Landlords And Losses: The Perils Of Capitalism In Jeremy Tyler’s “Fitting In”
There are a lot of times in Jeremy Tyler's memoir Fitting In that make you pause in the middle of a sentence and say, "Wait, what?" But not many parts hit as hard or as strangely as the one when a Section 8 renter planned her break-in to take the copper pipes from her rented residence.
Author:Darren McphersonReviewer:Habiba AshtonJul 29, 20257K Shares109.9K Views
There are a lot of times in Jeremy Tyler'smemoir Fitting Inthat make you pause in the middle of a sentence and say, "Wait, what?" But not many parts hit as hard or as strangely as the one when a Section 8 renter planned her break-in to take the copper pipes from her rented residence. After her anxious call, Jeremy rushed over, only to find her car parked outside with a strange mass of metal sticking out from under a cover. She kicked open the back door to make it appear as though someone had broken in. This isn't a story; it's one of many strange yet genuine tales from Jeremy's life as a young landlord in Indiana.
This story doesn't start with a man chasing wealth for the sake of luxury. It begins with a man chasing approval, security, and perhaps even love in a world that tells him he doesn't belong. Jeremy was 26 and owned 50 properties. He was dealing with tenants, contractors, lawsuits, and financial problems, all while fighting his demons. His path and ultimate disillusionment reveal a great deal about the cost of the American Dream and how capitalism can both benefit and harm us.
Jeremy didn't want to be a real estate billionaire; he just wanted to be a bank teller. He worked as a bank teller for his first job. Customers often made fun of him because they thought the job was "too feminine." For a young man who was already dealing with bodily dysmorphia and the wounds of years of bullying, it was another sign that he didn't belong.
He quit, then. He had no other choice but to work for his father. This man worked hard but was too generous, and he lost millions of dollars by lending money to others who never repaid him. Jeremy learned how to fix and paint houses, and soon he was buying and fixing up houses on his own.
By the time he was in his mid-20s, he had become deeply entrenched in the rental business, managing dozens of Section 8 properties, flipping houses, and taking calls from tenants at all hours of the day. Jeremy appeared to be a success story on paper. He had gone from being the "skinny kid" who was teased to a multi-millionaire who drove expensive automobiles and earned the respect of contractors who were twice his age. But as he says in Fitting In, that "success" came with a cost.
Jeremy talks about how he couldn't sleep because he was worried about broken furnaces, leaking pipes, and tenants who wouldn't pay rent. He became nervous every time the phone rang, fearing it might bring bad news. He felt increasing pressure as he acquired more houses. He writes, "I wasn't even at ground zero." "I was trying to get myself out of a deep hole."
He thought that his real estate empire would finally make him feel like he belonged. But it made him feel more alone than ever.
When Being A Landlord Becomes A Nightmare
Jeremy's narrative isn't just about running homes; it's also about running people and how that affects a person's soul.
Ralph is the old tenant whose furnace broke down. Instead of calling Jeremy to fix it, Ralph decided to use his oven to heat his home. What happened? A fire in the house burned Ralph's beard and destroyed both Jeremy's and the neighbor's stuff. Jeremy felt guilty. Why hadn't he looked at the furnace before? What was wrong with Ralph?
Michelle, a tenant, forged Jeremy's signature on bogus rent receipts and presented them in court, which prevented her from being evicted for months. Jeremy still felt like he was on trial, even though he had acknowledged the forgery in front of the judge. He remembers that "the judge still acted like it was my fault," which was the same thing that people had been blaming him for his whole life.
Each renter brought their own set of difficulties, some sad, some funny, but all of them were tiring. Jeremy says that tenants would flush socks down the toilet to damage the plumbing and then report it to Section 8, so they wouldn't have to pay their share of the rent. One renter even broke an old clawfoot tub by sliding through the floor below it, which turned the kitchen below into an indoor waterfall.
Every story shows how hard it is to be a landlord, especially when you're young and don't know what you're doing. Taking care of 50 homes wasn't simply a job; it was a mental marathon that lasted from dawn to dusk.
The American Dream Is A Lie
Jeremy's story is a classic American story of ambition: a young man with no college degree works hard, acquires real estate, and becomes a millionaire by the time he is 30. However, upon closer examination, Fitting In offers a warning about how capitalism exploits our weaknesses and perpetuates inequality.
Jeremy wanted to do well, not just for the money, but to show that he was good enough. People made fun of him all the time when he was a child because he was small and effeminate. He wanted to stop the people who dubbed him "the skinny fag" even as an adult, and he tried to fit in with a world that seemed to reject him at every turn.
But real estate didn’t save him. Instead, it threw him into a system complete with unfairness and inequality. He saw tenants having trouble paying their rent, and government programs like Section 8 exacerbated the situation for both landlords and tenants. He spent too much on contractors, renters cheated him, and courts took months to evict him. Jeremy felt like he was drowning, even though he was making millions.
His story is similar to the broader housing problem in the US, where owning a home and having financial means are generally considered the finest ways to demonstrate one's social standing and success. However, for many people, such as Jeremy, trying to accomplish these goals often leaves them feeling tired and despairing, rather than providing the safety they promise.
What We Learned From The Landlord Era
What can we learn from Jeremy's hard years as a landlord? Capitalism suggests that success doesn't always bring happiness. Jeremy still felt bad about himself, even though he owned several homes, drove nice cars, and had money in the bank. If anything, it made them worse.
Jeremy soon stopped managing rental properties. He hired someone else to deal with the continuous inquiries and sold off parts of his property. He realized later that his need to "fit in" had put him in a cycle of stress and self-doubt.
Fitting In isn't just about one man's journey as a landlord; it's also about the universal human need to belong and the false promises of money as a way to get acceptance. Jeremy's narrative is real, messy, and very human, and that's what makes it so powerful.
Jeremy Tyler'sbook tackles an unpleasant question in a world that urges us to work harder, buy more, and rise higher: What's the point of getting to the top if you still feel like an outsider? When the empire falls apart, the hardest part isn't building it; it's figuring out who you are.
Darren Mcpherson
Author
Darren Mcpherson brings over 9 years of experience in politics, business, investing, and banking to his writing. He holds degrees in Economics from Harvard University and Political Science from Stanford University, with certifications in Financial Management.
Renowned for his insightful analyses and strategic awareness, Darren has contributed to reputable publications and served in advisory roles for influential entities.
Outside the boardroom, Darren enjoys playing chess, collecting rare books, attending technology conferences, and mentoring young professionals.
His dedication to excellence and understanding of global finance and governance make him a trusted and authoritative voice in his field.
Habiba Ashton
Reviewer
Habiba Ashton, an esteemed professional in Digital Marketing and Business, brings over 10 years of experience to the table. She holds a Master's degree in Marketing Management from Stanford University and is a certified Digital Marketing strategist.
Habiba has authored numerous articles on SEO, Social Media Marketing, and Branding, published across reputable platforms.
Her impactful projects have consistently driven growth and visibility for businesses, earning her accolades from clients and industry peers alike. One notable achievement includes leading a digital marketing campaign that resulted in a 30% increase in online sales for a major retail client.
Looking ahead, Habiba is committed to pioneering ethical digital marketing practices that prioritize customer trust and engagement. Her vision is to lead initiatives that foster a transparent and sustainable digital ecosystem for businesses and consumers alike.
In her free time, she enjoys cycling, stargazing, and staying updated on digital entertainment trends.
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