Blackbird Spyplane’s Jonah Weiner on Substack, resisting selling out, and Obama’s pants legacy

Blackbird Spyplane’s Jonah Weiner on Substack, resisting selling out, and Obama’s pants legacy

49:05 Oct 3, 2025
About this episode
Blackbird Spyplane, a style and culture newsletter, launched in 2020 as one of the early adopters and success stories on Substack. This week, Ben and Max bring on co-author and longtime magazine journalist, Jonah Weiner, to talk about how the newsletter has evolved, how it changed his marriage, and why he’s ‘grossed out’ by affiliate links. They also talk about if he wants to expand the business further, and why Obama epitomizes ‘the state of the art of dad pants.’ Sign up for Semafor Media’s Sunday newsletter: https://www.semafor.com/newsletters/media  For more from Think with Google, check out ThinkwithGoogle.com. Find us on X: @semaforben, @maxwelltani If you have a tip or a comment, please email us mixedsignals@semafor.com
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