When Elon Went Broke, the Dark Side of Podcasting & Tales from the Tech Trenches | Jason Calacanis

Dave Rubin of “The Rubin Report” talks to the “All-In Podcast’s” Jason Calacanis about the origins of podcasting and how it evolved from blogging; his obsession with mastering every part of media production for independence; the early days of podcasting before mainstream adoption; the influence of figures like Howard Stern, Adam Curry, and Tom Green on new media; the emotional impact and asymmetrical intimacy of daily podcasting; how fame in podcasting differs from traditional celebrity; his extroverted nature and unique connection with fans; investing in startups like Uber and Robinhood with high risk but massive returns; his “mutant” ability to spot winners in angel investing early, like Uber's Travis Kalanick; how he looks for founder traits like intensity, awkwardness, and deep conviction; why his childhood poverty in Brooklyn fueled his drive for wealth and control; the emotional moment when he became financially secure; the dangers of post-exit depression for entrepreneurs; how true freedom comes from building without needing permission or investors; the importance of skills over vague dream-chasing; how Founder University helps teach practical startup essentials; how Silicon Valley figures like Elon Musk were initially dismissed in LA’s entertainment circles; how the tech industry evolved from being admired to viewed with skepticism after the rise of Facebook and social media toxicity; how Elon nearly lost Tesla and SpaceX during the 2008 crisis; how Jason offered to personally loan Elon money and pre-ordered two Model S cars to support him; how that Model S became a historic prototype worth over $1 million; and much more.

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