The Messy City Podcast

Bootstrapping Small Scale Affordable Housing

The Messy City Podcast

Show Notes

Terrell Jolly didn’t start out making it his mission in life to become a small-scale developer. But somewhere along the way, from Detroit to Kansas City, he made it happen. And boy is KC lucky to have him. TJ, as most people know him, is a unique guy in this town, and has a very unique process. But should it be unique, or should what he does be much more normal? He talks through how he bootstrapped his way into becoming a developer, how he works with Missouri’s Abandoned Housing Act in neighborhoods that the vast majority of developers avoid, and why he takes on such a difficult task. When I hear TJ talk, I think to myself, this is what our cities need. For a lot of cities in the Midwest in particular, we have a LOT of older homes and buildings that need renovation. We also have people who need affordable places to live. It’s people like TJ that figure out how to make it all economical, and are showing us a path towards something that can scale. But as he says, “you gotta have the guts.” It’s not easy. It’s not for the faint of heart. But it sure does have its rewards. Every city probably has a Terrell Jolly, and every city could use about a dozen 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”

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More from The Messy City Podcast

Oct 20, 2026

I first came across Chris Arnade with the rollout of his book, “Dignity: Seeking Respect in Back Row America.” It’s a terrific book, and explores community, human struggle and American cities and towns in ways that most books do not. He sort of became “the McDonald’s guy” after that book, but it’s really so much more. Over the last few years, Chris has been writing a Substack called “Chris Arnade Walks the World.” I might effusively compliment Chris too much in this episode, but I truly mean it. His writing and approach to writing is truly unique, often surprising and always interesting. In a certain way, Chris’s writing has filled a void, for perhaps just me personally, that was left by the death of Anthony Bourdain. Now, that may seem a strange comparison, and Chris might not even enjoy it. But what Bourdain often did was to use food (and later martial arts) as a lever to trying to understand people better all over the world. As time went on, he also explored more and more places off the beaten path as he sought understanding beyond the travel magazines or websites, or beyond what most of us see when we travel internationally. Food and cooking is not Arnade’s schtick, but his writing (and photography) follow his own curiosity about people and culture that I see as a bit analogous to Bourdain. Arnade is looking through his own lens, and his own unique set of curiosities, but as a reader, I feel it still converges on striving to more deeply understand humans. And as someone who also occasionally writes about walking, I find a strong connection to this approach. In this episode, we cover some of the ground and topics that Arnade frequently covers, and diverge to talk more about places that surprise him, and what his travels have taught him about life in the USA. I hope you enjoy. 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”

Oct 7, 2026

For most of my career, people in the urban planning, architecture and development world have almost completely avoided the discussion on crime and order in cities. We seem to like to pretend it’s either not important, or we have nothing to say about it beyond CPTED (Crime Prevention through Environmental Design) techniques. In many cases, I just have people hand-wave the issue away, as if it doesn’t really matter - “crime will happen no matter what, I’m not an expert,” blah blah blah. Let’s talk about zoning standards and street design instead. Today I discuss why this issue needs to be front and center, especially now as most suburbs build out their own downtowns and walkable neighborhoods. I discuss the importance of seeing your own city as others see it, and what the actual marketing proposition is for living in a city. I admit for most of my life, I have not cared enough nor focused enough on this issue. I’ve probably had the same, very typical attitudes you see in the professional, urban world. That’s simply no longer the case, as I’ve gotten much more of an insider’s view, and as my own city has suffered through demand destruction due almost primarily to this problem. And, it’s not unsolvable, either. Many of the solutions just involve making this a clear priority, and getting everyone focused on it as a team. Perhaps I’ll dive more into that in the future. For now, I rant. 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”

Sep 15, 2026

You might wonder how a podcast on urban planning, design and development could get interested in the arcane subject of property taxes. Except that, it’s all over the news lately, and its another fundamental issue than actual normies care about. People in my city have left it because of outrageous tax re-assessments. Developers and investors won’t invest in my County because of the same. And, frankly, we are a fairly no-drama, modest cost part of the world compared to many places. So I turned to Jaime Izurieta to start this conversation. Over at his Substack, The Vertical Sidewalk, Jaime recently authored a piece called “When the Levy Breaks,” which is a thorough introduction to how we got here with property taxation. I found the history incredibly interesting, and as a good a starting point as any for diving deep into this topic. As Jaime likes to say, “We don’t know that our way of doing this is the best. And we don’t know it isn’t.” But if we don’t start by understanding how we got here, we’ll never understand how to move forward. 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”

Sep 1, 2026

Returning champion Aaron Lubeck joins me to discuss his exceptional piece called, “Revisiting Euclid v. Ambler at 100,” which he posted on his Substack “On Housing.” Aaron also posts and helps curate “Southern Urbanism” - an excellent publication I highly recommend. While a lot of ink has been spilled and words shared about the impact of the Euclid v Ambler case, Aaron’s column adds some new wrinkles and information to it that even surprised me. We talk in some detail about the case itself, the arguments made, and the people you might be surprised that were considered the “out” groups in that era. We also talk some about what a post-Euclid world could look like, and the implications for the planning profession. Because Aaron and I can’t stop at just one topic, we also hit on some of the perverse consequences of building and energy codes, and how “The modern world destroys all that cannot be quantified” as he states. Oh also, Mel Brooks at 100, and the need for more satire in our lives. Enjoy. 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”

Aug 25, 2026

Architect, Author, Photographer and New Urbanist Steve Mouzon joins me to tell his story about the emergence of New Urbanism in a location that many would consider unlikely. Huntsville, Alabama might be known for Space Camp, but it’s not widely known as a place to find great urban design and architecture. And that’s a shame, because there’s more lessons to learn here for most cities than by flying to a big, coastal market. Steve talks about the emergence of the Village of Providence in the early 2000s, its unique characteristics, and how that project also influenced the rebirth of downtown Huntsville. He also shares some of his own travails and triumphs, asking “why not us?” For more on Steve’s work, please do check out his incredible resource at The Original Green. 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”

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