The Peel with Turner Novak Inside the All-In Podcast: Lessons from Elon, Trump, Oprah, Travis Kalanick, Investing in 100+ Startups per Year with Jason Calacanis
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Dec 18, 2025 
Jason Calacanis, an influential investor and founder, dives into captivating discussions about media and startups. He shares lessons from his experiences with interview legends like Oprah and Charlie Rose. Jason reflects on launching multiple media companies and the origins of the All-In podcast, revealing its impact on the 2024 elections. He analyzes Trump's media strategy and his early investments in Uber and Robinhood. Finally, he warns about job automation's rapid pace, urging founders to innovate for independence.
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Listen For The Next Question
- Listen deeply and let the guest's answer embed the next question, then double-click that thread.
- Slow down, pause, and follow up on the answer to create synchronicity with the audience.
Experiment With New Mediums
- Treat new mediums as playgrounds and try them without asking permission.
- Early experimentation wins when you assume "what if it works?" and iterate fast.
From Photocopies To A Media Business
- Jason printed a zine in 1995, sold subscriptions from a party tear-out page, and funded himself.
- That small photocopy experiment turned into a sustainable media business.