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NOTE: This interview was recorded on September 5, 2025.

I'm so excited for you to see this conversation I had with RT Rybak. He was the mayor of Minneapolis for three terms — one of the most successful and popular politicians the city has ever seen. He won his third term with over 70% of the vote. And this is the kind of guy who was able to run a city while also hosting pajama parties at the airport to protest noise pollution.

We got into a lot. RT talks about why he still goes to therapy after leaving office, and how being that close to the worst moments in the city — murder scenes, the bridge collapse, sitting with families of kids who'd been killed — leaves emotional barnacles that don't just go away. I wasn't expecting him to open up about that the way he did, and I think it's one of the most important parts of the conversation.

We also got into the state of media (RT was a journalist before he was a politician), why he thinks the current fracturing of news might actually be a good thing, the night before the primary when he first let himself believe he might really become mayor of this city, what it was like to walk into office in deep financial trouble, and what he's doing now running the Minneapolis Foundation.

We also got into where downtown Minneapolis goes from here — the empty office towers, the conversions to housing, and why he thinks winter might be our most underused asset.

The conversation flowed by so quickly. I really enjoyed it. I think you will too.

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