Today we’d like to introduce you to Garrett Ham
Hi Garrett, thanks for joining us today. We’d love for you to start by introducing yourself.
My journey to where I am today has been anything but linear. After law school, I worked in real estate, starting my career at the Walmart corporate headquarters in Bentonville, Arkansas. During this time, I joined the Army National Guard, where I served as a JAG officer. This role eventually led me to the active-duty Air Force, where I continued to serve as a JAG officer for four more years.
After completing my tour, I attended Yale University for graduate school, initially planning to earn a Ph.D. and pursue a career academia. However, in my final year, I pivoted toward business, when I started Weekender Management with my sister..
The idea for the company came about almost accidentally. I had always rented my properties out on a long-term basis, but I discovered a property in Northwest Arkansas that would cash flow as a short-term rental. When I couldn’t find a property management company specializing in short-term rentals willing to manage the property, I managed it myself with the help of my sister. Word spread quickly, and within a year, we were managing over twenty properties. Today, Weekender Management oversees about 50 short-term rentals and is expanding into new markets, including Florida and Missouri.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
One of the earliest struggles was building Weekender Management from the ground up without an existing template for short-term rental management in the area, as the industry was in its infancy. When we first started, we were essentially figuring everything out as we went—from pricing strategies to creating systems for cleaning and maintenance. It was a trial-and-error process that took a lot of time and energy to refine.
Scaling the business has also presented challenges. As we grew beyond just a handful of properties, the need for robust systems, specialized staff, and technology became apparent. Hiring the right people was a particular pain point. Finding team members who not only had the necessary skills but also shared my vision for exceptional customer service took time.
Another significant challenge has been competing in a saturated market. Large national firms often lure property owners with lower commission rates, but their quality of service doesn’t always match. Convincing owners that a local, high-quality management company like Weekender Management could bring them better returns wasn’t always easy, especially early on when we lacked a proven track record.
On the legal side, managing the complexities of short-term rental regulations has been a constant struggle. Navigating zoning changes, city ordinances, and licensing requirements while ensuring compliance for our clients has been demanding. Thankfully, my legal background has helped me tackle these issues more effectively, but I don’t anticipate these challenges letting up any time soon.
As you know, we’re big fans of Weekender Management. For our readers who might not be as familiar what can you tell them about the brand?
Weekender Management is a property management company specializing in short-term rentals, but we’ve recently expanded to include long-term rental management services as well. We’re based in Northwest Arkansas, with a growing footprint in Missouri and Florida. Our goal is simple: to provide property owners with expert management that maximizes their returns while offering guests exceptional stays that create lasting memories.
We handle every aspect of managing short-term rental properties. This includes expert pricing with daily rate adjustments, a superior cleaning and maintenance program, weekly payouts to owners, 24/7 guest support, and legal services through a partnership with a local law firm (that I also own).
Our specialization lies in creating a seamless experience for both property owners and guests. For owners, we make property management stress-free, handling everything from guest bookings to maintenance. For guests, we ensure their stays are unforgettable, with immaculate spaces and responsive customer service.
Several things make Weekender Management stand out from the competition:
High-Touch Service: Unlike many national firms, we provide a personalized approach. We treat every property as if it were our own, ensuring meticulous attention to detail and constant communication with our clients.
Comprehensive Expertise: My background as a licensed attorney and real estate broker allows us to offer a unique blend of services. We not only manage properties but also provide affordable legal support for property owners, from navigating local regulations to drafting agreements.
Proprietary Pricing and Fee Models: We’ve developed proprietary software to ensure cleaning fees and other charges reflect actual costs, helping owners retain more revenue. Our pricing model is designed to maximize revenue without sacrificing guest satisfaction.
Local Knowledge with National Vision: As a locally based company, we understand the unique markets we operate in better than national competitors. At the same time, we’re expanding strategically into high-performing markets like Orlando, Florida, and Southwest Missouri, bringing our expertise to broader audiences.
Commitment to Innovation: We continuously invest in tools, technology, and strategies to stay ahead of the curve. For example, we’re building a guest-facing website for direct bookings, aiming to reduce reliance on platforms like Airbnb and VRBO while increasing revenue for property owners.
We’re best known for our hands-on approach, exceptional guest experiences, and our ability to deliver higher-than-average occupancy rates and revenue per available room (RevPAR). Clients also value our transparency and the peace of mind that comes with knowing their properties are in capable hands.
What I’m most proud of is the reputation we’ve built for reliability, quality, and innovation. When property owners and guests speak about Weekender Management, they consistently highlight our responsiveness, attention to detail, and the high standards we set. Building this brand recognition in a crowded market has been one of our biggest achievements.
In terms of your work and the industry, what are some of the changes you are expecting to see over the next five to ten years?
The short-term rental industry is poised for significant change over the next 5-10 years. We’ll see increased regulation, pushing property managers to ensure compliance while maintaining profitability. Technology and automation, such as AI-driven customer service and smart home integrations, will become essential for efficiency and guest satisfaction. Direct bookings will grow as managers reduce reliance on platforms like Airbnb, and sustainability will play a bigger role as travelers seek eco-friendly options.
Secondary markets, like Northwest Arkansas, will thrive as travelers move away from crowded destinations, and hybrid models blending short- and long-term rentals will gain popularity. Guest expectations for hotel-like amenities and exceptional service will continue to rise, requiring property managers to elevate their offerings.
Finally, as short-term rentals grow in popularity, local governments are likely to introduce stricter regulations. We’ve already seen this in major cities, and smaller markets are following suit. These regulations could include permitting requirements, restrictions on the number of allowable rental days, or increased taxes. Successful property management companies will need to help property owners navigate these changes, ensuring compliance while maintaining profitability.
Contact Info:
- Website: https://www.weekendermanagement.com
- Instagram: @weekendermanagement
- Facebook: https://www.facebook.com/weekenderbnb
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