When I first heard about Airbnb—a vacation rental platform where you stay in someone’s home—I was intrigued. I can’t remember my very first stay as a guest, but with how much I travel, I eventually found myself booking through Airbnb more and more.
At first, I wasn’t sure what to expect. What does it even mean to stay in someone else’s home? Were they still living there, with their stuff shoved in closets or under the bed? Was it supposed to feel like a hotel? I didn’t have a clear picture of what the experience should be.
But over time, I began to pick up on the difference between hosts who really cared and those who were just riding the Airbnb wave without much thought. I learned quickly that hosting is an art—and not everyone’s great at it.
After each stay, guests and hosts review each other. (You can’t see their review until you submit yours—smart, right?) I usually lean toward kindness, even when the stay wasn’t perfect. I’d highlight the positives in my public review and save the constructive feedback for a private message, always hoping the host would take it to heart and improve their setup.
When I had a great stay, I started paying close attention to why. What made it feel so welcoming? Did they think through the little things—extra towels, cozy blankets, spare pillows? Was the Wi-Fi password easy to find? Were instructions posted clearly around the home? Did they stock coffee with creamer and sugar? Did it feel like home?
And even if a property checked all the boxes, I realized the host played an equally important role. Service matters. Were check-in and parking instructions clear? Was the host responsive if something went wrong? In the short-term rental world, you rarely get a second chance—one bad experience and your guest won’t return.
But going the extra mile? That’s how you earn glowing reviews, repeat guests, and even a little fanbase.
After a while, the guest experience had me curious—could I do this myself?
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So How did I go from Airbnb Guest to Airbnb Superhost?
Let’s back up a little.
I’ve had a natural eye for design since I was a kid (I know, we’re really going back here). Even though we didn’t have much growing up, I always took pride in keeping my space tidy and visually appealing. I’ve always had a knack for placement, color, and texture—and that creative instinct turned out to be a huge advantage when I ventured into real estate.
Now, you don’t have to be a designer to succeed in real estate, but you do need something to spark your interest. There are so many different paths within the industry—real estate is truly a launchpad for all kinds of opportunities. For me, I dove in headfirst and got my hands into just about everything: design, construction, sales, property management, flipping homes, new builds, and yes—you guessed it—Airbnb investing.
The first five years were wild.
After just one year in the business, I opened my own real estate company, which led me to purchase my first office. It was a small building with a few offices and a loft above. When I bought it, I sold my house and moved into the loft. Financially, it made sense—and I honestly loved being so close to work.
But I outgrew that space pretty quickly.
By year two, I purchased a historic building in downtown. The location was perfect, but the building needed a lot of work to function as an office. Still, I was up for the challenge. I had already flipped several properties at that point, including my first office, so I wasn’t afraid to take it on.
The building I bought—where my current office is located—came with a loft space, too. I’ve always loved mixed-use buildings. The loft had been beautifully renovated by the previous owners and was being rented long-term to a sweet couple. When they eventually moved out to buy their first home, I saw an opportunity.
I thought, Why not try Airbnb?
By that point, I’d spent plenty of time on the guest side. I knew what made a stay memorable, and I had a clear vision of what I’d want to offer as a host. The location was ideal, the loft had great character, and—let’s be honest—it gave me the perfect excuse to decorate.
So, I jumped in. I furnished the space and decided to give Airbnb hosting a try. Within a year, I earned the Superhost badge.
There’s really no secret to it. I created a space people loved returning to, and I stayed on top of communication. Simple as that.
My First Airbnb – The Historic Loft with a View
When you publish a listing on Airbnb, they encourage you to give it a name. I went with “The Historic Loft with a View.” From the beginning, I wanted to create a space people would want to come back to. Based on my own travel experiences, I knew that the places I remembered—and rebooked—were the ones with charm and a responsive host.
So, my first goal? Create that kind of environment.
Now don’t get me wrong—furnishing a 1,500-square-foot loft is no small task. It’s pricey, and you won’t see an immediate return. Like most real estate investments, Airbnb hosting is a long game. It typically takes about a year for your listing to really gain traction, so keep that in mind if you’re considering getting into it.
Back to decorating…
I love a good deal. Overpaying drives me crazy—even when I can afford it. That’s why Facebook Marketplace is my first stop. I’ll buy almost anything there (except mattresses, kitchenware, and toiletries). My second go-to? Amazon (cue the memes).
Comfort was a top priority, especially the beds. A pretty space means nothing if the mattress is terrible. I’ve had great luck with bed-in-a-box options from Amazon—surprisingly comfortable, and guests often asked where I got them.
Once the furniture was in, I added the décor. The style is a blend of old and new—antiques mixed with clean, modern lines. Stocking the space came next, and it was no small task. But the little details matter. Essentials shouldn’t be an afterthought.
On the backend, I focused just as much on systems. I started with Hospitable, which is perfect for new hosts. It helped me automate messages like check-in and check-out instructions and stay super responsive—something guests really appreciated. Later, I upgraded to Hostaway. Both platforms are great and make it easy to manage listings across multiple channels, keep communication smooth, and automate cleaning tasks.
Here’s how the loft turned out:
Once the listing went live, I was so excited to welcome my very first guest. From there, things really took off. As travelers came and went, I paid close attention to their feedback and made continual improvements—everything from small touches to major updates—to create an unforgettable guest experience. During Airbnb’s peak years, the loft became so popular it was nearly fully booked year-round. Guests were checking in and out faster than we could make the beds!
When Was Airbnb at Its Peak?
Airbnb’s prime years were undoubtedly 2015–2019. During that stretch, the platform was booming. Guest demand was high, competition was low, and regulations were minimal. Early adopters often saw strong returns without needing much more than a clean, charming space and good communication.
Then came 2020, and with it, a dramatic shift. The pandemic halted travel in many cities, but remote and rural Airbnbs took off. Longer stays became popular as people looked for escapes and worked from anywhere.
By 2022–2023, travel had rebounded—but so had the number of hosts. The market became more saturated, guest expectations rose, and many cities began enforcing stricter short-term rental laws. Some hosts struggled to keep up, leading to headlines about an “Airbnbust.”
Today, Airbnb is still a great opportunity—but success isn’t as easy or automatic. You need a thoughtful approach: strong design, comfort, clear instructions, and the kind of experience that makes guests want to come back.
My Next Airbnb – The Historic Manor
I ended up investing in another Airbnb, but this one came with a completely different story. I had partnered with one of my investor clients when the market was still strong. But partway through the remodel, my partner wanted out—right in the middle of it all. I hadn’t planned to take on the full investment, but I got creative, bought him out, and kept going. I wasn’t about to give up on the property.
The original plan was to flip it, but by the time it was ready, the market had shifted—yep, I’m talking about 2022–2023. The real estate landscape was shaky, interest rates were high, and buyers had vanished. I listed it anyway, but it just sat. No offers. No interest. Meanwhile, my balloon note was coming due, and I needed to make a move.
So I pivoted. I furnished the home and turned it into an Airbnb. This wasn’t the type of property suited for long-term rental—it was large and unique. And if I thought setting up a 1,500 sq ft, two-bedroom loft was tough… this one was a beast: 4,000 square feet, four bedrooms, three and a half baths, on half an acre. Brutal.
And of course, this was during a time when Airbnb wasn’t exactly booming either. But I had no choice.
Believe it or not, it actually performed pretty well. Enough bookings to cover expenses—and then some. And that’s all I could really ask for at the time.
While the Manor shared similarities with the loft—age, charm, and location—the guest experience was totally different. The loft attracted singles and small families. The Manor? It became a favorite for groups and larger gatherings.
Here’s how the Manor turned out:
The home was featured in the Denison Home Tours, in Better Homes & Gardens and the popular Facebook page – For The Love Of Old Houses.
What I Learned as a Superhost
I sold both of my Airbnbs in 2024, mainly due to my real estate business taking off and needing to invest that money in the growth of my property management company. But what I learned from being a Superhost with Airbnb are things I’ve taken with me—principles that now shape how we operate as a company and serve both our owners and residents. Airbnb taught me that hospitality isn’t reserved for short-term stays; it’s a mindset that can transform long-term property management too.
Here are my key takeaways from my experience on Airbnb:
- Details matter. Whether it’s fresh towels or a quick response to a message, the small things add up to a big impression. We apply this same attention to detail in every aspect of property management from move-ins to maintenance and more.
- Clear communication is everything. Guests want to know what to expect. The same is true for residents and owners. Setting clear expectations upfront and communicating openly builds trust and reduces frustration.
- Presentation is powerful. A clean, well-staged space photographs better and rents faster. We now approach our listings with the same eye we used for Airbnb—good lighting, thoughtful descriptions, and showcasing the home’s best features.
- Hospitality creates loyalty. Just like we had returning guests, we now have residents and owners who stick with us and refer others. People remember how you make them feel.
- Flexibility and problem-solving go a long way. No two guests (or residents) are alike. Being solutions-focused and ready to adapt has helped me grow a resilient and responsive team.
In short, Airbnb helped me see property management through a hospitality lens—and that’s a perspective I’ll never let go of.
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