Landlord Confessions: The Crazy Thing I Learned When I Started My Own Property Management Company

I’ve owned rental properties since I was in my twenties – and that means I’ve spent decades in the landlording business. Like most landlords and rental property owners, I started out managing my own properties and, as my portfolio grew, I began to explore other management options. After all, while you can feasibly manage one, three, or even a dozen (maybe) rentals on your own, when the number gets much higher than that even the most dedicated and talented individual will begin to get overwhelmed. When your portfolio hits the “tipping point” in terms of volume, it’s just time to make that move.

Well, that might sound good in theory, but it can be really, really hard to do in practice. As most rental property owners probably know, it’s very hard to find a property management company that feels the same way about your rental properties that you do. In fact, you’re basically “flying blind” when you hire a property management company in a lot of cases. Your relationship is built on a very thin foundation, and you probably do not have a lot of personal or direct experience with the company. And yet, you hire them to oversee your livelihood and/or the support system behind your retirement planning and passive income.

It’s a really, really tough place to be for both property managers and rental owners. In fact, it’s so close to impossible that I ultimately decided to start my own property management group, Olson Property Services, because I simply could not find a company that would provide me with the accountability and transparency I needed from a property management company!

Once I had started OPS, however, something really enlightening, surprising, and even crazy happened: Not all my investors immediately loved me.

Now, hear me out: I had expected OPS to basically be the answer to every real estate investor’s prayers because it was property management run by a real estate investor. After all, I knew what real estate investors needed! I knew what they wanted! I was equipped to provide it, and I had a sterling track record of upright business behavior stretching back years. I had a great reputation (and I deserved it)! So why was my company encountering so many combative clients? They were acting the same ways that I had acted and felt when I was working with other property managers.

I wondered what in the world was going on. After all, I had literally implemented every single thing that had been missing in the services provided by other property management companies. What was going on with my new clients? What was their problem?

As it turned out, the answer was simple: I had overlooked the thing that creates so much tension between real estate investors and their property management companies: communication.

When there is no shared experience or established personal trust, your relationship will rely on effective communication.

Of course, communication is the foundation. You still have to provide information, manage properties, and collect rents! But the first key to a good relationship with a property management client or a good property manager will be communication. Once I figured that out, my clients were much happier and, not surprisingly, so were the employees at OPS!

We established a series of guidelines for laying down effective avenues of communication with real estate investors that have stood the test of time, but first we had to figure out that communication was the heart of it all.

Learn more about Olson Property Services by clicking HERE or email Tom directly at

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