Legendary VC: This Learning Habit Separates the Winners

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May 2026

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Bill Gurley built a career betting on bold ideas: He was an early investor in Uber, Zillow, and Nextdoor. Those successes helped turn Benchmark, the VC firm where he’s general partner, into one of the most famous names in Silicon Valley. Now he wants to help other people make similarly bold bets — on themselves.

His new book, Runnin’ Down a Dream: How to Thrive in a Career You Actually Love, draws on lessons from the accomplished people that he’s met and invested in. They all share a similar quality, Gurley says: They have a relentless drive to get better at what they do, despite whatever barriers they face.

For example, he tells the story of Jen Atkin, a celebrity hairstylist who has worked with the Kardashians, Jennifer Lopez, and Katy Perry, and launched her own brand Ouai. People might see her biography and think: Well, business success came easy to her — because she already had access to famous people. But before she landed jobs with all those famous people, she arrived in L.A. with nothing but determination and $300 in her pocket. “She finagled her way into a front desk job at a salon and then attended a free vocational school in cosmetology that was offered in the city of Los Angeles,” Gurley says. “It is still offered, and most people don’t take the opportunity to go do those things. Then she parlayed this into an insanely successful career.”

Gurley joined me on the How Success Happens podcast, to share how to build an opportunity-seizing mindset. Here’s his playbook for activating your dreams.

A common fear among would-be entrepreneurs is: “I waited too long. The industry is too big now. I’ll never get in.” What do you say to that?

There’s a wonderful book by Daniel Pink called The Power of Regret. He says that, as we get older, our largest regrets — the ones that really weigh on our psyche — are not the mistakes we made. Instead, they’re what he calls “boldness regrets” — the bold moves we didn’t make at all. A lot of people might hesitate to do something and say, “I’m afraid I’m gonna do that and fail.” Yet, as you get to a later point in life, you’re much more likely to regret that you didn’t try.

Bezos has this thing called the regret minimization framework. It’s about imagining yourself later in life and asking: At that point, will you wish you had tried? For the book, I profile four people who started over age 40. My favorite might be Bert “Tito” Beveridge, the maker of Tito’s Handmade Vodka. He started his career as a seismologist and then as a mortgage broker, and came up with the idea to go do this at 40. Now he has, I think, one of the most successful spirit companies in the country.

What separates the people who really excel?

They’re constantly learning.

Many people quit learning at the college level, and then they just go do their job. But very successful people are constantly learning. I call it external learning. They’re spending their free time getting better at whatever this occupation is. Look at professional sports. Do you think Steph Curry still practices outside of games? The answer is yes, of course he does.

That’s why it’s so critical to do what you love. If you don’t love it, you’re not going to be motivated to keep learning. I think a great test of whether you’re actually targeting your dream job is: Would you spend your spare time getting better at it or learning more about it?

How have you worked on improving your own skills?

I was fairly unsuccessful in English and writing classes in high school, and developed those skills later in life by reading more. I had no experience in public speaking, but I leaned into it and did it more and more. So I’d say: Anything you think of as a weakness can be improved by simply doing it again and again.

That strategy can change as you get older. Early on in your career, work on your weaknesses. Then, by the time you’re 35 or 45, go nuts on your strengths. Exploit your strengths.

Image Credit: Bloomberg | Getty Images

You’ve written about the importance of mentorship. For someone who doesn’t have an obvious mentor around them, how do they actually make those connections?

When people think of mentors, they often want their mentor to be someone like Warren Buffett. And that’s not realistic. So I suggest they have two groups of mentors — what I call aspirational mentors and then realistic mentors.

For the aspirational ones, make a list of the people who really stand out in your field, who you want to attack and study and learn from. Through YouTube videos and podcasts, a lot of these people are out there talking about what they do, and you can go consume all that.

Then you should identify realistic mentors, who are people you’ll actually meet with. Just be more pragmatic about this. These are people two tiers down from the greats — the ones who no one ever calls. Find out who they are. They’ll be flattered if you’re studying them. They may not a