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This 37-Year-Old Makes 5 Figures/Month Renting Vacation Homes in Arkansas

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This 37-Year-Old Makes 5 Figures/Month Renting Vacation Homes in Arkansas

Garrett Ham had experience in real estate. He worked in the industry and obtained his license. And while in the Air Force, he started purchasing properties and then renting them out long-term.

When he decided to return to his native Arkansas, he ended up investing in a short-term rental. He had such success that he turned it into a business: Weekender Management.

Today he’s earning 5 figures per month managing 41 properties, and he has plans to add another 8 to his portfolio in the near future.

Keep reading to find out:

  • How he got started in real estate
  • Why he was hesitant to work with short-term rentals
  • What he’s learned while running that business
  • How he identifies the perfect client
  • How much he works per week
  • His marketing strategy for getting new clients
  • The resources he recommends
  • His biggest challenge
  • His greatest accomplishment
  • His advice for other entrepreneurs

Meet Garrett Ham

My name is Garrett, and I’m 37 years old. I hold a Bachelor of Arts from Ouachita Baptist University, a Juris Doctor from the University of Arkansas, and a Master of Divinity from Yale University. I hold both a license to practice law and a principal real estate broker’s license in Arkansas. 

After law school, I worked in Walmart’s real estate division for three years. During that time, I also joined the Army National Guard as a JAG officer. I left Walmart in 2013 to work in private practice before becoming a prosecutor in Benton County Arkansas. 

In 2015, I joined the active duty Air Force, spending four years as a full-time JAG officer. In that position, I was primarily responsible for military justice matters, including serving as a prosecutor in courts-martial. 

Most of my cases revolved around sexual assault and child pornography charges. I spent three years at Yale after leaving the military, and I founded my company, Weekender Management, with my sister during my last year there.

After graduation, I moved back home to Bentonville, Arkansas, where I run my business full-time.

My wife and I have been married for fifteen years, and we have two children: a daughter, who is eleven, and a son, who is nine.

Why He Created Weekender Management

This business was the result of an unexpected opportunity. 

I had a background in real estate, and I began investing in real estate myself when I was in the military. I would purchase a new home at each duty assignment, and then I would rent out when the Air Force moved me elsewhere. By the time I left the Air Force, I had three rental properties. 

While I was at Yale, I knew I wanted to return back home to Arkansas after graduation. So, I began looking to purchase my fourth rental property near home. The real estate market in northwest Arkansas had grown so hot, however, that it was difficult to find a property that would have a cash flow. 

I was finally able to find one that the owner was using as a short-term rental. It was the only property that I found that would have cash flow, but it would only provide a cash flow as a short-term rental. Short-term rentals were never something that I had ever considered, but I decided to give it a shot. 

My sister had just sold off a business that she had founded—a glamping company where she would set up luxury tents for clients wherever they wanted to stay—so I asked her to help me run my short-term rental until I could return home.

As we started gaining some success with the property, some people started asking us to help them with theirs, and we decided to start Weekender Management as a result.

This 37 Year Old Makes 5 FiguresMonth Renting Vacation Homes in Arkansas

We are a full-service short-term rental management company. We handle every aspect of running a short-term rental, from marketing, guest screening and communications, evaluating the market and setting prices, cleaning properties between guests, and just about anything in between. Our clients are able to receive returns on their investment without having to expend any of the effort that running a short-term rental requires.

It’s been a learning process along the way. 

We are always trying to improve how we do things, and that has led to some bumps along the way. We learned that there are some kind of clients that are a good fit for us and some that aren’t. I’d say most of our failures have revolved around failing to appreciate that in the beginning. 

When you’re just starting out, you want to say yes to everything, but that’s rarely a winning strategy. If you take on the wrong types of client, you’re unhappy and the client is unhappy. 

So, learning to identify who is a good fit for our offerings and helping those who aren’t find some alternative companies that may be a better fit has been critical to our growth. 

Focusing on a certain type of client makes it easier to laser focus on making them happy, which in turn results in their referring us to other potential clients like them. That has been the biggest source of our growth.

In that vein, we have found that our ideal client is an investor who is focused on maximizing the return on their property, regardless of whether they are new to the investment game or a seasoned professional. 

They prioritize guest satisfaction over sentimental attachment to the property and are open to decorating and pricing strategies that will appeal to potential guests. We are not a good fit for those who have strict rules for guests to follow or want to set minimum nightly rates based on their personal beliefs about the value of their property.

How Much Money Garrett is Making

We’re making 5 figures per month. It took about 18 months to reach that revenue level. I spend about 60 to 70 hours per week on the business.

His Main Marketing Strategy

We utilize Google ads to attract new clients, but we rely primarily on word of mouth and referrals. We currently only spend about $150 per month on Google ads. 

1679140204 252 This 37 Year Old Makes 5 FiguresMonth Renting Vacation Homes in Arkansas

There was a time when we were spending about $1,000 per night, but we were getting so many leads and bringing on so many clients so quickly, we had to scale back just to ensure we could keep up with our incoming business. We still get a steady flow of inquiries even at the lower spending level. 

We currently do all of our marketing ourselves. I discovered Google Ads by watching hours of YouTube videos and reading books about it. We’re looking to outsource this process in the near future, however. 

His Views on SEO

We utilize SEO, but we have not put a lot of focus in that direction. As we have received most of our business from referrals and Google ads, we’ve focused most of our efforts to date in that direction. 

His Email List

We have an email list and grow it by asking our guests to provide theirs. We also give away educational material on our website in exchange for an email address. We specifically offer a short ebook outlining five tips for becoming a successful Airbnb host for anyone who signs up to our mailing list.

Garrett’s Favorite Resources

My advice is to find as much educational material as possible, particularly books, and prioritize learning. 

Find podcasts by experts in your niche, “Get Paid For Your Pad,” and anything from Bigger Pockets, for example, is particularly valuable in my field. 

Take a basic accounting course at a local community college or university. Make sure you understand basic concepts such as the time value of money, and you can’t go wrong reading anything by Mike Michalowicz. 

Finally, while it requires a significant investment, take courses geared toward your particular niche. I’ve taken training from BeyondBnb and LegendsX, which are specifically designed for short-term rental owners, and was able to learn and immediately implement a lot of valuable advice that would have taken me years to learn on my own.

His Biggest Challenge

This would have to be learning what’s worth spending money on and what’s not. 

For example, we hired an accounting firm to help us draft owners’ statements every month. They did a good job, but they were very expensive. And we ended up having to audit the statements before they went out anyway. So, they weren’t saving us a whole lot of time and we were spending a whole lot of money. 

I’ve had enough graduate-level accounting courses to be able to do this myself, so that’s what I’ve started doing. We then hired a much cheaper bookkeeper to keep our books. While we will need to outsource this again soon, we’ve become a lot more aware of when a service brings real value and when the value it brings is less than what’s being expended.

“You’ve got to spend money to make money” may be true in some contexts, but it’s not universally applicable. When you’re just getting started, a better mantra is “You’ve got to spend money to go bankrupt.” 

Spend as little money as possible. Be as lean as possible. There is such a thing as being penny wise and pound foolish, so you shouldn’t forego necessary expenses. The question to ask, however, is whether you can still offer an exceptional service or product without spending money on a particular thing. 

If the answer is “No,” spend it. If the answer is “Yes,” which it almost always will be, then don’t. Be honest with yourself, and definitely don’t spend money on things just because you think you need them to be a legitimate business.

His Greatest Accomplishment

That would be surviving. With so many businesses failing within the first year, just surviving and turning a profit at this point seems like a huge accomplishment. 

What He Wishes He Knew When He Started

Be very careful how you spend money, and spend as little as possible. Make sure your spending is such that you have a profit from the very beginning. 

His Advice for Other Entrepreneurs

To succeed, you have to be a risk-taker, but you must be smart about it. Only spend money on something if failing to do so will hurt your business.  



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Red Lobster Speaks Out on ‘Misunderstood’ Bankruptcy Filing

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Red Lobster Speaks Out on 'Misunderstood' Bankruptcy Filing

It may be the end of an era for beloved seafood chain Red Lobster, which officially declared bankruptcy on Monday after months of speculation and dozens of abrupt restaurant closures.

Now, the company is speaking out to loyal customers — and investigating the role that its shrimp supplier may have played in its demise.

Related: Red Lobster Suddenly Shutters Dozens of Locations Without Warning Employees, Begins Auctioning Off Equipment

In a letter posted to social media, Red Lobster thanked customers for their nearly five decades of loyalty and assured the masses that the chain wasn’t going anywhere.

“Bankruptcy is a word that is often misunderstood. Filing for bankruptcy does not mean we are going out of business,” Red Lobster wrote. “In fact, it means just the opposite. It is a legal process that allows us to make changes to our business and our cost structure so that Red Lobster can continue as a stronger company going forward.”

Red Lobster noted that companies including Delta Airlines and Hertz “emerged stronger” after filing for Chapter 11 (Delta in September 2005, Hertz in May 2020) and found ways to bounce back.

“Birthdays, graduations, anniversaries, and yes, weddings. We’ve been here for them all,” the chain penned. “Red Lobster is determined to be there for these moments for generations to come.”

Red Lobster’s downfall was a slow burn, primarily blamed on an $11 million loss in November 2023 due to the chain rollout of an “Endless Shrimp” promotion. The deal offered customers all the shrimp they could eat for $20, and it proved to be a bit too popular.

Last week, it was reported that stores had begun shuttering without warning around the country, with dozens auctioning off all of their furniture and equipment online and some employees claiming they were given no notice ahead of time.

In a filing on Sunday, Red Lobster CEO Jonathan Tibus called out former CEO Paul Kenny and Red Lobster’s seafood supplier and owner, Thai Union, regarding decisions made surrounding the “Endless Shrimp” promotion and that Red Lobster is “currently investigating the circumstances” around the decision to make the promotion permanent instead of limited-time.

Related: Endless Shrimp Deal Is Too Popular, Red Lobster Loses $11M

“I understand that Thai Union exercised an outsized influence on the Company’s shrimp purchasing,” Tibus wrote. “[Red Lobster is] exploring the impact of the control Thai Union exerted, in concert with Mr. Kenny and other Thai Union-affiliated entities and individuals, and whether actions taken in light of these parties’ varying interests were appropriate and consistent with applicable duties and obligations to Red Lobster.”

Thai Union completed its purchase of Red Lobster in 2020.



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UMass Dartmouth Commencement Speaker Gives Grads $1000 Each

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UMass Dartmouth Commencement Speaker Gives Grads $1000 Each

The best commencement speeches are often motivational and thought-provoking, leaving new graduates optimistic as they head into the “real world.”

But for the Class of 2024 at the University of Massachusetts Dartmouth, new grads walked away with more than just a wealth of knowledge — they left their ceremony with an extra $1,000 in their pockets.

Related: ‘There Is More To Life Than Work’: Bill Gates Delivers Emotional Message To Graduates About Learning To Take A Break

Last week, the founder and CEO of Granite Telecommunications, Robert Hale Jr., spoke to grads at the University of Massachusetts Dartmouth about their futures and shared a story about a time when his business suffered a $1 billion loss in just one day to explain the importance of perseverance through failure.

“It’s okay to fail,” Hale told graduates. “Life will give you challenges and if you take those challenges you’ll fail from time to time — don’t worry about it … don’t fear failure, understand that it’s just part of the process, and if you use that fear of failure to motivate yourself, you’ll be better for it.”

Then, as he wrapped up, he shocked the audience by announcing he was giving each graduate graduate $1,000 — but there was a catch.

“These trying times have heightened the need for sharing, caring, and giving,” Hale told students. “Our community needs you and your generosity more than ever.”

The students were given two envelopes with $500 each — one was intended for the students to keep for themselves while the other was for them to give to someone else in need.

Related: Sheryl Sandberg’s Advice to Grads: Banish Self-Doubt, Dream Bigger and Lean In, Always

“As the degree conferral was about to begin, Hale came forward and let the graduates know he had one more bit of advice for them. He told the eager crowd that for him and his wife Karen, ‘the greatest joys we’ve had in our life have been the gift of giving,'” UMass Dartmouth said in a release. “Hale let the Class of 2024 know that the two large duffle bags being brought up on stage by security were packed with envelopes full of cash.”

There were roughly 1,200 students in UMass Dartmouth’s 2024 graduating class.

Hale’s current net worth is an estimated $5.4 billion.



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Stay Prepared on the Road with This $80 Tire Inflator

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Disclosure: Our goal is to feature products and services that we think you’ll find interesting and useful. If you purchase them, Entrepreneur may get a small share of the revenue from the sale from our commerce partners.

Business travel is inherently risky because driving poses certain innate hazards. If you’re a business leader sending yourself, team members, or employees out on the road, the least you can do is equip them with the tools they need to operate as safely as possible and get out of a jam if they happen to run into one.

A great tool that’s designed to help fix flat tires, this HOTO Air Pump Pro Portable Air Compressor and Tire Inflator, is on sale for just $79.99 (reg. $119). Promised to be 85% faster than competitors, this four-preset air pump is made to be able to fill a tire in at most five minutes.

Running on a 12V pump motor, this fast-working pump features a powerful battery life that can charge as many as 15 under-inflated tires within a single charge. When you’re filling up, the pump also prevents you from overdoing things with its worry-free automatic stop that ceases operations when the proper inflation is met.

This fantastic tire pump can serve as a great safety tool for business travelers. It can also promote exercise and recreation when used to pump up sports balls and bike tires.

The versatility and quality of this small, compact device have added up to make it a hit amongst users and critics alike. It’s even earned a coveted nomination from MoMa Design.

Don’t forget that for a limited time only, this HOTO Air Pump Pro Portable Air Compressor and Tire Inflator is on sale for just $79.99 (reg. $119).

StackSocial prices subject to change.

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