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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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We drive the Driftless after a late night with Umphrey’s McGee and let the road pull old stories loose, from bike crashes and basement slot cars to a wild cat named George and the quiet joy of becoming a grandparent. Along the way, Amish buggies, Frank Lloyd Wright, and the honest comfort of unpolished podcasts set the rhythm.
• festival glow at a grass amphitheater with Umphrey’s McGee
• why the Driftless landscape feels different and holds sound
• Hillsboro Brewing, Taliesin, and car-camping culture
• curiosity about Amish craft, parts, and Sunday routines
• the new cadence of grandparenthood and re-learning care
• bike freedom, concrete gutters, and gravel-pit adventures
• basement ping-pong, slot cars, and an orange VW dream
• George the cat’s wild streak and what he taught us
• walkie-talkies, voice as company, and low‑polish podcasts
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Chapters
1. Rolling Start & New Format (00:00:00)
2. Festival Recap: Umphrey’s McGee (00:00:46)
3. Driftless Region & Landscape (00:02:35)
4. Hillsboro Stops & Taliesin (00:04:20)
5. Amish Roads & Buggy Curiosity (00:07:30)
6. Camping Setup & Venue Vibes (00:09:20)
7. Summer Update: Becoming Grandparents (00:10:20)
8. Seeing Amish Sunday Routines (00:13:30)
9. On Podcasts: Production vs. Real Talk (00:16:00)
10. Granddaughter Milestones & Re-learning Care (00:19:20)
11. Winter Roads, Sleighs, And Rural Life (00:22:30)
12. Detour, Coffee Hunt, Quick Break (00:24:10)
13. Growing Up Across The Street (00:25:50)
14. Bike Crashes, Gutters, And Freedom (00:28:00)
15. Marshlands, Gravel Pits, And Exploration (00:31:10)
16. Basement Cars, Ping-Pong, And VW Dreams (00:34:10)
17. George The Cat: Wild To Domestic (00:37:10)
18. Fifth Grade, Feelings, And Walkie-Talkies (00:40:20)
19. Signing Off On The Road (00:43:00)
40 episodes
