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On with Kara Swisher

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

On with Kara Swisher

New York Magazine

Society & Culture

4.23.2K Ratings

🗓️ 26 February 2026

⏱️ 65 minutes

🧾️ Download transcript

Summary

Bill Gurley, accomplished venture capitalist, longtime Silicon Valley “worrywart,” and early Uber backer, joins Kara Swisher to discuss how to build a career you love and the tech industry’s sharp turn to the right.  Gurley’s new book Runnin’ Down a Dream, guides readers on how to find and nurture a truly fulfilling career — and his advice is the polar  opposite of Scott Galloway’s “follow your talent, not your passion.”  Kara and Bill talk about how to find your fascination, and why the best careers are built through craft, peers, mentors, and a willingness to start at the bottom. They also dig into AI-related job loss anxiety and Gurley’s growing focus on public policy — from regulatory capture to the concentration of power in the Mag 7. Plus: an expert question from Uber CEO Dara Khosrowshahi. Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

I learned a lot from the mailroom.

0:02.4

The key thing I learned is that really talented people were very generous and untalented people weren't.

0:19.1

Hi, everyone, from New York Magazine and the Vox Media Podcast Network.

0:22.5

This is on with Kara Swisher, and I'm Kara Swisher.

0:25.6

My guest today is Fain Venture Capitalist, an author of Running Down a Dream,

0:29.8

How to Thrive in a Career You Actually Love, Bill Gurley.

0:33.8

Bill was a top-rank research analyst on Wall Street.

0:36.1

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, next door, open

0:55.8

table, stitch fix, Zillow, and most notably Uber. After a long and successful career,

1:00.8

he's retired from venture capital and written a personal development book about finding the

1:04.2

career you actually love. I was surprised when I got it when he wrote me. I thought I was in a

1:10.2

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 we don't agree with him, he's always been a gentleman. And he actually reads and is an intellectual in many ways. He's always been that way. And 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.

1:28.4

So I'm curious 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

1:32.7

to do what you love. And of course, I'll ask him about President Trump in politics,

1:36.0

because now it's inescapably intertwined with everything in American life, especially the tech

1:41.4

industry. Our expert question comes from Dara Costa Shahi, the CEO of Uber.

1:46.3

So stick around.

1:59.8

Megan Rapino here.

2:01.1

This week on a touch more, we've got something for everyone.

2:04.3

We're talking about the U.S. women Olympians taking home more medals than the men,

2:09.8

the U.S. women's national team roster heading into the She Believes Cup,

2:13.4

and the latest on the WMBA-CBA negotiations.

...

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