Owning Short-Term Rentals as a Couple: The Airbnb Rental Diaries

If you’ve been around for a while, you might remember the birthday podcast episode I recorded with my daughter. That episode is still one of the most listened to, so I thought, why not turn it into a family tradition? This year, I’ll be featuring all the members of my family on the podcast around their birthdays. You’ll hear from my husband and our kids in April, August, September, and October. First up is Caleb, my husband, business partner in life, and today’s special guest.

Celebrating 34 Years of Caleb

Caleb’s birthday is coming up soon, he’s turning 34. And honestly, after 30, keeping track gets a little blurry. We joked that 30 might be the last milestone until 50… or is it 40? Either way, it was fun to reflect on some of Caleb’s past birthday memories. He didn’t grow up with big birthday celebrations like some of us, and when I asked about his favorite birthday memory, he took me down a different kind of memory lane—one that included brownies instead of cake and endless games of paintball.

We laughed about one of his less-than-favorite birthday experiences—his 30th, when we were in Kentucky touring properties and I may have forgotten it was his special day. Whoops. But to this day, Caleb still asks for brownies instead of cake, though he’ll make an exception for red velvet—sometimes.

As for this year? He doesn’t typically ask for anything tangible, but he mentioned wanting to try out this unique rail cart experience here in North Carolina—kind of like a bike that rides on train tracks through the mountains. Sounds like an adventure! That said, I was a little disappointed he didn’t mention the baseball game tickets I already bought for the Cosmic Glow game coming up. Apparently, he thought we were brainstorming additional gifts. Typical Caleb.

What Does I Even Do? According to Caleb…

Next, we shift gears to something I’ve always found entertaining: hearing Caleb describe what I do for a living. With all our moving in recent years, we’ve had to explain our jobs to a lot of new people, and I was curious what he tells others when they ask about me.

His response? “She runs her own business doing marketing.” Not wrong… but also a little vague, right?

He admitted that “marketing” is such a broad term that even when people ask him what that actually means, he struggles to explain it fully. But at least he knows it includes social media and websites! (Progress.) I went ahead and added a few more pieces to the puzzle: email marketing, brand design, strategic planning, and helping clients target their ideal audience—especially through Brand & Market.

We both agreed that we often forget to include our short-term rental business in that conversation, even though it’s one of our most consistent income streams. Funny how that works!

The Many Names of Me: Ali, Alex, or Ali Rae?

Now, here’s where things get fun and confusing. I’ve gone by several names over the years: Alex, Ali, Ali Rae… and my full name is Alexandra. Not super common, I know. So I asked Caleb what he tells people my name is, and his answer was gold: “Whatever you tell me to tell them.”

When we moved to our current state, he asked what I wanted to go by in this fresh start. I didn’t give him a straight answer then, and I still haven’t. These days, I’m usually “Alex” in everyday life, even though I introduce myself on the podcast as “Ali Haney.” And when I give my name at coffee shops? I go with Ali.

Even our friend who visited us got confused after reading one of our travel maps labeled “Alex.” He had just spent two days calling me Ali! We had to explain the whole name situation all over again.

The Great Podcast Mystery: Why Caleb Doesn’t Listen

I had to ask: does Caleb listen to my podcast? His answer? “You told me not to.” And, well… he’s not wrong.

I tend to be a bit secretive when I’m recording. I usually hole up in a closet with my mic and my notes. When we lived in Virginia, I recorded downstairs while Caleb watched the kids upstairs. Now, it’s usually in the closet again, and I definitely don’t want an audience while I’m mid-recording.

That said, he did listen to the birthday episode I recorded with our son, Huxley. So maybe there’s hope! But as for this episode? He says he’s living it in real time—no need to listen back.

And honestly, I don’t really listen to my episodes either once they’re edited. I record them, send them off to Haley at Gaffin Creative, and she works her magic. She edits the audio, adds the commercials, uploads, and schedules the episode. Once that’s done, I rarely revisit it.

Navigating the Pivot: From Wedding Dreams to Airbnb Reality

One of the biggest shifts we had to make as a family was deciding to walk away from our dream of launching a wedding venue in Kentucky and transitioning the property into an Airbnb. And let me tell you—it was a pivot full of emotional weight, logistical challenges, and an eventual sense of clarity.

The Original Vision (and the Wake-Up Call)

We took a big leap when we left the military. We moved eight hours away from any familiar face—further than we ever had while enlisted—and landed in rural Kentucky with two kids and no jobs lined up. I still had weddings booked as a photographer back in Virginia, so I was making frequent drives back and forth, and Caleb eventually found a full-time job with a paving company. His workdays were long—out the door by 6 a.m. and back around 6 p.m. Most nights, he still had to mow fields and maintain 90 acres of land. It was grueling.

But the toughest part wasn’t the workload, it was the isolation. Living that far out meant we were 30 minutes away from just about everything, and even worse, we were surrounded by neighbors who went beyond disapproval of our venue plans and into outright hostility. If you want the full deep-dive on that chapter, I break it all down in Episode 3 of the podcast.

Despite the sprawling acreage and our legal diligence, we were met with intense pushback. Our neighbors weren’t just indifferent; they made it clear they wanted no commercial activity anywhere near them, even if that activity was over the hill and out of sight. What began as disagreements turned into tension that constantly left us looking over our shoulders.

Pivoting to Airbnb: From Loss to Leverage

Ultimately, we pivoted. The dream of hosting weddings on that beautiful land was over. I remember coming back from a weeklong trip where I had back-to-back weddings to shoot, and Caleb had moved our entire family, while I was gone, out of the 6,000 square foot main house and into the 1,000 square foot carriage house. At the time, we were a family of four, and I was heavily pregnant with our third baby.

That move allowed us to get the main house Airbnb-ready, and looking back, it was the exact right decision.

The property is made up of three structures:

A 5,000 square foot metal shop, originally intended to serve the venue in some way.

When I asked Caleb if he was happy with how we pivoted, he was clear: “Yeah, I think Airbnb is a great idea.” And he’s right. Hosting weddings would have required us to sacrifice every weekend for the foreseeable future, and even though that was part of the short-term plan, the Airbnb model gave us freedom. We didn’t have to be on site all the time. We could call a plumber if something broke. We could get away for the weekend without worrying about guests needing us every moment they were there.

It gave us income and freedom—two things we were desperate for after the chaos we’d endured.

Systems Over Stress

At that point, this wasn’t our first rodeo with Airbnb. The Kentucky property was actually our second, and I was already co-hosting my mother-in-law’s Airbnb in Virginia. So I had systems in place: automations, templates, checklists. These made hosting manageable, even efficient. And that’s why, for us, Airbnb doesn’t feel like a traditional business.

It’s not grinding at a desk from 9 to 5. It’s not sweating deadlines or pitching clients. It’s passive-ish income. Sure, there’s work involved. But it doesn’t feel heavy. It doesn’t feel like survival mode.

It feels like peace. Like recovery. Like a quiet kind of success that doesn’t demand everything from us in exchange for financial return.

And when I get that payout notification in my inbox? It feels really, really good.

Quick Note on Branding and Business

Let’s shift gears for a second. You might’ve noticed how I mentioned systems, automations, and consistency. These are the same principles that matter when building a recognizable brand.

Here’s a quick tip for you entrepreneurs: a customer typically needs to come across your brand at least seven times before they make a purchase. But if your branding isn’t consistent.if they don’t know it’s your brand those seven times, then you’ve done all that marketing work for nothing.

That’s why I created the Brand Strategy Framework Mini Course so that you can build something cohesive, recognizable, and sale-converting. It’s a self-paced, budget-friendly resource for entrepreneurs who know something’s off but can’t quite figure out what. I’ll guide you through it, step-by-step. Check out the link in the show notes if you’re ready to stop guessing and start building something solid.

The Unforgettable Party and the Lessons It Taught Us

One of the most unforgettable, and unfortunate, events in our short-term rental journey was a wild party that resulted in police intervention. The guests were kicked out, some jumped the back fence, and the aftermath left us reeling. Thankfully, my brother Jeremy, who lived nearby, was able to assess the damage since we were stationed hours away. While the damage was minimal, the situation was chaotic. The neighbors noticed the commotion, and one even joked about grabbing leftover beer after the guests fled.

It happened in April 2020, right after the COVID-19 lockdown had begun. What made it even more complicated was the fact that the guest who threw the party was a Marine from Camp Lejeune. At the time, I was pregnant and found myself up at 2 a.m., exhausted and frustrated, trying to take screenshots of the Ring doorbell footage to send to the guest’s command.

That sleepless night taught me one of the most valuable lessons as a host: never accept one-night bookings. At the time, I required guests to message me before they could reserve, and this guest had told me his family was visiting from California. It seemed plausible, but in hindsight, it made no sense that someone’s family would visit for just one night. The guest lied, and I trusted him — a mistake I never made again.

When the cleaners came in afterward, they FaceTimed me, showing beer pong setups and sticky floors from spilled jungle juice. While no lasting damage occurred, the stress and emotional toll were significant.

Unexpected Guests and Surprising Solutions

One of our funniest stories came from a guest who reached out after their stay to ask if we had ever sensed a presence in the house. She claimed that every night at 2 a.m., she heard a sound that resembled a coffee machine starting up. It puzzled us at first, but then it hit me, it was Rhonda, our Roomba.

We had brought the robot vacuum from our home in Virginia, where it had been set to clean at 2 a.m. daily. When we plugged it in at the rental, it retained the original schedule. So, what the guest thought was a ghostly presence was actually Rhonda faithfully cleaning the floors. It’s a hilarious reminder that not all spooky noises in the night are paranormal but that sometimes it’s just smart tech doing its job.

Hosting short-term rentals has been a wild ride, from unexpected parties and ghost-hunting guests to respectful gamers and valuable life lessons. If there’s one takeaway from these stories, it’s that preparation, strong policies, and a sense of humor go a long way. Whether you’re a new host or a seasoned one, there’s always something new to learn, and laugh about, in the world of Airbnb.