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

“Jason would never stab you in the back. He might stab you in the face, though.”

— Douglas Rushkoff

Jason Calacanis (@jason) has invested in more than 300 startups in the past decade (Uber, Calm, Robinhood, and more), was Sequoia Capital’s first Scout, and is the author of the book ANGEL. He also hosts two podcasts, This Week in Startups and All-In.

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

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This episode is brought to you by House of Macadamias delicious and nutritious nuts! I love macadamia nuts and have been enjoying them often since keto expert Dr. Dominic D’Agostino recommended them on the podcast in 2015. They taste great, and with more healthy, monounsaturated fat than both olive oil and avocados, 27% fewer carbs than almonds, and more than 50% fewer carbs than cashews, they’re the perfect low-carb, keto-friendly, nutty snack. In fact, I just ate a handful of lightly white-chocolate-covered macadamias about an hour ago to keep me going through the afternoon until dinner. And I will say this: ​House of Macadamias produces the best-tasting macadamia nuts I’ve ever eaten… by far.

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Want to hear an episode featuring another incredible entrepreneur ? Have a listen to my conversation with Automattic’s Matt Mullenweg in Antarctica, where we discussed the surreality of perpetual daylight, the “patient” Antarctican landscape, rollicking penguin imitations, the grieving process, using smartphones to regularly record loved ones, existential revelations, cloned pets, how Matt expresses anger without cursing, gratitude, and much more.

What was your favorite quote or lesson from this episode? Please let me know in the comments.

SCROLL BELOW FOR LINKS AND SHOW NOTES…

SELECTED LINKS FROM THE EPISODE

• Connect with Jason Calacanis:

Website | Twitter

• Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 by Jason Calacanis | Amazon
• This Week In Startups with Jason Calacanis and Molly Wood
• The All-In Podcast with Chamath, Jason, Sacks, and Friedberg
• Patient Capital for Building Enduring Companies | The Sequoia Capital Fund
• The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss | Amazon
• QuickTime | Apple
• The Checklist Manifesto: How to Get Things Right by Atul Gawande | Amazon
• Bay Ridge (1982) | The New York Times
• Star Wars: The Empire Strikes Back | Prime Video
• Goodfellas | Prime Video
• Silicon Alley Reporter | Wikipedia
• Local Area Network (LAN) | Wikipedia
• Grandmaster Maurice Ashley Plays NYC Trash-Talker | The Tim Ferriss Experiment
• Paper Magazine
• Barneys New York | Wikipedia
• Blender CD-ROM Magazine | Internet Archive
• Pseudo.com | Wikipedia
• ​Before the Web: Online Services of Yesteryear | ZDNET
• Sony Online | Internet Archive
• Balthazar Restaurant New York
• The Roxy (New York City) | Wikipedia
• The Chemical Brothers
• The Orb
• The Terminator | Prime Video
• The 10 Greatest Punk Zines of the ’80s by Michael Hardy | Medium
• 2600: The Hacker Quarterly
• Roseland Ballroom | Wikipedia
• 1,000 True Fans by Kevin Kelly | The Technium
• Sliding Doors | Prime Video
• Forrest Gump | Prime Video
• Flickr
• Del.icio.us | Wikipedia
• Kozmo.com | Wikipedia
• An Italian Style Icon Since 1946 | Vespa
• Bedford-Stuyvesant NYC Neighborhood Guide | Compass
• Starrett-Lehigh Building
• Ellis Island | US National Park Service
• Latham & Watkins
• A Directory of Mostly Wonderful Things | Boing Boing
• paidContent | Wikipedia
• Travel News, Airline News, and Hotel News | Skift
• Inception | Prime Video
• Weblogs, Inc. | Wikipedia
• Amazon, Meta, Twitter Layoffs: The End of Silicon Valley’s 20-Year Boom | Slate
• New FTX CEO Calls the Crypto Exchange’s Corporate Control a ‘Complete Failure’ | The New York Times
• Automattic
• Gawker
• Engadget
• Gizmodo
• Farewell to TUAW – And to a Whole Era of Tech Blogging | Fast Company
• Opening the Kimono Event | Tim Ferriss
• Myers–Briggs Type Indicator | Wikipedia
• Enneagram of Personality | Wikipedia
• Blade Runner | Prime Video
• “Tears in Rain” Monologue | Blade Runner
• Calacanis Calls Time on the Internet ‘Me-Toos’ | The Guardian
• The Three Musketeers by Alexandre Dumas | Amazon
• A Rare In-Person Random Show with Kevin Rose — VR Workouts, I Bonds, Excellent Movies, Recent Books, Lessons from Amy Tan, How to Shape Your Mind, and More | The Tim Ferriss Show #622
• You Might Go Through Hell for Your Post-Ozempic Body | The Cut
• Fast with Zero | Zero
• The McLaughlin Group | Wikipedia
• The McLaughlin Group (Parody) | SNL
• Mark Zuckerberg on Long-Term Strategy, Business and Parenting Principles, Personal Energy Management, Building the Metaverse, Seeking Awe, the Role of Religion, Solving Deep Technical Challenges (e.g., AR), and More | The Tim Ferriss Show #582
• The Production Board
• AMC Stock Gains as House Report Reveals New Details on Robinhood | InvestorPlace
• Goop
• Athletic Greens | Tim Ferriss
• My Next Act: Democratizing Venture Capital | Launch
• The ProPublica-Vanity Fair Report on Covid’s Origins Is Explosive. Is It Reliable? | The Guardian
• Idiocracy | Prime Video
• Ow! My Balls! | Idiocracy
• Jackass: The Movie | Prime Video
• Red Scare Podcast
• Speak Freely | Signal
• Alley-Oop | Wikipedia
• Making Sense Podcast with Sam Harris
• The Reason Why Pink Floyd’s David Gilmour and Roger Waters Are Feuding | Far Out
• The Overton Window: How Politics Change | Conceptually
• Less Than Zero by Bret Easton Ellis | Amazon
• American Psycho by Bret Easton Ellis | Amazon
• The Bret Easton Ellis Podcast
• Psychedelics 101: Books, Documentaries, Podcasts, Science, and More | Tim Ferriss
• Colorado Proposition 122: Decriminalization and Regulated Access Program for Certain Psychedelic Plants and Fungi Initiative (2022) | Ballotpedia
• My Healing Journey After Childhood Abuse (Includes Extensive Resource List) | The Tim Ferriss Show #464
• Funding Cutting-Edge Scientific Research | Saisei Foundation

SHOW NOTES

• [05:39] Why is this only the first time Jason’s been on the show?
• [06:37] Never underestimate the power of checklists.
• [08:56] How Jason’s young life was steeped in blood and taxes.
• [11:57] How Jason entered the world of entrepreneurship.
• [29:32] What happened when Jason got fired from his own company.
• [34:05] Orchestrating a comeback the very next day.
• [37:49] The Mercury Club that never was.
• [41:37] The origin of “Calacanis.”
• [43:01] Building a blogging empire.
• [48:36] Finding blog writers.
• [52:51] Planning events and making memories.
• [58:39] Friendship, loyalty, and collaboration with close friends.
• [1:06:00] All-In: When a solo act gets tricked into joining a band.
• [1:13:39] Memorable times All-In has gone off the rails.
• [1:21:49] With greatly followed podcasts comes great responsibility.
• [1:27:38] KeepingAll-In running smoothly with four very different personalities.
• [1:34:53] Talent-wrangling techniques.
• [1:39:30] Bill Maher’s moderation style.
• [1:40:47] Friendly rapport can be contagious.
• [1:42:26] Can you see your comfort zone from the Overton window?
• [1:45:44] Transfering skills, building popularity, and co-existing with jet blockers.
• [1:52:16] What happens when you catch the car?
• [1:55:15] Psychedelic therapy and a big win in Colorado.
• [2:01:28] Jason’s billboard and parting thoughts.

MORE JASON CALACANIS QUOTES FROM THE INTERVIEW

“When I had no money and then became a millionaire, people treated me differently. All of a sudden, I got 30 more IQ points and I was two feet taller.”
— Jason Calacanis

“[On All-In], I have three partners, and all three of my partners on it have never had a boss. So you’ve literally got four of the most opinionated friends who’ve never had a boss who have four different directions they want to take it.”
— Jason Calacanis

“Have great friends. Build cool shit.”
— Jason Calacanis

“The system is so easy to win, and the system is set up for entrepreneurs to win in this country. Why on Earth would you cheat if it’s so easy to just have a win by just working hard?”
— Jason Calacanis

“It’s important to be, I think, a really good, loyal friend. I have been burned in this regard where I’ve been more loyal to certain people and they have not been loyal to me. And it’s very frustrating for some of the people around me when they see that happen to me. And for me, I say that is that person’s chance to learn how to be a friend. They just haven’t gotten there yet.”
— Jason Calacanis

“47 fucks given.”
— Jason Calacanis

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