Crazy Characters From My Real Estate Misadventures

Sometimes I find it hard to believe that I worked in real estate for a whole five years. I’ve written before about how the industry attracts some of the absolute worst people in the world: outright scammers and con artists, by-the-book operators with no ethical compass, and even the occasional gentle and moral person whose aggressive boringness makes them somehow worse than the criminals. (At least most of them are interesting.)

But not everyone in the real estate industry is a monster. Real estate—especially Detroit real estate, especially in the early 2010s—also attracts some of the absolute weirdest people in the world. And I’ve always had a soft spot for the weirdos. Thus, today I’m introducing a new and likely intermittent series in this newsletter, where I’ll tell you about some of the crazy people I encountered during my days in Detroit real estate.

Today: a character I’m calling the Renegade.


My friends and I often like to talk about how we moved to Detroit in 2012, before it was cool, but the Renegade really moved to Detroit before it was cool—in 2007, when the housing market collapse that would eventually hit the city harder than anywhere else was just in its earliest stages, and the so-called “Detroit renaissance” wasn’t yet a glimmer in the eyes of the businessmen and billionaires who would kickstart it a few years later.

He never told us exactly why he’d decided to make the move—I suspect he wasn’t even totally sure himself—but in a way it was obvious. Detroit, like Alaska and Las Vegas, is part of a small group of American places that exerts a magnetic pull on misfits and weirdos of all sorts. “Go west, young freak:” if you’ve never really fit in anywhere else you’ve lived, you end up trying your luck in a place that generates horrified looks in people’s eyes when you tell them you’re moving there. It could be a fishing boat off the coast of Juneau, or it could be Detroit in 2007.

The Renegade bought and fixed up a decrepit house in a part of East Detroit that’s considered dangerous now and therefore must have been considered even more dangerous at the time. But I got the sense that the Renegade wasn’t afraid of much. He was bearded and always looked a little unkept, and had an affinity for outdoorsy vests with lots of pockets; he seemed like he could talk to anyone, anywhere, and feel at home, a character trait I desperately envy.

The Renegade was a licensed realtor, but my impression was that he was more often hired as a sort of all-purpose fixer: the kind of guy you would turn to if you needed to not just sell a house, but also to clear out a family of raccoons, or broker a deal with a group of squatters who had claimed it as their own. He started a podcast about Detroit real estate, and made low-production-value YouTube videos where he’d tour neighborhoods and show off houses that were for sale to next-to-nothing. He eventually started a Detroit investors’ group that was miles away culturally from the rest of the buttoned-down Michigan real estate events, all of which met in barren suburban outposts that made the Boston suburb I grew up in look like Tokyo.

But my favorite story about the Renegade is undoubtedly the time he performed at at-home euthanization of his dying dog, using heroin he bought on the street.

He dropped this tale remarkably casually—in fact I think it may have even been while he was interviewing my cofounders and I for his podcast, though I don’t think this particular anecdote made the final edit—and he seemed to take a some delight in our obviously astonished reaction. The dog was terminally ill, but the Renegade was too poor to afford a visit to the vet, or maybe he just didn’t trust the medical establishment, even the one that caters to animals. How he could be sure of the dog’s condition without a formal diagnosis remained somewhat ambiguous, but the Renegade was confident in his knowledge, and he clearly loved the dog deeply. If he’d told me they’d had some kind of psychic connection, I would have believed him.

With vet-provided euthanasia off the table, the Renegade decided that the next best option was the homemade version. So he went out and bought some heroin—a sentence he said as casually as you or I might say we went out and bought some toothpaste. He had never used heroin, he clarified, but in his neighborhood it was clear even to non-users how to get it, at least if you were the kind of plugged-in guy the Renegade was. Then he shot up his dog (he looked up how to do it online), and held him as he died.

You could tell it had been an emotional moment for him , but you could also tell that he was proud of his ingenuity. In a way, what he’d done was no different from Detroit’s many other DIY projects, like the homemade streetlight our neighbor made to illuminate the block back in the days when almost none of the city’s real streetlights worked.

The Renegade obviously knew his story was crazy, but you could see that on another level he thought there was nothing unreasonable about it. He had taken initiative, been creative, solved a problem in a logical way. And most importantly of all, he had done right by his dog. All pets should be so lucky.


Now that I’m 31 and live in Brooklyn, a normal place for 31-year-olds to live, my life is much more boring than it used to be. There are crazy characters all over New York, of course, but here even the craziest of them are still familiar: if you haven’t run into them a million times on the subway or in line at D’Agostino’s, you’ve seen them on Broad City or High Maintenance or Seinfeld or Friends. As Tolstoy would have said, the weirdos in New York are all alike, but the weirdos in Detroit are all weird in their own way. And the Renegade and so many others I knew then have completed their slow fade from real people to stories. I reminisce about them occasionally, and that’s it.

I don’t think he’ll end up reading this, but it’s not totally impossible either. We might still be Facebook friends; he might stumble on it some other way. I’ve learned the hard way that when you write something on the internet, the person you least want to read it inevitably will.

If he does see this, I hope he recognizes himself in it; I hope he feels like I got him on the page right. And I hope he realizes how much I miss the days when everyone I met, everything that happened to me, didn’t need a single piece of exaggeration to make for a good story.

Yours in wondering how long I’m going to coast on “I once lived in Detroit” being one of the most interesting things about me,

Max