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February 3, 2023

Dreaming of Starting an Airbnb Business? Ask Yourself These 3 Questions First.

Vacation Rental

I get asked often about the success of our vacation rental cabins and I’m going to share the secret of our success with you today. This industry is full of educators talking about the logistics of running an Airbnb business. Agonizing over the details on the how and the what.

And to be honest, it leaves me feeling like it’s a cold transaction – almost a used cars salesy vibe – a landlord instead of building the business of your dreams. And that’s just not the way we do things around here.

3 questions to ask yourself before starting an Airbnb Business

If you’re dreaming of starting an Airbnb business, I think it’s important to start with a few questions first to really set the stage and know from the beginning just what type of business you ultimately want to run so that it can guide every decision you make from what property to buy to how you’ll market and attract your ideal guests. 

One of our cabins is really far north and in a place where it’s difficult to get help for cleaning or maintenance and it’s waaaayyyy off the beaten path from the normal touristy area that people visit. If you were a real estate investor, you’d likely not describe it as a slam-dunk investment decision. Someone who bought in the same area reached out recently because they were having trouble making their place successful and wanted to know if we could do it over, would we buy there again because they were regretting their decision.

Here was my answer: we don’t buy solely based on location but rather on the story we can tell. What experience can we curate for our guests there? What’s the special sauce of the area? What makes it unique? What will draw that perfect guest that we’re hoping to attract? Although this cabin was in a tougher area, it’s generating 250k/year for us – because it’s special and fits into our brand, our vision, and our clientele. 

Starting with our “why” and letting that be the heartbeat and compass as we scaled and grew was the difference maker and the secret to our success. So, here are the questions to ask yourself and the process we walk through long before even starting to look at properties. It’s how we’ve found diamonds in the rough, saw potential no one else did at the time – and now, people say how “lucky” we were to find the perfect places for our brand.

It’s not luck my friend, and here’s how we did it.


Start with your unique story and identify your “why”.

The truth is, YOU are going to be a main component when it comes to marketing your future vacation rental business. What do you bring to the table? People will want to know you and your story. They will want to feel like they are a part of something. Rising above the masses of all the options they have to choose from starts with them connecting with you

So, what story do you want to tell? What makes you different? What is your why for starting this business? Give your guests a reason to stay with you other than just the four walls of your vacation home.

For inspiration, here’s my example (and guess what? It shows up right on our about me page – the most viewed page of most websites):

It all started with an RV trip to Yellowstone with our best friends. One day, we parked the RV at a river and spent the entire day there. Sunup to sundown, we explored the river, fished, ate when we got hungry, and napped when we got tired. There was no wifi or screens, no work or laundry to distract us—just the simplest of days. This feeling is what I want for our guests at our cabins. Creating time to just be together in a beautiful space, with as few distractions as possible. I love the idea of creating a carefree, no-hassle, high-end experience for our guests, so they’re free to simply show up and make memories with their families.

You can read our full about page for further inspiration right here.

What problem are you solving and for who? Attracting your ideal future guest. 

Think through very specifically about the kind of person you want to serve in the future. This is important because it’s going to direct the type of properties you pursue that will attract this type of person. Keep this person in mind as you are deciding where to purchase. 

Free form write everything you can think about your ideal client. Try to visualize one person who would accurately describe a future guest you would want to host. Their age, their job, their interests, their pet peeves – get really specific. A lot of vacation rentals try to market to everyone, but narrowing down your ideal guest will allow you to speak directly to the exact people who are searching for your property allowing you to easily book dream guests.

What will your vacation rental offer this type of person you just wrote about? How will they benefit from staying with you? If it helps, you can even give them a name and a story to have in the back of your mind as you start to craft your Airbnb business and property search.

Here’s ours as an example:

The Jacobsen family lives in the Chicago metropolitan area in an old, upscale, renovated townhome. James is an attorney who often works 60-plus hour weeks, Meredith owns a boutique home decor store, and their two kids, Jake, 12, and Emma, 8, are busy keeping up with school and sports.

They rarely have time to sit down at the table for meals as a family, and Meredith feels like their kids’ lives are starting to slip by before their eyes. James grew up vacationing with his family in Door County but hasn’t been back in at least 15 years. He and Meredith have been craving a way to slow down with their children, reconnect with one another, and actually unplug from email, iPads, and Netflix—without having to fly to a beach 5 hours away or take 3 weeks off of work.

Ideally, they could pack up with a few bags and their 5-year-old labradoodle, Pogo, for a week or so every summer to escape somewhere convenient with water, good food, and simple family activities. They want somewhere that they could invite extended family to come with and that feels like the comfort of home—minus the crazy work demands and busy schedules, plus a slower pace and plenty of opportunity to relax and just be together.


Crafting an experience for your guests

Now that you know why you want to start this business and wrote a mission that elevates you above simply being a landlord, it’s time to bring it all together and think about crafting an experience.

If you don’t yet own a property, you might be thinking “how can I create an experience for anyone at this stage in the process?”. Valid, but here’s the thing: I want you to be envisioning that experience as you tour properties and find the perfect match for the type of business you want to build. The one that fits with your story, your mission, your ideal client, and the experience you want to market to them. 

What are your future guest’s goals in booking a vacation rental? Do they want to be in an area close to local attractions? Looking for a more unique property and setting? Isolated and private? Geared towards families? Geared toward couples? What will they do while they are there? What does a day look like? What’s close by that you can fold into the story of their experience at your property? 

When we toured our first property, The Point, other people saw the roof caving in, the 50 years of clutter that came with the place, the carpet in the bathroom, and multiple structures that made it kind of look like a junkyard… it was a lot of work. But, I saw there was a dock facing east and west – for coffee at sunrise and wine at sunset. I saw a private peninsula for kids to run free and barefoot off their devices, making memories. I saw an open space for a future large farm table for families to gather during dinners under twinkly lights. I saw a clubhouse for kids and a private guest house in those additional structures. People thought I was crazy and the cabin sat on the market for over a year before we bought it, and now it’s the #1 vacation rental in our area.

My point is, see the opportunity. See the story. See the experience OVER the real estate potential. This is what makes a brand you’re going to be proud of and sets you apart from the masses of other Airbnb options people have to choose from.

Ready for the next step in building that dream Airbnb business? I’ve got the perfect FREE guide 10 Strategies for a Wildly Successful Vacation Rental Business


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