Author Archives: somewhatjustin

At the end of 2021, I signed a bunch of papers and closed on The Flying Squirrel—a mountain cabin in Maggie Valley, NC. Shortly thereafter, I listed in on Airbnb. In this post I’ll share my learnings from the first ~90 days of business as a remote short-term rental host.

Get. Great. Photos.

When you list, photos are super important. Here’s an example of an early photograph I put on Airbnb:

At first glance, it might seem fine. And sure, it got me a couple of bookings. But after chatting with David over at Overlooked2Overbooked and using their Vacation Rental Assessment (highly recommend), I learned several things:

1. My photos were not bright enough
2. My photos did not show enough primary colors
3. My photos didn’t tell a story

So here’s some of my newer photos.

A bit better, yeah?

You don’t need a management company

Management companies like Vacasa will run your vacation rental for you and take a cut of the proceeds. Here’s why I don’t recommend starting with a management company:

• Once you set up some basic automation, the daily/weekly workload is actually quite low. I can spend as little as ~1-2 hours/week.
• Running a short-term rental is fun! I have the chance to introduce people to one of my favorite areas in the world.
• You can (probably) make more money on your own. Not only will a management company take a sizable cut from your payouts, they also won’t have the expertise on your property or even your market that you do. There are a lot of high quality free resources to help you improve your short-term rental game. Like this blog. 👀

Pick an area you know

When I decided to start a short-term vacation rental company, I knew ahead of time that I’d be looking in the Great Smoky Mountains area. Despite living in Texas my entire life, I do have some familiarity with the area from a month-long stay in Asheville in 2021 (via Airbnb, of course).

This gives me some advantages:

• Recommendations are much easier since I’ve spent time there as a guest
• I knew which areas to target. When I stayed in Asheville, I found myself driving through this little town called Maggie Valley to get to the best trailheads.
• More visits! I find myself visiting the North Carolina area quite often, so having a place to stay there is a nice bonus.

I got lucky in that the area I know well is great for short-term rentals. If you have a market in mind that you don’t know well, that’s fine too. Just make sure to follow my next tip:

Find an excellent local partner

This applies to anyone doing remote hosting.

I recommend finding the person who will be cleaning your property fairly early. This person can make or break the guest experience. I got very lucky because the first person I reached out to ended up being excellent.

While there are platforms like TurnoverBnB that will help you find and facilitate cleanings, for a single-property manager, this is overkill and expensive.

I found my cleaner by poking around on Facebook. I literally just searched “housekeeper maggie valley” and contacted the first person I found. It turns out that the person I found runs a short-term cleaning company. I see this as a major perk, because:

• She has experience with short-term rentals
• She has backup cleaners on her team
• Our incentives are aligned—if guests have a good, clean experience, that means higher occupancy in the future, which means more cleanings

Another major perk: My housekeeper is good at doing small repairs! When my brand new bed broke, my housekeeper fixed it right up, meaning I didn’t have to wait for someone else to take a look. Find you somebody that can do both.

Live in your property

If at all possible, live in your property as you get it set up. Because I work remotely, I was able to work from there as well. Having to cook, clean, recreate, be bored, etc in your property will help you get those “must-have” items you forgot to grab. You’ll have more ideas on how you can create an awesome experience. Your recommendations will be stronger as you find the best local spots. Plus, it’s fun.

You only need one tool (pricing)

If you listen or read in the STR space, you’ll no doubt hear about the various tools available to use. As a software nerd, I was tempted to pick out a few that sounded interesting and get them set up immediately.

What I recommend instead is to wait. Don’t purchase a tool until you feel the pain of not having it.

As a quick example, I thought I needed a platform to help with automated messaging. Since I only launched on Airbnb, I was able to use Airbnb’s built-in free tool. It does everything I need it to do.

The only tool I think you should start out with is a pricing tool. Pricing is crucial to your listing’s performance and requires a lot of effort to get right. I use Pricelabs, which provides some nice features:

• Automatic seasonality and occupancy based pricing
• Ability to set orphan day discounts (if there’s a space in between two other bookings, discount it)
• Last-minute discounts are helpful for increasing occupancy rate
• And more!

For about $20/month, this is a no-brainer.

If you’d like a screencast walking through Pricelabs, please reach out to me on Twitter!

Note: Airbnb does have a built-in dynamic pricing tool. However, I’m wary of it since their incentives don’t align perfectly with mine. Anecdotally, I’ve heard that they tend to focus on optimizing for occupancy rate, not overall revenue.

Why I launched on Airbnb only

Up until yesterday, I was only on Airbnb.

Being on one platform simplifies almost everything. With this being my first vacation rental, simplicity is key! It also helped me reach Superhost status before the April 1 deadline.

That being said, use something like AirDna to figure out which platforms your market uses. Here’s the breakdown for Maggie Valley:

I picked Airbnb over Vrbo because I prefer Airbnb for my own stays and knew the platform already.

Be available

I’m normally a heavy “Do not disturb” user on my phone. However, with owning a short-term rental, I’ve had to make some adjustments. You want to be able to respond to inquiries and guest problems as quickly as possible. It means more bookings and better reviews. I’ve already had multiple instances where had I not been available, a guest would have been locked out for hours.

The way I stay available is by bypassing my “Do not disturb” setting on my iPhone if the notification is coming from the Airbnb app.

The best reviews start before the guest visits

Looking at the best and kindest reviews I’ve received, they mostly come from guests that I’ve communicated with ahead of time.

I like to reach out a few days before my guests stay and ask if they have any questions or would like any recommendations. I do sometimes forget, which is why soon I’ll set this up as an automated message.

But by getting a conversation going with a guest, I get a chance to establish myself as a real person. One of my competitive advantages is that I’m a real person and not a faceless management company! Guests who know who you are will be more likely to, for example, crawl through a window to unlock a door that got locked from the inside (yes this happened).

Have backups for crucial items

Sometimes, you get a message from a guest saying the key broke off in the lock. 😬 If you have two lockboxes and a spare key, this is not a problem! I’d also recommend having backups for:

• All bedding
• Towels
• Heating/cooling

I 💖 consignment stores

You know what’s expensive? Furniture. Luckily, my area has these things called consignment stores and they’re amazing. Here’s the quick pitch: stuff, but used and cheap. Depending on your market, you might not be able to find what you need. But since I was building a mid-market mountain cabin, the consignment stores in my area were a perfect way to save some cash and find unique items.

Don’t worry about low rates (at first)

My first few nightly rates were abysmally low. As low as $60/night for a 3/1 in the mountains. However, these prices got guests in the door, which led to reviews and learnings. Since then, I’ve been able to charge as much as $179/night.

In the beginning, don’t worry about how much money you’re making. Just find a rate that will get guests to purchase, then focus on making an excellent guest experience and continuously tweaking and improving your listing.

In other words, optimize for occupancy, not revenue in the early days. Get those reviews, improve your listing, and soon you’ll be able to charge much more.

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I hope something in this guide was valuable, dear reader. I’m still very new to this game and will continue to learn. To follow along, please consider subscribing to my newsletter.

Maine is beautiful. I’ve had a blast exploring the different parks the state had to offer. Here are some recent highlights!

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Acadia

I’ve been heading out to Acadia with and without friends.

The Duck of Justice

Bangor, ME is more than just a small Maine city. It houses one of the most important ducks in the continental 48: the Duck of Justice.

After bothering an entire police department, I was able to get a photo with the local hero.

An Experience in Camden Hills State Park

The highlight of my trip arrived in Camden Hills State Park. After a long, uphill hike, I found a beautiful spot to watch the sunset.

It was an eye-watering beautiful scene to watch the sky shift from blue to a light orange. On my left, I could see a small fishing town, with small boats still on the water.

This was the spot I stayed at the longest during my adventures so far. I found a comfy rock and stayed for about 45 minutes. It’s easy to reach your destination, look around, and head back. But sometimes enjoying it means waiting and soaking up the beautiful landscape.

Fake McDonald’s

After leaving the park, I was super hungry. I found a very suspicious looking McDonald’s. Suspicious because it seemed to be in a weird spot, had no reviews, and no photos.

So naturally I headed towards it. There was no McDonald’s.

Instead, I drove through a beautiful coastal town and even found a tiny park with a strip of beach.

Baxter State Park

I went to Baxter State Park in hopes of seeing a moose. While I didn’t get the chance to see any, the hike to Chimney Pond was beautiful, and the pond itself was work the uphill trek.

I plan on climbing up to one of these mountains before I leave.

That’s it for now. More adventures await!

When visiting any modern technology news website, you’re going to see a lot of product-related posts. Reviews flood websites like The Verge, Engadget, as well as many tech YouTuber’s regular videos. Surely the average person isn’t looking to purchase this many gadgets at a time? Right?

Much of tech news is centered around hardware purchases. Affiliate revenue increases with large purchases. Everyone wants to know about the next great thing. People line up for pre-orders and complain when we can’t get them on time. We collectively hold our breath as we wait for Apple to release the latest version of their phone after months of rumors and speculation.

And for what? Do these new gadgets save us time, make us more productive, or provide another major benefit? In some cases, yes. Early phone iterations often brought substantial camera improvements that were immediately noticeable, even on small screens. Today, we have to place photos side-by-side and blow them up to 100% to find the differences. We use these differences to justify costly upgrades disguised as low monthly subscriptions. Other times, upgrading a device is necessary as the old one grows tired and slow. For people who rely on their gadgets to work as tools, such upgrades are understandable. What I lament are the rest of purchases that serve no immediate purpose other than to acquire the newest piece of hardware available, even if the cost can’t be justified.

I’m sure this all sounds judgmental. But I’m mostly writing this for myself. My previous post is an iPhone 12 review. I had the iPhone 11 Pro. I paid for a new phone because the sides were rectangular instead of curved. What. I am proud to announce that I returned the phone and for the first time in my entire lifeam planning on holding on to this phone for a second year. But don’t let me off the hook. After all, I’m typing this on Apple’s new M1 Macbook Air. Yes it’s fast, it’s great, but did I really need to upgrade? No.

In the past few months, the concept of the hedonic treadmill has been stuck in my mind. The idea is that as we accumulate money, we spend it on more things, and/or things of higher quality, thinking that it’s going to make us happier. Once the initial happiness wears off, we move on to the next level, waiting to purchase whatever is slightly better than what we already have. Many consumer-grade electronics seem built for this treadmill. It’s easy to get lost in the world of high-end audio, for example. Sure, you were happy with the computer speakers you got for Christmas, but you think you’ll really be happy when you can listen to the new Taylor Swift album on those mid-range Klipsch speakers. Same goes for cameras, phones, drones, keyboards, mice, PC hardware, laptops, and just about any other consumer-tech category you can think of. 

There’s always something better out there. Keep running on that treadmill, and you’ll find yourself exhausted and/or out of money. Get off the treadmill, enjoy what you have, and use that money to get your time back and experience the world.

I didn’t need this phone, but I bought it anyways. I like it. I’ve always gone for the top-of-the-line phone, but this year I wanted to downsize a bit. Feeling good about my choice, but ping me in 2 weeks when my return window is closing.

Also buy a fun color. I went with black. It’s cool, but red and blue are more striking. Life is too short to be subdued.