The guest
Jason Calacanis: Angel investor (300+ startups), Sequoia's first scout, author of Angel, and host of the This Week in Startups and All-In podcasts.
What this episode covers
Calacanis traces his arc from a traumatic Brooklyn childhood, where the feds padlocked his father's bar, through founding the Silicon Alley Reporter zine, surviving the dot-com bust, and selling Weblogs, Inc. to AOL for $30 million. He and Ferriss dig deep into the mechanics of podcasting and moderating, especially how Calacanis orchestrates the four-person All-In show like a basketball point guard. They explore the tension of building a hit project with close friends, why his partners refused lucrative ad money, and the loyalty he learned from his father. The conversation closes on the paradox of 'catching the car', the emptiness that can follow financial success, and the role of friendship, therapy, and psychedelics in confronting trauma.
Recommended on this episode
BookRecommendedISBN verified
The Checklist Manifesto
Atul Gawande
“you and I are obsessed with; And I make everybody read it, I'm obsessed with checklists”
“there's this book, The Checklist Manifesto, you and I are obsessed with, probably part of our kinship”— Jason Calacanis
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The Random Show
Tim Ferriss
“I snap that immediately, when The Random Show comes up in my feed”
“If I see Random Show, that's just like, I snap that immediately, when The Random Show comes up in my feed”— Jason Calacanis
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The McLaughlin Group
“It was the best Sunday morning political show of all time”
“It was the best Sunday morning political show of all time, The McLaughlin Group”— Jason Calacanis
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Red Scare
“the Red Scare podcast is hilarious; They're quite charming and hilarious”
“the Red Scare podcast is hilarious and Dasha always says, 'Oh, what's on the docket?'”— Jason Calacanis
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Signal
Signal
“it's pretty great”
“Signal is desktop and mobile now. Yeah, it's pretty great. And it's not owned by the Russians”— Jason Calacanis
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The Bret Easton Ellis Podcast
Bret Easton Ellis
“another podcast I like”
“another podcast I like is the guy who wrote Less Than Zero and American Psycho, Bret Easton Ellis”— Jason Calacanis
The guest's own work
BookBy the guest
Angel
Jason Calacanis
“is Sequoia Capital's first scout and is the author of the book Angel”— Tim Ferriss
MediaBy the guest
This Week in Startups
Jason Calacanis
“He also hosts two podcasts, we're going to talk quite a bit about, This Week in Startups and All-In”— Tim Ferriss
MediaBy the guest
All-In
Jason Calacanis
“He also hosts two podcasts, we're going to talk quite a bit about, This Week in Startups and All-In”— Tim Ferriss
BookBy the guestISBN verified
The 4-Hour Workweek
Tim Ferriss
“this 4-Hour Workweek goes from — you got paid nothing for that book and then all of a sudden”— Jason Calacanis
Also referenced (named, not recommended)
ProductReferenced
QuickTime
Apple
“we are both running backup QuickTime audio, so we have extra local copies in case something breaks”— Tim Ferriss
MediaReferenced
Spy magazine
“Why is this person on the cover of Spy magazine? Why is this person on the cover of Paper magazine?”— Jason Calacanis
MediaReferenced
Paper magazine
David Hershkovits
“He said, 'No, no. I'm the editor-in-chief. I'm David Hershkovits.' So I started writing for Paper magazine”— Jason Calacanis
MediaReferenced
Silicon Alley Reporter
Jason Calacanis
“I should be a reporter about Silicon Alley. I could do a Silicon Alley Reporter and it would just be me reporting”— Jason Calacanis
ProductReferenced
PageMaker
Adobe
“I got PageMaker, I started laying it out, I took pictures, I wrote a couple articles, and I went there and I printed it”— Jason Calacanis
ProductReferenced
Motorola StarTAC
Motorola
“imagine taking out your StarTAC, and I had seen a StarTAC phone, those little flip phones”— Jason Calacanis
MediaReferenced
Vanity Fair
“I need two packs of Marlboro Lights and bring me a copy of Vanity Fair or Esquire magazine”— Jason Calacanis
MediaReferenced
Boing Boing
“she started working on this Boing Boing thing. And I'm like, 'Boing Boing? What are you doing with your life?'”— Jason Calacanis
MediaReferenced
paidContent.org
Rafat Ali
“Rafat Ali was doing a blog on the site called paidContent.org and somebody ratted him out”— Jason Calacanis
ProductReferenced
WordPress VIP
Automattic
“He's now running WordPress for Matt Mullenweg. WordPress, like Pro, VIP like people like you and I use”— Jason Calacanis
MediaReferenced
Engadget
Weblogs, Inc.
“Engadget was crushing Gawker because we stole Peter Rojas from Gizmodo”— Jason Calacanis
MediaReferenced
The Unofficial Apple Weblog (TUAW)
Weblogs, Inc.
“we made the apple.weblogsinc, The Unofficial Apple Weblog, TUAW, which people fell in love with”— Jason Calacanis
ProductReferenced
Ozempic
Novo Nordisk
“I did a couple of series of Ozempics along with fasting that I learned about from you and Kevin”— Jason Calacanis
ProductReferenced
Zero (fasting app)
“I did a couple of series of Ozempics along with fasting that I learned about from you and Kevin and using the Zero fasting app”— Jason Calacanis
MediaReferenced
Goop newsletter
Gwyneth Paltrow
“Gwyneth Paltrow wrote about it in her Goop newsletter a couple weeks ago, that she's obsessed with the podcast”— Jason Calacanis
ProductReferenced
Google Docs
“Google Doc of topics. I make a docket every week with my producer, Nick”— Jason Calacanis
MediaReferenced
The Joe Rogan Experience
Joe Rogan
“I thought Joe Rogan did a really good job when they were like, 'Hey, you're having these people on'”— Jason Calacanis
MediaReferenced
Making Sense (Sam Harris podcast)
Sam Harris
“I got that from Sam Harris. I was listening to Sam's podcast. He gets people monologuing”— Jason Calacanis
MediaReferenced
Politically Incorrect
Bill Maher
“you might say, what's his name from Politically Incorrect? Bill Maher”— Jason Calacanis
BookReferencedISBN verified
Less Than Zero
Bret Easton Ellis
“the guy who wrote Less Than Zero and American Psycho, Bret Easton Ellis”— Jason Calacanis
BookReferencedISBN verified
American Psycho
Bret Easton Ellis
“the guy who wrote Less Than Zero and American Psycho, Bret Easton Ellis”— Jason Calacanis
MediaReferenced
Idiocracy
“You'll get Ouch My Balls. Literally Idiocracy, the TV show, Ouch My Balls”— Jason Calacanis
MediaReferenced
Blade Runner
“it's just like Blade Runner when the Nexus-6 is on the roof and he says like, 'Oh, my God, all my memories are going to be gone like tears in the rain'”— Jason Calacanis
MediaReferenced
The Empire Strikes Back
“if you remember in The Empire Strikes Back and Han Solo comes over to Chewbacca, he's like, 'Just take care of the Princess'”— Tim Ferriss
MediaReferenced
Goodfellas
“it was like out of a film like Goodfellas. Tim, I kid you not. I would have to go serve espresso to the bookie”— Jason Calacanis
MediaReferenced
The Terminator
“You know in The Terminator, you see from his view and all the words are going by and he's just processing everything really fast”— Jason Calacanis
MediaReferenced
Forrest Gump
“Everybody's going to be like, 'I guess life is like a box of chocolates, Tim.' I just turned into the Forrest Gump of the internet industry”— Jason Calacanis
ProductReferenced
Tesla Model S Plaid
Tesla
“I drive a Model Y and I prefer that to the Plaid”— Jason Calacanis
ProductReferenced
Tesla Model X
Tesla
“And I have a Model X, I enjoy sometimes the New York strip better than Wagyu”— Jason Calacanis
ProductReferenced
AirPods
Apple
“I think AirPods specifically, these little things that you can fall asleep in your ears or you have them in your ears all the time”— Jason Calacanis
Big reveals from this episode
- Calacanis's father's bar was padlocked by tax authorities when Jason was 17-18; his dad told him 'I probably going to jail... take care of your mom,' one of the great traumas of his life.
- Alan Meckler offered him $20 million for Silicon Alley Reporter in 1999, but he turned it down to keep his identity, then the dot-com bust hit and he lost everything.
- Dow Jones bought the scraps of his company, then fired him days later and handed him a $500,000 check paying out his contract, igniting 'Hulk-like rage' to prove himself again.
- In under 18 months he and Brian Alvey built Weblogs, Inc. into 87 blogs with $200K revenue and sold it to AOL for $30 million; investor Mark Cuban turned $300K into $6 million.
- All-In started during COVID from a weekly poker game; Calacanis says he was 'tricked into it' when Chamath proposed a two-person show that grew into the four-friend format.
- Calacanis estimates he forgoes roughly $25 million in advertising (his quarter ~$6-7 million) because his already-rich All-In partners refuse to run ads.
- Instead of ads, he raised his Launch4 venture fund publicly via the podcast, securing $44 million in commitments across five webinars from people he had never met in person.
- Ferriss reveals he founded Saisei Foundation (saiseifoundation.org) funding research into MDMA-assisted psychotherapy for PTSD and psilocybin for treatment-resistant depression.
Worth remembering
- Both hosts run backup QuickTime recordings; Calacanis asks guests 'how many seconds is your QuickTime running?' rather than whether they hit record, citing The Checklist Manifesto.
- He launched Silicon Alley Reporter as a photocopied zine, talking an overnight print-shop manager into a $1,750 job for $800 cash.
- His $90/year newsletter subscriptions started arriving as stacks of envelopes, soon $30,000-$40,000, letting him quit his jobs within 60 days.
- Calacanis means 'to have done well' or 'good for you' in Greek; his grandfather, a Merchant Marine captain, passed through Ellis Island 12 times.
- Weblogs, Inc. paid bloggers like Sean Bonner roughly $2-3 per post early on, scaling to a system of 450 bloggers pumping out thousands of posts a week.
- Inspired by Ferriss and Kevin Rose's Random Show discussion of Ozempic and the Zero fasting app, Calacanis lost 30 pounds over the past year.
- All-In nearly broke up multiple times; one fight had Calacanis threatening to replace Friedberg with Brad Gerstner as the 'fifth Beatle.'
- As moderator he tailors prompts to each co-host: 'science' for Friedberg (the 'Sultan of Science'), political 'red meat' for Sacks, and market 'alley-oops' for Chamath.
- He borrowed the 'Okay' interruption technique from Sam Harris and uses a finger-circle 'wrap it up' gesture to manage monologuers.
- Calacanis notes Colorado just passed (122) legalizing therapist-supervised psychedelics, and publicly discusses psychedelic potential for the first time.
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