3 Leadership Lessons I Learned from Being a Landlord for Nearly 20 Years

I grew up in a working class family in New York City. My father had a “side hustle” 40 years ago, long before the term was coined and became a?millennial trend. His after-hours gig was cutting and pruning trees for a tree company he ran when he came home from his day job at the New York City Parks Department. He worked late afternoons and weekends in order to provide for our family of six. My dad is the son of an immigrant––and I watched, as this man earned and saved, until one day he and my mom were able to purchase an investment property. It inspired me.

I moved to Florida back in 1995. I was in my mid-twenties and, like a classic?Gen-Xer, I was doing my best to climb up the proverbial corporate ladder. I was making close to $50,000 annually working as a manager for a Fortune 500 retailer––a nice income by most standards for a young women living in Florida at that time. I worked nights, weekends, holidays, and one very memorable 36-hour inventory shift, earning three promotions in my first two years. It wasn’t always blue skies, but I found the experience priceless and it helped lay the groundwork for my marketing career and entrepreneurial bug.

One of my hobbies when I moved to Florida was reading the classifieds. I was fascinated to see real estate listings in the 30, 40, and 50 thousand dollar range!? Could this be possible? That was unheard of in New York. From what I can recall, there were no apartments in the city for less than 100K …and most, much more.

After a couple years scouring the classifieds, I closed on my first investment property. It was a 600-square foot apartment for $27,000! A little gem in Boca Raton, with a great view of the train tracks out back (and accompanying tremors). I put a whopping $2,700 down, and took out a mortgage for the remaining 90%. I was officially a property owner. Yes! I happened to meet a girl who was going through a breakup so I rented it to her for $300 per month (about 50% less than fair market value at the time); but it was what she could afford… and, hey, I was still in the black!

Over the course of nearly 20 years, 17 closings and scores of tenants later (each with their own unique story and/or drama ;)… I forged lifelong friendships and learned some valuable lessons that have served me well in business too.

For example:

1-?“The first criteria of being a leader is to practice empathy – the ability to understand and share the feelings of another.”?–?Simon Sinek

That girl going through a rough patch who rented for a short stint at $300 soon became a dear friend. We created countless laugh-out-loud memories together! In an ironic twist, she later became my mortgage broker. And as fate would have it, a couple years later she would introduce me to my future husband. If I had not had empathy for her and put myself in her shoes, my life might be very different right now. I’m a big believer that in most cases, you get what you give––in business and in life.

2-?“Patience is a key element of success”?–?Bill Gates

When I first became a property-owner there were many times I was tempted to reduce the rent to fill a vacancy. And on several occasions, early on, I did. I look back now and realize that was a big mistake. With the exception of my first tenant, who became my friend (and never took advantage of me), I learned that waiting for the right tenant willing to pay the right price might be a bit daunting at times, but definitely worth it. The same holds true in business… if you are too quick to take the first deal that presents itself, and not wait for the right situation––one that puts a premium on your value (not your price), you may regret it.

3-?“People work better when they know what the goal is and why.” –?Elon Musk

The first few years getting tenants was trial and error for me (lots of errors ;). I can recall one time I rented to my hairdresser––regretfully with no lease. Needless to say that situation went south pretty quickly. Month after month he made up stories and gave me excuses instead of rent––and there were only so many times a month I could get another highlight treatment to my hair! After that, I made sure never to go into an agreement without a contract.

Eventually I graduated from using a template lease agreement (from Office Depot), to customizing one with a real estate attorney in order to eliminate any “gray areas”. I came to realize that setting clear expectations and putting rules (and goals) in writing helped to protect everyone’s interest. Gaining clarity up front made for smoother waters throughout the duration of the lease. I’ve carried that lesson with me in business too. If I’m working with a vendor, freelancer, client, employee, or employer, I’ve found if we both know where we are headed and why, it’s a winning formula. Whether it’s a job description, project authorization, or simple agreement, transparency and clarity benefit all parties.

Good leaders bring out the best in their team.

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This article was originally published on Cindy's Good Life Blog. Photo credit: Shutterstock