C-Suite Concerns: Garrett Ham Of Weekender Management On The Top 5 Issues That Keep Executives Up at Night

An Interview With Cynthia Corsetti

Cynthia Corsetti
Authority Magazine
19 min readNov 16, 2023

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Failing to innovate and falling behind our competition keep me up at night. We try to be on the cutting edge of things. In this market, even little ideas can make a big difference in terms of attracting guests and increasing revenues. My business partner and I are always striving to innovate and make things better, while keeping our ear to the ground to make sure that our competitors don’t beat us to the punch. There is no room for complacency, so no matter how well we do, there’s always the need to keep improving and keep pushing.

When it comes to business leadership, challenges are omnipresent. From rapidly changing market dynamics to technological disruptions, executives today grapple with multifaceted issues that directly impact their decision-making and strategic orientations. What really keeps the leaders of today’s corporate world awake at night? How do they navigate through these turbulent times to ensure the growth and stability of their organizations? As part of this series, we had the pleasure of interviewing Garrett Ham.

Garrett is the Principal Broker and CEO of Weekender Management, Inc., a company he co-founded with his sister, Stephanie Byrnes, that specializes in managing and investing in short-term rentals. His diverse career began in the real estate department at Walmart’s corporate headquarters, and he later worked as a corporate attorney, prosecutor, and JAG officer in the Air Force and the Army National Guard. He also leads the Ham Law Firm, Ltd., catering to short-term rental owners, and teaches part-time at the University of Arkansas. Garrett holds degrees from Ouachita Baptist University, the University of Arkansas, and Yale University.

Thank you so much for joining us in this interview series. Before we dive into our discussion about communication, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

My journey into short-term rentals was somewhat serendipitous. After completing law school, I began my professional career in the real estate department at Walmart’s headquarters in Bentonville, Arkansas. This experience laid the groundwork for my interest in real estate. I spent three years there before transitioning into private practice. Later, when I joined the military, I was able to become a real estate investor myself. Instead of selling my Bentonville home upon moving to my first duty station, I chose to rent it out, a decision that kickstarted my practice of purchasing and renting out homes with each move I made during my military career.

After leaving the military, I pursued graduate studies at Yale University in New Haven, Connecticut. During this time, I decided to purchase another rental property. I wanted to invest in Northwest Arkansas because by this time I knew that’s where I wanted to return upon graduation. Despite a hot real estate market that made cash flow-positive investments challenging to find, I discovered a promising opportunity in a property that was thriving as a short-term rental — a venture I had never before considered. So, I bought the property and enlisted the help of my sister, who had just sold a glamping company she had founded, to manage it for me until I could return home.

Her management efforts quickly garnered attention, attracting inquiries from other property owners who sought her expertise. Recognizing the demand for such services, we decided to leverage our combined experience and skillsets, culminating in the birth of our business. So, that’s how Weekender Management got started.

You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Gauging one’s own success can often be challenging, as it’s a measure not solely of personal achievements but also the success of the team and the business as a whole. If I had to name three traits, however, I would identify the following as key:

1. Willingness to Recognize my Failures — An example that encapsulates this trait involves our initial business model. My sister and I saw an opportunity to manage properties on a part-time basis. Our competitors did not offer this service, and we thought we could carve out a niche here. My sister referred to such part-time listings as “Weekender properties,” which inspired our company name. However, we soon realized why our competitors avoided this market — it’s not sustainable. Accepting that our original strategy was flawed allowed us to pivot quickly, which was crucial to our subsequent success. Had we not acknowledged our mistake and changed direction, our company’s story could have been very different. Additionally, were I unwilling to admit my mistakes, I would not be able to learn from or defer to individuals more knowledgeable and skilled than myself. My business partner, for example, excels in areas in which I am lacking, like customer service and client relations. Recognizing and respecting her superior skills in these domains means I step back and let her lead where she shines brightest, just as she lets me lead in areas in which I excel. This respect for her abilities has proven time and again to be a significant factor in our business’s growth.

2. Selflessness — This trait, for me, is aspirational, not descriptive. That is, I believe striving toward selflessness, even though I constantly fail miserably, has been key to my success. This aspiration is rooted in the Air Force’s core value of “Service before self,” which I’ve carried into my civilian life. During my military service, I sought to lead by example, taking on the less desirable tasks to show my team that no job was beneath me. If we were tasked with a particularly unpleasant task, for example, even though I was the officer in charge, I would try always to volunteer to perform the most undesirable task, so my people wouldn’t have to do it. In my current role, this translates into sharing the burdens of startup demands with my team. As we grow, I aim to continue demonstrating this value, reinforcing the message that I value their contributions and am willing to work alongside them, regardless of the task’s nature. My hope is that I’ll one day be able to attain this trait, rather than simply strive for it.

3. Keeping Perspective — I think one of the best things I can do as a leader is keep perspective. Often, the thing I think is the important, most pressing thing in the world really isn’t that big of a deal when I step back and look at it. I was a JAG officer in the military before I started this company. In that role, I worked sexual assault and child pornography cases day in and day out. That job required me to deal with some of the most horrific things the world has to offer and to speak with victims about the worst day of their lives. After having done that, stepping back from a stressful situation at work and taking stock of things has a calming effect. A moment of reflection makes me realize that the thing with which I’m dealing now is not, in fact, the most important thing in the world, and maybe I should not be putting so much pressure on my team over it. That doesn’t mean that there are never pressing issues in business that requires intense focus and dedication. Perspective is not the same as apathy. However, keeping things in perspective allows for a more deliberate decision-making process, as stress and panic are no longer drivers.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

One of the most formidable decisions we’ve faced involved a situation where we were at risk of compromising our service quality in one of our geographical areas due to the sudden loss of a key staff member: our housekeeping supervisor. The impact was significant, as this role was pivotal in ensuring quality and consistency within one of our key markets.

Faced with this challenge, we had to consider our options carefully. Ultimately, we decided to outsource our housekeeping needs in that area to a third-party company. This was no light decision, as it meant we would have to let our entire in-house staff go in that area. We offered them positions in different locations, but the distance between them and the available locations made this unfeasible for them.

This decision weighed heavily on us. The choice was not just a business decision; it was a personal one that affected the lives of our employees. It was necessary to maintain the high standards our clients expect from us, but it was also one of the most difficult choices we’ve had to make. It’s a stark reminder of the responsibilities that come with leadership. This decision reinforced my understanding of the complexities of leadership and the weight of the impact that decisions can have on individuals within the company. Even though I think we did the right thing, that decision still bothers me.

What do you believe are the top five concerns currently preoccupying the minds of C-suite executives, and why?

1. Well, the most obvious answer is the economy. Just like everyone else, I’m concerned about what an economic downturn will mean for our business. If people forego vacations or other trips because of economic uncertainty, that will have a direct impact on us. So, I spend a lot of my time trying to plan for such a downturn, so we can adapt as needed and perhaps target a different kind of traveler whose travel plans are less contingent on economic conditions.

2. Increased regulations also concern me. We specialize in short-term rentals, which have become the focus of many municipal governments who want to tamp down on the ability of people to rent out their property for short stays. I am an attorney, so I follow this closely, as I know that a city council could take action and close us out of a market. (Just look at New York.) I typically don’t mind reasonable regulations that allow cities to crack down on bad actors, but regulations that shut us out of a market or prevent growth can obviously have a significant impact on our business. We’re in a position to be able to fight such actions in court, but that’s a headache nobody wants if it can be avoided. We’re currently having difficulty with the city of Fayetteville — one of our biggest markets — because the city has suddenly become much stingier with its short-term rental licenses. I anticipate a court battle at some point over this issue.

3. Talent acquisition and management is a particular area of concern. We’re a small company, so payroll expenses can be a significant burden. So, we have to be careful not to hire too quickly, but we’ve grown large enough that we need to hire help. So, there’s this balance of needing to hire but needing to be responsible with company funds. Simultaneously, we struggle to balance the desire to pay our people well and rewarding performance with the practical financial constraints that we have. Solving this problem continues to beguile us, as I know it does a lot of businesses, including those much bigger than us.

4. Failing to innovate and falling behind our competition keep me up at night. We try to be on the cutting edge of things. In this market, even little ideas can make a big difference in terms of attracting guests and increasing revenues. My business partner and I are always striving to innovate and make things better, while keeping our ear to the ground to make sure that our competitors don’t beat us to the punch. There is no room for complacency, so no matter how well we do, there’s always the need to keep improving and keep pushing.

5. Then, of course, there’s concern about shifts in consumer demands and preferences. Perhaps tomorrow everyone decides they’d rather stay in hotels and motels again and forego short-term rentals. There has already been a growing movement against some of the more unsavory aspects of staying in short-term rentals, such as inconsistency in the quality of accommodations and endless chores to perform before checkout. Consequently, my business partner and I are always trying to think of ways to make ourselves stand out, so that even if consumer tastes change, there will be something different about us that will continue to attract people to what we offer.

In the face of rapid technological advancements and market shifts, do you find that you need to constantly recalibrate your strategies to ensure sustained growth?

Absolutely. Technology is always shifting and evolving. We are in the hospitality business, but it’s a segment of that business that grew out of technological innovation. Home sharing and online travel agencies, like Airbnb, gave birth to this business, or at least how it appears now. A business based on technology, however, has to monitor technological advancements carefully to avoid becoming obsolete. We take advantage of many technological tools at our disposal. There are some staples of the industry that we use, including Guesty, our property management software, and Price Labs, the tool we use to help us set pricing. But then there are new tools coming to market all the time that we evaluate and utilize when advantageous, particularly with the advancement of AI. Host AI, for example, helps us market our property through their unique AI-created landing pages. We have also been experimenting with AI tools to respond to guest communications. The technology is not to the point where it can respond to every message, but it can provide answers to the most commonly asked questions instantly, ensuring our guests receive nearly instantaneous responses 24/7. Our goal is to respond to all guest communications within five minutes, and we are always striving to cut that time down even more to increase guest satisfaction. These tools help us do that.

With the emergence of AI, blockchain, and other transformative technologies, how do you determine which tech trends are worth investing in?

It’s a lot of trial and error. If we encounter a new technology that looks like it could be beneficial for our business, we’ll test it out on a small scale. For example, when experimenting with an AI technology that would respond immediately to guests asking commonly asked questions, we implemented it at just a couple of our properties to see how it worked. If a technology doesn’t work out the way we had hoped, we cut our losses early. Fortunately, in this business, technological innovations are typically free or cheap to try, which means we can test out its usefulness in the business before we have to make a large financial commitment to roll it out to our entire portfolio.

With increasing digital threats, how are you prioritizing cybersecurity, and what measures are you taking to protect your organization’s assets?

Cyber security for us primarily focuses on safeguarding our guests’ and clients’ personal identifiable information. We don’t use our own proprietary software — except for some small custom software to help automate some tasks that don’t involve the storing or transport of sensitive information — so we stay secure by only utilizing tools that implement strict security protocols. In addition, whenever we can avoid having access to a guest’s sensitive information, we do. For example, we utilize Stripe to take online payments. Stripe stores and encrypts the guest’s credit card information, which we cannot access. Using a PCI compliant partner allows us to protect the privacy of our guests and safeguard their payment information.

When we do have to store sensitive information, we utilize encrypted cloud-based servers that limit access only to those who absolutely need it. This primarily consists of W9s from our clients, which we fervently safeguard. We rarely, if ever, store sensitive information on our local system, and when we do, we make sure it is stored only on encrypted hard drives.

Our approach is fundamentally about risk management — minimizing the amount of sensitive data we handle ourselves and entrusting it to those with the capability to ensure the highest possible protection. This way, we can devote our time and resources to our core services.

As a top executive, how do you manage stress and maintain mental well-being? Do you have any personal practices or routines that help you stay centered?

Founding and growing a company can be incredibly stressful. My business partner and I have invested an immense amount of time and effort to nurture our business from the ground up, often for little immediate reward. (We didn’t draw any salary at all during the first year.) Given the nature of running a small but growing company, my workday isn’t traditional by any means. It’s a continuum of work interspersed with short breaks. I can’t remember a single day that I didn’t work at least a little bit.

Because of this, finding ways to manage stress and prevent burnout is crucial. Passion for the work certainly helps, but the intensity is still draining. So, I’ve incorporated certain practices into my day to keep me going.

My faith is a crucial in this regard. As a devout Catholic, I strive to find time for daily prayer, with the rosary being a special respite that brings moments of calm and reflection. Although attending daily Mass more frequently remains a challenge, it’s something I’m working towards incorporating into my routine. These practices help maintain my perspective and nurture the internal stillness necessary to thrive amid the constant movement associated with this business.

My German Shepherd is another great source of balance. His need for daily exercise demands that I spend one to two hours outdoors, typically playing fetch. It’s non-negotiable — he becomes insufferable if he doesn’t get it. And while I still have my phone on me during these times, the activity offers a welcome counterbalance to my work.

Family also plays a crucial role. No matter the workload, dinner with my family is sacrosanct. It’s our dedicated time to connect with each other. I am keen to avoid the all-too-common trap where work creates distance within a family. I certainly don’t want my children to experience a ‘Cats in the Cradle’ type of relationship with me.

Evenings typically wind down with an hour of television with my wife. Though I might be tackling less demanding tasks during this time, such as responding to emails, it’s a period that helps signal the day’s end and allows me to decompress.

In essence, my life currently weaves between work and brief but critical breaks. These short periods of rest are vital, helping me to maintain the energy needed to manage both my business and personal life.

What habits or practices have been most instrumental in your personal and professional growth?

In my journey, both personally and professionally, there are several habits and practices that have significantly contributed to my growth. Paramount among these is my commitment to continuous learning. I read as much as possible, as I am constantly seeking knowledge and insights from a diverse range of sources. This habit has not only broadened my perspective but has also kept me informed about the latest trends and best practices in my industry.

Additionally, I place a high value on learning from those with more experience and knowledge than me. Seeking advice from others and absorbing their wisdom and understanding, has been instrumental in helping me get where I want to go. This practice has helped me to navigate challenges more effectively and to seize opportunities that I might not have recognized otherwise.

Furthermore, while it may seem unconventional in the business world, prayer plays a significant role in my life. It is not about seeking divine endorsement for my business endeavors — an idea I find a bit goofy at best and dangerous at worst — but rather about maintaining a sense of humility and perspective. Prayer serves as a constant reminder that I am just a small part of a much larger picture. It grounds me and keeps me aware that I don’t have all the answers, fostering a mindset of openness and continual growth. It also helps me fight against my worst impulses and guard against some of the pitfalls and unethical behaviors that plague many in business.

These practices have been the cornerstones of my personal and professional development. I believe they have shaped me into a more knowledgeable, empathetic, and effective leader. I also think that having a business partner has helped me in this regard. I am fortunate to have an extraordinary business partner who has strengths in my areas of weakness. Having someone with whom I have to share power, so to speak, helps keep me grounded and humble and forces me to see things from someone else’s perspective. I believe this is invaluable for continued growth and development.

The business world is evolving faster than ever. How do you ensure you’re constantly updating your knowledge and staying ahead of the curve?

My answer to this question is very similar to my previous one. Reading as much as I can helps me stay up to date and adjust to a changing landscape. I consistently invest time in reading not only industry-specific literature but also materials that help me maintain an acute awareness of current events, so that I can anticipate their potential impacts on the business landscape. This continuous effort to learn and become more aware of issues that may impact my business, very much in line with my earlier mentioned growth practices, are crucial in ensuring that I am always at the forefront of industry developments and changes.

The importance of diversity and inclusion in the workplace has been emphasized more than ever. Do you have any initiatives promoting diversity and inclusion in your organization?

As a small business with just a handful of employees, we don’t have a formal program. When we look to expand our team, our focus is on finding the most qualified individual for the position. However, qualifications for us go beyond just skills and experience; they also encompass the ability to bring diverse perspectives to our team.

We understand that having a team with varied backgrounds and viewpoints is essential to identify and address potential blind spots in our operations and decision-making. This approach ensures that our small team is not only highly skilled but also rich in diverse perspectives, which is vital for our business’s growth and adaptability. Having a diverse set of perspectives helps us reduce the number of things that we don’t know that we don’t know.

Can you share a piece of feedback or advice you received that significantly altered your leadership approach or philosophy?

One piece of advice that I consider often is to credit my team for our successes and take personal responsibility for our failures. This advice parallels the old adage that “success has many fathers, but failure is an orphan.” As a leader, I’ve learned that I have to own the failures. This means humbling myself before moving on to address those failures. This is important not just in terms of strategy correction but also in maintaining the morale and trust of my team.

This insight has led me to a deeper understanding of what true leadership entails. It’s not just about guiding a team towards objectives; it’s about engaging in constant self-reflection and evaluation of my own shortcomings. This was further underscored for me by one of the leaders I had when I was in the military. She would often reference the book “Leaders Eat Last” in a rather literal and superficial manner. That is, she would only follow its advice when we were actually eating. In every other scenario, however — every scenario that really mattered — she ate first. She would throw us all under the bus if it would advance her career or protect her reputation. This experience highlighted to me that effective leadership is not about catchy phrases, surface-level gestures, or the latest fad from the book du jour, but about genuine service to others, ongoing personal growth, and an unflinching willingness to acknowledge and learn from one’s shortcomings.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I would love for us to transform the landscape of affordable housing, particularly since short-term rental operators, like us, often take significant criticism as a contributor to housing unaffordability. While I dispute that claim, the accusations have helped me become more aware of this issue. In this business, I have gained a keen awareness of how regulations impact business operations, especially in the housing sector. Compliance is a big part of this business, as municipalities seek to impose more regulations and restrictions on short-term rentals. In the process of dealing with these issues, however, I have observed how regulations disproportionately affect the most vulnerable populations, often contradicting the political rhetoric around affordable housing. Politicians talk like the regulations they impose protect people from greedy corporations preying on the little guy, but much of the time, they hurt the people they’re supposedly meant to protect, while the corporations still get their money.

I would like to see us involved in reforming housing regulations to make the development of affordable homes more viable and cost-effective. The current landscape is laden with red tape and bureaucratic hurdles that inflate the costs of development, often to the point where only higher-end homes are profitable to build. Politicians talk about the need for affordable housing, all while imposing costly regulatory burdens and regularly disapproving housing projects. Then they turn around and decry the lack of affordable housing. This situation creates a significant gap in the availability of affordable housing, directly impacting those in greatest need.

My hope is that we would be able to work with industry experts, policymakers, and community leaders to identify and advocate for regulatory changes that encourage the development of affordable housing. By making it more economically feasible for developers to invest in such projects, we can create a more accessible housing market. People who need affordable housing don’t need — and typically don’t want — a handout. They simply need such housing to be built, which means we need to create an environment where developers will want to build them. No one is going to build homes if they lose money on each house, and the biggest cause of these economic disincentives are the politicians, bureaucrats, and central planners who are either unable or unwilling to see how their policies hurt the people who can least afford it.

My hope is that as our company grows, we aim to contribute to a solution that not only makes good business sense and protects property rights but also serves a greater social purpose by addressing one of the most pressing issues facing our communities today.

How can our readers further follow your work online?

You can learn more about our business on our website. We update our blog regularly with advice and updates about the real estate sector and short-term rentals in particular.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.

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