Can You Really Airbnb Your House While You Travel the World?
36 clever tools, apps, & services for hacking the system so you don't have to be physically present (AKA THE DREAM)
I’ve stayed in a *creepy* amount of Airbnbs.
According to my account—paired with my very astute calculations (by which I mean I am fully caffeinated and even took a shower)—I have stayed:
723 nights of my life in other people’s houses (always private, except for one time in Barcelona in 2012 when the app first came out)
In 62 different homes around the world
My favorites, by far, have been in London—and that’s because the British are stylish little wallpaper-and-marble-loving brats. Like, look at this.
Then again, this one in Dublin, Ireland was also magazine-worthy. Actually, it WAS in a magazine. Have been obsessed with brass cabinets ever since. 🤩
I have had the great pleasure of finding my passion for interior design because of Airbnb.
Some of the places I have stayed in Florence, Barcelona, Amsterdam, Mexico City—all design-forward, all teaching me little things about how to make a space look like a million dollars.
In short, I became obsessed.
So obsessed, of course, that I bought this farmhouse property in the Pennsylvania countryside with a matching miniature guest house so I can renovate it all and turn into an upmarket short-term rental—something that is sorely lacking in the area. (I should know; anytime I wanted to ever come visit my hometown, or my childhood friends and their babies, I had to stay in the Holiday Inn Express at the local Flying J truck stop—this is 75% of the reason why I invested in property here. I couldn’t take it anymore.)
If we were to calculate the number of nights I have stayed in hotels, I fear that this number would be multiplied by 3. That would be 2,169 nights staying in outside accommodations, or 5.94 years.
This tracks. I have been a career nomad for 15 years. I am not counting any of the long-term apartments I rented in different countries, like that time I spent years writing from Central America with copious amounts of pit sweat.
(Note for anyone who saw my poll, below ⬇️, and was curious about my usage of “papas bravas” instead of “patatas bravas”: it’s the same dish, just informal Central American shorthand that’s been drilled into my skull!)
ANYWAY, DARLING.
I’m on a mission to turn this farmhouse property into an short-term rental (STR) for a few reasons:
As a part of the long-term travel community, being able to feel like you are “at home” in a place so far away has greatly improved my quality of life—and I want to return the favor for others.
It’s a big part of my identity. And, if you’ve ever studied marketing, you’ll know that people do the things that help them reinforce their identity.
Thanks to platforms such as Airbnb and One Fine Stay and Plum Guide and Home Exchange, real estate & design has become a passion of mine.
I enjoy meeting other globally-minded people. You never know when a CEO is going to be making an omelette in your kitchen.
And, of course, from a financial standpoint: if you can earn enough rental income to cover your costs, you’re essentially using other people’s money to build your own real estate ‘empire’
If you can earn more than your breakeven number, you are profiting—and earning the elusive ‘passive income’ that the travel community is always so hot for
The traveler’s problem, of course, is that unlike my other digital businesses, a piece of real estate isn’t exactly mobile. And, operating a guest house out of one is less so. There are *physical, in-person things* that must be done: bedding needs changing, houses need cleaning, supplies need filling, and guests need managing. Not to mention the other joys, like landscaping, and lawn mowing, and changing air filters.
On its face, these things sound…really heavy. They are precisely the kinds of things I didn’t want to deal with in my 20s and 30s. Re-grouting a tub? No thanks, I’d rather re-make a martini.
But, when you turn 40 and you’re seriously into real estate and you seriously still are just as obsessed with the world as you always were, you find ways to combine your interests. So, this is an experiment I’m running here on the newsletter in 2025 and I’m excited to bring you on this journey!
The #1 goal of our mission: learn hacks for operating a guest house from anywhere.
Which is why I’m calling it: The AnywhereBNB.
We love real estate, but not at the cost of our freedom. And, we love freedom, but not at the cost of fun, passionate investments that bring us joy.
So, without further ado, here are 36 incredibly clever tools, apps, services, companies, and courses I’m looking into using to achieve the goal of running an Airbnb guest house from anywhere. 🏆 🗺️ 🏡 🧹 🛁 🪄
(Seriously save this list if setting up an Airbnb is even vaguely on your mind. You will refer to this over and over again!)