The Messy City Podcast

Unpopular Ideas to Fix the Housing Market


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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



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The Messy City PodcastBy Kevin Klinkenberg

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