The Messy City Podcast

Kevin Klinkenberg
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Dec 30, 2025 • 1h 2min

Transforming Your Own Backyard

For a guy that never intended to be a developer, Steve Nygren is having a remarkable impact on development and so much more. Steve led the development of Serenbe, which is a “biophilic” community southwest of Atlanta. This story is nothing short of remarkable. Even if nothing more had happened than getting 500+ property owners that control about 60 square miles of land to agree on a framework for future development, that alone would be incredible.But when you start to learn more and experience the town of Serenbe itself, it becomes quickly apparent this is a model worth emulating. Serenbe employs a more historic model of a rural village that is walkable and fairly dense, mixed with land set aside for agriculture and experiencing nature. Along the way, the community has touched the world of regenerative agriculture and New Urbanism both, along with a deep dive into thinking about healthy living.Steve talks about using your influence when you have the opportunity, and how to help the next generation. His book, “Start In Your Own Backyard: Transferring Where We Live with Radical Common Sense” dives deep into this philosophy and work. I would add, he’s also got a lot to share about how to bootstrap a large, master planned development.Find more content on The Messy City on Kevin’s Substack page.Music notes: all songs by low standards, ca. 2010. Videos here. If you’d like a CD for low standards, message me and you can have one for only $5.Intro: “Why Be Friends”Outro: “Fairweather Friend” Get full access to The Messy City at kevinklinkenberg.substack.com/subscribe
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Dec 17, 2025 • 1h

Brooklyn Doesn't Need Your Butt

One of the mantras of small or incremental development workshops for years has been, “no one is coming to save you.” The solution to your neighborhood’s or community’s problem isn’t some outside force. It’s you. A similar mantra has been, “Brooklyn doesn’t need your butt.” Make it more colorful at your own leisure. We are often attracted by the allure of the sexy place, but it’s the not-sexy places that really need time, attention and effort from people who care.This episode gave me a chance to talk with someone who feels both those mantras deeply, and is doing something about it. Justin Pregont, from Pomeroy Development in Atchison, Kansas has taken up the mantle himself. He’s solving problems through real estate in his town, and in other rural towns across the state of Kansas. Justin was eager to see the types of interesting buildings and tenants he saw in bigger markets in his own town. So after realizing no one else was going to do it, he decided to figure it out himself. There’s a lot of inspiration, and a lot of hard reality in this episode. Maybe you think, I live in California or New York or Florida - what can I possibly learn from someone in small-town Kansas? Give it a listen, and then let me know.Find more content on The Messy City on Kevin’s Substack page.Music notes: all songs by low standards, ca. 2010. Videos here. If you’d like a CD for low standards, message me and you can have one for only $5.Intro: “Why Be Friends”Outro: “Fairweather Friend” Get full access to The Messy City at kevinklinkenberg.substack.com/subscribe
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Dec 10, 2025 • 52min

Unpopular Ideas to Fix the Housing Market

One of the most shocking pieces of information I’ve seen in the last year is how high the average age of all homebuyers has become. Depending on the source, I’ve seen between 59 and 62 years old. This is the *average* age. We’ve never seen a housing market quite like this, so I turned to Charlie Bilello, the Chief Market Strategist for the firm Creative Planning to help me understand it better. While I talk at length about the regulatory, design and policy aspects of housing on the podcast, Charlie is an expert in the financial side.We trace a bit of the history of how we changed the idea of housing from shelter to a financial product, and then hit on how those policy changes have created the mess we are in today. Charlie has a wealth of ideas that are admittedly unpopular, but could go to great lengths to fix the housing market over the short and long term.Along the way, we talk about fifty year mortgages, the impact of this issue on everyone under forty years old, the concentration of wealth with Baby Boomers, and why it’s so hard to make changes.If you want more from Charlie, check out his excellent YouTube channel.Find more content on The Messy City on Kevin’s Substack page.Music notes: all songs by low standards, ca. 2010. Videos here. If you’d like a CD for low standards, message me and you can have one for only $5.Intro: “Why Be Friends”Outro: “Fairweather Friend” Get full access to The Messy City at kevinklinkenberg.substack.com/subscribe
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Nov 25, 2025 • 51min

Can California Forever begin to cure the state's housing woes?

About forty years ago, the New Urbanism came on the scene with bold and creative ideas for building entirely new towns. The founders of the movement intended to prove that we could really build beautiful, walkable new places in America, much like some of our historic norms. Those early communities captured incredible attention, far beyond their actual size. And they’ve influenced a couple generations of people in the planning and development world.But it’s also true that most of the new places built were fairly modest in scale. Seaside, Florida, the famous community on the Florida panhandle, is just sixty acres in size. Many other new communities were the size of a suburban subdivision, or a smaller master-planned community. This isn’t a knock on the projects, it’s just the reality of what could be achieved and who the clients were.In recent years, an even bigger and more audacious proposal has come forward called California Forever. The founders have acquired over 50,000 acres in the Bay Area in Solano County. I speak with Gabriel Metcalf, the Head of Planning, to discuss the plans for this new community - the whys, whats and hows. This is a massive effort, and one that’s intentionally trying to renew notions of what can be done in a state that’s become famously difficult in which to build.Gabriel and I talk about not just the specifics of the proposed community, but how this effort fits into the historic context of new towns, and what he sees as precedents. Can we still build new places in America that are inspiring and solve 21st century problems? And what do new towns say about our existing cities and their struggles? We discuss all this and more.Find more content on The Messy City on Kevin’s Substack page.Music notes: all songs by low standards, ca. 2010. Videos here. If you’d like a CD for low standards, message me and you can have one for only $5.Intro: “Why Be Friends”Outro: “Fairweather Friend” Get full access to The Messy City at kevinklinkenberg.substack.com/subscribe
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Nov 11, 2025 • 1h 8min

How to Unleash the Swarm

Andrew Burleson asks us to think about, “what is the system that creates space for people to live?” Systems thinking may seem terribly wonky, and in reality, it is. But systems thinking gave us the Constitution and the Bill of Rights and a whole host of ideas that underpin western civilization. Systems thinking was behind the movement that created administrative city planning and zoning in the 19-teens and 20s. YOU might not be thinking about systems, but someone else is. So the question is, what kind of systems do we want and need, that produce the best outcomes for human beings?Andrew is a man of many hats, not the least of which is he’s the Board Chair for Strong Towns. Beyond that, he’s a terrific thinker in his own right, and writes a Substack called The Post-Suburban Future. This episode is an outgrowth of a post he wrote called, “Could we create land use rules that work better for everyone?” If the episode intrigues you, read the post, too. He goes into even more detail with images there.The main focus of our conversation is a notion I described a few years ago, which is we need to “unleash the swarm” to solve our housing and development issues. Andrew does an exceptional job of describing the problem (all development now is discretionary and professionalized), and that our land use regulations essentially require stasis. Stasis sounds comforting to many, but it actually works against our intentions when practiced in reality.In this episode, we talk about how to de-professionalize housing, which is a phrase I really like, and how to drive incremental change by the context of a block or neighborhood. Andrew’s phrase that I love is, “the individual project is small, but the collective output is enormous.” As I reflected on that, it occurred to me that’s the entire spirit of the American experience, and one we’ve gotten away from to our detriment.Find more content on The Messy City on Kevin’s Substack page.Music notes: all songs by low standards, ca. 2010. Videos here. If you’d like a CD for low standards, message me and you can have one for only $5.Intro: “Why Be Friends”Outro: “Fairweather Friend” Get full access to The Messy City at kevinklinkenberg.substack.com/subscribe
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12 snips
Oct 28, 2025 • 1h 6min

Talking Abundance and Strong Towns

In this engaging conversation, Seth Zeren, a developer and housing advocate known for his practical insights on placemaking, discusses his thoughts on merging the Strong Towns and Abundance movements. He explores the benefits of localized empowerment versus larger-scale reforms, emphasizing the need for state support alongside grassroots initiatives. Seth provocatively questions the legitimacy of municipalities in decision-making, while advocating for a return to historical building practices and a renewed focus on design quality. Tune in for an enlightening dialogue on housing and urban growth.
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Oct 21, 2025 • 55min

Reflecting on Leon Krier

A few months ago, we lost Leon Krier, one of the all-time greats in the world of architecture and urban design. I’m joined by Dan Parolek of Opticos Design to reflect on Krier’s work and influence, and his personal experiences working with him on multiple projects. Krier’s work and his many drawings have been foundational for so many of us that came through the world of New Urbanism. His simple, elegant way of dissecting what’s wrong with modern cities angered a lot of people in the architecture and planning establishment, but appealed to so many of us that knew something was wrong. In the end, there’s almost nothing about Krier’s work that should be controversial. He approached everything from the perspective of what is actually good for human beings. He felt we could and should learn from the acquired wisdom of the past and generations of people before us. That any of that should be controversial says so much about the era in which we live and how the design professions have mutated over the years.If you don’t know Krier, I hope this is an introduction. Please go check out his books. They’re incredibly easy to understand and read, and many are good for a laugh, too.Find more content on The Messy City on Kevin’s Substack page.Music notes: all songs by low standards, ca. 2010. Videos here. If you’d like a CD for low standards, message me and you can have one for only $5.Intro: “Why Be Friends”Outro: “Fairweather Friend” Get full access to The Messy City at kevinklinkenberg.substack.com/subscribe
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Oct 14, 2025 • 1h 4min

Reframing the Housing Discussion

Chuck Marohn, founder of Strong Towns and author of Escaping the Housing Trap, brings a fresh perspective on housing finance and policy. He critiques the 30-year mortgage's distortive impact on the market, exploring its historical evolution and systemic risks. The conversation dives into the role of yield curve control and how political motives manipulate interest rates. Chuck also emphasizes the importance of social trust in urban resilience and advocates for revitalizing struggling neighborhoods instead of pursuing high-rise developments.
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Oct 7, 2025 • 1h 46min

Episode 100: What is Your "Why?"

I’ve been an avid podcast listener since the early days of podcasting. It’s probably one area where I was a bit of an early adopter for technology. My guess is this is in part due to the fact that I grew up listening to a lot of radio, especially radio shows in the car when my parents were driving. So I suppose you can say I’ve always been interested in the audio side of conversations and entertainment.Back a few years ago, my brother finally nudged me into trying to do a podcast, after he’d gotten his started. His is all about the Mississippi River and the culture, environment and communities along it. Take a listen, it’s really good! He’s an incredible wealth of information about the river, and was even featured recently on Rick Steves’ podcast.But when Dean got me started, I wasn’t sure exactly how this would go, or if I’d enjoy having a podcast. Now here I am a few years later, with thousands of subscribers, and a milestone in episode #100. It’s been a wild ride, and getting more enjoyable all the time.So for this one, I decided to have some fun with two of my good buddies - Jason Carter-Solomon and Shomari Benton. Both have been on before, and both frequently offer great insights into life as well as the sorts of topics I delve into routinely - planning, development, design and small-scale real estate investment.We take some time on this episode to look back at our own lives, and we get a little personal. They even bring the questions to me, as we discuss our “why” for doing what we do, talk about career regrets, and think about what the future holds for each of us. I hope you enjoy it - we had a lot of fun doing this episode.Thanks so much for listening to these first 100 episodes.Find more content on The Messy City on Kevin’s Substack page.Music notes: all songs by low standards, ca. 2010. Videos here. If you’d like a CD for low standards, message me and you can have one for only $5.Intro: “Why Be Friends”Outro: “Fairweather Friend” Get full access to The Messy City at kevinklinkenberg.substack.com/subscribe
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Sep 30, 2025 • 1h 5min

Incremental Success, One Not Sexy Project at a Time

One thing that’s really obvious when you talk with Johnny Youssef is that he’s just a very positive and happy guy. And, frankly, it’s amazing what he’s accomplished at a still-young age. Johnny started his journey in Egypt, and eventually landed in Kansas City as a small developer and rental property owner. We talk about how he focused on the not-sexy parts of our region, and quickly built an income portfolio that has served him well.Johnny is the closest thing to a social media star that I’ve had on the show. In fact, almost everything we talk about can be seen on his channels, and I’d certainly recommend checking out his videos. In particular, his story of buying and renovating and old church here in Midtown KC is fantastic.There’s so much to learn from people like Johnny that just get in the game, take risks, and build. It’s a spirit we could use a lot more of, and in Johnny’s case I can’t wait to see what else he accomplishes.Find more content on The Messy City on Kevin’s Substack page.Music notes: all songs by low standards, ca. 2010. Videos here. If you’d like a CD for low standards, message me and you can have one for only $5.Intro: “Why Be Friends”Outro: “Fairweather Friend” Get full access to The Messy City at kevinklinkenberg.substack.com/subscribe

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