The Career Advice That Ruins Lives (And What Actually Works) - Bill Gurley

The Career Advice That Ruins Lives (And What Actually Works) - Bill Gurley

Today on Open Book, I’m joined by legendary venture capitalist Bill Gurley, whose new book Runnin' Down a Dream challenges a lot of the career advice we give young people. Bill argues that the safest career path isn’t the “safe job” at all—it’s finding something you’re genuinely fascinated by and chasing it relentlessly. We’re going to talk about curiosity, regret, and how to build a career you actually love. Bill Gurley is a general partner at Benchmark, a leading venture capital firm in Silicon Valley. Over his venture career, he has invested in and served on the board of such companies as Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow. Gurley has written about technology and other subjects on his popular blog, Above the Crowd, for over 20 years. This is a sensational book. Get your copy of Runnin' Down a Dream: How to Thrive in a Career You Actually Love here: https://amzn.to/46X4rEc Anthony Scaramucci is the founder and managing partner of SkyBridge, a global alternative investment firm, and founder and chairman of SALT, a global thought leadership forum and venture studio. Pre-order my next book, All the Wrong Moves: How Three Catastrophic Decisions Led to the Rise of Trump, out on the 17th of September in the UK and the 22nd of September in the US: ⁠https://linktr.ee/anthonyscaramucci⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Episoder(259)

Jun 2026 Q&A: Breaking From Trump, Reforming American Democracy & Book Recs

Jun 2026 Q&A: Breaking From Trump, Reforming American Democracy & Book Recs

It's the June Q&A on Open Book, and you came at me with everything this month: aliens, whether there's a reckoning coming when Trump's term ends, and the honest reason it took me so long to break from...

30 Jun 26min

The Coach Everyone Called a Failure (He Proved Them Wrong) - Monte Burke

The Coach Everyone Called a Failure (He Proved Them Wrong) - Monte Burke

Pete Carroll was written off as a flake, a fraud, and a two-time NFL failure, but then he built one of the greatest dynasties in college football history. This week on Open Book, Monte Burke and I get...

25 Jun 28min

America Repeats the Same Crisis Every 80 Years. Here's How We Overcome It - Bob Crawford

America Repeats the Same Crisis Every 80 Years. Here's How We Overcome It - Bob Crawford

Does America face a defining crisis every 80 years? In this episode, I sit down with musician and author Bob Crawford to explore the remarkable life of John Quincy Adams, why history may be rhyming on...

23 Jun 33min

Historian: The Untold Story of WWII's Most Fascinating Person - Geoffrey Roberts

Historian: The Untold Story of WWII's Most Fascinating Person - Geoffrey Roberts

Kathleen Harriman was there at the center of it all, at Churchill's side in the Blitz, in Stalin's Moscow, at Yalta, and somehow history almost forgot her. My guest today, renowned historian Geoffrey ...

18 Jun 27min

High Performance Psychologist: The #1 Fear Holding You Back From Your Full Potential

High Performance Psychologist: The #1 Fear Holding You Back From Your Full Potential

What if the biggest thing standing between you and your best life isn't failure, it's what other people think of you? Today, I sit down with world-renowned high-performance psychologist Michael Gervai...

16 Jun 33min

The Rise and Fall of a Tech Titan - Katie Prescott

The Rise and Fall of a Tech Titan - Katie Prescott

Mike Lynch was a working-class kid from East London who built one of Britain's greatest tech companies, and then watched it all collapse in a fraud scandal that stretched across two continents, two co...

11 Jun 29min

You Can't Understand America Without Understanding New York - Russell Shorto

You Can't Understand America Without Understanding New York - Russell Shorto

Before New York was New York, it was New Amsterdam, a Dutch colony built on pluralism, capitalism, and a radical idea that tolerance could be a competitive advantage. Russell Shorto joins me on Open B...

9 Jun 30min

The AI Expert Who Will Change Your Mind About AI - Josh Tyrangiel

The AI Expert Who Will Change Your Mind About AI - Josh Tyrangiel

I've been saying it for years, AI is the most important conversation we're having right now. Josh Tyrangiel spent a year hunting for the people actually using it to save lives, and what he found will ...

4 Jun 31min

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