Dealing with tenants

General Advice

MAR 19, 2022

Last week, I made a very difficult choice. I rejected a rental application of a tenant who was going through a rough divorce. He was required to vacate his current home, which he shared with his wife of 30 years, by the end of the month. If he doesn’t find a place by the end of March, he’ll be homeless.

On paper, he was a strong tenant (A+ credit/income/employment). In person, however, there were a lot of red flags. I trust my gut instincts with non-quantifiable decisions; we’ve evolved to pickup on the intangibles of every situation. The realms of reality and fantasy are different — in fantasy land, everyone’s great and all is fair. But in reality, you can do everything right and still fail.

With that being said, in reality: I make business decisions devoid of emotions.

My walk-through & interview with him was a 6/10, but something I’ve learnt from my sales background: If a client is difficult at the onset, then your headaches will only get worse. In sales we learn this the hard way and have a saying: small deals cause big headaches. The best thing to do is walk away, it’s not worth the small payday.

Here’s a few of the red flags: wanting to move in prior to start date to ‘work’ on the property (painting, minor remodeling, DIY stuff — lol wtf don’t ever tell your landlord you’re going to remodel their property), standoffish attitude about paying prorated rent for starting lease early, talking over me during the tour, etc.

I initially accepted him as a tenant because he was great on paper, but after our interactions, I passed. I got into an argument with him about paying rent for the days he wanted access before the lease started. Man was such a nightmare to deal with before signing, I doubt it would get better after. To give you an idea where a landlord’s head is at during tenant screenings: I don’t want to be in a situation where he doesn’t pay rent, and I have a hard time communicating with him about it.

Through the experience, I learnt that it’s illegal in New York for a landlord to require her tenants to pay rent electronically. If your tenant wants to pay in cash or checks, you can’t force them to use an electronic management tool, but you can ask them.

Overall, the experience was a helpful reminder on the realities of investing. It’s a heavy human-interaction industry, both investor & customer facing — with the good comes the bad. Below is a screenshot of the text he sent me after I turned him down. Not going to lie he had me in the first half.

An update: My journey towards closing my first commercial deal has, expectedly, taken a few turns. As of last week, I’m a free agent! I’ve decided to resign from my job and dive into real estate with full force. I’m scared, anxious, but extremely happy with my decision. This feels like the right thing to do, and regardless of whatever happens at least I won’t be stuck with regret in the future.

A few weeks ago, I wrote about the quickest ways to start earning cash in real estate: wholesaling, and agent representation. Wholesaling is going to be my lowest hanging fruit because a lot of my startup sales skills port over well into this process. Cold calling, prospecting, discovery conversations and the most fun: closing! I’ve been submerged in so many tutorials and online content about wholesaling that it all feels incredibly overwhelming — as it should.

As things begin to materialize (and get realer!) I’m piecing together a few bits of my psyche to keep myself grounded: there’s a difference between being incapable vs. uncomfortable. For the most part, I confuse the two. Just because something is uncomfortable (like quitting my job to pursue my passion), doesn’t necessarily mean I’m incapable of doing what needs to be done to win — I’m just out of my comfort zone, not my ability zone. My next update regarding the road to my first deal should be a lot more concrete in terms of the targets and KPIs I’ve set for myself, stay tuned!


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