Meet The Journalist Every Tech Billionaire is Afraid Of (Ft. Kara Swisher)

Legend. Disruptor. Tech’s sharpest critic. Kara Swisher doesn’t just cover Silicon Valley—she holds it accountable.

On this episode of The Burnouts, Kara sits down with Phoebe and Sophia for an unfiltered conversation about building a career on her own terms (and never waiting her turn). From calling out mistakes at The Washington Post as a college student to becoming the most feared interviewer in tech, Kara shares the bold decisions, brutal lessons, and behind-the-scenes power moves that shaped her journey.

She gets real about the early days of tech reporting, navigating anti-gay and anti-women environments, the importance of always asking for more (and walking away if you don’t get it), and what it really takes to own your IP in a world built by and for powerful men.

Plus: Why women need to ask for more (and not wait their “fucking turn”)

Come for the stories about Steve Jobs, Elon, and Succession-style media drama—stay for Kara’s hard-won wisdom on surviving, thriving, and never selling yourself short.

Also: why “fuck you money” only matters if you’re willing to use it.

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Chapters
02:30 – Getting hired by criticizing The Washington Post
06:00 – Losing her dad young & finding independence
09:15 – Money mistakes and financial advice for women
12:30 – Learning to negotiate, ask for more, and own her IP
18:00 – Walking away from Dow Jones and the New York Times
21:30 – Why power makes tech moguls weird
27:00 – The shrinking world of billionaires and “cashmere prisons”
29:00 – On grilling Zuckerberg, interviewing Jobs, and the point of journalism
32:00 – Advice for building a career in media today
35:00 – Kara’s blueprint: Be useful, be entertaining, be unique

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Subscribe to The Burnouts for exclusive conversations with today’s top founders and culture-shaping entrepreneurs. Hosted by former Stanford roommates turned startup co-founders, Phoebe Gates and Sophia Kianni, this isn’t just another founder podcast—it’s untold conversations and the unfiltered reality of what it takes to build your dream career in your 20s. Guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and more visionaries defining the brands—and blueprints—of our time. Whether you’re dreaming big or building now, these are the conversations that will show you how it’s done (and what no one else tells you).

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