Kyle Chayka is a freelance writer who writes for Businessweek, The Verge, Racked, The New Yorker, and more.

“I love that idea of form and content being the same. I want to write about lifestyle in a lifestyle magazine. I want to critique technology in the form of technology, and kind of have the piece be this infiltrating force that explodes from within or whatever. You want something that gets into the space, and sneaks in, and then blows up.”

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The Legacy

Real-estate mogul Charles Kushner had been cast out of power, found guilty of a strange bundle of crimes including “secretly setting up [his brother-in-law] with a prostitute, then taping the encounter.” His son Jared, then 23, was left to carry the ambition for the both of them.

Susan Casey is the former editor of O and the author of three New York Times bestselling books. Her latest is Voices in the Ocean: A Journey into the Wild and Haunting World of Dolphins.

“The funny thing is people often say, ‘You must be fearless.’ I’m always afraid of whatever it is. But for whatever reason—I think it’s partly naïvety, partly just overwhelming curiosity—I am also not going to let fear stop me from doing things even if I feel it. Unless it’s that pure…you do have to listen to your body sometimes if it tells you not to do something that could result in you really never coming up from falling on that 70-foot wave.”

Thanks to MailChimp, HelloFresh, and Squarespace, and for sponsoring this week's episode.