I’ve been an avid podcast listener since the early days of podcasting. It’s probably one area where I was a bit of an early adopter for technology. My guess is this is in part due to the fact that I grew up listening to a lot of radio, especially radio shows in the car when my parents were driving. So I suppose you can say I’ve always been interested in the audio side of conversations and entertainment.

Back a few years ago, my brother finally nudged me into trying to do a podcast, after he’d gotten his started. His is all about the Mississippi River and the culture, environment and communities along it. Take a listen, it’s really good! He’s an incredible wealth of information about the river, and was even featured recently on Rick Steves’ podcast.

But when Dean got me started, I wasn’t sure exactly how this would go, or if I’d enjoy having a podcast. Now here I am a few years later, with thousands of subscribers, and a milestone in episode #100. It’s been a wild ride, and getting more enjoyable all the time.

So for this one, I decided to have some fun with two of my good buddies - Jason Carter-Solomon and Shomari Benton. Both have been on before, and both frequently offer great insights into life as well as the sorts of topics I delve into routinely - planning, development, design and small-scale real estate investment.

We take some time on this episode to look back at our own lives, and we get a little personal. They even bring the questions to me, as we discuss our “why” for doing what we do, talk about career regrets, and think about what the future holds for each of us. I hope you enjoy it - we had a lot of fun doing this episode.

Thanks so much for listening to these first 100 episodes.

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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