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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)

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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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For more than a year, I’ve been talking with Steve Grove about the future of news, the Minesota Star Tribune, and what it means to lead a civic institution in 2025.

In this conversation, I finally got to ask him the questions on the record: the role of billionaire owners in journalism, whether local news can survive the digital age, what really happened inside DEED during Covid, and why he chose to write a memoir that reads suspiciously like a political launch.

Steve is the CEO and publisher of the Star Tribune and former head of DEED, and he spent years at YouTube shaping the early creator era. This isn’t a surface-level media interview. It’s a deeper look at how journalism actually works, how power moves behind the scenes, and what’s at stake for Minnesota.

If you want more conversations like this, subscribe to One Hour Detours. And if you want more of my regular Minnesota stories, you can always find them on One Minute Tours.

You can purchase Steve's book, "How I Found Myself in the Midwest" here: https://amzn.to/49efESL (affiliate link).

⸻

Chapters

00:00 Who Steve Grove is and how long we’ve been talking

01:03 Writing a book while running the Star Tribune

04:20 The accidental political energy of his memoir

07:53 What government service really looks like from the inside

10:14 Why bureaucracy frustrates people but still matters

12:19 How polarization affects Minnesota differently

17:15 Has our culture actually recovered from Covid

20:10 The Minnesota paradox and the gaps we don’t talk about

23:23 Steve’s move from government to running the Star Tribune

24:31 Closing the printing plant and what that means

27:01 How digital subscriptions changed the business

29:00 The value of print, serendipity, and the E-edition

33:48 How the Star Tribune sets the agenda

36:03 The Pete Hegseth text messages story

39:47 What a publisher actually does inside an investigative scoop

41:14 The editorial independence question

41:35 Is it good for America to have media owned by billionaires

43:33 Conflicts of interest and whether they matter

44:31 Who should own the news in the future

46:09 How creators changed the landscape

47:20 Should creators be doing the job journalism used to do

49:04 What Steve learned from the early YouTube era

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Comedian MJ Matheson joins One Hour Detours to talk about breakups, open-mics, and the absurd joy of crying at Wisconsin Dells’ Noah’s Ark waterpark. We get deep on what makes Minnesota’s comedy scene unique, how trauma turns into timing, and why the suburbs are the true villains of the Twin Cities.

MJ also helps me workshop my own stand-up material about Minneapolis vs St. Paul — and things get unexpectedly emotional (and hilarious).

Chapters:

00:00  Intro – Meet MJ Matheson

02:30  Art, aesthetics & the set design

03:00  Crying at Wisconsin Dells during a break-up

05:10  The music that hurts so good

07:00  How MJ started in comedy

08:40  Open mics, sociopaths & surviving the scene

10:50  Love Island UK vs American reality TV

11:40  Catholic mass in a football stadium

13:00  What it takes to be a comedian day-to-day

16:00  Why open mics can be brutal (but essential)

20:00  Hosting Easy Speak at Volstead Emporium

24:00  When MJ called me out in the crowd

26:00  Workshopping my bit on Minneapolis vs St. Paul

35:00  The suburbs are the real enemy

40:00  Comedy as therapy and math equation

45:00  Holding for laughter & timing the beat

46:00  Laughter as a way to break tension

49:00  Collaborating on bits & ending the hour

Wall art by Genel Jumalon (https://www.jumalon.art/)

Filmed at Kickernick Building (https://www.kickernick.com/)

Hosted by John O’Sullivan (One Minute Tours, Hidden Middle)

Filmed at the One Hour Detours studio in beautiful downtown Minneapolis

To see the stand-up set that was performed later that night, see: https://www.youtube.com/watch?v=DJ7dOl5ZwBM