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(272)

Chicago Is at a Breaking Point (But She Says She Can Fix It) - Susana A. Mendoza

Chicago Is at a Breaking Point (But She Says She Can Fix It) - Susana A. Mendoza

Today on Open Book, we're not joined by an author, but by a woman fighting to become the next mayor of Chicago. Susana Mendoza grew up in Chicago learning how to stand up to bullies, fight for what sh...

14 Aug 28min

The Secretive Family Behind a $13 Trillion Financial Empire

The Secretive Family Behind a $13 Trillion Financial Empire

Fidelity is one of the most powerful financial institutions in America, but the story of the family behind it has largely remained hidden. Justin Baer joins me to reveal how the Johnson dynasty built ...

11 Aug 35min

Ex-CIA Officer: America Has a 20% Chance of Splitting Apart - James Telfer

Ex-CIA Officer: America Has a 20% Chance of Splitting Apart - James Telfer

A former CIA officer sat down to write a "fun airport novel" and ended up putting a 20% probability on America actually splitting apart. James Telfer joins me to talk about what he saw from the inside...

6 Aug 29min

America is Deeply Broken (Here's How We Can Fix It) - Rye Barcott

America is Deeply Broken (Here's How We Can Fix It) - Rye Barcott

What does real courage look like when the cameras stop rolling, and the tribe wants you to fall in line? On this episode of Open Book, I sit down with Rye Barcott, Marine, author, and founder of With ...

4 Aug 34min

He Repaired My Marriage And Then We Lost Him Forever - Mike Maimone

He Repaired My Marriage And Then We Lost Him Forever - Mike Maimone

I got fired from the White House, my marriage was falling apart, and the guy who talked me off the ledge was my publicist, Howard Bragman, a man so full of life he'd call you 'numbnuts' one minute and...

30 Jul 30min

July 2026 Q&A: Will I Run For Office? How I Read So Much? How To Fix The American Education System?

July 2026 Q&A: Will I Run For Office? How I Read So Much? How To Fix The American Education System?

You send me the questions, I give you the answers, no filter, no spin, straight from the gut. This month: would I actually run for office, how I manage to read a book a week, why Independence Hall is ...

28 Jul 31min

The Heartbreaking Atrocity of The Ukraine War (And Why You Should Care) - James Verini

The Heartbreaking Atrocity of The Ukraine War (And Why You Should Care) - James Verini

After reading his book on the war in Ukraine, you will understand the significance of this conflict as you never have before. Putin thought he could topple Kyiv in days and convinced himself Ukraine w...

23 Jul 31min

The Truth About Guns In America They Don't Want You To Know! - Mike McIntire

The Truth About Guns In America They Don't Want You To Know! - Mike McIntire

Three-time Pulitzer winner Mike McIntire joins me to talk about his new book Ricochet (out today), and this one hit me hard. We've got more guns than people in this country, and I wanted to know how w...

21 Jul 31min

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