Bill Gurley on Failure, Mentors, and Why You Need to Relax About Your Career

**Dan Bova** (0:00)
One of the biggest struggles for entrepreneurs trying to achieve success is time. There's not enough of it. You're stuck in the weeds doing too much. You definitely don't have time to be chasing down office supplies or tech gear from five different stores. That's why there's Walmart Business. With one free account at business.walmart.com, you get access to a huge selection of business essentials, from cleaning supplies and office tech to workwear and even fresh food, all at Walmart's everyday low prices. You can set up multi-user accounts for your team, automate your orders with subscriptions, and even track spending with built-in tools. Your stuff can be delivered or you could pick it up at your local Walmart. Want to make things even easier? Well, with Walmart Business Plus, you get free shipping with no minimum, rewards on large orders and powerful spend analytics to help you make smarter decisions. Walmart Business is built for entrepreneurs, saving you time, money, and hassle, so you can get back to what matters, growing your business. Sign up today at business.walmart.com. Terms apply.

**Bill Gurley** (1:21)
AI is incredible. It can teach you how to fry an egg and even write a poem.

**Dan Bova** (1:26)
Pirate style.

**Bill Gurley** (1:28)
But it knows nothing about your work. Slackbot is different. It doesn't just know the facts. It knows your schedule. It can turn a brainstorm into a brief. And it doesn't need to be taught. Because Slackbot isn't just another AI. It's AI that knows your work as well as you do. Visit slack.com/meetslackbot to learn more.

**Dan Bova** (1:50)
I've read a lot of interviews with you. Invariably, somebody asks you about Google. And you missed the opportunity to become an early investor.

**Bill Gurley** (1:58)
I've never been upset by that. In fact, I've often told that story. It's quite a lesson, right? Like in venture, missing something like that is the biggest kind of mistake you can possibly make. Investing in something that doesn't work, you lose one time your money. But here, you missed out on an opportunity to make 10,000 times your money. Having lived through that, I think it was motivating. Like, I'm not going to let that happen again.

**Dan Bova** (2:26)
Hey, everyone, welcome to How Success Happens. I'm Dan Bova, writer and editor at entrepreneur.com, and I've got a cold. But more importantly, I've got an incredible guest today. Bill Gurley is a legendary investor, general partner at Silicon Valley VC firm Benchmark. He's invested in and served on the boards of such companies as Nextdoor, OpenTable, Uber and Zillow. I've heard of a few of those, so he must be pretty good at what he does. He has written and spoken extensively about the intersection of business and technology, and has a new book coming out called Runnin Down a Dream that will be available on February 24th. Welcome, Bill.

**Bill Gurley** (3:11)
Thanks for having me, Dan. Greatly appreciated.

**Dan Bova** (3:13)
Bill, my first question is, I looked at your bank account, and I'm fairly certain that you're probably the most financially successful person who has come on the show. My first question is two parts. What made you want to write a book, and more broadly, what makes you want to do anything anymore? You could obviously just stop and live a very comfortable life for the rest of your life.

**Bill Gurley** (3:39)
I was in a moment in my life where I was reading a ton of biographies. I imagine a lot of your listeners have had that journey or go through part of a journey like that. And I noticed this kind of common thread across these three dissimilar biographies, people from far away fields. One was a restaurateur, one was a folk singer, and one was a basketball coach. And they all started from zero with a lot of intentionality, and they all ended up at the top of their field. And I noticed that they were adopting a similar playbook. As an idea and a writer, like, the minute it clicked, I felt like I had to, I literally have a place where I keep notes for new ideas, and I wrote it down. And I did it as a presentation at the business school where I went, and they posted it online, and a couple people noticed, like James Clear, who wrote Atomic Habit, saw it and said, this is fantastic.

**Dan Bova** (4:34)
You're being a little bit humble with your video. A few people sort of, a few million people saw it, but you know, it is an incredible video, and I definitely suggest people track down this talk that Bill gave. So who did you speak to when you talked to people for the book? Who did you talk to?