The Messy City Podcast

Kevin Klinkenberg
  • 4.9 (25)
  • DESIGN

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

  1. 1D AGO

    The Case for Optimism and Beauty

    Social media is an unlikely place to find truly positive and optimistic people. But occasionally you find one. Today’s example: the charming and determined Coby Lefkowitz, whose relentless optimism can only rub off on you. Coby is a developer in New York state, and a prolific writer, poster and speaker on the value of beauty in the built environment. He’s written a book called “Building Optimism” and has a Substack by the same name. In his Substack, you can read more about his forthcoming project in Kingston, NY, and what all he’s trying to accomplish. Coby and I discuss the role of optimism in a longer, healthier life, whether or not building beautifully is actually more expensive, and the intriguing benefits of thinking of your social media audience as just yourself and your Mom. Coby’s story is also a great example of how a young person can gain valuable experience working for someone else for a few years, grinding it out, and refining your skills before embarking on your own. You can find Coby on X/Twitter here. 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

  2. MAR 17

    The Best Life Hack, Ever

    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

    51 min

  3. MAR 3

    Do our communities need better hardware or better software?

    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

    1h 8m

  4. FEB 10

    What is a Starter Home?

    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

    45 min

  5. FEB 2

    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

  6. 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
  7. 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

  8. 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
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4.9
out of 5
25 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
    118
  • Rating
    Clean
  • Copyright
    © Kevin Klinkenberg
  • Show Website
    The Messy City Podcast

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