12 Things I Learned After 90 Days on Airbnb

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:

Living room of The Flying Squirrel

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:

Where my competition lives

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.

Only Airbnb and a timer app can get through DND

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.

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.

More Adventures in Maine

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


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

Jordan Pond in Acadia
More Jordan Pond
On the way to Otter Point
Otter Point, Acadia

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.

In case you couldn’t tell I was super nervous to meet him. But he’s super nice in person.

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!

Accidental Night Hiking in Acadia

For my very first hike in Acadia National Park, I decided to start out by hiking the Dorr Mountain Ladder Trail. It’s not a long trail, but with over 1,000 feet in elevation gain, I figured I was in for a workout. I was right.

I was, of course, delighted to see some of the unique features of this trail that I had never seen before. At one point, I had to squeeze through narrow rocks, while at another I found myself climbing an actual ladder.

I had arrived after work, so it was delightful seeing the island and forest on my way up as the sun was making its way down.

I was also introduced to another new trail element: carins.

One of many carins on this trail.

Carins are man-made rock formations used to guide hikers along a trail. While there were also blue spray-painted stripes every 20-50 feet to mark my path, I found the carins to be helpful.

I thought this tree looked cool.

One thing I found unique about this trail was the amount of rock-walking I did. Large patches of this trail found me walking on bare rock instead of gravel or grass.

Top of Dorr Mountain

After a few breaks and a lot of inhaling, I reached the top of Dorr Mountain.

The mountain afforded some neat views of the surrounding area.

Cadillac Mountain on the left

But when I looked across the way, I saw an even taller mountain. Cadillac Mountain. How could I resist?

Well at first I did. It was getting late and I didn’t want to return to my car in the dark. So I started to head back to my car.

But I didn’t drive thousands of miles to turn around, I thought. It was adventure time. So I turned around, making a beeline for Cadillac Mountain.

Race to Cadillac Mountain

Cadillac Mountain took me in the opposite direction of my car, and the sun was getting low.

Checking the map, I saw that Cadillac Mountain was only about 300 feet higher than Dorr Mountain. I figured I’d just be doing a slight uphill climb and I’d be at the top in no time.


Very quickly, I found myself descending, until I bottomed out in a dark forest.

Then I found myself climbing again at a steep incline. The views were even better as the sun set lower and lower.

Reaching the top of Cadillac Mountain was worth it. While the sun had mostly set by this point, I enjoyed seeing people for the first time on my hike. I even found a group of friends gathered around a guy with a guitar, which I found particularly beautiful.

With the sun almost gone, it was well past time for me to return to Dorr Mountain and then complete the journey back to my car. But on my way back from Cadallic to Dorr, I saw something that surprised me.

A Fun Surprise

I was very excited.

What I at first thought was a duck, then a skunk was waiting for me. Directly in my path. Afraid of the consequences of getting stuck by one of those sharp quills, I kept my distance and let the little guy amble away.

While the primary animal-sighting goal of this trip for me is to see a moose, I was very excited to see my first porcupine in the wild.

At Night

Pretty quickly, things got dark. I hadn’t seen a single soul on my way to Dorr Mountain, and I was sure hoping not to see anything spooky on my way back.

Some town idk

The real scary idea was getting lost. Besides the carins, I also had these blue marks to help me out.

Armed with my weak iPhone flashlight I worked my way back along the trail. I chose to take the faster way back to my car to avoid spending more time in darkness.

It was dark.

On my way back I definitely heard some nearby rustling in bushes, which could have been anything from a baby squirrel to a hungry ‘squatch. I was only a little scared.

After what felt like forever, I made it back to my car, safe and sound. Despite the added danger of unprepared night hiking, I’d recommend it. I’m glad I pushed myself to climb another mountain. The porcupine made it well worth it. Thanks, little guy.

Pinnacle Overlook at Crowder Mountain

Today, I had the pleasure of driving to the Charlotte Airport to drop off some folks. On the way back, I decided to stop in at the Crowder Mountain State Park and take on the 2-hour long Pinnacle Trail. The 767 ft elevation gain encouraged some sweat, but seeing the overlook at the top made the trip well worth it.

Hard to see here, but this was a large drop to the forest floor below. I looked down.

Along the way, I saw a few lizards!

he cute, he fast
good camo, friend


Yesterday, I received my second dose of the COVID-19 vaccine. This feels like the beginning of the end for my pandemic arc. Today, let’s go back to the beginning.

I’m taken back to the moment when I realized that COVID was here to stay. I was with my family in East Texas. We had just eaten dinner at a restaurant following my grandfather’s funeral. I looked up at the TV, which was set on a news channel, and saw the headline that the W.H.O had declared COVID-19 a global pandemic. My dad made me laugh by remaking on how confused he was at the headline at first. “Who declared it a pandemic? Who?? Why are they asking?”

As the news continued, I felt my anxiety rise as it finally started to hit me. This was real. This would affect my life.

For the previous couple of weeks, I, like many others, passed COVID off as another flu. Another H1N1. Nothing too scary, just something we’d hear about on the news. It was wishful thinking.

This was obviously a lapse in judgement. Even late into the game, I ignored the signs telling me that COVID was real and that I needed to prep. Over the past year, I’ve tried to analyze myself and ask why I missed something so big.

One of the traps I fall into is giving more weight to an outcome or decision because that’s the reality I wish to live in. I wanted it to be true that COVID wasn’t a big deal, so in my reality, it wasn’t. Eventually, I had no other choice than to accept what was going on.

Over the past year, I’ve been employing this trick of trying to remove my own wish fulfillment from my decision-making process. The key is seeing reality as it is, and not as you want it to be. This is a core tenet of many spiritual practices like Buddhism and meditation, both of which I’ve grown interested in over this past year.

But this tool—seeing reality as it is—isn’t just helpful when looking inward. When I disagree with someone, or think they’re acting irrationally, I try to look at their incentives. Their wishes. To return to the COVID example, I’ve heard and seen people who don’t wish to wear masks. I hear them say they aren’t effective, or that they aren’t worried about COVID so they’re not worried about protecting themselves. In their own eyes, they aren’t doing anything wrong. Humans are self-justifying machines. Look at the split left-right brain experiments to see just how good we are at justifying actions. For people choosing to not wear a mask, I truly believe that their reality is one in which COVID isn’t a big deal, that masks aren’t going to help, and/or masks are only effective at protecting oneself.

But just to be clear: wear a mask.

When evaluating decision-making, try to look at motives. What is the world that this person wants to live in, and are they constructing their own reality to match it? The bubbles and communities we’re a part of go a long way to altering our perceived reality. That’s why it’s important to make sure you’re receiving inputs that counteract your own reality. Approach them with a sense of humility. Who are you to say that you’re right? Even if you don’t change your mind, you’ll have a better understanding of those who disagree with you. Let’s have some empathy.

Tech Media & the Hedonic Treadmill

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.

iPhone 12 Review

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.

Create like nobody is watching

Is anyone else out there an unknowing perfectionist? I’ve never thought of myself as someone who needed “perfection” in the things that I do. My apartment is normally a mess, my organizational skills leave much to be desired, and if you’ve seen my handwriting you’d see how good of a third example this is. But what I’ve failed to realize is that in some ways I am a perfectionist, just in a different sense.

For several years, I was a YouTube Creator. I put videos out on a near-daily basis as I progressed through high school. I even made some cash from it. Looking back at the videos… they were bad. Not gonna lie. However, I greatly enjoyed my work and built a small following off my exploits. I even made enough money to buy half of my first car. Shoutout to mom and dad for the rest.

Fast-forward to today, and my creative output has been… lacking. I’ve created and scrapped several videos, started blogs and never published to them (hi!), and had countless ideas for side projects that I’ve started and quit. I saw myself as a quitter, someone who couldn’t follow through. And perhaps there is truth to that. But as I try to be more gracious with myself and learn from others, I’m seeing now that the reason for my lack of output wasn’t just lack of motivation (if that at all). It was my own fear. Fear of putting something out there that’s subpar. I’m afraid of being a beginner again.

The inability to start as a beginner is extremely limiting. The most popular content out there is often the most refined and polished version of what a particular creator has been working on for years. Content-survivorship-bias leads us to only see the good stuff. How many people have seen the early, shoddy work of a creator you look up to? During the first 1-2 years of my YouTube career, I made terrible videos. Luckily, almost nobody watched them! I distinctly remember being excited when I reached 100 views. On a video. I’m convinced that nobody remembers my early work, and I find that incredibly refreshing. So here I am, making a blog post that I don’t think anyone will read. And that’s ok. I’m not writing for people, I’m writing for me.

Today, I’m ok with publishing mediocre content (👋). As long as I learn and grow, the next thing I create will be better. But if I wait until I can create this finely tuned gem of a project on my first try, that day will never come.

Next up:
I haven’t read them yet, but The War of Art & Paul Graham’s essay Early Work seem like good next places to go.