“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.
The transcript of this episode can be found here. Transcripts of all episodes can be found here.
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.
Now, listeners of The Tim Ferriss Show podcast can use code TIM20 to get 20% off all orders and a free box of their best-selling Namibian sea-salted macadamia nuts worth $35! If these are not the best macadamia nuts you have ever eaten, House of Macadamias will give a full 100% refund, guaranteed.
This episode is brought to you by LinkedIn Jobs. Whether you are looking to hire now for a critical role or thinking about needs that you may have in the future, LinkedIn Jobs can help. LinkedIn screens candidates for the hard and soft skills you’re looking for and puts your job in front of candidates looking for job opportunities that match what you have to offer.
Using LinkedIn’s active community of more than 900 million professionals worldwide, LinkedIn Jobs can help you find and hire the right person faster. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit LinkedIn.com/Tim.
This episode is brought to you by Eight Sleep! Eight Sleep’s Pod Cover is the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced (and user-friendly) solution on the market. Simply add the Pod Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. It also splits your bed in half, so your partner can choose a totally different temperature.
Go to EightSleep.com/Tim and save $250 on the Eight Sleep Pod Cover. Eight Sleep currently ships within the USA, Canada, the UK, select countries in the EU, and Australia.
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:
- 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
- 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
- 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
- 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
- [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
- Chris Sacca
- Atul Gawande
- Jack Dorsey
- Jason’s Dad
- Han Solo
- Leia Skywalker Organa Solo
- Josh Harris
- David Hershkovits
- Christine Muhlke
- Esther Dyson
- Kevin Kelly
- Heather Jackson
- Alan Meckler
- Douglas Rushkoff
- Charlie Rose
- Allan Houston
- Caterina Fake
- DJ Spooky
- Rafat Ali
- Howard Stern
- Xeni Jardin
- Marvin Minsky
- Robert Brockman
- Brian Alvey
- Mark Cuban
- Peter Rojas
- Sean Bonner
- Matt Mullenweg
- George Harrison
- Paul McCartney
- John Lennon
- Nick Denton
- Steve Jobs
- Jony Ive
- Evan Williams
- Dave Goldberg
- Tony Hsieh
- Kevin Rose
- Travis Kalanick
- Chamath Palihapitiya
- John McLaughlin
- Mark Zuckerberg
- David O. Sacks
- Donald Trump
- David Friedberg
- Gwyneth Paltrow
- Brad Gerstner
- Chris Ashenden
- Vladimir Putin
- Joe Biden
- Volodymyr Zelenskyy
- Joe Rogan
- Dasha Nekrasova
- Rachel Maddow
- Sam Harris
- Bill Maher
- Roger Waters
- David Gilmour
- Bret Easton Ellis
- Jade Calacanis
- Debbie Millman
The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.
Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)
One Reply to “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 (#635)”
Two word impression of this episode: High energy. Loved catching the nuggets of insight scattered like tracer rounds throughout the machine gun barrage that is Jason Calacanis.