The Messy City Podcast

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

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

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

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

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