In my conversation with Bill Gurley, we talk about how to pursue your passion, how your peers can be your mentors, why gratitude matters, and how a zero-sum mentality will get you nowhere fast.
Bill Gurley joins us as a general partner at Benchmark, a leading venture capital firm in Silicon Valley. Over the course of his career, he has influenced some of the most transformative companies including OpenTable, Uber, Zillow, Grubhub, Stitch Fix, and Snapchat. Bill earned a bachelor’s degree in computer science from the University of Florida and later received an MBA from the University of Texas at Austin.
In his book Runnin’ Down a Dream, Bill wants you to do exactly that. He writes, “If you’ve only got one shot then why not do what makes you happy?”
Tune into my conversation with Bill Gurley to learn how to do what makes you happy on Find Your Passion Career Podcast!
From Blog to Book
Bill didn’t begin with a book in mind. He started with a blog in his field, learning how systems worked, synthesizing information, and writing it up. He also read a ton of autobiographies and noticed a trend he wanted to capture. That idea eventually became a speech he gave at the University of Texas. The speech resonated, and that same message became the book.
In Runnin’ Down a Dream, Bill highlights stories of people who started at the bottom, often in nontraditional fields, and shares the principles behind their success. Bill himself spent years in other fields before venture capital. He points to those experiences to remind listeners that it’s okay if you’re not in your dream job right now. In fact, he says it’s often easier to know when you’re not in your dream job.
Bill suggests checking in with yourself regularly. “At least once a year raise your head up and say, ‘Do I want to do this for the next 30 years?’” And don’t feel like you’re stuck, it’s ok to leap—most people change their careers.
One signal that you may be moving toward your dream? You find yourself constantly learning on your own time.
Tell People Where You Want to Go
Bill’s journey was shaped by paying attention to what he was drawn to after the workday. He found himself researching stocks for fun, which inspired him to go to business school. He worked at a high-growth tech company and liked the experience and the disruptive nature of the industry. He even points to his times counting cards playing blackjack in Vegas and how thinking a lot about gambling with an edge helped to point him toward his passion.
He knew venture capital was where he wanted to go but that it was ultra competitive. He went to Wall Street with venture capital in the back of his mind. Finally, he decided to make the career change, and he told someone what he wanted to do. With a promise to work for them first, they offered to help Bill get there.
Sometimes the next step starts with simply saying your dream out loud.
Your Peers Are Not Your Competitors
This idea may surprise you. Bill encourages a reframe: your peers are not your competitors—they are your peer mentors. In the book, he talks about a group of young Athletic Directors who started a WhatsApp thread and supported each other over decades. They shared what worked, exchanged advice, and opened doors for one another.
Peers can help you learn at a rapid rate and expand your network exponentially. “Find likeminded people that are trying to achieve the same thing you are and hang out with them as much as you can and support them as much as you can,” says Bill.
A zero-sum mentality will get you nowhere fast. When you believe there’s only one seat at the table, you isolate yourself. When you believe there’s room for others to win too, you build something much bigger.
On Rejection and Feeling Unqualified
Bill reflects on moments of doubt. Surrounded by University of Florida basketball players who went on to the NBA, he knew as a benchwarmer that he wasn’t going to get there.
And again in his career, when he changed companies and the area he was covering, he said, “I really felt like a fraud.” Reflecting on these moments, Bill shares that this is all part of the career experience. As you gather information, you can start to feel like you know even less than before. But that’s often what growth feels like.
“If you’re sticking your toe into learning something new, just know there’s going to be a lot of anxiety, and don’t judge yourself too early.”
Rejection and discomfort don’t mean you’re unqualified. They mean you’re growing.
Future-Proof Your Career
Bill is a big proponent of continuous learning in every way: reading, YouTube videos, podcasts, AI. “You can learn all the time, anytime,” he says.
He explains that humans evolve with their tools and encourages people to think about AI in that same way. Think of AI as the Excel and PowerPoint of today, he shares. Future-proof yourself by knowing as much as possible and staying curious.
Form the Habit of Always Give Back
One theme of Bill’s book that stood out is the idea of always giving back. Don’t wait until you’re wildly successful to give back either. Start with this mindset early. “You’re going to build more relationships, stronger relationships,” he says.
Bill encourages taking the time to send that thank-you note. And that 15 minutes a mentor gave you? Pass it on. Offer it to someone else.
It’s not just the right thing to do—it’s also a helpful technique. When people feel genuine gratitude from you, they’re more inclined to help. Over time, that habit of appreciation and generosity can become a superpower.
After listening to Bill’s story, one lesson is clear: runnin’ down your dreams isn’t a solo act. It involves reflection, courage, continuous learning, peer mentorship, and gratitude. To tune in to Bill’s full interview, download the episode here on Spotify or Apple Podcasts.
FYPC Podcast Ep. 65: Lori Bumgarner, Career Coach and Author