The Messy City Podcast

Kevin Klinkenberg
  • 5.0 (23)
  • DESIGN

Embracing change, uncertainty and local initiative for our cities and towns kevinklinkenberg.substack.com

  1. 3D AGO

    A Conversation with Ross Chapin

    One of the great trends in housing from recent decades has been the revived interest in micro-communities, especially those organized around shared courtyards. I first started to learn about this in the late 1990s, and am delighted to say it’s really picked up steam since then. Ross Chapin has been at the forefront of all this, and taught many of us how to do it well. In this episode, Ross talks about how in some sense he accidentally got into doing this kind of work, how it changed his practice, and then importantly we explore key approaches to design and details that make it all work. Ross likes to say, “If you’re in your happy place, you’re going to sing.” But do we achieve that just by lining up a bunch of buildings around a lawn space? No, the details really matter, and Ross takes us through how to balance security and connection, how to think about layers of space, and how to design small homes and spaces that feel great. Every once in a while, I get in trouble with diehard YIMBY (Yes In My Backyard) activists because I insist that design of housing matters, and we need to build housing that actually satisfies human needs. Yes, we need to make it vastly easier to build just about everything. But too often we overlook human well being, and ignore aspects of our human nature that determine success or failure in new developments. Ross Chapin has blazed a path for all of us to better understand this all. Take a listen. 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

    1h 7m

  2. JAN 27

    Reality in the Rust Belt

    Jason Segedy returns for his third appearance on the show, as Jason now works in North Canton, Ohio as the Deputy Director of Administration. Jason has also gotten more active on LinkedIn in recent months, with his usual provocative and insightful thoughts on a variety of topics. I highly suggest you look him up! We hit on why a huge supply of older homes may not be an advantage, especially in a weak housing market, the challenges of population decline (and why people shouldn’t be so blase about it), and what it might take to actually recruit people to the region. We also manage to discuss my pet issue as it relates to the management of cities - at what scale is best for communities to operate? What’s it like on the inside, working at larger and smaller scales? Jason is also always thoughtful on the big picture and what he sees happening in the culture and the country. We talk about why he thinks this is a big moment for a lot of change. 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

    1h 3m
  3. You Have Agency

    JAN 20

    You Have Agency

    After three years of podcasting, I share some thoughts on why I do this, and what I hope to achieve and share. Maybe you like it, maybe you don’t - either is fine, really. But my focus is and will continue to be on people who take concrete action, not on obsessive policy wonkery. It’s not that policy wonkery doesn’t matter - it’s just that too many people waste too much time focusing on it, when life has so many more productive ways to pass the day or the years. Similarly, my focus is on the so-called Flyover Country. It’s what I care about, it’s what I love, it’s the people and places I want to succeed. If that’s not your cup of tea, if that limits the reach of this Substack and podcast, that’s just fine. It’s not possible to be all things to all people, and each of us has to find where to direct our intentions. In this episode, I share a story about St. Joseph, Missouri, and how it ties to this focus and a mindset of what really makes a difference in life. Live your life somewhere that needs you and wants you. Build things. Create life and activity. It’s what we are meant to do. 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

    44 min

  4. 12/30/2025

    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

    1h 2m

  5. 12/17/2025

    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

    1 hr

  6. 12/10/2025

    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

    52 min

  7. 11/25/2025

    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

    51 min

  8. 11/11/2025

    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

    1h 8m
See All (114)

5
out of 5
23 Ratings

About

Embracing change, uncertainty and local initiative for our cities and towns kevinklinkenberg.substack.com

Information

  • Creator
    Kevin Klinkenberg
  • Years Active
    2023 - 2026
  • Episodes
    114
  • Rating
    Clean
  • Copyright
    © Kevin Klinkenberg
  • Show Website
    The Messy City Podcast

You Might Also Like