We were lucky to catch up with Garrett Ham recently and have shared our conversation below.
Garrett, appreciate you joining us today. How did you come up with the idea for your business?
The story of how I started Weekender Management began almost by accident. After law school, I began my career in Walmart’s Real Estate Department at its home office in Bentonville, Arkansas. There I developed a real interest in real estate. My personal real estate journey started a few years later, but it wasn’t until I joined the military that the pieces really started falling into place. With each military relocation, I’d buy a home, live in it for a while, and then rent it out when the military moved me to a new location. This process allowed me to accumulate properties over time, leveraging VA loans to build a portfolio.
When I finally had enough equity in my properties, I pulled out funds to purchase my first true investment property—one that was purchased solely as an investment rather than as a primary residence. I was living in Connecticut at the time, pursuing graduate studies at Yale University, but I always knew that I wanted to return to Arkansas. While planning for my eventual return, I began searching for investment properties in Northwest Arkansas. However, I quickly realized that the real estate market had become extremely competitive, with housing prices rising rapidly. The long-term rental strategy I had always employed suddenly wasn’t making financial sense anymore because cash flow was becoming difficult to achieve.
Then, I found a property that the owner was renting on a month-to-month basis. This was when I had my first realization that a different strategy might work. I saw the potential for positive cash flow using the short-term rental model, so I decided to take a chance and purchased it.
That’s when the challenge came in: I had always used property management companies for my long-term rentals, so I assumed it would be a simple process to find one for this property. To my surprise, I struggled to find any property management company in the area that specialized in short-term or month-to-month rentals. One company I approached even declined to take on the property because they said it wasn’t a good fit. (Interestingly enough, this same company recently reached out with marketing materials asking if I’d be interested in their services for that very same property.)
Not being able to find a suitable property manager, I turned to my sister, who lived in Northwest Arkansas, and asked if she would help me manage the property. Together, we figured things out. She was instrumental in navigating the day-to-day operations, and as we gained experience, something unexpected happened: other people in the area began reaching out, asking if we could help manage their properties as well. It was one of those moments where you realize a need existed that wasn’t being adequately met.
Within a year, we were managing more than twenty properties, and that’s when I knew this was a worthwhile endeavor. The logic was simple: there was a significant gap in the market for short-term rental management, and by filling that gap, we were solving a problem that no one else seemed to be addressing. The management companies that existed at the time were servicing mostly only high-end properties, leaving many smaller investors without support. Now, Weekender Management has grown to managing 50 properties, most for other people, but some of which are owned by me personally or have been acquired with capital partners. We’ve even expanded into Missouri.
Looking back, it was a mix of personal circumstances, the right opportunities, and the recognition of a market need that led to the creation of Weekender Management.
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
In addition to what I’ve shared about how my business began, my journey into real estate and property management is rooted in both strategic decisions and unexpected opportunities. My background spans several fields, from law and real estate to military service, which gave me the skills to operate in multiple disciplines. My career began after law school, where I specialized in real estate during my time at Walmart, but my real estate experience deepened when I started purchasing homes as I moved around with the military. Each relocation was an opportunity to invest, and soon, real estate became more than just a side pursuit—it became a core focus.
While the story of Weekender Management’s founding started somewhat by accident, there were critical factors that shaped its growth. First, the Northwest Arkansas region was undergoing a rapid transformation, with increased tourism and business growth driving demand for short-term rental properties. There was clearly a market gap when it came to professional property management services catering to this sector. The excitement came from knowing that I could build a company that didn’t just address a need but did so in a way that brought a fresh perspective to an evolving market.
Beyond Weekender Management, my experience as a lawyer—both in private practice and as a civilian and military prosecutor—shaped how I approached challenges in real estate. Understanding the legal and regulatory complexities that often accompany property investment, especially for short-term rentals, allowed me to guide clients through these hurdles with precision. What separates our company from others in the field is this combination of real estate management expertise and legal acumen, which enables us to provide comprehensive services to my clients.
At Weekender Management, we solve several problems for our clients. First, we offer peace of mind. Many of our clients are out-of-state or have limited time to manage the day-to-day operations of their properties, and they rely on us to handle everything from guest communication to property maintenance. Our services ensure their properties remain profitable and well-maintained without the hassle of managing them personally. We also solve the problem of market navigation—many property owners want to maximize their rental income but don’t know how to position their properties for success. We bring a data-driven approach to pricing and marketing, ensuring our clients’ properties stay competitive in the market.
What sets Weekender Management apart from others is not only our focus on short-term rentals but also our deep commitment to offering personalized, hands-on service. Many property management companies operate at a distance, but we treat each property as if it were our own, which resonates with clients who value that extra level of care.
One of the things I’m most proud of is how we’ve been able to grow organically, based purely on the results we’ve delivered and the trust we’ve earned from our clients. We started with one property, and now we manage around 50, which speaks to the value we provide. Another key aspect of our success is our adaptability—real estate is constantly changing, and whether it’s adjusting our strategies to match market shifts or incorporating new technologies to improve guest experiences, we stay ahead of the curve.
As a brand, Weekender Management stands for reliability, expertise, and innovation in the property management space. For potential clients, I want them to know that when they work with us, they’re not just hiring a service provider—they’re gaining a partner who is fully invested in their success. Whether it’s managing a vacation rental or offering legal advice through my law firm, my team and I bring a depth of knowledge and a personal commitment that I believe is unmatched in the market.
Ultimately, my work is about creating value—both for the properties we manage and the people we serve. That’s what motivates me every day, and it’s what I want our clients and partners to know as they consider working with us.
Can you talk to us about how you funded your business?
When it came to funding Weekender Management, I was fortunate to have already laid the groundwork through years of real estate investing. By the time the business started, I had built up a portfolio of rental properties, and that provided the financial foundation I needed. The initial capital came from two main sources: personal savings I had accumulated over the years and an equity line of credit I took out on one of my existing rental properties.
This allowed me to avoid the typical challenges many new entrepreneurs face when trying to secure funding from outside sources. I didn’t have to go through the process of pitching to investors or applying for loans, which gave me more flexibility and control over how I wanted to grow the business.
In hindsight, the fact that I had built up this equity and savings through years of disciplined real estate investment was a key advantage. It allowed me to start the business with confidence, knowing I had a stable financial foundation from which to grow. This early financial independence also meant that I could focus fully on providing the best possible service to my clients without worrying about immediate financial pressures or external investor expectations.
Can you tell us about a time you’ve had to pivot?
My life has been full of pivots, each leading me in a direction I never anticipated. The first major pivot came when I was in college. I had planned to become a pastor, dedicating my life to ministry. However, during my senior year, I made the unexpected decision to attend law school instead. It was a significant shift in my path, one that changed the entire course of my career. After graduating from law school, I began working in real estate, but my journey didn’t stop there.
I decided to join the Army National Guard and move into private practice. After that, I became a civilian prosecutor and eventually joined the active duty Air Force. There was a time when I thought I might make the Air Force my career. I enjoyed the work and believed it could offer long-term fulfillment. But after my first tour of duty, I felt compelled to move in a different direction and separated from the Air Force to pursue graduate studies at Yale University.
At Yale, my intention was to pursue a Ph.D. and a career in academia, which seemed like a natural fit given my background and interests. During the last year in my master’s program, however, I found myself drawn toward business and entrepreneurship. I shifted my focus and took as many classes in Yale’s School of Management as I could, learning everything I could about the world of business. This was another unexpected pivot, but one that opened the door to a completely new set of opportunities.
The most significant pivot came shortly after, when I unexpectedly fell into the property management business. It wasn’t something I had planned for or even thought about pursuing, but once the opportunity presented itself, I embraced it fully. Starting Weekender Management was never part of the grand plan, but it has turned out to be one of the most fulfilling endeavors I’ve taken on.
Looking back, it’s clear that each pivot was essential in leading me to where I am now. While I still teach part-time at the University of Arkansas School of Law, my plan for a career in academia has given way to the business opportunities I never expected. Each turn, whether in the military, law, or business, has contributed to the skills and experience that now drive my work.
Contact Info:
- Website: https://www.weekendermanagement.com
- Instagram: @weekendermanagement
- Facebook: https://www.facebook.com/weekenderbnb/
- Linkedin: https://www.linkedin.com/in/garrett-ham-3333a439/
- Twitter: @WeekenderMgmt
Image Credits
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