YouTuber Natalie Wynn, better known as ‪@ContraPoints‬ , may be the internet’s most persuasive political commentator. Known for her carefully produced, elaborate video essays, Natalie has an uncanny ability to attract and deradicalize viewers with reactionary, right wing politics. She sits down with Jon to talk about the importance of style in political persuasion, explain how the internet became fascist in 2017, and teach what it takes to actually change minds online.

00:00 Intro
01:20 Interview start
06:44 How the internet “became fascist in 2017”
11:58 Ad break
14:35 what YouTube comments reflect about society
16:31 How she approaches persuasion
25:30 why humor is an important tool for persuasion
31:28 Ad break 2
34:39 Natalie’s thoughts on “cancel culture”
43:52 the presence of envy in our culture
49:48 How do you unplug?

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Crooked believes that we need a better conversation about politics, culture, and the world around us—one that doesn’t just focus on what’s broken, but what we can do to fix it. At a time when it’s increasingly easy to feel cynical or hopeless, former Obama staffers Jon Favreau, Jon Lovett, and Tommy Vietor have created a place where people can have sane conversations that inform, entertain, and inspire action. In 2017 they started Crooked with Pod Save America—a nobullshit conversation about politics. Since then, we continue to add shows, voices, and opportunities for activism, because it’s up to all of us to do our part to build a better world. That’s it. End of mission.

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