The guest
Jason Calacanis: Angel investor and entrepreneur, early backer of Uber, Robinhood, and Calm. Host of This Week in Startups and co-host of the All-In Podcast.
What this episode covers
Lex Fridman talks with angel investor Jason Calacanis just days after the GameStop/Wall Street Bets short squeeze. Calacanis, an early Robinhood investor, explains the liquidity crisis behind Robinhood's trading halt and the public spat with his All-In co-host Chamath. The conversation ranges across capitalism versus China, the cult of the entrepreneur, the dangers of engagement-driven social media, and what makes great founders like Elon Musk and Jeff Bezos. It closes on a personal story of Calacanis sending Musk $100,000 to keep Tesla alive, and a meditation on loyalty, gratitude, and love.
Recommended on this episode
ProductRecommended
Chess.com
Chess.com
“they literally have puzzles yeah so i was like oh and it's a hundred dollars a year for this product”
“i've been playing chess and trying to get that going again after watching queen's gambit and i got chess.com”— Lex Fridman
BookRecommendedISBN verified
Can't Hurt Me
David Goggins
“that book is amazing and the audiobook's amazing”
“that book is amazing and the audiobook's amazing when he's talking about how fat he was and how he just had to go and keep running”— guest
The guest's own work
BookBy the guest
Angel: How to Invest in Technology Startups
Jason Calacanis
“jason calacanis who's an entrepreneur investor author of angel how to invest in technology startups”— Lex Fridman
BookBy the guest
Angel: How to Invest in Technology Startups
Jason Calacanis
“so i wrote a book on that angel and then i do a course called angel university that i teach six times a year”— guest
Also referenced (named, not recommended)
ProductReferenced
Robinhood
Robinhood
“in full disclosure i was an angel investor in robin hood before they launched and when i met the founder vlad”— guest
ProductReferenced
Uber
Uber
“i mean uber i introduced to about 25 investors and three of us said yes”— guest
ProductReferenced
Tesla
Tesla
“when elon was investing in tesla and some other guys were running it and he was trying to save the company”— guest
ProductReferenced
Airbnb
Airbnb
“something like airbnb is another perfect example of something that should really not work in practice but it does”— guest
MediaReferenced
The Queen's Gambit
Netflix
“i've been playing chess and trying to get that going again after watching queen's gambit and i got chess.com”— Lex Fridman
MediaReferenced
The Dark Knight
Christopher Nolan
“it really feels like the dark knight series of films where like some people just want to see the world burn”— guest
MediaReferenced
The Last Dance
ESPN
“did you see the michael jordan documentary the last dance like half of it okay i'm still working”— guest
MediaReferenced
Contagion
Steven Soderbergh
“before that bill gates was banging his fist and jeff skull was doing the movie contagion”— guest
MediaReferenced
Game of Thrones
HBO
“have you did you watch game of thrones and they're like yeah watch breaking bad like yeah”— guest
MediaReferenced
Breaking Bad
AMC
“have you did you watch game of thrones and they're like yeah watch breaking bad like yeah”— guest
ProductReferenced
Clubhouse
Clubhouse
“look at clubhouse this thing went from being a private beta six months ago to being the number one app in germany”— guest
ProductReferenced
Calm
Calm
“the first deal we ever did was calm.com the meditation app we put 378 thousand dollars into it”— guest
ProductReferenced
Amazon Prime
Amazon
“and you're like wow and it's like yeah you're paying 13 a month for the privilege of shopping at amazon yeah”— guest
ProductReferenced
Peloton Tread
Peloton
“my usage of clubhouse is going on my peloton treadmill putting clubhouse on taking a room and just listening”— guest
BookReferencedISBN verified
The Purpose Driven Church
Rick Warren
“i read this book by i've got his name rick something um he wrote the purpose driven church”— guest
MediaReferenced
Blade Runner
Ridley Scott
“you ever see blade runner yes of course do you remember what rucker harrah says at the end all of these memories gone”— guest
ProductReferenced
Tesla Model S
Tesla
“and he shows me the model s and nobody knew that he was working on the model s”— guest
ProductReferenced
Tesla Roadster
Tesla
“i had my orange tesla roadster and he had his p1 or p2 like the red one that i think is in space now”— guest
BookReferencedISBN verified
Authentic Happiness
Martin Seligman
“it turns out martin seligman in uh was it authentic happiness anyway the guy who really studied happiness and joy”— guest
Big reveals from this episode
- Calacanis met Robinhood founder Vlad at a dive bar (Antonio's Nut House) while having drinks with Elon Musk, and invested on the spot.
- Robinhood was on the brink of insolvency during the squeeze and raised about $3.5 billion in a week to cover trades.
- His syndicate's first deal, Calm, was bought into at a $5M valuation and is now worth $2B; he still owns ~5%.
- He claims Chamath's accusation that Robinhood halted trading because hedge funds told them to is 'not true', it was a liquidity crisis they legally couldn't discuss.
- Says he may actually be in favor of Trump being banned from social media because of how peaceful the discourse became after.
- During Tesla's near-collapse Musk privately showed him the unreleased Model S on a BlackBerry; Calacanis wrote two $50K checks to pre-order and keep payroll going.
- Calacanis owns Tesla reservation number 0000001, which Musk gave him as the first person to order the Model S.
- Compares ambitious workers to samurai versus rice pickers, arguing brutal startup cultures aren't for everyone.
Worth remembering
- Calacanis introduced Uber to about 25 investors and only 3, including himself, said yes.
- Praises Tim Ferriss's skill-acquisition method, recalling teaching the 'fabulously uncoordinated' Ferriss to shoot hoops in Italy.
- Argues the top ways Americans die now, obesity, suicide, heart attacks, show how 'soft' the country has become.
- Warns that if China 'wins capitalism' over the US it is an existential threat to humanity.
- Traces engagement-driven feeds to a Facebook decision to rank by likes/comments, which he says birthed outrage and cancel culture.
- Venture capital funds less than 1% of US startups; 7 of 10 startups he invests in go to zero.
- David Goggins is unpaid; he fights forest fires for a few months a year and just does 'hard shit all the time.'
- Tells a story of de-escalating a man who doxxed him by appealing to shared connections and the man's wife and newborn.
- Cites Martin Seligman's research that gratitude letters are one of the greatest amplifiers of joy in life.
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