How a Six-Figure Side Hustle Inspired my Pandemic Career Change

I am a "Wayfarian". After 16 wonderful years with IBM, I've decided to start a new adventure. Let me backup.

It was summer 2019 when a knock on the door of my childhood home in Helena, Montana caused my parents to sell their home of 28 years to a young family. My parents were both retired from the Montana state government and had been commuting multiple times a month from Helena to Bozeman to help out my brother and sister with their small children. So when they were left without a home, I thought it'd be the perfect time to invest in some real estate in Bozeman to get them closer to their six grandchildren, allowing them the freedom to spend summers in Florida, while I'd try my hand at real estate investing. A new duplex came on the market, one side a 4-bedroom, the other side a 1-bedroom. Both with full kitchens, baths, and garage space - critical for Montana winters. It was outside my price range for the investment, but zoned for vacation rentals -- which is rare in Bozeman! My logic was that the income would help offset the larger than expected mortgage. Plus Bozeman was booming as the fastest growing micropolitan city in the United States. We closed in October.

A few short months later, the COVID-19 Pandemic crippled the world. My family was forced to redefine what life was like. My husband, a molecular scientist, took on most of the distance learning responsibilities as his lab was shut down. Our kids, two in pre-K and two in 1st grade, learned by watching a computer screen. It was hard. For me, I had always worked remotely, so I was used to the "Zoom fatigue". However, I wasn't used to kids busting into my office telling on their siblings or proudly showing off something important to them... and the heartbreak of shooing them away. We knew this new lifestyle wasn't sustainable but we continued for a couple months until we reached our breaking point. With no end in sight and Baltimore public schools announcing remote learning for the remainder of the school year, we packed our Honda Odyssey and drove 48 straight hours to my parents in Bozeman.

We lived as a multi-generational family, the eight of us, in that 4-bedroom duplex. Four adults made the distance learning more reasonable, and the kids got the attention they had been craving. Next door a new, nearly identical duplex was being built by the same builders. It was August 2020, and our duplex was doing alright financially. Despite the pandemic, we had renters. Others just like us, escaping the pandemic and taking advantage of their new found ability to work remotely around the world. We decided to grow our business and hopefully spread out our family across the two properties, giving everyone a bit more space. Our offer was accepted and we closed right before Christmas last year.

Now, if you recall, we drove to Montana with a frantically packed minivan, four kids, and two dachshunds. This meant we had to start over furnishing our new home. Scratch that - We GOT to start over! I loved the freedom of a blank slate, designing a space knowing that it was for others who were experiencing the beauty of Montana and making unforgettable memories -- how could I make it special for guests through design and personal touches. Five-star review after five-star review we knew we were onto something. We've now broken the six-figure mark for 2021 (screen shot is only Airbnb)!

There is more than meets the eye when it comes to running a successful vacation rental. It's a data optimization challenge that was satisfying to tackle. Below you'll find a few of my best practices if you're thinking about starting a vacation rental side hustle, but I'd love to hear in the comments from other hosts on what's worked for them or anything I may have missed.

1. List on multiple platforms

When we first started our vacation rental business I only listed on Airbnb. I figured most people looked on Airbnb and it was a duplication of efforts to cross list and manage on other sites. Boy was I wrong! As soon as I listed on VRBO, my booking rates soared. There are different audiences across the two services depending on which region of the country and the world you are in. I wanted to attract both the parents of Montana State University students as well as the younger crowd exploring the world. For Bozeman, I also noticed VRBO had an appetite for a higher price point. There is a site called AirDNA where you can see stats on different active short term rentals based on a zip code. As you can see from this screenshot of Bozeman, MT most rentals in my area are only on Airbnb (49%) vs. VRBO (21%) vs. both (30%). The lower inventory on VRBO could account for why my booking rates scaled on cross listing.

2. Automate Management

Early on with our vacation rental business, my mom did all of the cleaning flips between renters. She painstakingly spent hours perfecting the cleanliness of our units. As much as I valued her help, I also wanted her to enjoy her retirement. I had a business idea. What if using the vacation rental calendars we could automate cleaning jobs for local cleaners? When I was searching for competitors, I found Turnoverbnb.com. I decided to try it out and it was exactly what I wanted. Completely hands-off, it streamlines organizing cleaners between renters and payouts. Best tool I found!

When we first started listing our spaces, we listed low in hopes of getting some fast five star reviews. The price point resulted in guests who did not respect our property, there were multiple beer stains left on the furniture. I quickly learned that pricing high attracted more of the clientele we desired. But choosing a price point has always been a guessing game. I've recently been trying out Pricelabs to automate pricing. It's hard to keep track of all of the local events, especially being in a college town. Pricelabs uses demand in areas to help with dynamic pricing. The builder of our duplexes, who also runs some vacation rentals in Bozeman, shared a trick that if you "touch" the listing description it'll promote your listing in searches. Sure enough when I made a change, I'd notice a booking shortly after. Maybe it was a coincidence, but managing a daily listing change is time consuming. Using a tool like Pricelabs, the system automates a daily sync of price changes which has the same technical effect as a change to the listing.

Use the automated messages within Airbnb and VRBO to make responses to guests quick. I noticed similar questions across guests "Do you have any recommendations for places to eat?" or "How far are you from Yellowstone?". There is also the ability to add variables to personalize with first names and property listing details. I also saved my messages into a Google Doc so I could copy and paste them quickly for my business website or direct text messages to guests as well. You can even splurge and get a full service channel manager that handles communication for you through services like beds24. When it comes to automation of listings it goes without saying that it's critical to sync calendars, which all major vacation rental services provide.

3. Automate the Spaces

My inner nerd has been unleashed on our spaces. We've got an Amazon Echo in every bedroom, smart light bulbs, smart televisions, smart thermostats, smart locks, a Roomba, connected garage doors, and smart blinds - everything is controllable by voice. However, I sometimes regret going all in on the smart devices because technology needs more hand holding. Many of our guests can't figure out how to download the August Smart lock app and connect over bluetooth to unlock the doors. We made sure to pair the locks with a keypad for a low-tech entry point and temporary access codes, but the batteries die. We purchased Alexa controlled Yoolax smart blinds for our modern space, but they need to be charged and are finicky with voice commands. For each IoT device we provide a manual backup like a good old fashion garage door remote.

In general, by not giving out a physical key to our home I feel more comfortable and our guests feel safer. Those guests that figure it out, definitely appreciate the high tech touch. However, I wouldn't recommend it for remotely managed properties.

4. Add personal (and local!) touches

One day, my mom and I were having lunch at a hole in the wall burrito joint when I noticed some local artwork hanging on the walls. It's not a new concept, artists having rotating work hanging across town in hopes to sell a few pieces. I jotted down the name of the artist that grabbed my attention with her unique and quirky Montana style, Alexis Hove. I sent Alexis an email asking if she'd be willing to hang some of her pieces in our spaces. She said yes! With my crafty DIY skills, I created some acrylic signs that served as a living guide for things to do around Bozeman and secured them underneath the artwork on the walls. Each plaque includes a QR codes to buy the art using Venmo and take it right off the wall for guests to bring home.

Another artist, Allison McGree, who went to my high school growing up, also was willing to share her gorgeous mountain landscapes which perfectly compliment that playful style of Alexis. The art is a fun touch that highlights and supports local artists.

I also splurged and bought some Samsung "The Frame" televisions that look like a piece of art hanging on the wall. They allow you to rotate photos as a gallery. Bozeman photographer's Loneman Photography shared many gorgeous Montana digital photos which the TV cycles through to give our space an extra local touch. (Side note: if you do get "The Frame" and want to upload your own photos make sure the ratios are exactly 16:9 or 3840 x 2160 pixels to achieve a full screen effect)

For other personal touches I turned to Etsy. A coat rack with railroad ties, an industrial metal switch for the fireplace, and handmade soap that I wrapped with our business name are just a few of the little things we added for a comforts of home feel - always putting the customer first.

5. Rules

Not all parts of running a vacation rental business have been fun. The hardest parts have been dealing with neighbors and bachelor parties. Be sure to check local rules and go through the proper licensing if you decide to run your own short term rental. I have one neighbor who has harassed my children, submitted false complaints to the city about our short term rental, and told me to my face she was going to "shut [me] down" when I confronted her. I've gotten 24 hour notices from our homeowners association to stop advertising or I'd be fined $100 a day followed by them directly taking money out of my checking account. Luckily, within a couple weeks they did refund me after investigating the issue. But it was stressful.

On the other hand our renters haven't always been ideal. On two separate occasions we had bachelor parties where drunk men have tried to open a neighbors house (all the homes in our neighborhood look the same, but still!) in the middle of the night. We've had broken dishes, visits by the police, upset renters when they realized we only offered streaming services vs. full cable, and bad reviews because we didn't have cooking spray. We've gotten better at proactively warning larger groups that we're in a residential neighborhood and reinforcing how we'd like them to treat our spaces through past guest horror stories. Many hosts add extra insurance policies from companies such as Proper specifically targeted at issues related with running a short term rental business. Being a host is not for the faint of heart - you'll need to be able to take the glowing reviews with the critical feedback and decide for yourself whether you really need to "add a coffee table" or whether or not "the bedroom really needs a huge flat screen television".

At Wayfair, we are a community of innovators, risk-takers, and trailblazers who celebrate our differences, and know that our unique perspectives make us stronger, smarter, and well-positioned for success.

6. Design

Throughout this process is when I really fell in love with Wayfair. They had everything I needed for the interior design of our vacation rentals and the customer service was second to none. Buying furniture online is intimidating, but during a pandemic, we opted to avoid unnecessary trips to the store before the vaccines were available for our children and their grandparents. Wayfair was sympathetic when something arrived with missing pieces or a quality issue and they made the process of visualizing how a piece will complete your intended look easy. Amateur cellphone pictures of actual products in someone's home are way more impactful than professional photos. I was impressed with their search results and found the contextual recommendations felt relevant in my inbox. There is an art to e-commerce and it's an incredible big data and machine learning challenge to perfect personalization.

I was intrigued and drawn to them, not only as a user and their target persona but as an innovator, product executive, and engineer.

I am a Wayfarian

“You have brains in your head. You have feet in your shoes. You can steer yourself any direction you choose. You're on your own. And you know what you know. And YOU are the one who'll decide where to go...”

― Dr. Seuss, Oh, the Places You'll Go!

Now, don't get me wrong, my mortgages are high so my PTI is far from six-figures. I won't be leaving the day job any time soon, but with a 15 year mortgage, I'm hoping to supplement the cost of sending four kiddos to college someday. But I was inspired! With so much room for technical innovations in the home space -- for me the decision to join Wayfair was easy, marrying my creative and technical side.

You've heard the stories of the Great Resignation. Mid-life crisis?!? Nah, I believe the pandemic has taken us all back to the basics, opened our eyes to what matters most in life, and is inspiring all of us to take happiness risks.