The Endless Benefits of Risk-Taking

Robert Dell’Osso from MasterKey PM talks about what he’d tell himself when he started his business eight years ago.

I’ve always been involved in real estate, but I bought my first rental property when I moved to North Carolina for a corporate job. Taking that initial leap into property ownership helped me discover just how much I enjoy managing properties. I realized that managing properties for others would be my next best move, so I obtained my North Carolina broker’s license after buying that first rental property.

I started my single-family residential property management company, MasterKey Property Management, in Raleigh in 2016. We now manage around 450 homes for a diverse mix of clients ranging from accidental landlords with a single property to seasoned investors with larger portfolios.

While the majority of our clients own just one or two properties, we don’t handle short-term rentals, vacation homes, or large apartment complexes.

Our staff is equally diverse: We have two assistant property managers handling move-ins and outs; two remote team members to take phone calls, draft leases, communicate with tenants, and handle renewals; and an on-staff handyman to deal with maintenance requests. We also have our business development manager (BDM), who’s been with us for years.

Ultimately, we’re fortunate enough to be able to run a sizable operation with lean production methods.

What Would You Tell Yourself Back in 2016? 

The first thing I would do is remind myself that I don’t have to do everything alone. When I was first starting out, I handled the bookkeeping, the property repairs, and just about anything else that required attention.

At that time, I didn’t have relationships with any vendors, but I realized that trying to do everything yourself may seem like a tenable short-term solution, and yet, I realized just how much of a costly error it would prove to be down the road.

Don’t try to be your own BDM. I soon became overwhelmed and started dropping the ball on even the most mundane of responsibilities. Now, I know with confidence that I can rely on my experienced BDM to help me manage my time efficiently.

Then, hire a bookkeeper. Unless you’re an expert in that field, hiring someone to help you manage your books will go a long way for only a couple hundred bucks a month. Compare that cost with spending thousands to have someone clean up your books because you can’t reconcile them yourself.

Enlisting expert assistance for foundational business responsibilities and other low-cost tasks will go a long way in preventing unnecessary stress and expensive mistakes.

The other thing I’d tell myself is to stick with the management software I was using at the time.. From the beginning, you should take the time to research and select a software package that will scale with your business and accommodate its growth from the get-go.

Begin with the “end” in mind. Plan for long-term growth, even when it’s uncertain at the time. Be proactive rather than reactive.