Why ‘Playing It Safe’ In Your Career Doesn’t Pay with VC Bill Gurley

Kara Swisher (0:00)

I learned a lot from the mailroom. The key thing I learned is that really talented people were very generous and untalented people weren't.

Hi, everyone from New York Magazine and the Vox Media Podcast Network. This is On with Kara Swisher and I'm Kara Swisher. My guest today is famed venture capitalist and author of Runnin Down a Dream, How to Thrive in a Career You Actually Love, Bill Gurley. Bill was a top-rank research analyst on Wall Street. When I met him, he covered the PC industry. He worked as the lead analyst on the Amazon IPO before decamping for Silicon Valley. There, he became a general partner at Benchmark Capital, a celebrated VC firm known for early-stage investing and very tall venture capitalists. Bill was an investor in companies like GrubHub, Nextdoor, OpenTable, Stitch Fix, Zillow, and most notably Uber. After a long and successful career, he's retired from venture capital and written a personal development book about finding the career you actually love. I was surprised when I got it, when he wrote me. I thought I was in a beef with Bill Gurley, because I'm in a beef with all the Silicon Valley people, but I wasn't because Bill is thoughtful. He's a great debater. Even when you don't agree with him, he's always been a gentleman. He actually reads and is an intellectual in many ways. He's always been that way. So I'm excited to talk to him. He's also the polar opposite of what Scott preaches on Pivot, so that's a relief. So I'm curious to hear Bill explain why it's actually important to do what you love. Of course, I'll ask him about President Trump and politics because now it's inescapably intertwined with everything in American life, especially the tech industry. Our expert question comes from Dara Khosrowshahi, the CEO of Uber. So stick around.

SPEAKER_3 (2:01)

This episode is brought to you by Nespresso. Introducing Virtuo Up, the latest in a long line of innovation from Nespresso. It's innovation you can touch, sense and taste in every single cup. With a three second start, easy open lever, and dedicated brew over ice button, it's even easier to enjoy your coffee your way. Sip for yourself. Shop Virtuo Up exclusively at nespresso.com.

Rabindranath Son (2:28)

When things get hard, how do you talk to yourself?

I'm Rabindranath Son, VP of Fitness Programming and Head Instructor at Peloton. This week on my new podcast, Project Swagger, I'm sharing my strategies for how to build better self-talk. It's time to work on befriending yourself. Follow Project Swagger wherever you get your podcasts.

SPEAKER_5 (2:51)

For a lot of Americans, credit card debt feels like a fact of life.

SPEAKER_6 (2:55)

I think it's just important for people to understand how credit can work for you or against you.

SPEAKER_5 (3:02)

Why that little piece of plastic has so much power. That's this week on Explain It To Me. Find new episodes Sundays wherever you get your podcasts.

Kara Swisher (3:22)

Bill Gurley, thanks for coming on On.

Bill Gurley (3:25)

Thanks for having me on, Kara.

Kara Swisher (3:26)

I'm gonna get into a bunch of stuff, but let's start with you. Within Silicon Valley, you're incredibly well known as a renowned former VC. I met you when you were investing.

Bill Gurley (3:35)

I was a stock analyst, and then I spent a year and a half at Hummer Wimblad, and then I went to Benchmark. I think it was probably back when I was a stock analyst.

Kara Swisher (3:42)

It was when you were an analyst. I did, I met you when Mary Meeker was also a stock analyst, and then you both became investors. And then I think I ran into you again at Hummer, and then I think I wrote the story when you went to Benchmark, and then you invested in eBay. But fans of the show, people who know you, actually know you from Superpump, is the fictionalized version of you played by Kyler Chandler. Tell people who don't know who you are, who you are.

Bill Gurley (4:04)

I grew up in Texas. My father was a very early employee at NASA, which was, I think, quite influential on me that he did that and had such a ride. I was a end of the bench D1 basketball player that didn't get very many minutes.

I got a lot of experiences and became a computer scientist, worked at Compaq, which you'll remember, but most people won't, as an engineer for two years. Then business school, then Wall Street Analyst for three years in New York City and then a year with Frank Quatrone. He's the one that took me out to Silicon Valley.