Why I became a landlord: people, safety, and the feeling of home

If you asked me where home is, I honestly don’t have an answer. We moved every two years during my childhood which meant different houses, different schools, different friends, and feeling like life was constantly starting over. Moving from one small town to the next in the rural midwest in the 90’s meant most of the people I went to school with had known each other since kindergarten. I, on the other hand, felt like an outsider. I would start to make friends only to move the next school year. I was unable to relate to my peer’s experiences because my family was simply too poor and my parents were too busy working to play an active role in our lives. As a kid, it’s almost impossible to understand exactly why you’re different, but it was obvious to me that I was without really understanding why. This alienation, although difficult to articulate, is how I developed my fascination with the idea of “home” and the feelings associated with it.

Why was my life like this? The best context I can give starts with my mother. As a rebellious seventeen year old, my mom dropped out of high school, met a guy, and got pregnant. I honestly don’t know most of the details of this story as it’s too painful for my mother to share. Yet, on October 10th, 1987 here I was in the world. By my first birthday, my mother had married, divorced, moved out, and placed a no contact order on my father such that I didn’t even know I was estranged from my biological father until I was a teenager. Soon after these events my mom met the man that I call dad and was pregnant with her second son. Not long after came a third. When I was five years old, my mother moved out on her own, again, because my dad had a gambling addiction that left us hungry most nights.

One memory that stands out in particular is when, as a six year old, I went to the gas station a couple blocks from the house to buy some milk. My mom had just finished a long day of work and was lying on the couch exhausted. I went up to her, timidly, and told her we were out of milk. After lifting her arm and looking at me through weary eyes, she gave me a couple dollars from her pocket and told me to go get us a gallon of milk. I knew where to go so I walked the three or so blocks by myself to the gas station. After grabbing the milk from the bottom shelf in the refrigerator, I walked over to the lady behind the counter and gave her the money my mom had given me. She called me back because I didn’t even realize that I was supposed to get change. After reaching the curb to cross the street, I tripped, causing the milk container to hit the ground, split open, and get milk all over myself and the sidewalk. I started crying and went back into the store to explain to the lady what had happened and to ask if I could get another gallon of milk. I believed I couldn’t go home empty handed because I knew my mom didn’t have any more money for milk. Luckily, the cashier was kind and gave me another gallon to take home. I was extra careful this time and slowly hauled the gallon home taking frequent stops because my arms kept getting tired. Thinking back on this event, what sticks out is how traumatizing poverty can be. The smallest things, such as a replacement gallon of milk, can make or break a person’s day. Especially that of a six year old.

It’s with this reflection on the soul crushing impact of poverty that I found further inspiration to become a landlord. The largest individual expense for families, especially poor families, is rent. Living paycheck to paycheck sometimes means choosing between keeping a roof overhead or putting food on the table. As someone who had witnessed this firsthand, I believed I could be the landlord that compassionately supported the human being on the other side of the transaction. Knowing that many people have no choice but to rent, why couldn’t I be that compassionate landlord? I didn’t have to be the world’s best landlord, I simply had to do a better job than what else was available and from my experience as a child, I knew that bar was pretty low.

So, after winding down my first company, I decided to make the transition back home to South Dakota. I won’t tell this story today but suffice it to say, my decision to leave the Stanford / Silicon Valley / Y Combinator ecosystem was for a host of reasons, many of which stemmed from my own poverty mindset and the insecurity of not doing enough to create value. I was also craving that feeling of “home”, of security and I believed that by returning to the environment in which I grew up I could make a difference for the little boy in me who sought safety and acceptance.

Striving to be an understanding landlord was honestly my favorite part of the job. I got the chance to do this early on in my business when one of my first tenants had been late on his rent three months in a row. He was a single dad with three kids and had been able to consistently pay what he said he’d pay every two weeks, when he got his paycheck, but not when the rent was due at the beginning of the month. After the third time this happened, I reached out to him and suggested that we change how his lease was structured. Instead of the back and forth about waiving late fees, I suggested that we modify the lease so that he instead paid half his rent every paycheck. He agreed, telling me that he felt stressed about late fees and wondered when my generosity would run out and result in him getting evicted. I then told him the story of my mom being a single mother of three boys and that having a deal like this would have helped her immensely.

After we signed the new lease, I felt like I had created a true win-win. The win of helping a single parent worry a little less about money because I knew how hard it was living paycheck to paycheck. The win of the little boy within me feeling pride in helping other little kids have a dad who could be a little more present instead of stressed about money. And the win of compromise that helped both myself and the tenant succeed.

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