build is a podcast with the same goal as his book, helping people find work they love. So when I trace Bill's own path from a NASA kid in Texas to an engineer at Compaq, then to Wall Street, and finally Silicon Valley, I wanted to turn the lens around on him. His first principle is find your passion. But how did Bill actually find his?
Speaker 1:He had five fascinations pulling in different directions. During business school, he saw the venture capital held most of them. And he spent twelve years chasing that role. But he also put his own spin on it, adding a public writing practice that wasn't part of the VC playbook at the time. The thing that told him when the current version still wasn't right was boredom, something most people try to suppress.
Speaker 1:I think Bill's own story fills in the hardest part of the advice that he gives. Not how to chase your passion, but how to define it in the first place. Here is my letter to Bill Gurley. Bill, leading up to the release of your book, I wanted to turn the lens on you. Your first principle is find your passion.
Speaker 1:And your own path shows exactly how you did that. You didn't have just one passion. You had five interests, and even the role that came closest didn't use all of them until you made it your own. You grew up in Dickinson, Texas, a small town outside Houston that most people have never heard of. Dickinson was a NASA bedroom community, filled with engineers and scientists who'd moved there when Johnson Space Center opened in the early nineteen sixties to run the Apollo program.
Speaker 1:Your father, John, was one of those early NASA employees. It was his dream job. He'd started working at Langley Research Center in 1958, before NASA even existed as NASA, and transferred to Clear Lake when the manned spacecraft center was established. As you've described it, half the fathers on our street worked at NASA. Gene Krantz, the flight director who guided Apollo 13 home after the oxygen tank explosion, was actually your neighbor.
Speaker 1:Growing up on a street of NASA scientists shaped how you learned to think. You grew up surrounded by systems thinkers, people who solved impossible problems by breaking them into their component parts. Engineers who worked together on seemingly impossible challenges proved that big things happen through the careful accumulation of small advantages. It would have made a lot of sense for you to go into aerospace. But the spark that set your career in motion didn't come from your father's world at NASA.
Speaker 1:It actually came from your sister. Beth went to Rice University as an electrical engineering major, and then she became employee number 63 at a little company called Compact Computer. '63 was early enough to get meaningful stock options. Meaningful enough that when Compaq went public in 1983, those options were worth real money. You've described what that was like.
Speaker 1:I was seeing the stuff I wouldn't have seen otherwise. You got a glimpse of the future through your sister. Wealth created by getting close to exponential growth in technology, rather than wealth created by climbing a corporate ladder. And once you saw it, you couldn't look away. This was the first of your many interests.
Speaker 1:You had what you've called a love affair with tech. You studied computer science at the University of Florida, playing basketball for the Gators because at six foot nine, how could you not? But you were always going to work in technology. But just as growing up in a NASA neighborhood didn't put you on a path to aerospace, seeing your sister's windfall didn't make you a software developer. As you've described it, I had a love affair with tech, I had seen my sister do well off of options, and I had this gambling bug.
Speaker 1:There it is, the gambling bug. You ended up at Compaq in the late eighties, where you read Peter Lynch's book about investing in what you know. You started trading stocks on Prodigy, one of the first online services. When the technology company Borland went public, you bought shares on IPO day because you'd use their products every day at work. Tools like Turbo Pascal and Quattro, tools you loved.
Speaker 1:The stock went from $12 to 80, and something clicked. You were hooked on the asymmetry. The possibility that being right about something could compound in ways that salary never would. This dabbling in the markets revealed a third interest. You wanted to understand how markets worked.
Speaker 1:How companies were valued. How capital allocation decisions shaped entire industries. As you've put it, I had gone from, okay, I like computers, to watching Compaq and Borland go public, and wondering, how does this Wall Street thing work? The fourth interest is a little less obvious. You had an urge to explain what you saw.
Speaker 1:To translate complexity into clarity you could share. As you've described it, putting words on paper makes you smarter. Sometimes you realize you were wrong. Writing wasn't just output for you. It was how you thought.
Speaker 1:This would show up later in your Wall Street research reports, in your blog, above the crowd, and now in the book. The drive to encode what you saw into prose was there early. And the fifth interest. You wanted to get wealthy. Nothing wrong with that, and you've never hidden it.
Speaker 1:Your sister's success planted the seed. Your early wins in the market added fuel. You wanted to apply your interests with leverage. Your first principle is find your passion. You've already evolved past that word.
Speaker 1:In your book, you borrowed Seinfeld's fascination. As you told Rick Rubin, the word passion got overused a bit. I think you're right. Five fascinations. A love affair with technology, a gambling bug, a deep curiosity about markets, a need to write, and a desire for wealth.
Speaker 1:Most people would look at those five things and see five separate career paths. Engineer, trader, portfolio manager, journalist, entrepreneur maybe. Most people would feel pressure to pick one and commit. You didn't pick. You held all five, with no idea yet how they'd fit together.
Speaker 1:Which is when the boredom started. After graduating from the University of Florida, you went to work as a design engineer at Compaq, working on the four six fifty and their first multi processor server. This should have been perfect. You were inside the company that changed your sister's life. You were doing technical work at the most exciting PC manufacturer in the world.
Speaker 1:Check the Fascinations. Love affair with tech? Absolutely. You were building computers, working with cutting edge processors, solving real engineering problems. But everything else?
Speaker 1:No. No investing, no writing, no asymmetric bets. The work was interesting. The company was successful, but something was missing. Here's how you've described what happened.
Speaker 1:It should have been a dream come true, but I was surprisingly bored. Bored at Compaq in the late eighties when personal computers were eating the world and Compaq was leading the charge. That's quite a statement to be bored in that environment. By your third project at Compaq, another computer with a slightly faster clock speed, a better Intel chip, everything else the same, you reached a conclusion. After about three years, I reached a point of near certainty.
Speaker 1:I don't want to do this the rest of my life. Most people here bored at work and think, something's wrong with me. I should be grateful. I'm not trying hard enough. But your boredom was a signal.
Speaker 1:You were feeding one fascination and starving the other four. And you listened. You went to business school at the University of Texas, and something started to crystallize. You had these five fascinations. Technology, investing, riding, risk, and wealth.
Speaker 1:And you began to see that there might be one role that held all of them. You started to voice that you wanted to be a venture capitalist. You were direct with everyone about it. But the response from the industry was clear. Austin Ventures, the local firm, wouldn't even give you an interview.
Speaker 1:Other firms were more explicit. Go work for twenty years, and then we'll talk. Most people would have taken that as a sign to find a more accessible path. Consulting, corporate strategy, something respectable that you could get hired to do as an MBA. But the job you wanted didn't come with a career track.
Speaker 1:Nobody was recruiting engineers from Texas into venture capital. So you started building one yourself. You begged your way into a job at Credit Suisse First Boston as a Wall Street research analyst covering the PC industry. Check the Fascinations again. Love affair with tech?
Speaker 1:Yes. You were covering Dell, Compaq, Microsoft, all serious technology companies of the day. Deep interest in investing? Yes. You were analyzing businesses, understanding competitive dynamics, building financial models, living and breathing the markets.
Speaker 1:Writing? Also, yes. Research reports were the craft. And you'd borrowed an idea from a rival analyst at Kidder Peabody. A weekly fax newsletter that the buy side loved.
Speaker 1:Two weeks after that analyst left the scene, you launched your own above the crowd. It became a defining element of your career. How about gambling bug? Not really. You were making recommendations, but other people took the risk.
Speaker 1:And well, also no. Analyst salary, no meaningful ownership, no participation in the upside of the recommendations you made. So three out of five fascinations is closer, but something was still off. At one point, you did something audacious. You attended Stuart Alsop's Agenda Conference.
Speaker 1:The most important gathering in tech at the time. Every person who mattered was there. At this particular conference, they sold a PalmPilot. Remember those? Preloaded with the contact information of every single attendee, including their fax numbers.
Speaker 1:This is unthinkable now, but back then, times were simpler. So you bought the Palm Pilot, you did the math, about 70¢ per name for the 350 most important people in the technology industry. And then, you spammed the entire list with your above the crowd newsletter. I love that. Think about the guts that took.
Speaker 1:A Wall Street analyst from Texas trying to break into the Silicon Valley network. And your move was to blast your newsletter to the entire power structure of the tech industry using a contact list from a Palm Pilot you bought at a conference. The legendary investment banker, Frank Quatrone, noticed. He was the guy who'd taken Cisco and Netscape public. He called you and asked a question.
Speaker 1:What is your dream job? You told him you'd always dreamed of being a venture capitalist. He said, move to Silicon Valley. Come work for me covering Internet companies, and I'll introduce you to every venture capitalist I know. So you immediately moved to California.
Speaker 1:You became the lead analyst on the Amazon IPO at only 31. You built a relationship with Jeff Bezos that would last decades. And you made institutional investors all American research Team two years in a row. By any conventional measure, you had absolutely made it. But the boredom signal came back.
Speaker 1:One night at 10:30, on a trip to the firm's New York office, you walked the 36th Floor of Park Avenue Plaza from office to office. Looking at the senior analysts, some of whom had been doing this for twenty years, these people represented the future version of the path you were on. And you asked yourself a question. Do I want to be this person when I'm 60? The answer was clearly no.
Speaker 1:Three years on Wall Street, just like the three years at Compaq, and the same signal. The boredom, the restlessness. Each time telling you that not all your fascinations were being served. Every exit was teaching you something, but unlike most people, you listened. You kept building.
Speaker 1:Nobody handed you a career in venture capital. You assembled the path yourself from an analyst, from the newsletter, the Palm Pilot, Frank Quatrone, relationships you built from nothing. True to his word, Quatrone introduced you to every venture capitalist he knew. You were so eager to enter the world you'd been dreaming about since business school that when Hummer Winblad offered you a position in 1997, you said yes immediately. John Hummer was a six foot ten former NBA player, and you hit it off right away.
Speaker 1:A year and a half later, you landed at Benchmark Capital, your dream firm. Twelve years after that first glimpse of what technology and equity and asymmetric outcomes could mean, and after so many times of being told, not yet, go get some experience first, you finally brought your five fascinations together into a single role. Your partner Kevin Harvey has a phrase that you love. Life is a use it or lose it proposition. I suspect that's part of what kept you pushing forward.
Speaker 1:And this role really did use everything. Love affair with tech? Yes. You were investing in the future of technology at one of the most interesting times in history. Meeting founders, building things that didn't exist yet, talking to some of the brightest people in the world about where the industry was going before the market understood it.
Speaker 1:Deep interest in investing? Yes. Pattern recognition across companies and markets became your daily work. You were analyzing network effects, understanding business models, and making serious capital allocation decisions. Writing?
Speaker 1:Yes. Above the Crowd grew from that fax newsletter into one of the must read voices in technology. You wrote essays on marketplace dynamics, on the perils and pitfalls of going public, on regulatory capture, essays that still stand as foundational thinking in the industry. How about the gambling bug? Early stage VC is maximum asymmetry.
Speaker 1:Most bets go to zero, some struggle along, while the very few special ones go to the moon. That element of risk is baked into the work. And wealth? For those who do it well, there's real wealth to be earned through carried interest and ownership. Direct participation in the value created.
Speaker 1:So all five fascinations were held in one role. A role nobody wanted to give you permission to do. A role that you built your own career track to. But it wasn't immediate bliss. The transition to being a GP was jarring.
Speaker 1:You've described what happened after your first investment didn't work. Walking around the benchmark office, anxiety spiking to the point of nearly breaking out in hives, thinking, what have I gotten myself into? How could you ever possibly be successful in this industry? Your partner said something that reframed it. They said, it's going to be okay.
Speaker 1:Get back out there. You're good. You're doing fine. They gave you permission to try and fail, and try again. The permission that Austin Ventures wouldn't give you when you were 25 knocking on their door.
Speaker 1:The permission you'd spend twelve years earning for yourself. Then, after spending a quarter century in a dream job at Benchmark that you built by hand, you declared victory and stepped back. As you've described it, you'd accomplished everything you aspired to. You knew the business bends towards youth, and it was time to start giving back. But here's what I didn't expect from someone who had built their dream job and written a book about it.
Speaker 1:That signal came back a third time. You went on a listening tour. You talked to everyone who'd made a similar transition out of venture capital. You explored angel investing, sitting on boards, managing your own money. You crossed all of them off.
Speaker 1:The boredom, the restlessness, the same feeling you had at Compaq and Park Avenue returned. And then you said something to Tim Ferriss that I think is the most revealing thing that you've ever said about your career. I couldn't discover something that got me excited. Slowly, I've come around to an idea that I made up. It's not a career that other people have.
Speaker 1:There it is. You made it up again. Bill, I think that phrase explains your entire career. You didn't invent every role from scratch. Venture capital existed before you got there.
Speaker 1:But you never settled for a version that left your fascinations unserved. At compact, one out of five. On Wall Street, three out of five. When you saw that venture capital held most of them, nobody would hand you the job, so you built the path to it yourself. And then you layered above the crowd on top.
Speaker 1:A public writing practice that wasn't part of the VC playbook. Making the role fully yours. Now, post benchmark, you've gone even further. You've built something that doesn't even yet have a name. You're turning that UT talk into a book.
Speaker 1:You're building a foundation to give people who can't afford to chase their dreams the resources to try. You're developing a policy institute around the issues you care most about. None of this existed before you built it. And I think that's because after a quarter century, your fascinations have evolved. You've got new ones now.
Speaker 1:And you're running those down too. Bill, fascination is hands down a better word than passion. But your own story teaches something that even fascination doesn't capture. Most people I talk to aren't single threaded. They love technology and they're fascinated by markets.
Speaker 1:They want to write and they want to build things. Maybe they're intellectually curious, but also financially ambitious. And they're bored at work. They assume the boredom means something is wrong with them. Standard career advice is to pick one fascination, to focus, to specialize.
Speaker 1:Most of the time, far earlier than we're prepared to make such a consequential choice. And when the boredom comes, the advice is push through it. Be grateful. Stop being so restless. Your story says something different.
Speaker 1:Listen to the boredom. It's telling you that not all of your fascinations are being served. The role that comes closest might need your own spin. And if nothing out there fits, you make it up. That's what you did three times and each time, the boredom was the signal that got you moving again.
Speaker 1:What's interesting is that even the book needed permission. Brian Koppelman met you at a conference in the mountains going around asking everyone, what creative project are you doing outside of your career? When you told him about the speech at UT, he looked at you and said, you have to make this a book. Someone gave you permission to create a work whose purpose is giving other people permission. You told Rick Rubin you want it to disinhibit people.
Speaker 1:Bill, I can tell you that it does, at least it has for me. Your book gives people timeless advice for chasing a dream. But your own story teaches the harder part. How do you define it in the first place? What do you do when you've got multiple fascinations pulling in different directions and no existing job uses all of them?
Speaker 1:You chase roles that satisfy more and more of them. You trust the boredom that tells you when the current version isn't right. And when nothing out there fits, you make it up. If this letter finds you, Bill, the invitation stands. I'd love to record an episode together.
Speaker 1:This has been a Craftsmith Letter to Bill Gurley. If you saw yourself in that story, here's something you can do this week. If you're bored at work, try something before you dismiss it. Write down the parts of you that aren't being used. The fascinations you have that your current work doesn't touch.
Speaker 1:Don't edit yourself. Don't force them into a narrative. Just list them. That boredom might be the most useful signal in your career. It's not saying that you're ungrateful.
Speaker 1:It's telling you that not all of your fascinations are in play yet. If you think Bill should hear this letter, you can help me deliver it. Send him this episode. I'll put links to his site and socials in the show notes. And if you want to know whether it reaches him and what happens if it does, follow Craftsmith wherever you're listening to this podcast.
Speaker 1:I'm Bill Allred. Thank you for listening to Craftsmith.