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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)

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I sat down with Hope Walz just hours after her father announced he would not run for re-election as governor of Minnesota. It was a strange moment to talk. The decision was still fresh, and the reasons behind it were still settling.

We talked about what it’s actually like to grow up in a political family, how the last year changed her life, and what happens when politics stops being abstract and becomes personal. Hope opens up about receiving threats, briefly living with Secret Service protection during the national campaign, and what it felt like to lose that safety overnight.

She also shares how the decision not to run came together inside her family, why her dad believed stepping aside might lower the temperature around Minnesota, and how she thinks about media, social platforms, and responsibility now that she has an audience of her own.

00:00 Recording on the day of the announcement

02:43 What family conversations around stepping away actually looked like

04:36 Threats, harassment, and stepping back from social media

06:34 Living with Secret Service during the national campaign

09:43 Choosing life without security afterward

16:37 Being part of the decision not to run again

18:38 Minnesota as a national political target

37:08 Dating and having a normal life under Secret Service

44:24 Becoming a content creator after the election

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I went into this conversation thinking we were going to talk about billboards.

If you live in the Twin Cities, you already know the image — arms out, face everywhere, so many billboards they’ve become a regional inside joke. Kris Lindahl built one of the most recognizable personal brands in Minnesota, and I wanted to understand how that actually happened.

But once we sat down, the conversation went somewhere else.

It turned into a discussion about obsession, control, grief, and the strange psychology of becoming unavoidable. At times, Kris drove the conversation with sheer force of personality. At other times, I tried to slow things down and get into the weeds — sometimes successfully, sometimes not.

Did I do a good job pressing where it mattered? I’m genuinely curious what you think.

This episode goes into trauma, rumors, early hustle, and the parts of success that don’t fit cleanly on a billboard.

🎙 One Hour Detours is a long-form conversation series with exactly one rule: one hour, no edits.

Chapters

00:00 – Why Kris Lindahl Is Everywhere

03:45 – How Billboard Saturation Actually Works

10:30 – Selling Wristbands for Spring Break Trips to Mexico

18:55 – Building a Business Around Pure Visibility

26:40 – The Murder of His Father and How It Shaped Him

35:20 – Grief, Healing, and Personal Responsibility

43:10 – Did Kris Lindahl Swindle His Ex-Wife to Pay for Billboards?

51:40 – What Comes After Total Visibility

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CORRECTION: We recorded this interview on a Friday afternoon. The following Saturday morning Kathleen reached out to me and asked me to correct the record. At 57:15:41 she says "81st Airborne" when she meant the 82nd. The fact that she remembered this the detail in the early weekend morning speaks a lot to her commitment to getting the details right. Thanks Kathleen!In this episode, I sit down with Kathleen Hennessy, the Managing Editor of the Star Tribune, to talk about how news is actually made in Minnesota. Kathleen has worked everywhere from the Associated Press to The New York Times, and now helps run the largest newsroom in the Upper Midwest.We talk about who really holds influence inside a modern newsroom, how breaking-news decisions happen, the difference between transparency and anonymity, and why Minnesota struggles to have hard public conversations. Kathleen also walks me through the morning of the Melissa Hortman shooting and how the Star Tribune mobilizes behind the scenes at moments when the state is watching.CHAPTERS00:00 — Why Kathleen Hennessy came to the Star Tribune01:40 — How newsroom leadership and ownership actually work04:10 — Covering power in Minnesota: business, politics, and influence07:22 — Inside the newsroom during breaking news12:03 — The morning of the Hortman assassination16:02 — How stories get written now (live blogs vs. traditional reporting)20:00 — Minnesota’s relationship with hard conversations24:15 — Guns, politics, and generational echoes30:57 — Journalism vs. creators: authenticity and independence37:04 — How the Star Tribune decides what gets covered49:42 — What content actually converts subscribers51:48 — Why and when they use anonymous sources

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In this episode of One Hour Detours, I sit down with Liz Collin — Alpha News reporter and creator of "The Fall of Minneapolis" — for an unfiltered conversation about our city. We debate whether Minneapolis is a “failed city,” what it means to actually live here today, and why Liz uses such strong language to describe political opponents and local leaders.We cover: • Liz Collin’s controversial documentary The Fall of Minneapolis • Claims about Governor Tim Walz, Alpha News reporting, and media bias • How Minneapolis is portrayed as a “failed city” vs. lived experience • The future of new media, political rhetoric, and local journalismThis isn’t a softball interview. We challenge each other on how the media frames crime, politics, and public safety in Minnesota. Whether you agree or disagree with Liz Collin, you’ll come away with a deeper understanding of the debate over Minneapolis’ future.Recorded at the Kickernick Building in beautiful, downtown Minneapolis.Art by Megan Moore - you can see her works at https://www.meganmoore.com/"The Fall of Minneapolis" can be viewed at https://www.youtube.com/watch?v=eFPi3EigjFA⸻Chapters:00:00 Intro01:00 Am I “platforming” Liz Collin?08:00 Dehumanization, “the mob,” and political rhetoric15:00 Is Minneapolis a failed city?25:00 Alpha News and the rise of new media37:00 Why The Fall of Minneapolis went viral45:00 Living in Minneapolis vs. political framing55:00 Closing thoughts⸻#LizCollin #Minneapolis #AlphaNews #FallOfMinneapolis #TimWalz

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Minneapolis Mayor Jacob Frey joins me in a candid, emotional conversation just one week after a mass shooting shook the city. We talk about the immediate aftermath, his role on the ground, the nationwide struggle over gun reform, and what it means to lead a city through crisis. This episode covers everything from the father running barefoot to save his child, to the politics of assault weapon bans, to Frey’s personal reflections as a parent and mayor.