Uploaded July 2026 | Updated September 2026, 2 weeks ago
Dave Eggers (Contrapposto, The Circle, and A Heartbreaking Work of Staggering Genius) is a bestselling author, founder of McSweeney’s, and Pulitzer Prize finalist. Dave joins the Armchair Expert to discuss the strange family lore behind McSweeney’s, growing up in John Hughes-era Illinois, and falling in love with writing and designing books as a kid. Dave and Dax talk about moving to Berkeley to help raise his little brother after his parents died, shaking up literary readings with They Might Be Giants, and building a creative community out of rejected magazine pieces. Dave explains why kids should be published, how writing can give order to chaos, and why the happiest creative life might be the one with the least preciousness.
Check Allstate first for a quote that could save you hundreds: allstate.com
Watch Armchair Expert episodes: youtube.com/playlist?list=PLzPEuwClyOzDdlrAmU-IwKncG87qrF7Vw
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About the Show:
Hi, I’m Dax Shepard, and I love talking to people. I am endlessly fascinated by the messiness of being human, and I find people who are vulnerable and honest about their struggles and shortcomings to be incredibly sexy. I invite you to join me as I explore other people’s stories. We will celebrate, above all, the challenges and setbacks that ultimately lead to growth and betterment. What qualifies me for such an endeavor? More than a decade of sobriety, a degree in Anthropology and four years of improv training. I will attempt to discover human “truths” without any laboratory work, clinical trials or data collection. I will be, in the great tradition of 16th-century scientists, an Armchair Expert.
Watch Armchair Expert every MONDAY, WEDNESDAY, and FRIDAY here on Youtube!
Listen to episodes ad-free by joining Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/shows/armchair-expert-with-dax-shepard
Chapters:
0:00 - Trapper Keepers
5:02 - Comedians
9:27 - Young Writers
14:29 - Seeing the Magic Trick
20:04 - The Vince Vaughn Talent Show
26:23 - Elevating New Voices
33:17 - Starting McSweeney’s
38:21 - Doing What You Love
46:14 - Casuals
52:52 - Common Ground
1:03:27 - Contrapposto
1:09:20 - The Snooty Art World
1:21:30 - The Ambition Gap
1:33:10 - 826 Valencia
1:38:33 - Jetpack Academy
#armchairexpert #daxshepard #daveeggers #contrapposto
Dave Eggers (Contrapposto, The Circle, and A Heartbreaking Work of Staggering Genius) is a bestselling author, founder of McSweeney’s, and Pulitzer Prize finalist. Dave joins the Armchair Expert to discuss the strange family lore behind McSweeney’s, growing up in John Hughes-era Illinois, and falling in love with writing and designing books as a kid. Dave and Dax talk about moving to Berkeley to help raise his little brother after his parents died, shaking up literary readings with They Might Be Giants, and building a creative community out of rejected magazine pieces. Dave explains why kids should be published, how writing can give order to chaos, and why the happiest creative life might be the one with the least preciousness.
Check Allstate first for a quote that could save you hundreds: allstate.com
Watch Armchair Expert episodes: youtube.com/playlist?list=PLzPEuwClyOzDdlrAmU-IwKncG87qrF7Vw
Follow Armchair Expert on social:
instagram.com/armchairexppod
facebook.com/ArmchairExpPod
twitter.com/armchairexppod
Connect with Wondery
wondery.com/shows/armchair-expert-with-dax-shepard
facebook.com/WonderyMedia
twitter.com/WonderyMedia
instagram.com/WonderyMedia
tiktok.com/@wonderymedia
About the Show:
Hi, I’m Dax Shepard, and I love talking to people. I am endlessly fascinated by the messiness of being human, and I find people who are vulnerable and honest about their struggles and shortcomings to be incredibly sexy. I invite you to join me as I explore other people’s stories. We will celebrate, above all, the challenges and setbacks that ultimately lead to growth and betterment. What qualifies me for such an endeavor? More than a decade of sobriety, a degree in Anthropology and four years of improv training. I will attempt to discover human “truths” without any laboratory work, clinical trials or data collection. I will be, in the great tradition of 16th-century scientists, an Armchair Expert.
Watch Armchair Expert every MONDAY, WEDNESDAY, and FRIDAY here on Youtube!
Listen to episodes ad-free by joining Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/shows/armchair-expert-with-dax-shepard
Chapters:
0:00 - Trapper Keepers
5:02 - Comedians
9:27 - Young Writers
14:29 - Seeing the Magic Trick
20:04 - The Vince Vaughn Talent Show
26:23 - Elevating New Voices
33:17 - Starting McSweeney’s
38:21 - Doing What You Love
46:14 - Casuals
52:52 - Common Ground
1:03:27 - Contrapposto
1:09:20 - The Snooty Art World
1:21:30 - The Ambition Gap
1:33:10 - 826 Valencia
1:38:33 - Jetpack Academy
#armchairexpert #daxshepard #daveeggers #contrapposto
