Appearances

• 
  Lex Fridman Podcast

  #161 – Jason Calacanis: Startups, Angel Investing, Capitalism, and Friendship · Feb 2021

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• 
  Modern Wisdom

  How Does Angel Investing Work? - Jason Calacanis - #154 · Mar 2020

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• 
  The Twenty Minute VC (20VC)

  20VC: Jason Calacanis on The 4 Questions Investors Must Ask Founders, Whether YC Have Scaled Their Process Successfully & Why Early Founder Liquidity Is Good Not Bad · Aug 2017

  Jason Calacanis: The World's Greatest Angel Investor · Jun 2015

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• 
  Decoder with Nilay Patel

  Recode Decode: Jason Calacanis · Mar 2020

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• 
  My First Million

  #150 - Jason Calacanis Joins The Brainstorm To Talk Robinhood, Gambling and the Opportunities He's Investing In · Feb 2021

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• 
  The Knowledge Project

  #81 Jason Calacanis: Intelligent Risk · Apr 2020

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• 
  The Tim Ferriss Show

  #635: Jason Calacanis on Brooklyn Grit, Big Asks, Angel Investing (Uber, Calm, Robinhood, and more), The Magic of Thinking Big, and St*bbing People in the Face but Never in the Back · Nov 2022

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• 
  TRIGGERnometry

  What Does This Mean for America - Jason Calacanis · Nov 2024

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• 
  Plain English with Derek Thompson

  Market Meltdown: Why Tech and Crypto Are Crashing - and What Happens Next · May 2022

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• 
  Odd Lots

  Jason Calacanis On the Expensive Lesson Coming to Silicon Valley · Jul 2022

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• 
  The Bulwark Daily

  Jason Calacanis: The Silicon Valley Vibes Are Still Pro-Trump · Jun 2026

  Jason Calacanis: Anarcho Capitalism · Aug 2025

  BONUS EPISODE with Jason Calacanis: The Civil War in Silicon Valley · Oct 2024

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• 
  The Megyn Kelly Show

  Power of Trump 2.0, Why Elon and DOGE are Working, and Independent Media's Impact, with Jason Calacanis and Chamath Palihapitiya of All-In | Ep. 1008 · Feb 2025

  Crime and Chesa Boudin's Recall, and Elon Musk's Twitter Plan, with Jason Calacanis and David Sacks | Ep. 337 · Jun 2022

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• 
  The Logan Bartlett Show

  EP 39: All-In’s Jason Calacanis Joins, Breaking Into Media, Tech in Journalism and the Kanye Controversy · Oct 2022

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• 
  The Meb Faber Show

  Jason Calacanis on Democratizing Venture Capital, How to Handle Large Winners, & Why The Price You Pay Matters...Even in Venture Capital | #469 · Mar 2023

  #69 - Jason Calacanis - “This is a Little, Secret Way... A Dark Art of Becoming Truly Wealthy... Massive Wealth" · Aug 2017

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• 
  The Peel with Turner Novak

  Inside the All-In Podcast: Lessons from Elon, Trump, Oprah, Travis Kalanick, Investing in 100+ Startups per Year with Jason Calacanis · Dec 2025

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• 
  The Jordan Harbinger Show

  100: Jason Calacanis | Advice from the Most Successful Angel Investor · Sep 2018

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Others on Lex Fridman Podcast

• DHH
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• Anthony Kaldellis
• Jensen Huang
• Jeff Kaplan
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• Paul Rosolie
• Irving Finkel
• Michael Levin
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Others on Modern Wisdom

• Sasha Hamdani
• Stan Tatkin
• Codie Sanchez
• Kanika Batra
• David Sinclair
• Johnny Chang
• Daniel Lieberman
• Jimmy Carr
• Peter Santenello
• Bill Thompson
• Jett Franzen
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Others on The Twenty Minute VC (20VC)

• Demis Hassabis
• Marc Andreessen
• Aravind Srinivas
• Mark Cuban
• Sam Altman
• Yann Lecun
• Bill Ackman
• David Friedberg
• Bill Gurley
• Bryan Johnson
• Jake Paul
• Winston Weinberg
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Others on Decoder with Nilay Patel

• Demis Hassabis
• Sundar Pichai
• Aravind Srinivas
• Steve Aoki
• Ro Khanna
• Eugenia Kuyda
• Ronan Farrow
• Mustafa Suleyman
• Brian Chesky
• Joseph Cox
• Ben Smith
• Casey Newton
• all 827 guests

Others on My First Million

• Saagar Enjeti
• Pieter Levels
• Andrew Huberman
• Tom Freston
• David Friedberg
• Michael Saylor
• Alex Hormozi
• Codie Sanchez
• David Senra
• George Mack
• Ben Askren
• Mark Manson
• all 281 guests

Others on The Knowledge Project

• Brad Jacobs
• Gio Valiante
• Giulia Enders
• Bill Gurley
• Winston Weinberg
• Greg Brockman
• Mario Harik
• Joe Liemandt
• J.W. Marriott
• Phil Knight
• Nicolai Tangen
• James Clear
• all 224 guests

Others on The Tim Ferriss Show

• Michael Levin
• Janna Levin
• Robert Rodriguez
• Marc Andreessen
• Jordan Peterson
• Jordan Jonas
• Andrew Huberman
• Lisa Randall
• Chris Young
• Mike Birbiglia
• Sarah Silverman
• Bill Burr
• all 480 guests

Others on TRIGGERnometry

• James Holland
• Dave Smith
• Douglas Murray
• Jordan Peterson
• Vivek Ramaswamy
• Cenk Uygur
• Roman Yampolskiy
• Bassem Youssef
• Tulsi Gabbard
• Dana White
• Bill Ackman
• Michael Malice
• all 541 guests

Others on Plain English with Derek Thompson

• Darby Saxbe
• Daniel Lieberman
• Robert Wright
• David Epstein
• Ezra Klein
• Richard Reeves
• Nir Eyal
• Cal Newport
• Oliver Burkeman
• Paul Eastwick
• Morgan Housel
• Ken Burns
• all 219 guests

Others on Odd Lots

• Saagar Enjeti
• Mark Cuban
• Ben McKenzie
• Michael Saylor
• Ezra Klein
• Morgan Housel
• Steven Rinella
• Ro Khanna
• Brad Jacobs
• Dylan Patel
• Reiner Pope
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• all 808 guests

Others on The Bulwark Daily

• Derek Thompson
• Saagar Enjeti
• Mark Cuban
• Ben McKenzie
• Ben Stiller
• Chris Hayes
• Pete Buttigieg
• Ezra Klein
• Ken Burns
• Ro Khanna
• Sam Harris
• Fiona Hill
• all 247 guests

Others on The Megyn Kelly Show

• Dave Smith
• Douglas Murray
• Saagar Enjeti
• Jordan Peterson
• Vivek Ramaswamy
• Andrew Huberman
• Tulsi Gabbard
• Mark Cuban
• Tucker Carlson
• Bill Ackman
• David Friedberg
• Robert Pape
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Others on The Logan Bartlett Show

• Derek Thompson
• Dario Amodei
• Aravind Srinivas
• Mark Cuban
• Sam Altman
• Benedict Evans
• Eliezer Yudkowsky
• Tim Urban
• Robin Hanson
• Joe Hudson
• Ben Lamm
• Kara Swisher
• all 146 guests

Others on The Meb Faber Show

• Will Guidara
• Morgan Housel
• Gio Valiante
• Bethany McLean
• Peter Zeihan
• Andrew Schulz
• Kevin Kelly
• Nick Maggiulli
• Louisa Nicola
• Jim O'Shaughnessy
• Annie Duke
• David McWilliams
• all 526 guests

Others on The Peel with Turner Novak

• Celine Halioua
• Josh Miller
• Matt Mullenweg
• Aaron Levie
• Adrian Aoun
• Alex Bouaziz
• Ali Partovi
• Baiju Bhatt
• Charles Hudson
• Chetan Puttagunta
• Chris Olsen
• Ed Sim
• all 158 guests

Others on The Jordan Harbinger Show

• Paul Rosolie
• Marc Andreessen
• Charan Ranganath
• Andrew Callaghan
• Mark Cuban
• Annie Jacobsen
• Christopher Whitcomb
• Rachel Zoffness
• Amir Levine
• Justin Garcia
• Chelsea Handler
• Seth Godin
• all 583 guests