#166 What I Learned From Bill Gurley
What I learned from reading "Runnin’ Down a Dream: How to Thrive in a Career You Actually Love” by Bill Gurley.
Today’s Chapter is based on the book “Runnin’ Down a Dream: How to Thrive in a Career You Actually Love” by Bill Gurley.
Bill Gurley is an American venture capitalist and longtime general partner at Benchmark, a prominent Silicon Valley firm, known for early investments in companies like Uber, Zillow, OpenTable, Grubhub, Stitch Fix, and Nextdoor.
Here’s what I learned:
Find Your Fascination
“The best job is the one you’d do even if you didn’t need the money— the one that makes you tap dance to work every day.”
— Warren Buffett
Bill Gurley has studied many successful people from different industries and have found a common pattern among all of them. Among them, he believes in the importance of pursuing what genuinely fascinates you. He argues that true success often stems from an obsessive interest that drives people to learn and work without feeling a burden. Curiosity and a perpetual desire to learn should lead you toward working in a career that energizes you.
Gurley believes that the term “Follow your passion” has become a bit of a cliche, but that “Fascination might be a better word because it suggests giving real, substantial thought to something, rather than relying on surface-level vibes. And it invokes an equally important word—curiosity. If you are fascinated with something, you yearn to understand every bit of detail about it. And that desire to know more will be endless.”
One example Gurley provides is Magnus Carlsen, the chess champion who didn’t just practice but lived and breathed the game from a young age. Unlike other kids who treated chess practices as homework, Carlsen found it enjoyable which set him apart. This intrinsic motivation is what separates thriving professionals from those who burn out. Gurley explains that “Most of the top chess players in the world study the game for several hours a day. Magnus Carlsen, often considered the greatest chess player of the modern era, has said that from a young age, his preparation has been more focused on the joy he gets from the game.”
“I would still spend a bunch of time reading books, playing—the things I still do, but I do them for fun. That was the difference between me and the other kids. They would go to chess practice. They would maybe even do their homework. But they weren’t living and breathing the game in the way that I was.”
— Magnus Carlsen
Based on this premise, Gurley stresses that a college major is not a life sentence, it is more than acceptable to pivot away from it. The key is to view your formal education as a starting point rather than a dead-end. He writes, “It is important to realize that most people will end up doing something outside their college major. And that is perfectly fine. Said another way, the “major” decision need not be as daunting as it seems. I would think of it as one of the first stops of many on the path to finding your eventual career. If you love it, great. If not, there will be ample opportunity in the future to expand your career horizons. And you will still benefit from the journey.”
And so, how does one know if you have found a deep fascination that’s worth pursing as a career? Gurley believes that the best test comes from what he learned from the legendary college basketball coach Bobby Knight who once said, “The will to win is not nearly as important as the will to prepare to win. Everyone wants to win, but not everyone wants to prepare to win.”
“When you are thinking about what fascinates you, run through this in your mind. Does the idea of doing whatever your chosen field requires for an indefinite amount of time sound tedious—or does it sound like fun? To be truly successful, your work needs to feel joyful—the way chess feels to Magnus Carlsen. It must be fulfilling all on its own, not just because of the potential outside rewards.”
— Bill Gurley
Finally, Gurley suggests trying the Compass Exercise designed by Bill Burnett and Dave Evans from their book “Designing Your Life” to find out what you are curious about. He elaborates that the Compass Exercise “is similar to “loves and strengths” but is more focused on alignment with your own values—what you define as happiness and success. They recommend you write two short 250-word essays. The first is titled “What is work for?” and the second is titled “What is a good life?” As above, the goal is then to search for careers that create coherence between the two. This exercise is more about identifying your core values and making sure there is alignment with your actual career direction.”
This reminds me of what we have previously learned from Kazuo Inamori, the founder of Kyocera who believed that the purpose of life is to elevate our minds and to refine our souls. He elaborates that refining one’s soul can only be done through hard work. As a matter of fact, he explains that “Working diligently does much more than fulfill us. It also builds and refines our character and helps us hone our philosophy for living.”
As such, he believes that it is one’s duty to be persistently striving to make each day better than the one before. This is the key in finding purpose and value in life. And you only achieve this, if you are working in a career that you have a fascination for. This reminds me of this following quote from Charlie Munger: “Spend each day trying to be a little wiser than you were when you woke up. Day by day, and at the end of the day-if you live long enough-like most people, you will get out of life what you deserve.”
Furthermore, Inamori explains that “the path to refining one’s character can be found in one’s daily work.” As such, no matter role or job is in front of you, make sure you do your best. Similarly, whether you are a carpenter, a tailor or a fisher, you need to work hard in order to refine your soul and to elevate your character.
This reminds me of the important lesson Lee Iacocca learned from his father. Once at a restaurant, Iacocca recalls that the waitress was being rude and his father gave her the following speech:
““I’m going to give you a real tip,” he’d say. “Why are you so unhappy in this job? Is anyone forcing you to be a waitress? When you act surly, you’re telling everybody you don’t like what you’re doing. We’re out for a nice time and you’re wrecking it. If you really want to be a waitress, then you should work at being the best damn waitress in the world. Otherwise, find yourself another line of work.””
— Lee Iaccoca
Learning Machine
“I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines. They go to bed every night a little wiser than they were when they got up, and boy does that help, particularly when you have a long run ahead of you.”
— Charlie Munger
Once you have identified your deep fascination, Bill Gurley mentions that the next step is to commit to a lifetime of learning. He emphasizes that the titans of any industry, whether it is Danny Meyer in the restaurant business or Stephen King in literature, they never stop being students of their craft. They do not rest on their laurels or assume that their past successes guarantee future victories. Instead, they continuously consume information, study their predecessors, and look for new edges to sharpen their skills.
Gurley writes, “You can see this pattern of deep and continuous learning repeated in the titans of almost every industry. Danny Meyer studied every element of the restaurant business—and continues his studies of the field, even after all his success. Lorrie Bartlett, the Hollywood agent, consumed as many stories as she could as a kid and still reads every script she can. Jerry Seinfeld studied the best comics in the world.”
The beauty of this continuous learning process is that, if you have truly found your fascination, it will not feel like a chore at all. The pursuit of knowledge becomes an engaging and almost playful endeavor. You find yourself going down rabbit holes of information simply because you want to know the answer, not because it was assigned to you as a task.
“You want learning to be fun. You need it to feel like play. We’ve all been drawn down a rabbit hole of knowledge trying to answer some question or understand something that happened—knowing even in the moment that the entire endeavor might be a waste of time. But sometimes you really want to know something. Studying your field needs to feel like that. You would do it even if it weren’t your job. The knowledge is its own reward. Your curiosity and drive have to come naturally. You cannot force it.”
— Bill Gurley
Furthermore, to structure this lifelong educational journey, Gurley outlines a comprehensive framework for how you could approach your intellectual development. It is not enough to simply read, you must be intentional and multifaceted in your learning strategy. He mentions that there are four learning types: industry history for credibility, continuous updates for edge, specialization for uniqueness, and outside fields for breakthroughs. He elaborates that “First, you should learn the history of your chosen field. Then you need to commit to learning continuously, in a self-propelled way, throughout your career. What’s evolving? Who else in your field has big new ideas that you should know about? Third, you need to go deep in some specialized, unique way. In other words, you will develop unique insights and skills in your field that separate you from the rest. And, finally, you need to learn outside your chosen field—following other fascinations—because that type of far-away learning is actually the most likely to spark novel and truly impactful breakthroughs.”
By understanding the history of your field, you avoid repeating past mistakes and gain an appreciation for the foundational principles of your work. By learning continuously about current trends, you stay relevant and adaptable. By developing a specialized niche, you make yourself indispensable and create a unique value proposition.
Finally, by exploring entirely unrelated fields, you allow your brain to make novel connections, leading to the kind of innovative thinking that can redefine an entire industry. This relentless, multi-pronged approach to honing your craft ensures that you are always growing, always improving, and always moving forward.
“The illiterate of the 21st century will not be those who cannot read and write, but those who cannot learn, unlearn, and relearn.”
— Alvin Toffler
If you want to become a learning machine, you must be reminded of the principle of compounding as we have learned previously from Warren Buffett. As a matter of fact, the power of compounding is a mental model that shouldn’t be only used in investing. Compounding also works in terms of seeking wisdom or obtaining good habits. As a matter of fact, a one percent improvement every day leads to 37x improvement in a year.
Alternatively to investing, Buffett also uses it to think about his mind and body’s health. As a matter of fact, bad habits can also compound negatively. Even more concerning is the fact that you only get one mind and one body to last a lifetime. As Buffett once said, “It’s what you do right now, today, that determines how your mind and body will operate ten, twenty, and thirty years from now.” Buffett often mentions snowball as an analogy to understand compounding.
“I packed my little snowball very early, and if I had packed it ten years later, it would have been way different than where it stands on the hill right now. So I recommend to students that if you start out a little ahead of the game—it doesn’t have to be a lot, but it’s so much better than starting out behind the game. And credit cards really get you behind the game.” — Warren Buffett
“The snowball just happens if you’re in the right kind of snow, and that’s what happened with me. I don’t just mean compounding money either. It’s in terms of understanding the world and what kind of friends you accumulate. You get to select over time, and you’ve got to be the kind of person that the snow wants to attach itself to. You’ve got to be your own wet snow, in effect. You’d better be picking up snow as you go along, because you’re not going to be getting back up to the top of the hill again. That’s the way life works.”
— Warren Buffett
Find Mentors
“If I have seen further, it is by standing on the shoulders of giants.”
— Isaac Newton
Bill Gurley views mentorship as a supower, allowing you to accelerate your learning by borrowing from others’ experiences. He cites notably the example of Warren Buffett who learned about value investing through his mentor, Benjamin Graham. Great mentors can share with you hard-earned lessons so that you can avoid the pitfalls. Gurley writes, “Good judgment comes from experience, which comes from bad judgment. Why relearn things others already learned the hard way? A good mentor will share hard-earned lessons and industry insights, helping you learn in weeks or months what might otherwise take years. No matter how successful you become, it never hurts to ask for advice from people you trust when you are making hard decisions.”
Another example of the importance of mentorship is Mark Zuckerberg, who used to take long walks with Steve Jobs during the early days of Facebook. The two would discuss about everything from management approaches to Facebook’s overall company mission. In the current day and age, you don’t even need to be in direct contact with your mentors. Everyone can be studied remotely through books, interviews and social media.
“Start today by studying the greats in your field. Read their books, listen to their interviews, watch their videos on YouTube. If they are on social media, you can follow them and comment on their posts. If they ever follow you back, you can direct-message them—which is an incredibly powerful means to contact someone you idolize directly. If you charm someone, they might just respond.”
— Bill Gurley
This approach also works by having great relationship with senior colleagues at your current company. Gurley writes, “If you are early in your career at a company, you might approach a more experienced colleague for advice over coffee. If you are shifting careers, reach out to people in your new industry. Many mentorships start through informal conversations.”
The key is taking initiative. Mentors are busy people. They’re unlikely to chase you. But if you show up prepared, demonstrate that you value their time, and let your ambition show, many will be genuinely happy to help. As Tim Ferriss once said, “To learn and grow quickly, identify who inspires you, then reach out. The best mentors respond to ambition.”
Gurley elaborates that “This is a critical insight. Make sure your own ambition is on display during this process. If you are at this point in your journey, where you are searching for mentors, you have nothing to lose and everything to gain. Later in life, many of these people will be your co-workers and peers. But if you are just starting out, put your curiosity, your earnest (and ambitious) desire to learn, on display.”
Finally, Gurley believes in having multiple mentors or what former Facebook COO Sheryl Sandberg calls a “personal board of advisors.” It is often important to find different successful people to mentor you on different aspects. One can teach you about leadership while another can teach you about communication. Different people may have different areas of expertise and have different views on things which is extremely useful.
This reminds me of Shane Parrish’s concept of creating a board of directors in his head in order to help him with decision-making. Even better, he believes that this fictional board can include people from the present and the past. What better way of thinking about a problem than to do so under the lenses and advices of great ones like Charlie Munger.
Here’s what my personal board of directors would look like:
Warren Buffett
Charlie Munger
David Ogilvy
Henry Singleton
Thomas Mellon
Naval Ravikant
Benjamin Franklin
Thomas J. Watson
What about you?
Beyond the Book
Listen to "#413 How To Run Down A Dream" by Founders Podcast
Read "“Runnin’ Down a Dream: How to Succeed and Thrive in a Career You Love”" by Bill Gurley
Read "Become A Learning Machine" by Farnam Street
Read "Standing on the Shoulders of Giants" by Farnam Street
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