Property Manager Roundtable – Hear From The Pros

Property Manager Roundtable – Hear From The Pros

In the world of property management, there’s always something new to learn. Whether you’re just starting out or have years of experience, gaining insights from industry experts can be invaluable.

That’s why we recently gathered a group of seasoned property managers for a roundtable discussion to share their knowledge and experiences!

In this article, you’ll discover the key takeaways from our Property Manager Roundtable webinar — where the pros reveal their insights and advice on various topics related to property management.

Table of Contents

Starting a Property Management Company

Starting a property management company can be an exciting venture, but it requires careful planning and research to ensure success. To kick off our roundtable discussion, the experts shared a bit about their foray into the industry:

Matthew Whitaker, Evernest’s Founder and CEO, started his company at the beginning of the 2008 economic crisis by default. When the bottom fell out of the housing market, he was left holding 30 rental houses that he wanted to sell, but couldn’t. So he set out to find a property manager with similar beliefs and management preferences as to his own. Later that year, Matthew started Evernest and opened our doors for business.

Duke Dodson of Dodson Companies has a similar story. He says, “I got into the business in 2007. I had purchased two or three rental properties and was looking for a property management company. I couldn’t find one that I thought would do the job the way I wanted it done. I knew I needed to figure out what I was going to do with my life and I knew I wanted to start a business at some point. And the stars aligned in 2007!”

Tim Wehner, also of Dodson Companies, was dragged in by Duke! Tim says, “I graduated college in 2008 and was laid off, like many many people, at the very start of 2009. I moved back to Richmond, started doing odd jobs here and there, and met Duke. He asked me to come fill in for about a week until he hired somebody. That one week turned into three weeks, and then one day he kind of sheepishly came to my desk and asked if I wanted to stay on full-time. I said sure, and here we are 13 years later!”

Vince Deorio of redT Homes took a different approach. Vince says, “I was buying houses at the courthouse with cashier’s checks right out of college. I learned a lot about the entire process, but we didn’t do the management well. We tried and filed repeatedly to find a good property manager and eventually decided we just needed to do it ourselves. That was my way in.”

Finally, Michael Krause of Atrium Management Company shared his background. According to Mike, “I got started as a maintenance tech back in 2003 and the rest is history! I worked in maintenance for a decade or so and eventually connected with my business partner. We quickly became best friends and decided we wanted to get into business together. We now manage over 4,000 single-family houses in apartments.”

All that to say, there are so many ways one might find themselves in this dynamic industry. But, once you’re here, what exactly do you do next? Our guess: Learn and grow.

Lessons Learned Early in Property Management

The experts started out by sharing their experiences and the valuable lessons they learned early in their property management careers.

One recurring theme was the importance of hustle. “Whether it was showing a house or posting rents, I did everything. As you’re growing a business, you need to be out there hustling and grinding,” said Matthew

Other important lessons learned revolved around dealing with those first difficult clients. Duke says that, when you’re first getting started, you don’t have a ton to offer. So, you might get saddled with a few problem owners. “You’re pulled in so many directions, it’s a very difficult business and industry. And so, early on, you have to figure out where you draw the line with clients.”

The experts also stressed the importance of providing exceptional service. “We bought a company that had a really good reputation,” Mike said. “The former owners had done a great job and all their clients loved them. It was like we were never good enough, so it just took real hustle. Being willing to do anything for those first clients, eventually systematizing things, and doing anything to not lose a client in the first year was key.”

Greatest Pain Points for Property Managers

Our experts then candidly discussed the greatest pain points they have encountered throughout their careers as property managers.

One common challenge mentioned was communication. “Communication, being upfront, and providing more information helps a lot,” said Mike.

Another pain point highlighted was automating manual processes. According to Tim, “We’re trying to automate everything, but people still want to chat with us. There’s really no great answer. We’ve set up so many systems to automate things, but people still want to call you and have that conversation.”

The topic of leasing also came up. “One of our big friction points is days on market creeping up,” said Matthew. “We’re trying to figure out why that is — is it COVID? That’s probably some of it, but that’s one of our big internal conversations right now.”

New Prop Tech Making Positive Impacts

Technology has revolutionized the property management industry, so our roundtable experts had to share their thoughts.

One innovation that was unanimously praised was the improvement of fraud-detection tech. “One of the big challenges we’re starting to have in the industry is fraud around documentation,” said Matthew. “Today, there’s tech that can identify and cut down on that fraud.”

The experts also highlighted the benefits of AI. “We use ChatGPT all the time,” said Mike. “Owner emails that used to take a half hour? You can now do those much quicker. We also started using for rent collection. Highly recommend it.”

If you’re interested in implementing tech tools, check out our recent blog roundup, which includes!

Final Thoughts: What You Can Learn From an Expert Property Manager Roundtable

Our Property Manager Roundtable provided a deep dive into the world of property management, with insights from industry experts who have years of experience in the field. From starting a property management company to navigating pain points and embracing prop tech, there is much to learn from their collective wisdom.

Ready for More?

We know what it’s like to grow a property management business from 30 doors to more than 16,000. The journey was anything but easy, and we learned tons of lessons along the way. Our desire to share that knowledge with you motivated us to start the Evernest Property Management Show podcast, a weekly newsletter, and our monthly webinar series for property managers.

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