Jason Calacanis: Behind the Scenes of This Week in Startups – Inside Podcasting

Key Takeaways


Jason’s Crazy Childhood

  • Jason grew up in Brooklyn, NY in the 1970s/80s
    • “Our entire goal was to not be from Brooklyn; we just wanted to get out”
  • One particular set of memories: hanging around his dad’s bar/restaurant (which Jason describes as a very violent environment – “guns, Hells Angels, cops, drug dealers, and bookies”)
    • Jason started helping out at the bar when he was just 7-years-old
    • “I’m trying to think of my earliest memories; they’re all violent”
  • “All the fighting my parents did was over money”
  • Because of the above – “My entire goal in life was to have power, not to get beat up, and to have money because everything in my childhood was about not having money and not having power”
    • It took Jason until he was near 50 to understand these roots of his driven personality
  • Jason, a middle child, has a younger and older brother: his younger brother is a firefighter, and his older brother works in the finance industry
  • “Forget about helicopter parents, we were free-range. From a very early age, my dad would get home in the early morning hours from the bar with my mom being at work and say, ‘Everyone out of the house; I need to sleep.'”
    • Jason and his brothers would then hit the streets of Brooklyn with minimal money for 12 hours or so on their own (remember, this was the 80s)
      • “You can imagine the type of trouble a bunch of boys would get into; we were doing terrible things… shoplifting, fighting, vandalism… We were punks.”

How Jason Discovered His Discipline, Drive, and Persuasive Abilities

  • Jason attended Xaverian High School, an all-boys Catholic high school 
  • When he was 15, Jason was almost thrown out of high school for having such horrible grades
    • A science teacher stuck up for him, insisting to the principal to let Jason stay in school as long as he joined the taekwondo club 
      • Jason got very good very quickly 
      • The experience also spawned Jason’s interest health/fitness, leading him to run his first NYC marathon at age 17 (he actually had to lie about his age – the minimum age for running was 18)
        • “That’s when I started to get the inclination that I could get away with ANYTHING”
          • “It was a very early lesson I learned that I was an incredibly convincing person… I had persuasion, I had discipline, and I had drive. That is a wicked combination.”
          • “I learned that I could convince myself or other people of anything”
  • Jason’s grades also began improving – he went from a GPA of 64 (out of 100) during his freshman year to a 94 at the close of his senior year
    • “I had learned discipline through the martial arts and marathon running that I didn’t know I had”
  • Around this time, Jason also began reading about the benefits of positive visualization
    • “I would go through every mile of a marathon and imagine it. I imagined myself in first; I imagined myself in second. I told myself, ‘My body’s a machine controlled by my mind and I have control of my mind; I can do anything.’ I’d repeat that to myself every mile.”

The Magazine Space

  • In the 1980s/90s, magazines were very popular and Jason became fascinated, particularity with the power structure associated with them (editors, editors in chief, associate editors, managing editors, editor at large, etc.)
  • A realization that changed Jason’s life:
    • “You can either be the person who’s on the cover a magazine or you can pick who’s on the cover”
      • This doesn’t go where you think – “In my warped mind, I thought the person who picks who’s on the cover is more important”
  • Jason then dove in and created a series of magazines – “Which for me was just a way of getting power”
    • One of those was Silicon Alley Reporter, one of the top internet magazines at the time
      • Jason was once offered $20 million to sell it, but famously turned it down (he later sold it for ~$300k shortly after 9/11)

Into the Depths of Depression & PTSD

  • “I had PTSD from 9/11 that I didn’t know I had at the time” – Jason was diagnosed ~5 years afterward
    • Just how bad was it? – He’d cry when an ambulance drove by and he couldn’t bring himself to watch any 9/11 TV/anniversary coverage
      • It wasn’t severe depression by any means, but his mood was definitely altered
    • He eventually went to therapy with the encouragement of his wife
    • “This sense of injustice of 9/11 really just hit me very hard”

Weblogs Inc.

  • After selling his magazine, Jason still had a fire he needed to fuel, so he built Weblogs
    • “Blogs were going to be huge; it was so obvious to me. I wanted to build a $20 million company and sell it as soon as possible.”
      • (Jason actually sold it for $30 million 18 months after conception to AOL)
        • Jason cried when the bank wire it – “I no longer had to worry about money”

Jason’s Current Role as a Startup Investor and Advisor

  • “A lot of what I do now is sit with founders and talk to them about their fears and dreams. I then work with them to take their fears, dreams, and startups, which are a manifestation of their entire lives, and see if they can become successful knowing that 70% of the time a startup goes to 0.”
  • Nowadays:
    • “Every day I get a phone call from a founder telling me that I’m going to lose $300k from some investment or that their company’s shutting down… and that’s okay”
      • Jason, you could say, has become immune to failure


  • Jason’s first podcasting experience came when he launched “Calacanis Cast”
    • He released ~30 episodes over 2 years
  • He eventually changed the name to This Week in Startups (named after This Week in Tech, another popular podcast)
    • For early episodes, Jason would just record his lunch/dinner meetings with interesting people in the startup space
  • “This Week in Startups” just turned 10-yeas-old
    • They’ve released 950 episodes to date
    • They now have their own studio and 6 full-time employees

Jason Calacanis = Donald Trump?

  • In Jason’s book, he describes his investing style as “judgmental and combative” 
  • “I have enough self-awareness to know I was a bit insane as a magazine editor and an iconoclastic loudmouth earlier in my career”
    • “I see the power in being candid with people”
      • Kara Swisher has actually compared Jason to Donald Trump in this regard
        • Jason adds – “I’d like to think I’m more intellectually honest and well-researched. I think he’s a compulsive liar and narcissist. I’m a minor narcissist.”
  • “Part of my brand is to be aspirational. I work with entrepreneurs, and in order for us all to succeed, they need to be aspirational as well. I want the most aspirational and aggressive winners to come to me.”
  • Jason claims he’s one of the top-5 angel investors of all time (“But I’m the number 1 active angel investor”)

When Jason’s on his death bead looking back at his life, what will he say gave him the most joy?

  • Raising a family and productive children in the world who are happy, self-actualized, and doing great work
  • But secondly: Helping a massive number of founders succeed
    • “I truly believe that entrepreneurs and capitalism are both worth fighting for; same thing for fighting against socialism, communism, mediocrity, people not pursuing their dreams, and not solving problems.”
    • “I love founders. I love these people; I love entrepreneurs… Boy do they solve a lot of problems and make humanity better, and the state of humanity has NEVER been better.”
      • Even the most impoverished people today are better off than middle class/wealthy people were ~100 years ago

Jason’s Favorite Podcasts

Additional Notes

  • Jason took the NYC police department test and almost joined the Police Academy, but decided at the last minute to attend Fordham University as part of a night school program
    • He was forced to work multiple jobs during the day to cover tuition
  • Jason was once a volunteer EMT worker
  • Jason was once approached to work on a TV show with Harvey Weinstein centered around his role as a tech investor (Jason says it would have been similar to The Voice)
    • NBC bought the rights to the show, but after recording a few pilot episodes, it was never released (mainly due to Harvey’s scandal)
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Notes By MMiller

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