Jason Calacanis on Brooklyn Grit, Big Asks, Angel Investing (Uber, Calm, Robinhood, and More), The Magic of Thinking Big, and St*abbing People in the Face but Never in the Back | Tim Ferriss Show #635

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Check out the Episode Page & Show Notes

Key Takeaways

  • “That’s a pretty scary thing when you’re 17 years old and your dad says, ‘I’m sorry, son. I don’t have money for college, I’m probably going to jail. I tried to make this business work, but it didn’t work. Take care of your mom.’” – Jason Calacanis
  • While working two jobs to pay for night school, Jason began to write a column on a new thing called the Internet for Paper Magazine; he then started his own magazine called Silicon Alley Reporter which covered things people were doing with the internet 
  • Within 60 days of launching it, Jason was able to quit his job and go full-time, generating $40K in revenue (sent through the mail) and becoming important to CEOs overnight 
  • The Dot Com Crash happened after he turned down a $20 million offer to be acquired, he ended up selling it to Dow Jones for scraps and was soon fired 
  • Within two years of being fired, he founded and sold Weblogs, Inc. to AOL for $30 million in 2003 
  • Jason believes that the human experience is a series of memories you collect over time 
  • “Jason would never stab you in the back. He might stab you in the face, though.” – Douglas Rushkoff 
  • The All-In Podcast has become a top 30 podcast in the world and could do $25 million per year in ads, but the cast (minus Jason) refuses to monetize it 
  • “I’m like, ‘Guys, let me have a jet. You’re standing between me and private aviation.”Jason Calacanis on the besties’ refusal to monetize 
  • “People think Sacks and I hate each other. Sacks and I love each other deeply, even though he can’t say it. I can say I love Sacks, and I know he loves me.” – Jason Calacanis
  • Jason is the point guard on the superteam; he knows what gets each of the cast members going, and throws them alley-oops to get the best out of them regarding their particular interests  
  • Beyond a certain amount, money is not the right scorecard; the right scorecard is, “Did you wake up and couldn’t wait to get out of bed?”  
  • Whether you’re a millionaire or a billionaire, the steak tastes the same
  • It is a terrifying moment when you’ve made the $50 million and realize that all of your pain, anxiety and depression is still there 
  • Some people tend to mask their suffering with performance because they don’t want to face the pain and suffering that is driving the performance 
  • “The two best things I’ve done in my life is having great friends and build cool sh*t.”Jason Calacanis

Intro 

  • Jason Calacanis (@jason) is the World’s Greatest Moderator, angel investor, entrepreneur, and founder of TheSyndicate.com. Jason has invested in over 300 startups in the past decade and hosts two podcasts, This Week in Startups and All-In.  
  • In this conversation, Jason Calacanis and Tim Ferriss discuss how Jason’s young life was steeped in blood and taxes, how Jason entered the world of entrepreneurship, got fired from his own company, orchestrated the $30 million comeback, why memories are all we have, loyalty, the trials and tribulations of the All-In Podcast, why the besties are leaving tens of millions on the table, the responsibility that comes with having a massive audience, talent-wrangling techniques, catching the car, trauma, psychedelics, Jason’s message for a billion people, and more 
  • Check out these Podcast Notes from Jason’s performance as the World’s Greatest Moderator 
  • Host – Tim Ferriss (@tferriss)  

The Power of Checklists 

  • Jason and Tim both run QuickTime in the background as they record podcasts in case something goes wrong
  • Jason and Tim both love The Checklist Manifesto, which is a book that Jack Dorsey would give to all of his new Twitter employees too 

Jason Calacanis’s Young Life 

  • Growing up, Jason worked at his father’s bar in Bay Ridge, Brooklyn 
  • His father was late on paying taxes, and the Feds came and padlocked the place, taking everything and almost sending his father to prison 
  • Jason calls this one of the great traumas of his life
  • “That’s a pretty scary thing when you’re 17 years old and your dad says, ‘I’m sorry, son. I don’t have money for college, I’m probably going to jail. I tried to make this business work, but it didn’t work. Take care of your mom.’”Jason Calacanis  
  • The violence and craziness in Brooklyn made the business world appear much easier
  • Jason didn’t know that there were other worlds out there beyond the types of people that visited the bar, which included the mafia, the Hell’s Angels, cops, and Wall Street people
    • “It was like out of a film like Goodfellas.” – Jason Calacanis 
  • Serving the people that visited the bar made Jason really good at dealing with people from an early age 

How Jason Entered the World of Entrepreneurship 

  • Jason worked two jobs to pay for college: fixing laser printers and building computer networks with cables
  • Jason worked in Manhattan during the day and went to school there at night
  • He was quasi-plugged into the tech scene in NYC because he knew about the internet and had friends working on various internet-related projects
  • Jason bumped into the founder of Paper Magazine David Hershkovits at a party, and helped him set up his dial-up connection 
  • David told Jason that he should write a column on the internet for Paper Magazine, and that’s how Jason broke into the world of business, technology, and entrepreneurship
  • “I was like this little nerdy kid. I didn’t know how to write, I didn’t know how to spell, I didn’t know how to put a comma in a sentence.” – Jason Calacanis 
  • All of his friends were starting internet stuff, and there was an emerging magazine culture in New York, so Jason decided to launch a magazine called Silicon Alley Reporter, which was a term used to describe the growing tech scene in NYC 
  • Jason was $900 short to have the first issue of Silicon Alley Reporter printed; the guy working at the printer shop let it slide 
  • Jason took the first issue to a party and just started handing them out to people; within minutes, everyone at the party stopped what they were doing and began to read the zine
    • This is the moment when Jason realized he had power 
    • This experience gave Jason the confidence to believe that he could be an entrepreneur and do something in the world
  • Within 60 days, Jason had enough subscribers to Silicon Alley Reporter that he was able to quit his job and go full-time 
  • Within 60 days from launching, Jason received $30K-$40K in the mail from people subscribing 
  • He became “important” overnight: all of a sudden every CEO in the internet ecosystem wanted to talk to Jason 
  • The timing of it was critical; this was at a time when the internet browser was yet to support graphics, so Jason was very early 

What Happened When Jason Got Fired From His Own Company 

  • By 1999, Silicon Alley grew to become a 300-page magazine, and the company had 100 employees 
  • The magazine was generating about $8 million per year, plus hosting events that brought in another $3 million  
  • The founder of internet.com Alan Meckler offered Jason $20 million for Silicon Alley Reporter 
  • The magazine was Jason’s identity and so he decided not to sell it because he didn’t want to give up his identity
  • Then the Dot Com Crash happened, and Jason lost everything
  • All of the companies advertising in Silicon Alley went bankrupt  
  • He sold Silicon Alley to Dow Jones for scaps 
  • Shortly after acquiring the company, Dow Jones bought Jason out of his contract and effectively fired him
    • He was given a $500,000 check 
  • “I’m looking at a $500,000 check – which is an extraordinary amount of money, obviously – and the only thing I can think is, ‘I want to beat the sh*t out of this guy.” – Jason Calacanis
  • He went from being a nobody to living the peak New York experience, to everything being gone overnight 
  • Jason felt Hulk-like rage after his firing and wanted to prove to everyone that he could do this again – that he was not a fluke
  • Jason started his next venture the very next day after being fired from the Silicon Alley Reporter  

Mercury Club That Never Was  

  • Jason wanted to create a service where rich people could pay $100 per month for four hours of deliveries
  • Mobile phones had just come out, so people could dial an 800 number and have things delivered to them 
  • “If you get to a medium first, you can exploit it.”Jason Calacanis 
  • Mercury, as in the Greek god with wings on the feet  
  • Jason never ended up building Mercury Club 

The Meaning Behind “Calacanis”

  • Kalakanis means “to have done well” or “good for you” in Greek
  • The K’s were switched to C’s when Jason’s grandfather came through Ellis Island 

 Building a Blogging Empire 

  • A lot of people began writing blogs instead of magazines because they were faster, better, cheaper, and cooler 
  • Blogs used to be called “weblogs” because they were logs kept on the web 
  • Jason and his friend Brian Alvey started Weblogs, Inc. in 2003 
  • They began writing weblogs on topics like Wi-Fi and Apple, and within 18 months, they had 87 blogs and did $200,000 in total revenue
  • AOL acquired Weblogs, Inc. for $30 million in 2005 
  • Two years after turning down the $20 million offer for Silicon Alley Reporter, Jason got a $30 million offer  
  • Jason realized that he was good at building and selling businesses; he might fail two out of three times, but he could do it 

Planning Events and Making Memories

  • Understand your personality when planning an event
  • If you’re an introvert, ensure you have enough time to “recover” in-between stage appearances 
  • Jason loved creating events because they connected many people and resulted in relationships that changed people’s lives forever  
  • The speech about memories in Blade Runner is the most powerful moment in movie history for Jason 
  • Jason believes that the human experience is a series of memories you collect over time 

Friendship, Loyalty, and Collaboration With Close Friends 

  • “Jason would never stab you in the back. He might stab you in the face, though.” – Douglas Rushkoff
    • Jason put this quote on the back of his book Angel 
  • Jason’s loyalty to his friends today stems from his father teaching him about the importance of loyalty as a child
    • His father emphasized the importance of loyalty between him and his brothers
  • “One of my superpowers is being there for my friends.”Jason Calacanis 
  • Have a large number of acquaintances, and a close number of close friends
  • The world gets smaller and smaller as you become more successful 
  • You can get burned if you’re loyal to someone and they don’t return the same level of loyalty 
  • Jason dropped 30 pounds doing the Tim Ferriss-Kevin Rose Program: a couple of cycles of Ozempic, lifted weights, and intermittent fasting using the Zero App  

The All-In Podcast 

  • The All-In Podcast is a podcast of four friends, who are all capital allocators, modeled after The McLaughlin Group style show where a wide variety of perspectives are shared 
  • Jason, Chamath Palihapitiya (@chamath), David Sacks (@DavidSacks), and David Friedberg (@friedberg) all played poker together and decided to launch a podcast together where they discuss the topics of the day 
  • The podcast launched around the start of the Covid pandemic and immediately connected with people because of the group’s candid and opinionated discussions 
  • The All-In Podcast has become a top 30 podcast in the world 
  • Each person has their own group of fans, and the following has grown beyond a level that Jason could ever imagine 

Memorable Times The All-In Podcast Has Gone Off The Rails

  • It’s hard to keep a super-team together, and the All-In Podcast has famously gone off the rails on several occasions in its short existence 
  • The most memorable flare-up was over the All-In Summit, an in-person event hosted by the cast with guest speakers, all planned by Jason 
  • David Friedberg was scared that the All-In Summit would flop and hurt the podcast’s reputation, and arguments ensued amongst the crew about the event 
  • Jason told David Friedberg that if he wasn’t enjoying the podcast, and didn’t want to attend the event, then he should leave the podcast 
  • The team ultimately decided to stick to the podcast and limit the outside noise 
  • The All-In Podcast is Jason’s biggest media success to date, and yet the other members of the show refuse to do ads
  • The show could do $25 million per year in advertising, but Chamath, Sacks, and Friedberg refuse to do ads 
  • “I could use another $7 million a year. This is big cash. After taxes, it would be a jet. I have no jet.”Jason Calacanis 
  • “I’m like, ‘Guys, let me have a jet. You’re standing between me and private aviation.”Jason Calacanis    
  • The team agreed to let Jason plug his fund on the pod, and he has since gotten thousands of emails from wealthy people wanting to invest
  • Jason has gotten $44 million in commitments in the last five weeks from doing five webinars 
  • Some things the All-In cast has come to peace with:
    • They hit lightning in a bottle
    • Trust and love each other
    • Put on a good show
    • Root for each other 
  • “People think Sacks and I hate each other. Sacks and I love each other deeply, even though he can’t say it. I can say I love Sacks, and I know he loves me.”Jason Calacanis 

With Great Podcast Numbers, Comes Great Responsibility 

  • The cast members are experts in venture capital and markets; when they talk about anything else (Covid, Ukraine, politics), they are just as informed as the everyday person
  • There is a strange dynamic going on in the world today where people think Joe Rogan and Tim Ferriss shouldn’t talk about certain things because their shows are popular 
  • “You are allowed to have a conversation. And people need to come to their own truth.” – Jason Calacanis    
  • Tim Ferriss’s protocol for discussing hot-button issues: include a strong disclaimer and do not look at Twitter for a week  
  • There is a responsibility on the part of the audience 
  • Tim does a lot of fact-checking and vetting on guests before having them on the show; if there is evidence that someone is playing it too fast and too loose, Tim won’t have them on 
  • For this conversion, Tim has 20 pages of notes despite him and Jason being close friends 
  • Jason thinks Joe Rogan should start a second podcast called “After Joe”, where a group of subject matter experts vets whatever subject was discussed in the main show
  • “You do great notes. And there are people who do show notes of both our shows once in a while that are pretty good.”Jason Calacanis
    • We have to break the fourth wall here: Jason, our headphones are burning!!

How All-In Runs Smoothly With Four Very Different Personalities 

  • There is a docket each week for the episode, an idea Jason took from Dasha of the Red Scare Podcast  
  • The group shares links throughout the week in a Signal group chat and builds the docket from that using Google Docs  
    • The messages in the P2P encrypted Signal chat disappear within a week of being sent
  • “Signal is desktop and mobile now. Yeah, it’s pretty great. And it’s not owned by the Russians.” – Jason Calacanis 
  • Jason knows what gets each of the cast members going, and throws them alley-oops for their specific interests 
  • Jason is the point guard on the team
  • He will go to each member after the show and “very quietly” give them notes on their performance 
  • Jason is not disagreeing with Sacks when he challenges him, he is trying to help Sacks clarify his position  

Talent-Wrangling Techniques and Some Inside Baseball 

  • If you’re engaging in a group discussion about a certain topic and there are five good points to make, don’t hog all of the five good points
    • After making one or two good points, pass the ball to your teammate and let them make a good point 
  • Jason gives the members “the wrap up sign” by circling his index finger in the air, but also nods to indicate that what they are saying is interesting 
  • Jason got the “oh-kay” from Sam Harris after a guest goes on a long monologue, which indicates to the guest that you understand what they said and that you have something to add 
  • Tim slows down his question when he asks it to draw the listener and guest in, almost including them in the formation of the question happening in his head  

The Overton Window  

  • The Overton Window is the societal consensus on what is allowed to be discussed openly in society writ large
  • Imagine if the group chats you have with your close friends were shared with the world

Translating Skills and Building Popularity 

  • Jason had done thousands of podcasts prior to doing All-In, so much of his skill set transferred despite it being a slightly different playing field 
    • It was like ping-pong skills transferring to tennis skills 
  • He had a 10-person podcast team from This Week In Startups  
  • Whether you’re a millionaire or a billionaire, the steak tastes the same 
    • After realizing this, the scorecard for cash stopped mattering to Jason, which was freeing to him 
  • Money is not the right scorecard (beyond a certain amount); the right scorecard is, “Did you wake up and couldn’t wait to get out of bed?”  
  • “It is hard for me to go to bed sometimes because my enthusiasm for life is so high.” – Jason Calacanis 
  • You run on adrenaline in your twenties and thirties, but you start to question what is left when you enter your forties and fifties 

What Happens When You Catch The Car?

  • You have to ask yourself if you’re happy after you catch the car and the adrenaline rush has subsided 
  • There is a ton of self-deception that goes into convincing yourself that you need $20, $30, $50, or $100 million dollars 
  • It is a terrifying moment when you’ve made the $50 million and realize that all of your pain, anxiety and depression is still there 
  • People panic when they realize that making the $50 million didn’t fix all the things that are wrong in their lives 
  • All things being equal, it is better to have the money than to not have the money 
  • It’s worth studying why the prevalence of depression in “successful people” increases after they’ve caught the car 

Psychedelic Therapy and A Big Win In Colorado 

  • Jason believes that not enough people have looked inside themselves to identify where their trauma is and try to understand it 
  • Psychedelics taken in a therapeutic setting may help more people look inside themselves and process their trauma 
  • Colorado passed Proposition 122 which will allow therapists to use different psychedelics to treat trauma and PTSD  
  • Some people tend to mask their suffering with performance because they don’t want to face their pain and suffering that is driving the performance 
  • For some, the hot coals that fuel the engine consist of pain and suffering 
  • Check out these Podcast Notes on psychedelics, psychedelic experiences without drugs, and these notes on psychedelics and neurostimulation for brain rewiring  
  • You are working with nuclear power when you’re working with psychedelic compounds 

Jason Calacanis’s Billboard and Parting Thoughts 

  • If Jason could put any message on a billboard that would reach millions of people, he would put “Just Give It A Shot” or “Be Kind To Each Other” or “Have Great Friends; Build Cool Sh*t” 
  • Jason wants to see people be kinder to each other and have more open-hearted discussions with each other 
  • You can have productive discussions with people with that you disagree with
  • “The two best things I’ve done in my life is having great friends and building cool sh*t.”Jason Calacanis 
  • Someone is not telling the truth if you don’t have disagreements with your friends  
  • Tim has considered taking a break from the podcast after hitting a billion downloads, which should happen in the next few months or so 
  • Tim would seek out interesting people to have conversations with regardless of if he was doing the podcast or not, so he might as well record them (thanks Tim!)
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Notes By Stan Rizzo

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