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Tim FerrissJason Calacanis on Brooklyn Grit, Big Asks, The Magic of Thinking Big, and More
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CHAPTERS
- 0:15 – 4:13
Podcast Prep Tactics and The Checklist Manifesto
Tim introduces Jason and the two compare notes on podcasting. Jason shares a trick for confirming a guest's backup recording is running and praises The Checklist Manifesto.
- •Jason has long listened to Tim's show and takes notes on it
- •Asking 'how many seconds is your QuickTime running?' confirms the backup is actually recording
- •Both are fans of The Checklist Manifesto
- •Jason makes everybody read the book because people forget
- •Surgical checklist example: a tent on a clean scalpel signals it is sterile
- 4:13 – 7:22
Growing Up in a Brooklyn Bar: Blood, Taxes and Adaptation
Tim asks about Jason's childhood, and Jason describes his dad's bar in Bay Ridge and the tax raid that padlocked it. He explains how a world of mobsters, Hells Angels and cops made him good with people.
- •His dad's bar was padlocked by the feds and tax authority in 1988 after the stock market crash
- •Jason's dad told him he had no money for college and might go to jail
- •The bar's regulars included the mafia, Hells Angels, cops and Wall Street people
- •The experience made him good at dealing with people
- •Business later felt easier because there was no violence
- 7:22 – 13:44
From Fixing Printers to Paper Magazine and Björk
Tim asks how Jason became an entrepreneur despite what happened to his dad. Jason describes night school, wanting to be on a magazine cover, and the downtown tech scene that led him to Paper Magazine's David Herskovitz.
- •Jason fixed laser printers and built networks while paying for night school himself
- •He grew curious about who was on magazine covers and what a masthead meant
- •He met the Paper Magazine founder at a party in the basement of Barneys
- •He started writing an internet column for Paper
- •A night out with Herskovitz led to meeting Björk
- 13:44 – 21:24
Launching Silicon Alley Reporter and Learning to Ask
Inspired by zine culture, Jason photocopied the first Silicon Alley Reporter and talked a print-shop manager into a deal. He handed copies out at a Roseland party and got his first taste of power.
- •Zine culture and Herskovitz's foldable Paper inspired the format
- •The print shop bill was a surprise, and the overnight manager helped him anyway
- •Jason learned that asking for things, even outrageous things, often works
- •The whole party stopped to read the zine, which he describes as a feeling of power
- •Subscription postcards at $90 brought in cash within weeks
- 21:24 – 24:07
Overnight Success and the Strangeness of Speaking Fees
Jason and Tim trade stories of sudden success. Tim recalls getting the call that The 4-Hour Workweek hit the bestseller list, and both talk about how odd it feels to be offered huge speaking fees.
- •Jason's rise happened within about 60 days of that party
- •Tim learned his book made the list while exhausted from radio satellite tours
- •Speaking fees of $30,000 to $40,000 matched what each earned in a year
- •Jason felt guilt because the fee was what his parents made in a year
- •Sudden success makes it hard to stay grounded
- 24:07 – 29:23
Turning Down $20 Million, the Crash, and Getting Fired
Tim asks about the January 1999 offer for the magazine. Jason explains why he declined, how the dotcom bust took everything, and how Dow Jones fired him while paying out his contract.
- •Internet.com's Alan Meckler offered $20 million for Silicon Alley Reporter
- •Jason refused because the magazine was his identity
- •The dotcom bust wiped him out and he sold the remains to Dow Jones
- •Dow Jones then fired him and handed him a $500,000 check
- •He felt a berserker rage and vowed to prove it wasn't a fluke
- 29:23 – 36:20
Mercury Club and Reading the Post-Bust Landscape
The day after the firing, Jason got a desk and started calling people to find out what was being built. He then describes his abandoned Mercury Club idea, a messenger service for rich New Yorkers, and his belief in getting to new mediums first.
- •He started the next day by calling people to see what was happening after the bust
- •He met people building Flickr, Delicious and early blogs
- •Tim and Jason joke about Tim learning basketball layups
- •He saw that getting to a medium first earns outsized credit
- •Mercury Club would have delivered items by Vespa and bike messenger for $100 a month, but was never built
- 36:20 – 37:46
The Origin of 'Calacanis' and Grandfather's Ellis Island Trips
Tim asks about Jason's Greek surname. Jason explains its meaning, the story of how it was spelled at Ellis Island, and what he found about his grandfather online.
- •Calacanis means 'having done well'
- •Jason says immigration officers spelled the name incorrectly, and that bananas were handed out at Ellis Island
- •His grandfather was a Merchant Marine engine captain
- •The Ellis Island archive shows his grandfather passing through about 12 times
- 37:46 – 47:43
Building Weblogs Inc. and the $30 Million AOL Sale
Jason explains how blogs caught his eye through two former employees and how he and Brian Alvey built Weblogs Inc. They reached 87 blogs and sold to AOL for $30 million within 18 months.
- •Rafat Ali's blog and another former employee's blogging income showed him how well blogs could pay
- •He pitched Brian Alvey on weblogs for business at a Knicks game
- •Writers were paid a few dollars per post, later raised to $10
- •They built 87 blogs, including TUAW, and AOL paid $30 million
- •The sale proved to Jason that he could build a business again
- 47:43 – 53:31
Why Jason Loves Events: Memories and Tears in the Rain
Tim asks about producing events. Jason contrasts extrovert and introvert styles, then explains that he builds events to create lasting memories, citing Blade Runner's 'tears in the rain'.
- •Jason calls himself an ENTJ and Tim an INTJ
- •Jason compares himself to a morning radio host and Tim to a weekly 60 Minutes
- •Events let people meet and create life-changing moments
- •Tim's Open the Kimono event is still remembered as a peak experience
- •The deaths of friends make him count how many memories he has left
- 53:31 – 1:02:28
Loyalty, Friendship, and Jason's Ozempic Story
Tim asks where Jason's loyalty comes from. Jason credits his dad's Three Musketeers rule and talks about transactional relationships and fame. He then shares the weight-loss program he took from Tim and Kevin Rose's show.
- •Jason's father taught him that he and his brothers must never leave each other behind
- •Success makes your world smaller and people more transactional
- •Jason says he has been burned by friends who weren't loyal back
- •Jason lost 30 pounds with Ozempic, fasting and weightlifting
- •The loss came from advice he picked up from Tim and Kevin Rose's show
- 1:02:28 – 1:15:49
How All-In Started and Its Chaotic Super Team
Jason explains what All-In is and how it grew out of his friendship with Chamath, plus Sacks and Friedberg. He describes the show's popularity, the clash over the All-In Summit, and why the partners refused ads.
- •All-In features four friends who are investors and business builders
- •Jason modeled the format on The McLaughlin Group
- •Chamath proposed the show, and Sacks and Friedberg joined during COVID
- •A dispute over the All-In Summit nearly led to a split
- •His partners decline ads, but the show helped him raise $44 million in commitments for a new fund
- 1:15:49 – 1:23:13
Responsibility of Big Podcasts and Handling Controversial Topics
Jason and Tim discuss the responsibility that comes with large audiences. They compare how each handles controversial topics, vetting, and the role of the audience.
- •Jason says All-In's panel are experts on markets and startups but only as informed as listeners on other topics
- •Jason describes how COVID lab-leak talk drew calls to take a podcast down
- •Tim adds strong disclaimers and stays off Twitter for a week after sensitive episodes
- •Tim vets guests heavily and rejects many
- •Jason suggests a companion show, 'After Joe', to vet episodes
- 1:23:13 – 1:35:27
Moderating All-In: Docket, Talent-Wrangling and Technique
Tim asks Jason to walk through his preparation as moderator. Jason covers the weekly docket, setting up each partner with the topics they like, giving private notes, and managing monologues.
- •The docket is a Google Doc fed by a Signal group chat
- •Jason feeds Friedberg science topics and Sacks political red meat
- •He feeds Chamath financial and market topics he can explain well
- •He gives private notes after shows
- •He uses a wrap-up hand circle and a short 'Okay' to manage monologues
- 1:35:27 – 1:41:51
Bill Maher's Style, Friendship on Display and the Overton Window
Tim asks who stands out as a moderator, and Jason names Bill Maher's use of humor. They then discuss why audiences love seeing friendship and talk about the narrowing Overton window.
- •Maher drops a funny line into a heated debate to break tension
- •Jason says there are few good moderators and Tim could do an All-In-style show
- •Friendship on display is a draw for audiences, with fans upset when the show nearly broke up
- •Tim says friends talking freely lets listeners take off their 'psychological corset'
- •Jason defines the Overton window and laments how narrow it has become
- 1:41:51 – 1:51:55
Ingredients of Success and Catching the Car
Jason attributes All-In's success to accumulated reps, then reflects on money not being the right scorecard. He describes the question of what happens when you catch the car and how Tim sees success driving depression.
- •Reps from years of podcasting prepared him, like going from ping pong to tennis
- •Beyond a point, the scorecard of cash doesn't matter
- •His true scorecard is waking up eager for the day's activities
- •His new book is about money and what happens when you catch the car
- •Tim says depression can rise after achievers cross the money threshold
- 1:51:55 – 1:58:36
Psychedelic Therapy, Research Resources and Colorado
Jason praises Tim's psychedelic research work and says many people haven't done the inner work. They discuss Colorado's new law and Tim shares resources, including the trauma episode and the Saisei Foundation.
- •Jason has never talked publicly about psychedelics and says many suffer because they haven't looked inside
- •Jason notes Colorado allowing therapists to use psychedelics in safe settings
- •Tim points to his trauma episode with Debbie Millman
- •Saiseifoundation.org lists research institutions and projects
- •Tim describes the legal landscape as in flux and psychedelics as powerful
- 1:58:36 – 2:06:34
Jason's Billboard and Closing Thoughts
Asked what he would put on a billboard, Jason offers 'have great friends, build cool shit'. The two close with praise for each other, thoughts on podcasting's intimacy and where to find Jason.
- •Jason's head says give it a shot, while his heart says be kind to each other
- •He wants more open-hearted discussions across disagreement
- •Tim says disagreement and repair are part of good friendships
- •Jason urges Tim never to stop podcasting
- •Jason says podcasts create a lifelong friendship with a personality you've never met
