The Art of Property Management: Garrett Ham’s Blueprint for Success

Garrett Ham, CEO and principal broker of Weekender Management, Inc., brings a unique vision to the world of property management. His company doesn’t just oversee properties — it curates experiences. In an industry where detail is key, and quality is paramount, Ham’s approach ensures that each property under their care reflects excellence. They’re committed to managing spaces while also crafting memorable stays and ensuring guest comfort. This is evident in the company’s approach to vacation rentals, property management, and regulatory support.

The interview below is a treasure trove of insights for anyone interested in property management or looking to start a business. Join us as we uncover the story of a visionary leader and his journey to redefining excellence in property management.

Background and Inspiration

SBS – What inspired you to start Weekender Management, Inc., and how did your background prepare you for this venture?

Garrett – I had been investing in real estate for several years while I was in the military (I would purchase a home at each new duty location and then keep it when I moved to rent out). When I got out of the military, I moved to Connecticut to start graduate school. After two years into a three-year program, I decided that I wanted to move back home to Northwest Arkansas when I graduated. So, I started looking for investment property there.

However, the real estate market was hot at that time, so I found it extremely difficult to find a property that would cash flow as a long-term rental. After looking for a while, I came across a property that was doing well as a month-to-month rental, so I purchased that property and decided to put it up on Airbnb.

When I tried to find a local property manager to manage it for me, however, I couldn’t find anyone willing to take it on because of its location. Fortunately, my sister had just sold a glamping business she had founded, so I asked her if she could manage my property for me until I returned home. She did such a good job that other people began asking for her help with their short-term rentals, and we decided to turn it into a business.

As far as my background, I started my career after law school in Walmart’s real estate department at its corporate headquarters in Bentonville, Arkansas. I had the opportunity to learn a lot about real estate during that time. The three years I spent there were a great experience to prepare me for the role I have now. As discussed above, I became a real estate investor myself during my time in the military, which further honed my real estate acumen.

When we started the business, I was in graduate school at Yale. Yale’s graduate programs are relatively flexible, so I was able to take several classes in the Yale School of Management that I could apply directly to the business. This helped me focus on subject matters in which I thought my knowledge would be lacking, which helped us as we were just getting started.

Challenges and Solutions

SBS – What were the biggest challenges you faced when starting your business, and how did you overcome them?

Garrett – When we started our business, I had experience in real estate, and my sister, who became my business partner, had experience starting a company. But this was something different. Short-term rentals were not something with which I was that familiar. We didn’t have any mentors or really anyone from whom we could seek advice. We had to learn everything as we went, and we’re still learning.

We overcame this by being willing to take risks, try things out, and figure out what works. We also consumed whatever resources we could get our hands on. We read books, listened to podcasts, sought out-of-state mentors — anything we could do to learn from the experience of others, despite having no one around us from whom we could learn. And then, we tried out what we learned and saw what worked. And if it didn’t work, we abandoned it quickly. We were willing to try and fail and learn from that failure, which I think has provided us the greatest chance of success.

Business Model and Strategy

SBS – Can you describe the business model of Weekender Management, Inc.? How did you decide on this particular approach?

Garrett – Our business model focuses on managing short-term rentals on behalf of owners and attempting to maximize their income. We take a share of the total revenue, so it’s in our best interest to act in our clients’ best interest. The more we earn for the clients, the more we earn. Choosing this business model was relatively easy, as it’s the most common model in property management, short and long-term alike. Although some companies charge a flat rate, we wanted to make sure our interests aligned with our clients’ interests. The thing that caused regular evaluation and decision-making was not the fee structure but setting the criteria for the type of property that we took on.

When we first got started, my sister got a lot of inquiries from people who wanted to rent out their homes occasionally to make some extra money, such as on weekends or during special events, like the University of Arkansas football games. They didn’t want to rent out their homes full-time. As such, the few property managers in our area that would manage short-term rentals would not accept them. So, we decided we could create a niche for ourselves by managing these types of properties. My sister called these homes “weekender properties,” which is how we got our name.

After some time, however, we realized that there was a reason no one else was willing to manage these types of properties. It’s not sustainable. The number of properties we would need to make it a viable business model was simply beyond what our market could support. So, we abandoned this approach and no longer accept these types of properties.

However, we did keep a remnant of this model. We allow our owners to use their properties as much as they want, which is unusual in the industry. So, we do manage some properties that are owners’ vacation homes. We’ve found offering this service is a good middle ground between our initial business model and the more traditional one. While we found that managing “weekender properties” was not viable, we discovered that offering owners the ability to use their properties as much as they wanted was a nice benefit that they appreciated. It does cost us revenue, but we found the tradeoff in terms of customer satisfaction to be worth it.

Market Analysis and Trends

SBS – How do you analyze and adapt to the evolving market trends in property management?

Garrett – This is a tough one. The landscape of short-term rentals is always changing, particularly as city governments become much more active in regulating them. Some regulations are reasonable, but some are unnecessarily draconian. We deal with these issues by keeping up to date on what’s going on in the news that will affect us. When things get too bad, we also consider a wider array of options. I own and operate my own law firm that exists to serve investors in short-term rentals. Through my law firm, I am in the process of filing a lawsuit against one of the cities in which we operate over their short-term rental regulations. While we don’t like to go that route, sometimes we find it necessary to fight back against regulatory overreach.

Beyond regulations, we’re also monitoring shifting demand and customer expectations. As short-term rentals have become more popular, what guests expect has changed, and we have to keep up with that. We do this through reading news articles to monitor overarching trends, but we place the greatest emphasis on evaluating and responding to the feedback we get from our guests.

Pricing is the same thing. Setting prices is a never-ending process of learning and iteration. We’re constantly monitoring average rental rates in our markets — particularly with comparable properties — and our booking rates to determine what pricing should be, and making the appropriate adjustments. The market is changing constantly, so we have to change along with it.

Client Acquisition and Retention

SBS – What strategies have been most effective for acquiring and retaining clients in your business?

Garrett – The best way we have found to attract new clients is to perform well for our current clients. While we do advertise and market our services, many of our clients come by word of mouth. To retain clients, we must perform. It’s really as simple as that. If we maximize the revenue of our current clients, they’ll typically stay with us and refer other people to us. If we don’t, however, they won’t.

We also emphasize customer service, attempting to answer any questions that they may have or address any concerns they may have as quickly as possible. I make sure emails from clients go to my VIP folder, for example, so I can prioritize responding to them over addressing other emails. It also means constantly monitoring pricing and the market to maximize their income as much as possible. Unfortunately, we are not perfect in this regard, and sometimes we are unable to keep up with the expectations of our clients. But we do give it our all, and we believe most of our clients are satisfied with the service they receive.

Financial Planning

SBS – How did you approach financial planning and management in the early stages of your business?

Garrett – In the beginning, we were pretty much flying by the seat of our pants. We had a trust account to keep client money as it came in from their properties — as is required by state law — but it was a learning process otherwise. We tried to spend as little money as possible without damaging the business. I put up the money to get the business started, and we operated on that until the income from the business overtook our expenses.

We did take some risks during this time. To generate income while we were still trying to acquire a sufficient number of clients, we engaged in rental arbitrage. This is where we would sign a long-term lease on a property and then rent it out as a short-term rental, pocketing the difference in rent. This helped get us through the hard times in the beginning and allowed us to learn more about this business before we had the pressure of clients. So, as we got clients, we already had a lot of experience under our belts.

Technology Integration

SBS – In what ways has technology been integrated into your business operations, and how has it impacted your efficiency and service quality?

Garrett – Technology has been an essential part of our business from the beginning. Operating in a market that was transformed and made possible by online travel agencies like Airbnb and Vrbo, it was inevitable that technology would be essential. In the beginning, we utilized property management software to manage our bookings. This helped ensure that we didn’t double book by taking one reservation on Vrbo for the same dates as a reservation on Airbnb, for example.

We also began using pricing tools to help us monitor the market and adjust pricing as demand ebbed and flowed on a daily basis. We’ve utilized technology in whatever way we thought would improve our operations. Sometimes it worked out well; sometimes, it didn’t. If it didn’t, we abandoned it and moved on. Now, with the advancement of AI, we are excited to see what potential new tools may soon become available to improve our operations further.

Team Building and Leadership

SBS – What qualities do you look for when building your team, and how do you foster leadership within your company?

Garrett – When we hire people, we look for people with good attitudes and people skills. This is, above all, a hospitality business, which means good customer service is necessary. This is particularly true since this business requires dealing with unreasonable and unpleasant people from time to time. So, a good attitude and a generally pleasant demeanor are more important than anything else.

However, we also look for some kind of experience, and we like to hire people that we think will fill in the gaps that my sister and I have. Someone who excels at what we excel in, through no fault of their own, won’t be able to contribute as much as someone who excels where we lack. Once we hire people, we try to give them as much autonomy as possible so that they can take ownership of programs and make them their own, keeping in mind George Patton’s quote, “Don’t tell people how to do things, tell them what to do and let them surprise you with their results.” We believe that telling our people the end result we want and then letting them figure out how to get there can unleash all kinds of innovations and ideas that we would never have considered ourselves.

Risk Management

SBS – How do you identify and manage risks in your business operations?

Garrett – We have to be vigilant about monitoring what’s going on in the news and in our local area to assess risks. This can be something as obvious as the implementation of new regulations to something a little more removed, such as an economic downturn. We prepare for these risks by running through as many scenarios of possible problems we may face and formulating game plans for addressing them.

For example, if a recession causes travel to slow, we may shift our marketing focus toward those looking for a staycation or toward business travelers coming to Walmart headquarters who are less likely to be affected by a mild recession. In this, we appreciate the old mantra that plans are worthless, but planning is everything. We know things may not work out quite the way we planned, and we’ll have to adjust. However, already having thought about these things in advance and having a game plan in place will allow us to pivot and adapt much easier than if we were starting from scratch.

Growth Strategies

SBS – What strategies have you implemented for growth and scalability in your business?

Garrett – One way we have adapted for growth is by removing aspects of the business that need particular focus and spinning them off into their own subsidiaries or partner organizations. For example, my sister has been providing design services to our clients from the beginning. However, she has since opened up her own design firm, allowing us to continue to make that service available to our clients without it taking up the time and resources of Weekender and our team.

Similarly, we spun off the cleaning part of the business into a subsidiary/joint venture with a new partner who is able to give that important part of the business the central focus that it needs to help Weekender be successful. This has allowed us to maintain the core part of our business inside of Weekender without any distractions that other services may cause. This makes for fewer moving pieces to adjust as we grow.

In addition, we’ve created standard operating procedures for as much of our business as possible. These written procedures provide very clear, detailed instructions as to how to do things so that new hires can refer to them easily as needed and hit the ground running.

Customer Satisfaction

SBS – How do you ensure high levels of customer satisfaction and service quality in your property management services?

Garrett – We try to treat other people the way we want to be treated. That is, we try to put ourselves in the customer’s shoes — whether guest or client — and ask what kind of treatment we would like to receive from the property manager. That brings us a long way to preventing unhappy customers in the first place. But if problems do arise, we apologize and try to make it right.

This is a tricky business because we have two customers with sometimes competing interests: the guests and the property owners. So, we have to balance their interests against one another. That is not an easy process, and it is one with which we continue to struggle.

Of course, our primary focus is on the client, but performing well for the client also means performing well for the guest. So, we let our clients know upfront the efforts to which we will go to ensure guest satisfaction, and we do everything we can to ensure guests have a great stay with us. However, we do have to draw lines sometimes with guests and tell them there is a limit to what we can do for them. We cannot give them a full refund if a lightbulb burns out or the grill runs out of propane, for example. Sometimes, we just have to accept that there are some people who are just impossible to please, but following these strategies helps us reduce that number to as few as possible.

Advice for New Entrepreneurs

SBS – What advice would you give to someone looking to start a business in property management or a related field?

Garrett – Learn as much as possible about real estate and investing as you can. In addition to being a hospitality business, this is a numbers business. Numbers have to work, and owners have to get a return on their investment. While you don’t need an MBA, you need to have an understanding of this type of thing if you’re going to do well.

You also have to be prepared to deal with unreasonable people. They will be the minority, but they will be out there. You’ll have owners who think their one-bedroom condo in a mid-sized market should make $1,000,000 per year, and you’ll have guests who will pay $50 per night and expect a level of service to rival the Ritz Carlton. You sometimes have to be firm, but you always have to be professional. If you have a short fuse, this isn’t the business for you.

Finally, I would make sure that you have a clear understanding of your state’s laws. In my home state, you have to have a real estate license to be a property manager. So, you can get in some serious trouble by opening a property management business without a licensed person on board.

Future Vision

SBS – Where do you see Weekender Management, Inc. in the next five to 10 years, and what are your long-term goals for the company?

Garrett – I see us becoming a full-service management company for investors in short-term rentals. We already provide management services and housekeeping services, and through our partnerships, we provide design and legal services at significantly discounted rates. We have also just opened up an investment arm with the intent to raise funds from investors to purchase lucrative short-term rentals and manage them at reduced rates. Finally, we hope to open a realty arm soon as well, so we can help investors find and secure properties that would work well as short-term rentals.

Down the road, we hope to form a maintenance subsidiary with our own in-house maintenance staff focused on our clients and their properties and maybe even establish a subsidiary to serve as a hard money lender to help clients finance their purchases. We want real estate investors to be able to come to us and have all their needs met without having to rely on outside parties for anything.