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Episodes from The Messy City Podcast

The Case for Optimism and Beauty

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...

Mar 31, 20261h 8m
The Best Life Hack, Ever

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...

Mar 17, 202650 min
Do our communities need better hardware or better software?

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...

Mar 3, 20261h 7m
What is a Starter Home?

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...

Feb 10, 202644 min
A Conversation with Ross Chapin

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 ap...

Feb 2, 20261h 7m
Reality in the Rust Belt

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 re...

Jan 27, 20261h 2m
You Have Agency

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 th...

Jan 20, 202643 min
Transforming Your Own Backyard

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 emul...

Dec 30, 20251h 1m
Brooklyn Doesn't Need Your Butt

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 bo...

Dec 17, 20251h 0m
Unpopular Ideas to Fix the Housing Market

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.<...

Dec 10, 202552 min
Can California Forever begin to cure the state's housing woes?

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 Flor...

Nov 25, 202550 min
How to Unleash the Swarm

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 huma...

Nov 11, 20251h 8m