Can You Really Airbnb Your House While You Travel the World?

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!)

1. AirDNA is THE platform for researching investment properties, getting amazing short-term rental data, and getting a higher return on your investments.
2. Fractional, for co-owning rental properties with others. (This just looks very cool.)
3. Landwatch is neat if you want to buy property to put a tiny home or cabin!
4. Here.co is curating great Airbnb property investment deals & sending to inbox.
5. HSBC has a special expat mortgage! Particularly if you’ve been traveling abroad and don’t have the kind of history on paper that traditional mortgage companies want to see. (I bet there are more of these.)
6. Latchel for hands-off property maintenance & guest issues - in LOVE with what they’re doing here! Dreammmm situation.
7. Hire Sofia is VAs (virtual assistants) who do remote property management.
8. Extenteam also does remote staffing solutions for property management.
9. Operto is like having superhero powers for automating cleaning staff schedules, maintenance staff schedules, maintenance requests, and so much more (but you hire the peeps—then they follow checklists and get notified if people extend their stay, etc.)
10. Flexkeeping looks super great, too: also for automating things like cleaning.
11. Breezeway is another one for automating cleaning, maintenance & requests.
12. Cleanster and Turno helps you find, schedule & pay vacation rental cleaners.
13. This VERY interesting white glove management service from Wander, where you partner with them and they take care of *everything*.
14. Price Labs for optimizing your pricing strategy.
15. Keystone Bookkeepers or Thuro for accounting and bookkeeping services specifically for vacation rentals.
16. AutoRank for optimizing your Airbnb listing for SEO.
17. Akia is a text-messaging platform for automated guest communications and making it feel luuuxe.
18. Remote Lock for managing locks & codes from anywhere via the internet.
19. And HERE is how you handle it if you live in an apartment and have a door buzzer. :)
20. This fun course from The Staging Studio on styling & furnishing your short-term rental. (And remembering rules like: SCOTCHGUARD EVERYTHING.)
21. Hostaway and Hostfully for property management automation software.
22. Guesty also for property management, with automated guest messages, automated pricing adjustments, and tonnsssss of features.
23. Guesty Capital for renovating properties & investing in new amenities. (What a cool niche.)
24. Loans specifically for real estate investors.
25. Modern insurance for short-term rentals & property investors.
26. This booklet on taxes for short-term rentals.
27. Accountable for bookkeeping and money management for your property manager.
28. Superhog for safety, guest screening, ID verification.
29. Minut for cigarette detection, indoor and outdoor noise levels, motion detecting, temperature and humidity, and monitoring.
30. HostGPO helps you source & furnish your rental.
31. Public Goods gives you eco-friendly products with which to furnish your rental.
32. Fulhaus for one-click “buy that room” furnishing for rentals - very cool concept!
33. Keycafe is amaaazing for leaving keys at a public place for guests to pick up. I used this in Edinburgh, and it was seamless. Then, you drop the keys back off to the location.
34. Stayfi for offering guests Wifi AND ALSO building your email list for direct bookings later. (Otherwise, the booking platforms like Airbnb are the only ones who get their email.)
35. The Host for offering a cute little on-site store to give your property hotel-like amenities! (Especially useful if your property is remote.) But, also upsells like in-home massage, private chef, fresh flower delivery, and firewood. LOVE.
36. Lugless for having your guests ship their luggage, skis, snowboards, golf clubs, boxes, and more. Isn’t that neat?

Have you ever hosted an Airbnb or short-term rental?

Help me out!

What’s the #1 thing you learned NOT to do? All advice & wisdom welcome. 💥