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Jason Calacanis's book club picks and book recommendations
Across 6 podcasts. Every show Jason Calacanis appears on, in one place — not just one.
Jason Calacanis’s book club picks
Jason Calacanis has picked 8 books for the book club on This Week in Startups. The latest is The Nvidia Way by Tae Kim, first picked in December 2024. Every pick, newest first:
Jason Calacanis’s most recommended books
- The Lean Startup by Eric Ries
- The Checklist Manifesto by Atul Gawande
- No Rules Rules: Netflix and the culture of reinvention by Reed Hastings
- The Ride of a Lifetime by Robert Iger
- Working Backwards by Colin Bryar
- The Power Law by Sebastian Mallaby
- Good to Great by Jim Collins
- Who is Michael Ovitz? by Michael Ovitz
- Unreasonable Hospitality by Will Guidara
- On Writing by Stephen King
Jason McCabe Calacanis is an American podcaster, Internet entrepreneur, angel investor, and author. On his podcast This Week in Startups, Calacanis frequently references and recommends books that span business history, memoirs, fiction, and psychology. He brought up Steven L. Peck's novella A Short Stay in Hell after seeing it highlighted by an online influencer. When talking with a young caller, Calacanis recommended a reading list for a well-rounded education, which included Akira Kurosawa's Something Like An Autobiography, Phil Knight's Shoe Dog, Steve Martin's Born Standing Up, Peter Biskind's Easy Riders, Raging Bulls, and Stephen King's On Writing as a way to unlock inspiration. In other episodes, Calacanis praised Abigail Shrier's Bad Therapy during a conversation with a guest and highlighted Bill Perkins's Die with Zero while arguing that affluent individuals should actively put their capital to use rather than sit on it. Across these episodes, Calacanis used literature to impart lessons on business, creativity, and personal philosophy.
Books recommended by Jason Calacanis
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The Lean Startup
The Lean Startup by Eric Ries is a foundational business guide that advocates for validated learning, rapid experimentation, and minimum viable products to help entrepreneurs build successful companies without wasting time or resources.
Discussed“So uh Steve Blank and Eric Reese created this methodology called lean startup. He's an entrepreneur and he's just really awesome and he created this methodology along with Eric Reese. Eric Reese wrote the book Lean Startup and you want to create a hypothesis and run an experiment”
Where to get it
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The Checklist Manifesto
The Checklist Manifesto by Atul Gawande is a nonfiction exploration of how simple checklists and systematic processes can dramatically reduce human error and prevent catastrophic failures in complex fields like medicine and aviation.
Recommended“And uh you know, that's why I talk about the Checklist Manifesto all the time. And you wanted to see who's hungry to get things done and who's a detail person in startups.”
Where to get it
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No Rules Rules: Netflix and the culture of reinvention
No Rules Rules: Netflix and the Culture of Reinvention by Reed Hastings and Erin Meyer details the radical management philosophy and unconventional corporate culture behind Netflix.
Discussed“and they have a culture deck and then they have no rules rules which um Erin Mayer did she was also on the program I haven't had read Hastings yet but Patty McCord had hers and uh then Reid Hastings did one”
Where to get it
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The Ride of a Lifetime
The Ride of a Lifetime by Robert Iger is a business memoir by the former Disney CEO detailing his professional journey, leadership philosophies, and strategies for navigating massive corporate transformations and creative challenges.
Discussed“and then you read uh ride of a Lifetime by Iger and then you put the CIA in between it and now you got the entire story and all the characters interweaving”
Where to get it
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Angel
Angel by Jason Calacanis is a comprehensive guide to early-stage investing, offering practical advice for startup founders and prospective angel investors navigating the venture ecosystem.
Discussed“Hey, Jason wrote this great book, Angel. It's in 12 languages. I would like permission. And I know this because Microsoft called my publisher, Harper's Business”
Where to get it
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Working Backwards
Working Backwards by Colin Bryar and Bill Carr is an insider account of Amazon's unique management practices, operational discipline, and customer-centric business strategies.
Discussed“And so then people started anticipating that person's questions and they said in the book working backwards which is the Amazon book that everybody's game got really higher because they knew that person was prepared had looked at the numbers and would always ask the question how did you come to that number”
Where to get it
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The Power Law
The Power Law by Sebastian Mallaby is a comprehensive history of venture capital that examines the legendary firms and high-stakes investments that shaped the modern tech economy.
Recommended“It'll explain, you know, the power law. It'll explain diversification. It'll explain the time horizon. It's called Angel. Or you can just read the power law and understand that like I don't know, 29 of 30 bets, 39 of 40 bets will return no capital”
Where to get it
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Good to Great
Good to Great by Jim Collins is a prominent business and management book that investigates what makes companies transition from being merely good to achieving sustained greatness.
Discussed“it's kind of like that good to Great Book Jim Collins wrote I don't know if you ever read that one but yeah for sure back when there were only like you know 100 business books that was one of the ones that always the the lesson there”
Where to get it
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Who is Michael Ovitz?
Who is Michael Ovitz? by Michael Ovitz is a compelling memoir by the legendary Hollywood superagent detailing the rise of Creative Artists Agency and the mechanics of the entertainment industry.
Recommended“Michael Ovitz was there for a bit read have you read the book who is Mike Ovitz I have not read that book actually just read it it's a great read”
Where to get it
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Unreasonable Hospitality
Unreasonable Hospitality by Will Guidara is a bestselling memoir and guide that details how exceptional, customer-focused service can transform businesses and leadership.
Discussed“Will G uh Gado who wrote unreasonable hospitality I had him on the program. Yeah, I do remember that.”
Where to get it
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On Writing
On Writing by Stephen King is a celebrated memoir and masterclass that blends the author's personal experiences with practical, no-nonsense advice for aspiring writers.
Recommended“Stephen King has a great one on writing. Stephen King's on writing. Really interesting.”
Where to get it
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Grinding it Out
Grinding it Out by Ray Kroc and Robert Anderson is the candid autobiography of the man who built McDonald's into a global fast-food empire through relentless persistence and operational discipline.
Discussed“I showed myself taking the screenplay yeah for founder the founder and the book rinded out the PDF of the book rinded out about Ray Croc and a bunch of other Ray Croc business case studies”
Where to get it
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The Anxious Generation
The Anxious Generation by Jonathan Haidt is a prominent non-fiction book that explores the profound psychological impacts of smartphones and social media on youth mental health.
Discussed“and if you read um what is Jonathan ha's book gosh sorry my shortterm memory anxious Generation Um and I had him on uh the Allin interview series you going see it over there Jonathan hate Allin”
Where to get it
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Antifragile
Antifragile by Nassim Nicholas Taleb is a groundbreaking exploration of systems that not only withstand shocks and disorder but actually thrive and grow stronger when exposed to volatility, stress, and uncertainty.
Discussed“This is a great book. And what anti-fragile means, people think it's not being fragile. I think it actually the more proper uh definition and my my gentleman here, my co-host will look it up exactly what Nim TB means by it.”
Where to get it
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Bad Blood
Bad Blood by John Carreyrou is an immersive investigative non-fiction book that uncovers the massive corporate fraud behind Elizabeth Holmes and her blood-testing startup, Theranos.
Discussed“well a bunch of walgreens executives apparently according to bad blood felt a lot of pressure that they were going to lose the deal and they didn't do their diligence”
Where to get it
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How to Win Friends and Influence People
How to Win Friends and Influence People by Dale Carnegie is a classic self-help manual focused on interpersonal communication, relationship building, and effective social influence.
Discussed“You need to productize how to win friends and influence people. Like, if you just do that And you know, that book has a negative connotation to it cuz it has influence people on it, but it actually has some good things, which is if you show interest in people, you'll be an interesting person is the basic thing.”
Where to get it
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Rework
Rework by Jason Fried and David Heinemeier Hansson is a provocative and influential business manifesto that challenges traditional corporate wisdom, offering unconventional insights into productivity, remote work, and running a lean organization.
Discussed“they literally wrote a book rework telling other companies how they should work and they were right they told companies they should do remote work it'd be better for employees”
Where to get it
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Amp It Up
Amp It Up by Frank Slootman is a direct management guide focused on building a high-performance execution culture, raising expectations, and driving hypergrowth through urgency and intensity.
Discussed“it was episode 1362 the book amp it up leading for hyper growth by raising expectations increasing urgency and elevating intensity”
Where to get it
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Hillbilly Elegy
Hillbilly Elegy by J.D.
Recommended“and if you haven't read JD's book I read your book long before all of this and I just want to say your book was so inspiring and I I have recommended it long before today to you know literally hundreds of people it's a fantastic read if you haven't read it”
Where to get it
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Red Notice
Red Notice by Bill Browder is a gripping memoir detailing the author's financial career in Russia, his subsequent battle against state corruption, and his campaign to pass the Magnitsky Act following the tragic murder of his lawyer, Sergei Magnitsky.
Recommended“you know in Russia obviously uh if you've read red notice your lawyer will be murdered like that book by the way incredible incredible I mean it just if you want a incredible book to read this summer or listen to the audio book's fantastic as well”
Where to get it
- Shoe Dog by Phil Knight
- Thinking in Bets by Annie Duke
- Creativity, Inc. by Ed Catmull
- Born Standing Up by Steve Martin
- Something Like An Autobiography by Akira Kurosawa
- Man's Search for Meaning by Viktor E. Frankl
- The Black Swan by Nassim Nicholas Taleb
- The Five Dysfunctions of a Team by Patrick Lencioni
- Never Split the Difference by Chris Voss
- Radical Candor by Kim Malone Scott
- The purpose driven church by Rick Warren
- The Bell Curve by Richard J. Herrnstein
- The Contrarian by Max Chafkin
- Alchemy by Rory Sutherland
- Billion Dollar Loser by Reeves Wiedeman
- The Kid Stays in the Picture by Robert Evans
- I Love Capitalism! by Ken Langone
- Powerful by Patty McCord
- All Tomorrow's Parties by William Gibson
- Crossing the Chasm by Geoffrey A. Moore
- Idoru by William Gibson
- Atlas Shrugged by Ayn Rand
- Range by David J. Epstein
- The adventures of Tom Sawyer by Mark Twain
- The Hobbit by J.R.R. Tolkien
- Zero to One by Peter Thiel
- Chaos Monkeys by Antonio Garcia Martinez
- The Fish That Ate the Whale by Rich Cohen
- Maus I: A Survivor's Tale by Art Spiegelman
- The chickenshit club by Jesse Eisinger
Questions about Jason Calacanis’s book recommendations
What book does Jason Calacanis recommend most?
The Lean Startup by Eric Ries. Jason Calacanis recommended it in 15 episodes, with 6 explicit recommendations.
How many books has Jason Calacanis recommended on podcasts?
We have found 257 books Jason Calacanis recommended or discussed, across 326 episodes of 6 podcasts. Ad reads and passing mentions are not counted.
What books are on Jason Calacanis's reading list?
The books Jason Calacanis has recommended most on podcasts are The Lean Startup by Eric Ries, The Checklist Manifesto by Atul Gawande, No Rules Rules: Netflix and the culture of reinvention by Reed Hastings, The Ride of a Lifetime by Robert Iger and Working Backwards by Colin Bryar. The year-by-year lists below have all 257.
What books has Jason Calacanis picked for the book club?
The Nvidia Way by Tae Kim, The Power Law by Sebastian Mallaby, Working Backwards by Colin Bryar, No Rules Rules: Netflix and the culture of reinvention by Reed Hastings, Never Split the Difference by Chris Voss, The Hot Hand by Ben Cohen, The Fish That Ate the Whale by Rich Cohen and The Ride of a Lifetime by Robert Iger, newest first.
What did Jason Calacanis recommend on This Week in Startups?
The Lean Startup, The Checklist Manifesto and No Rules Rules: Netflix and the culture of reinvention, among 228 books in all.
What is the latest book Jason Calacanis recommended?
A Short Stay in Hell, recommended on This Week in Startups (2026-10-24).
People who recommend the same books
Books Jason Calacanis wrote
Jason Calacanis’s latest episodes with books
Jason Calacanis’s book recommendations by year
All 257 books Jason Calacanis recommended or discussed across 326 episodes, filed by the year each episode came out. Each year goes episode by episode, with the minute every book came up.