The Messy City Podcast

We take a break from our routine conversations today to have some fun, and talk about the wonders of travel hacking with my sister, Cindy Weir. Cindy epitomizes how to really leverage having a system for travel hacking, as she made the most of her small business to rack up points. It’s paid off incredibly for her, as she’s traveled to 22 countries in just the last five years, in addition to doing so in style.We go over how she got there, some of the many little tips and tricks we’ve learned over the years, and even share insider knowledge on airline lounges, lodging, and more.Are you someone that loves to travel? Do you own a small business or have an active side hustle? If you can say yes to both of those, then you need to listen to how Cindy it, and you can as well.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

Longtime friend-of-the-pod Abby Newsham returns, on her hiatus from the popular Upzoned podcast. Abby is a practicing planner in Kansas City with Olsson Associates. Abby is very active working with communities leading planning charrettes, and we talk at length about what a charrette actually is, the value of it, and why doing charrettes can actually give you hope that people can solve problems together.Then we talk about Billy Cooney’s article that was republished in Southern Urbanism, called, “Zoning Won’t Save Us,” which is basically on piece on why we over-rely on technocratic solutions to problems that are actually very human. I might say, you can’t solve a culture problem with a technical manual.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 perils of being in a profession or field for many years is how you see beyond simple dualities. By that I mean, you hear people argue confidently and vehemently about X vs Y, but you know there’s actually a Z they’re not even thinking about. Sometimes people talk about this as a “third way” solution. I confess that my whole life and career I’ve mostly been interested in those “third” ways, since I find they tend to have much more wisdom and insight than the other two.This came to mind recently when I was very kindly asked to speak with a group from ULI-Nashville about starter homes - the need, the barriers and the solutions. Because I can’t help myself, I opted to talk more about what I think we mean by starter homes, and some options for them that don’t get enough play in the conversation.This episode is a longer version of that talk, including the three different ways I look at starter homes. The issue is very timely, and it’s critical. We’re having a terrible time getting people into home ownership right now. A lot of this I covered in a previous conversation with Charlie Bilello, on the financial causes and barriers. But I’m at heart still an architect, so I think a lot about buildings and building types as part of this, and search for ways to talk about the problem in concrete terms.Let me know what you think in the comments. What type of starter home do you wish to have, or did you have? How about your parents and grandparents? What is truly missing in the marketplace, and how do we get to solutions in your opinion?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 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

Reflecting on three years of insights, the host emphasizes the importance of taking action over mere policy discussions. Conversations beyond personal bubbles are vital for community growth. A case study from St. Joseph, Missouri illustrates how local culture, affordability, and revival efforts can transform smaller cities. Focusing on Flyover Country, he champions local doers, urging individuals to create change without waiting for approval. The creative repurposing of obsolete properties and the human side of community building are highlighted as essential elements in fostering belonging.

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

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

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