On the heels of Mark Zuckerberg’s live interview with the Acquired podcast, hosted at a packed Chase Center in San Francisco, Ben and Nayeema explore the icy relationship between traditional media and big tech.

Why are Silicon Valley’s CEOs more likely to be found gabbing on a podcast about their fashion choices than quoted in the New York Times? When did the media and tech breakup, who is to blame, and who wins and loses when hard questions are optional?

To answer these questions, they talk to a podcast host, creator, and investor who has been on the winning side of this dynamic: Jason Calacanis host of This Week in Startups and co-host of All-In. On All-In, Jason has interviewed tech titans and political figures including Marc Benioff, Elon Musk, JD Vance, and Donald Trump. Ben and Nayeema ask whether anything is lost when “CEO safe spaces” replace hardball interviews.

To wrap things up and bring the temperature down, Max Tani brings on an ESPN blindspot.

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Find us on X: @semaforben, @nayeema, @maxwelltani or on Instagram @nayeemaraza

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A Safe Space for CEOs (and Politicians?) with All-In’s Jason Calacanis 51:08 Share

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A Safe Space for CEOs (and Politicians?) with All-In’s Jason Calacanis