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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.
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.
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.
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.”
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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Cut Costs, Not Features with This Microsoft Bundle Deal
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.
Software subscription fees can quickly add up, and for small-business owners, entrepreneurs, or freelancers, these costs can eat into profits. Businesses spend approximately 29% of their IT budgets on software, according to a 2023 survey by Gartner.
For business professionals who are looking to streamline workflow without paying steep subscription fees, the Ultimate 2019 Microsoft Bundle might be the perfect solution. For just $71.94 (regularly $927), this comprehensive four-part bundle offers Microsoft Office Professional Plus 2019, Windows 11 Pro, Project 2019, and Visio 2019.
While it’s not the newest version of Microsoft’s software, it can deliver tremendous value for anyone seeking tools to manage their business, boost productivity, and work efficiently. The bundle offers a lifetime license, meaning you’ll get all the functionality you need without the recurring costs associated with subscription services like Microsoft 365.
However, it does come with Windows 11 Pro, which includes the recent AI updates. Windows 11 Pro delivers a modern, intuitive interface with enhanced security features such as biometric login and Smart App Control, making it ideal for professionals who prioritize privacy and usability. It’s also equipped with tools that support multitasking, such as Snap Layouts and Virtual Desktops.
For companies looking to reduce overhead without compromising essential functionality, making a one-time purchase of slightly older software is a smart financial move. This includes Office’s most popular productivity tools, Word, Excel, PowerPoint, and Outlook.
Project 2019 is a must-have for anyone who is managing large or small projects. It helps track tasks, timelines, and resources, making it easier to stay on top of deadlines and ensure your team moves in the right direction. Project 2019 gives you the tools to streamline processes and manage tasks efficiently.
Visio 2019 is ideal for creating professional diagrams, flowcharts, and organizational charts. It’s particularly valuable for visualizing complex data or workflows, which is essential for business owners looking to improve operational efficiency.
If you need a productivity boost without eating into savings, take a closer look at this bundle.
Get the Ultimate 2019 Microsoft Bundle with Office, Project, Visio, and Windows 11 Pro for $71.94 (regularly $927).
StackSocial prices subject to change.
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3 Trends That Will Change the Future of Entrepreneurship
Opinions expressed by Entrepreneur contributors are their own.
The most recent data from the new Global Entrepreneurship Monitor report reveals a powerful trend for the future of entrepreneurship.
Young adults, aged 18-24, had both the highest entrepreneurial activity and entrepreneurial intentions in the United States, according to the Global Entrepreneurship Monitor 2023-2024 United States Report. With similar results in 2022, this is not just a minor shift — it’s a fundamental change that could have lasting impacts on the economy and society.
I serve as the chair of the board for the Global Entrepreneurship Research Association, the entity that oversees GEM, which was founded in 1999 as a joint venture of Babson College and the London Business School. As the GEM U.S. team co-leader and a professor of entrepreneurship at Babson, I see firsthand the impact of the research created by the Global Entrepreneurship Monitor.
Here are three entrepreneurship trends from the new GEM report that are changing the landscape for the future.
Related: 21 Success Tips for Young and Aspiring Entrepreneurs
1. Young entrepreneurs on the rise
For years, entrepreneurship has been dominated by older, more experienced individuals, but this year’s report shows that the youngest adults are now at the forefront. According to GEM, 24% of 18- to 24-year-olds are engaged in some form of entrepreneurial activity, a higher rate than any other age group. What’s driving these young entrepreneurs is equally remarkable: They aren’t just starting businesses to make money; many are deeply committed to making a positive impact on society and the environment.
These young entrepreneurs make sustainability a key priority. They are more likely than entrepreneurs from older generations to build businesses with sustainability as a core focus — whether that means reducing their environmental footprint or focusing on social causes. This shift toward impact-driven entrepreneurship isn’t just anecdotal. GEM data shows a significant number of young entrepreneurs taking real, measurable steps to create businesses that align with their values. With sustainability as their north star, young entrepreneurs appear to be simultaneously pursuing societal impact as well as profits.
However, it’s not all smooth sailing. While young people are leading the way in starting businesses, they are also discontinuing them at higher rates than their older counterparts. The discontinuation rate for 18- to 24-year-olds is 15%, the highest among all age groups. This is not surprising, given the challenges of inexperience and more limited access to capital. Starting a business is tough, and sustaining one is even more challenging. But despite these hurdles, the enthusiasm and energy that young people bring to entrepreneurship are undeniable, and with the right support, this generation has the potential to drive substantial change.
2. Tech gender gap narrows
One of the most promising findings in the GEM report is the narrowing gender gap in the technology sector. Historically, tech startups have been dominated by men, but 2023 saw a record-low difference in the number of men and women starting tech companies. The gap has narrowed to just 1%, with 8% of women compared with 9% of men launching businesses in the Information and Communication Technology (ICT) sector.
This is a significant step forward and reflects broader efforts to support more women technology startups. Still, it’s important to recognize that while progress is being made, continued focus on providing equal opportunities is essential to ensuring this trend continues.
3. Optimistic outlook for Black and Hispanic entrepreneurs
Another highlight from the report is the optimistic outlook among Black and Hispanic entrepreneurs. These groups showed stronger confidence in their entrepreneurial abilities and lower fear of failure compared to their white counterparts. Black respondents, in particular, demonstrated high levels of resilience and self-assurance, which is vital in overcoming barriers faced in starting and sustaining businesses. This optimism is encouraging, but there’s still much work to be done in assuring ecosystems offer equal opportunities for all aspiring entrepreneurs, regardless of their background.
Related: I Wish I Received This Advice as a Young Entrepreneur
A promising future
Reflecting on the key findings of this year’s GEM report, it’s clear that the entrepreneurial landscape is changing in meaningful ways. The rise of young, sustainability-driven entrepreneurs signals a future where business is not only about profit but also about making a difference. These young entrepreneurs are launching businesses at a time when the world is looking for solutions to some of its most pressing challenges — climate change, poverty and economic recovery.
Yet, to fully realize the potential of this next generation, there must be more focus on addressing the challenges they encounter. Young entrepreneurs need access to the right resources — whether it’s funding, education or mentorship — to turn their innovative ideas into sustainable businesses. The narrowing gender gap in tech is encouraging, but we must continue to foster environments that support women and other underrepresented groups in entrepreneurship.
The GEM report paints a picture of an entrepreneurial future driven by purpose, diversity and innovation. But it also reminds us of the work that lies ahead in making entrepreneurship more accessible and sustainable. If we can provide young entrepreneurs with the tools and support they need, we will not only see more businesses being created — we’ll see businesses that are making a lasting, positive impact on the world.
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These Are the Top Side Hustles to Work Less, Make More Money
In the best-case scenario, a side hustle could turn into a multimillion-dollar business that generates a passive income stream — but at the very least, starting a side gig could help pay some bills.
A new survey from personal finance software company Quicken shows that almost half (43%) of Americans with a side hustle, or an extra source of income added to a primary income, make more money and clock in fewer hours overall than those without a side hustle.
The three most popular side hustles pursued by those who work less and make more money were personal assistance (20%), cooking and baking (16%), and caregiving (16%). One in five people with side hustles said they were business owners, too, selling products online or offering services like photography.
The majority of people with side hustles (82%) said starting a side gig helped them financially, and kept them from living paycheck to paycheck. Most with side hustles (57%) had savings equal to at least four months of living expenses.
The survey also found that, for younger side hustlers, a way to an extra income doubles as a path to becoming more employable. 44% of Gen Z (born between 1997 and 2012) choose to start a side hustle in order to obtain skills for long-term careers, much higher than the overall 18% of Americans who started a side hustle with the same motivation.
Quicken conducted the survey online, gathering responses from more than 1,000 Americans.
Additional research on side hustles, released in August by NEXT Insurance, showed that three out of five people bring in less than $1,000 monthly in side income, while 22% make $1,000 to $10,000 a month, and 15% make more than $10,000.
Related: Starting a Side Hustle Should Come With a Warning Label — Here’s What You Need to Know