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

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).

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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

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

Minneapolis City Councilwoman Latrisha Vetaw joins me for a candid, unfiltered conversation about the state of City Hall, why the council feels broken, and how politics can sometimes feel more like theater than public service. She opens up about trust issues on the dais, her fight for Northside representation, and yes—her unforgettable Usher cherry story.

This episode of One Hour Detours goes deep into what it means to serve a divided city, how national issues clash with local responsibilities, and the personal costs of being in public life.

Chapters

00:00 – Intro: Who is Latrisha Vetaw?

02:00 – Running for office vs. serving

05:00 – Mentors, training, and how to start in politics

08:00 – Facial expressions, performance, and being “real” on the dais

09:20 – Northside representation and standing her ground

11:00 – How an idea becomes law at City Hall

14:00 – Tobacco policy, coupon bans, and city attorneys

18:00 – Is City Council “broken”? Division and dysfunction explained

19:30 – Who represents constituents vs. themselves

20:45 – The encampment debate: healing camps or public danger?

23:00 – Talking openly about homelessness and addiction

27:00 – Third-term mayors, incumbents, and political fear

31:00 – Political violence, safety, and threats to electeds

36:00 – Why some people won’t run for office anymore

41:45 – Life in the spotlight: sports games, fans, and recognition

42:00 – The Usher cherry story

44:30 – Public vs. private life: when you’re always “the councilwoman”

47:00 – Drinks, social life, and the human side of City Hall

48:00 – Closed sessions and what really happens behind the scenes

50:00 – Can council members be friends? Division by voting block

52:00 – Dinners with colleagues and broken trust

54:00 – Why the council feels like “cosplay”

55:00 – Generational divides at City Hall

57:00 – Wrapping up

Minneapolis is at a crossroads. With the mayoral election approaching, three challengers sat down for a one-hour roundtable debate unlike any other — no stump speeches, no canned talking points, just a candid conversation around the dinner table.

From the role of money in politics, to the future of ranked-choice voting, to deep frustrations about racial inequities and North Minneapolis, this is a raw look at the candidates who want to replace Jacob Frey.

Omar Fateh — the leading challenger — was invited but did not attend, leaving an empty chair and questions about his record.

Watch this to hear unfiltered perspectives on the biggest issues facing Minneapolis.

Chapters:

00:00 – Introduction & Empty Chair: Why Omar Fateh didn’t show up

01:10 – Setting the stage: A dinner table debate, not another forum

05:00 – Who are you ranking #2? The games of ranked-choice voting

15:00 – Narratives of crisis: Is Minneapolis “at the bottom of the barrel”?

25:00 – Policing, safety, and the city’s trust deficit

35:00 – The role of money: Jacob Frey’s massive fundraising advantage

45:00 – Political identity: race, representation, and the mayor’s role

55:30 – The question I would have asked Omar Fateh about Uber/Lyft

01:00:00 – Closing thoughts: Leadership, trust, and who actually runs this city

Dallas Goldtooth has taken one of the most unusual career arcs in entertainment — from Minnesota rez-based comedy sketches with the 1491s, to Reservation Dogs, to the Fallout TV show, to starring alongside Jason Clarke in Apple TV’s The Last Frontier.

We talk about his viral beginnings, the transition from indie comedy to blockbuster streaming action, and what it means to represent Native voices on screen while raising a family of six.

Chapters:

00:00 – Intro & Dallas Goldtooth’s Hollywood leap

02:00 – Growing up on the Lower Sioux Reservation

07:30 – Comedy as survival: The 1491s & viral sketches

13:00 – Minnesota history, monuments, and reckoning with the past

20:00 – Landing roles in Reservation Dogs and Rutherford Falls

25:00 – Breaking down The Last Frontier

29:00 – The “copaganda” question and conflicted roles

34:00 – Representation, identity & Native roles in Hollywood

41:00 – Acting in Fallout with Walton Goggins

45:00 – Family life with six kids while acting

55:00 – Reflections on culture, comedy & the future

Former Minneapolis Mayor R.T. Rybak joins me for an unfiltered conversation about what it really means to lead a city and why authenticity is now the most powerful tool in politics. We cover the emotional cost of leadership, the changing face of Minneapolis, and how social media is reshaping civic power.

If you care about democracy, media, or the future of cities, this episode is for you.

No edits. No prep. One hour. Let’s go.

Chapters

00:00 Intro, One Hour, No Edits

01:48 “Disheveled” as a Media Strategy

04:15 The Power of Authenticity in Politics

08:23 Are TikTok Creators the New News Anchors

13:10 R.T.’s Career from Journalist to Mayor

17:00 Why He Ran for Mayor and Thought He’d Lose

21:45 Pajama Party Protests and Playful Politics

25:02 “I Was in Over My Head”

30:30 Trauma, Therapy, and the Emotional Toll of Public Service

36:12 The Cultural Shift in Minneapolis Politics

39:50 Should Outsiders Run for Office

44:10 How the Minneapolis Foundation Actually Works

50:40 Donor-Advised Funds Explained Simply

53:15 The Future of Minneapolis: Hope or Decline

56:33 Downtown Real Estate Collapse and Reinvention

59:58 Why Minneapolis Is Better Than Portland