Triple Win Property Management Blog | Second Nature

Why I Quit Property Management: Real-World Insights

Written by Tony Cline | May 1, 2025 1:45:00 PM

Tony Cline has over 20 years of experience in property management. After purchasing a real estate and property management brokerage in Denver, Colorado, he spent more than two decades as managing broker. Today he's focused full time on his work as a Property Management Success Coach. Tony is a Second Nature Triple Win Mentor.

Most people in property management will tell you that it’s an industry with high turnover, especially for newcomers. As someone who found property management as a second career and launched my own business, I’ve seen that struggle firsthand.

It’s not common to stick around in property management for two decades, but that’s what I did before choosing to sell my business and focus on coaching. So why did I quit property management to run a consulting and coaching business?

My journey to property management

I didn’t start my career in property management. I actually focused mainly on process and data management for technology companies. Eventually I was part of an exit, and I decided that I wanted to try my hand in the real estate world.

I ended up buying a brokerage in 2000, and in the due diligence process, I discovered that they were also loosely managing 31 properties. When I say “loosely managing,” I mean that everything was very manual and the company didn’t have a lot of systems in place. Given my background in data and processes, I knew there was a lot of room to improve.

But back in 2000, property management wasn’t really seen as a profession. It was just looked at as something that real estate agents did on the side when they couldn’t sell houses. But to me, real estate sales meant big paychecks occasionally, followed by a month with no income. Property management provided consistent, predictable income each month, which is what I wanted.

Establishing my company

When I first bought the company, I immediately knew the property management side had a lot of potential. From day one I was focused on growing door count.

We were explicitly targeting loft condos in downtown Denver, Colorado. That was the profile of properties that the company was already managing, and I knew that I wanted to keep the focus narrow. We only had a couple of people on the team, but we had a clear target client profile and a strong sense of what we wanted our company to be. Because property management wasn’t nearly as popular then as it is now, we also didn’t have a whole lot of competition, which gave us an opportunity to dominate the market.

What I enjoyed most about working in property management

There was a lot of upside to running my business. First off, we were really good at what we did. Because we had such dominance in the market, it gave us an extra level of confidence in what we were doing, and inspired us to keep building. Plus, working in an emerging industry was very exciting, even if it came with some downsides.

More importantly, though, I really enjoyed the relationships I built with local property owners. We had a lot of repeat customers, so we got to know them well. We’d sell them a property, and then the client would realize the size of the investment opportunity, so they’d buy another one from us, and then we’d manage it as a rental.

On the flip side, we had clients that we were managing properties for who eventually decided to sell. When you already have that trusted relationship with someone as their property manager, you have the inside track on selling their property when the time comes. They’re not going to go shopping around for other brokers, or looking to nickel and dime you.

The most challenging aspects of property management

Almost anyone who’s worked in property management will tell you that it’s not always sunshine and roses. There are a lot of challenges, and my business was no exception.

For my company, one of the biggest learning curves in the beginning was learning to work with HOA management companies. Because we were focused on lofts, almost all of our units were in buildings that had HOA boards and professional HOA management companies. That creates certain challenges with certain repairs and renovations, move-in and move-out processes, and even small things like pet friendliness.

The other factor was that, like I said, it was 2000, and property management wasn’t nearly as common as it is now. I didn’t know anyone else who had done property management at that level. I didn’t even know about NARPM for about the first 11 years that I had my company, so in a lot of ways I was on an island of my own, trying to figure the whole thing out.

Eventually I ended up getting together with a few other property managers I knew in the area to form the Denver Independent Brokers Group. Even though a lot of our early members were only doing leasing, it still provided us all with a little bit more of a network and a group to learn with and from.

Growing and maturing as a business

The business was pretty successful pretty quickly, thanks to our specific market. I ran the company for nearly twenty years, and we grew to about 330 doors.

We hired more staff, and at our peak we had about eleven full-time employees. That seems like a lot for a company with 330 doors under management, but most of them worked in the brokerage arm of the company. Some worked across teams, selling real estate but also showing rentals. We only had about four dedicated property management employees.

Eventually we decided that the next stage of growth was to create a national brand. We knew that what we were doing was working well, and I had a network of other broker/owners who had similarly successful companies in other areas. So in December of 2019, we signed the paperwork to merge my company with four others across seven different markets. 

Stepping away from property management

Deciding to step back from property management—and from the business I had been building for two decades—was not easy. But in 2022, we decided to do it.

It had been a couple of years since the companies had merged, and it hadn’t been all smooth sailing. We had tried to standardize things across the country, and that didn’t always work. We had also elevated people who were thriving in their local markets into national positions, but that meant that the local offices no longer had the institutional knowledge that lived with those individuals. As a result, we struggled both at the local and national levels to adjust.

We weren’t exactly looking to sell at that point, but we were approached with an offer that was pretty strong. We realized that the merger had created a tough situation for a lot of us, and selling was a good way to untangle that. We ultimately decided to sell the business in order to decouple the partnerships that we had formed.

My advice to those in property management

After the decades-long property management journey I’ve been on, my biggest piece of advice to anyone who’s just starting out in the industry is to always continue to expand and grow your knowledge. Property management is a lot more mature now than it was twenty years ago, and it’s moving faster than ever. You want to make sure you’re staying up to date, because even if you don’t own a company now, you might in the future. The people who do own the company are eventually going to want to retire, so they’ll be selling at some point. Or you may want to go out on your own and start a company.

If you’re already a business owner, my advice is to design a business that can run without you, rather than design a business around you. In some ways, you want to be the least essential member of your team. Step away from tactical processes so you can focus on making strategic improvements and growing your bottom line.

Regardless of where you are in your career, my advice is to build wealth by building your own portfolio. Property management isn’t usually a high-margin industry, but when you start to build your own portfolio, you diversify your income rather than relying entirely on your business.

What I’m doing now

I’ve stepped away from actively managing properties, but I’m still in the property management world. I currently run a coaching business, ONYX, where I help property managers grow their businesses by getting more strategic.

In a lot of ways, I’ve been a coach my whole life, whether in business or Little League. I’ve been connecting with people in the industry since I first started, and part of NARPM since 2011, including serving as my local chapter president. I felt I had a good sense of the challenges other property managers were facing, so I decided to do some consulting on the side, starting in about 2017.

My coaching business was up and running as a side gig while I was still running my property management company. When we decided to sell that business, coaching worked well for me as a logical next step. I knew it was something I wanted to do more of, and suddenly I had the time and space for it. Now, with my company well established, I’ve been able to help nearly 200 companies improve their processes and become more effective.

 

If you want to learn more about my management philosophy, check out my recent episode of the Triple Win Property Management Podcast.

 

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