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Tim FerrissJason Calacanis on Brooklyn Grit, Big Asks, The Magic of Thinking Big, and More
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At a glance
WHAT IT’S REALLY ABOUT
Jason Calacanis on Brooklyn Grit, Comebacks, Friendship, and All-In
- Calacanis describes growing up in Bay Ridge, Brooklyn, in his father's bar, where he saw the mafia, Hells Angels and cops, and where tax authorities padlocked the bar when he was 18, an experience that shaped his drive for power and security.
- He built Silicon Alley Reporter from photocopies handed out at a party into a company worth roughly $11 million, turned down a $20 million offer, lost nearly everything in the dotcom bust, and was fired by Dow Jones.
- Fueled by rage after being fired, he started Weblogs Inc. the next day, scaled it to 87 blogs in 18 months, and sold it to AOL for $30 million, which he says proved the earlier success was no fluke.
- He explains how All-In grew out of poker-night friendships with Chamath, Sacks and Friedberg, how he moderates and coaches three strong personalities, and how the show survived conflict over events and ad revenue.
- Both men discuss the paradox of 'catching the car': money stops mattering past a point, Calacanis measures success by enthusiasm for getting out of bed, and he closes with the billboard message 'Have great friends, build cool shit.'
IDEAS WORTH REMEMBERING
5 ideasAsking boldly often works
Calacanis says a printer manager let him walk away with 1,000 copies for $800 against a $1,750 bill, and he learned early that people will often do what you ask, even outrageous things.
Rage after a setback can fuel a comeback
After Dow Jones fired him and handed him a $500,000 check, he got an office the next day and later sold Weblogs Inc. to AOL for $30 million within 18 months.
Get to new mediums first
He argues that arriving early on a medium such as zines, blogs or podcasting earns disproportionate credit, much like buying a cheap loft in a neighborhood before it becomes popular.
A good moderator tailors prompts to each person
Calacanis feeds Friedberg science, Sacks politics and law, and Chamath markets questions, gives private feedback after shows, and uses a finger-circle wrap-up cue or a calm 'Okay' to manage monologues.
Loyalty is a core principle learned from his father
His father taught him and his brothers to never leave one another behind, and Calacanis says being a loyal friend is one of his superpowers, even when it isn't reciprocated.
WORDS WORTH SAVING
5 quotesI, I don't know, it's like I, the two best things I've done in my life is have great friends and build cool shit.
— Jason Calacanis
the right scorecard is, did you wake up and couldn't get, couldn't wait to get out of bed?
— Jason Calacanis
we call it podcasting, but it's really like this, like, lifelong friendship you have with a personality you've never met.
— Jason Calacanis
It's a big failing of human nature, that we have this weird thing with the scorecard, that we think the s- the scorecard of dollars is, like, important. It's not.
— Jason Calacanis
I would really like to see people be kinder to each other and just have, like, really open-hearted discussions with each other.
— Jason Calacanis
High quality AI-generated summary created from speaker-labeled transcript.
