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I sat down with Comrade for exactly one hour, and it turns out when you put an iconic awkward comedian on the pod, you get… well, it nearly broke the show.

Comrade is a prolific comedian who’s also building something real in the world, and we talk about how he balances performing, creating, and actually paying rent while trying to make meaningful work. We get into where his comedy comes from, why discomfort is kind of the point, and what it looks like when you keep showing up even when you don’t feel ready.

If you want to check out what Comrade is building (and support his work), start here:
👉 https://www.comradetripp.com/

And if you like conversations like this, the best way to support what I’m doing is to become a supporter at oneminutetours.com. That support is what lets me keep sitting down with interesting people and seeing where the hour takes us.

Thanks for watching, and I’ll see you on the next detour.

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Support the show and get behind-the-scenes access at oneminutetours.com.

This week I sat down with Richard Carlbom, the chair of Minnesota’s Democratic Party, in the middle of one of the most volatile weeks this state has seen in years.

A woman had just been killed in south Minneapolis during a federal operation. ICE activity was escalating across the metro. Schools were shutting down. Protesters were flooding the streets. At the same time, Minnesota’s governor announced he wouldn’t seek reelection, throwing the state into an open race for power.

Richard is one of the people quietly responsible for holding all of that together — managing the party’s response, keeping elections functioning, and figuring out how a democracy operates when pressure keeps rising.

We talk about what his job actually looks like when a crisis hits, why language and outrage suddenly matter so much in politics, and where the line is between protest, civil disobedience, and real political change. We get into misinformation, the way entire communities become scapegoated, and why Minnesota keeps finding itself at the center of national political flashpoints.

We also talk candidly about how candidates are really chosen, what an open governor’s race means behind the scenes, and what lessons he took from leading Minnesota’s marriage equality campaign — especially about listening instead of lecturing voters.

This is a grounded, honest conversation about power, fear, responsibility, and what it actually means to try to protect democratic systems when they’re under stress.

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Grammy-winning musician Joe Mailander of The Okee Dokee Brothers joins John O’Sullivan for an uncut, one-hour conversation about music, fatherhood, faith, and finding meaning in the simple things. From their early canoe trips that inspired a Grammy, to turning down another nomination in protest, this episode dives deep into the power of family folk—and why the songs we sing with our kids often hit hardest as adults.

New Album: Little Old You — out now
Album debut show: Ordway Theater January 10 & 11. Tickets available at https://ordway.org/events/the-okee-dokee-brothers/

Learn more at https://www.okeedokee.org

📍 Chapters:

00:00 Intro — Why The Okee Dokee Brothers matter

03:00 “Nature’s Music” (live performance)

06:00 The art of family folk

08:00 When kids’ music makes adults cry

14:00 Faith, simplicity, and the folk tradition

20:00 Saint John’s Abbey, brutalist architecture, and belief

31:00 Parenting, spirituality, and emotional honesty

38:00 Turning down a Grammy nomination

46:00 Fatherhood lessons and “Little Old You”

57:00 “Through the Woods” (live performance)