Trevor is joined by entrepreneur, Dallas Mavericks owner, and television personality Mark Cuban. Mark recently announced that he’s selling his majority stake in the team and that he’s leaving the long-standing show Shark Tank after 15 seasons. Mark and Trevor talk about why he’s making these life changes, his Twitter battle with Elon Musk, and how he’s planning to positively shake up the American healthcare system.

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Trevor is joined by tennis champion Nick Kyrgios, who is known both for his prodigious talent and his “bad boy” reputation. They discuss how Nick feels about that label, the challenges he's faced on the road, and finding a kindred spirit in Naomi Osaka. Trevor and Nick also nerd out on gaming, and talk about what Nick's girlfriend thinks of his new OnlyFans account.

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To start off the new year, Trevor and his friends chop up some of the biggest news stories of the week. Just hours before its release, they make predictions about Jeffrey Epstein’s infamous “list,” discuss the controversial resignation of Harvard’s president Claudine Gay, and share their hopes and worries for 2024.

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Trevor sits down with Los Angeles mayor Karen Bass on the anniversary of her first year in office. In 2022, Bass upset a well-financed opponent to win the election and return to the city where her activism began. Mayor Bass discusses her work as a high school student on Bobby Kennedy’s campaign, why she cut a London trip short because of Angela Davis, LA’s homeless crisis, and whether she’d ever run for President.

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Trevor is joined by Tristan Harris, a tech ethicist and entrepreneur who is probably best known as "the guy from 'The Social Dilemma' documentary” and who has dedicated himself and his company to aligning technology with humanity’s best interests. Tristan debunks the myth of his Burning Man epiphany and unpacks both the promises and the perils that lie ahead with AI.

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Trevor is joined by genre-defying artist and performer, Janelle Monáe, whose 2023 album, The Age of Pleasure, was recently nominated for two GRAMMYs, including Album of the Year. Janelle shares her reaction to that honor, her rebellious youth, and why she used to be scared of mentor Prince and Grace Jones. Trevor also shares an exclusive GRAMMY update of his own, and his theory on why Beyoncé was late to the last one.

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Trevor has a candid and revealing conversation with Sam Altman, who was ousted and then reinstated as CEO of OpenAI just 12 days ago. Sam recounts where he was when he received the brutal phone call, how it all really went down, and its emotional toll. Trevor and Sam also discuss ChatGPT’s explosive release last year, Sam's hopes for AI to better humankind, as well as its potential for evil if not governed properly.

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Trevor sits down with Grammy-nominated rapper DaBaby, who just a few years ago was the face of hip-hop with multiple hit singles to his name. Then a controversial moment at the Rolling Loud festival in 2021 changed everything. Trevor and DaBaby face that moment head-on, as well as DaBaby’s challenging upbringing in North Carolina, how he understands his own role as a father, and whether he has any regrets.

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Trevor is joined by Bill Gates, the co-founder of Microsoft and one of the world’s foremost philanthropists. The two talk about how he and Paul Allen schemed to get computer time as teens, the dangers AI may play in our future, what it’s like to be at the center of so many conspiracy theories, Bill’s love of pickleball, and more.

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Trevor is joined by actress/producer/author Kerry Washington. The good friends unpack the end of the Hollywood strikes, the shocking family secret Kerry shares in her newly published memoir, the responsibility of being first on the call sheet, why James Corden is concerned for Kerry, and the one feature Trevor inherited from his family. Trevor also catches up with friend Christiana Mbakwe Medina about their different life choices and the reason she wants Trevor to marry and have kids.

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