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Courtney Levy: “Trustworthy Property Management”

Trustworthy Property Management- You do need a team in the area that will work 365 days a year and will go above and beyond in between stay cleanings to help you with repairs, maintenance and be available in case of emergencies. Many people dream of becoming an Airbnb host but don’t know where to start. […]

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Trustworthy Property Management- You do need a team in the area that will work 365 days a year and will go above and beyond in between stay cleanings to help you with repairs, maintenance and be available in case of emergencies.


Many people dream of becoming an Airbnb host but don’t know where to start. In this series called “5 Things You Need To Become A Highly Successful Airbnb Host” we are interviewing successful Airbnb hosts who share lessons from their experience about how to run a very successful Airbnb property. As part of this series I had the pleasure of interviewing Courtney Levy.

A Massachusetts native, Courtney Levy leads a team of Sales Operation managers and analysts at HubSpot. Prior to her role at HubSpot, Courtney spent 10 years holding Corporate Finance positions at General Electric. Courtney has spent the majority of her career relishing in data and analysis, making sound business and financial recommendations, and leading sales planning cycles.

In her evenings and weekends, she has partnered with her husband, Jake, to launch a small but mighty short term rental business that specializes in chic family friendly spaces in New England. Courtney and Jake’s first rental launched in 2019 in North Conway, NH, and has booked at an average of 95% occupancy since their opening with a 4.9 rating on Airbnb. Courtney and Jake expect to close on their second cabin in 2021, and are excited to expand their business to include shoppable rentals, consulting, and design.


Thank you so much for joining us in this interview series. Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”?

I was born and raised in Massachusetts. Like most suburban Mass kids, I ended up at UMASS Amherst for my undergraduate degree. I was a pretty mediocre student in high school, but kicked my learning into high gear in college and ultimately landed a spot in a finance leadership program at General Electric. I spent the first 5 years of my career obsessed with climbing the corporate ladder as fast as I could, until my boyfriend, now husband, and I found out we were expecting a child. I exited the fast lane of my company and spent a few years trying to “make up for it” as a first time mom and career woman, being promoted into management roles to prove that I could do both.

What led you to first start becoming an Airbnb host?

Like I said, I was stuck in a corporate finance job and I didn’t see what other path there was other than fighting to move up to the top. It was almost like a third-life crisis at 30 where I had gotten married, had a kid, but was terrified that the majority of my life was spent with my nose stuck in a spreadsheet. I knew that I had an internal desire to create something. I went into undergraduate business school with a desire to be an entrepreneur, but instead got distracted by the allure of a cushy finance salary. I had hired a wonderful life and business coach who told me to stop waiting and to make the jump. I love interior design and the feeling you can create with spaces. Combining my artistic side with my love of travel led me and my husband down the path of looking at real estate in New England that would make for great short-term rental spaces. We bought our first cabin in North Conway, New Hampshire in early 2019 and started renting it in September of the same year.

Can you share the most interesting story that happened to you since you started this?

I was really determined to make the start up of our AirBnB different from all the rest, so I had come up with the idea to host a design competition for the cabin before we started renting it. I got in touch with local designers in the Boston area and encouraged them to submit a vision board for the NH cabin. The designs were all amazing and I was so lucky to make these new connections in the industry. Instagrammers voted for design and we ultimately implemented it into the space!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

No matter what Shea McGee from Dream Home Makeover says, DON’T PAINT THE WOOD PANELS IN YOUR CABIN WHITE. Seriously, don’t do it. It takes ten coats of paint, thousands of dollars in labor, and you need to upkeep it. I shed many tears and had many disagreements with my husband about the fact that I had to have white walls. The lesson that I learned is that you can design chic spaces without trying to replicate the clean white aesthetic that’s trendy as of late. You just need some ingenuity and a bit of creativity and inspiration. You’ll also save a ton of dough.

What are some of the common mistakes you have seen people make when they first start hosting with Airbnb?

A lot of AirBnB hosts live far away from their rental, and as a result, need to hire locally for the maintenance and upkeep of their space. If you’re thinking about starting, don’t overlook this step. You want to trust the people that may be interacting with your guests and taking care of your property. You also have to make a decision between a local property manager that is self-employed versus a property management company. Both have their advantages and disadvantages and I’ve seen hosts not treat this step with enough care, which will ultimately show up in your reviews, especially around the cleanliness of your space.

What are some of the things that can be done to avoid these errors?

I recommend taking the time to interview, collect references, and evaluate the market cleaning rates and typical house rules. We spent way too much time with our first property manager who ultimately wasn’t the right fit for our space, and when we were looking for our second, we spent a lot more time upfront vetting applicants which paid off tremendously in the long run. We now have a property manager that we love and trust, who has become more of a business partner than an employee.

Can you share with our readers about the innovations that you are bringing to the Airbnb experience? In your opinion, what makes you different from the rest?

More and more travelers are expecting AirBnBs to be hotel quality but with the same value you’d expect from renting a house on that type of platform. When I look at my competition in the area, what’s made us stand out has been our attention to the aesthetics and the feel of the space. We want you to come to our cabin and feel like it’s your second home that you would have designed with inspiration from Joanna Gaines or Shea McGee. As a result, we pay very close attention to every detail, down to the quality of the sheets and beds. We top this off with making sure our photographs on our site are of professional quality, just like a hotel would.

Wonderful. Here is the main question of our discussion. Can you share “5 Things You Need To Become A Highly Successful Airbnb Host”? Please share a story or example for each.

  1. Great Location — First, you need a great location for your guests. There needs to be top things to do in the area. Secondly, you need a location that’s going to be profitable for you. If you have a beach property but it’s in Massachusetts, know that this is only going to rent at premium rates for 12 weeks a year. If you’ve got both skiing and water, then you’ve all of a sudden maximized your occupancy rates.
  2. Trustworthy Property Management- You do need a team in the area that will work 365 days a year and will go above and beyond in between stay cleanings to help you with repairs, maintenance and be available in case of emergencies.
  3. A Great Aesthetic and Professional Photos — This is really what makes your listing stand out. There are a LOT of postings out there on AirBnB and a lot of them feel like they haven’t had much thought put into the space. Even worse, it looks like the photos on the listing were taken with a first generation iPhone. A great design with high quality professional photos makes all the difference in getting your place rented.
  4. Attention to Detail — Guests appreciate the small details that you invest in; quality soaps, shampoos and lotions, cooking supplies, beautiful coffee table books. These are small investments that you need to pay attention to. Reading messages on the app will also help you get to know your guests. They will offer up hints like “anniversary weekend” where you can wow them with a small bottle of champagne.
  5. A Customer First Lens — Not everyone will love your space or appreciate what you’re going for. While you can’t control every situation, you can maintain a customer first focus. If someone is unhappy, acknowledging that you didn’t meet their standards is a great first step in customer service in the travel industry. Creative ways to accommodate them also go a long way, like a free night in the future, or a gift card to a restaurant or coffee shop nearby.

You are a “travel insider”. How would you describe your “perfect vacation experience”?

COVID has forced us to reimagine what a perfect vacation experience is for our family. We used to think that traveling to exotic or faraway places would be our perfect vacation, but we’ve come to realize that what’s just within 2 hours driving from us is worthy of exploration. Our perfect vacation in this new era we live in is to rent an RV, take the dogs, and travel up and down the East Coast. Most recently we visited Acadia in Maine, which after 33 years of being a New England woman, I had never explored. I think the RV lifestyle is going to continue to explode as more people want access to travel in the future.

Can you share with our readers how you’ve used your success to bring goodness to the world?

Gosh, this is a great question and I hope that I truly have brought goodness to the world with this venture. We had our son on the younger side for the average millennial. There was a period where, as a couple, we felt like we had missed some of the more adventurous or experimental times of our mid to late 20s. When we started to become more confident as parents, we got out and traveled again, this time with our son in tow. I’ve noticed that the service and travel industry has opened up a lot more to families since then, and we wanted to be a part of that when we set up our AirBnB. We work hard to make our space a place that families with young children in particular feel is accommodating to their needs. We want them to feel like they are “away” but have all of the same amenities that home has to make traveling with kids comfortable.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

We were very fortunate through COVID to be able to continue paying the mortgage on our second property despite a sudden decline in rental income last March and April. In fact, it was a blessing, because as we became more confined in quarantine, we had a space to escape to a few times that gave us a sense of normalcy. The pandemic has hit employment hard, especially for women and single mothers. There are a lot of families out there that can’t afford a weekend away to escape the daily stressors of the pandemic. I’m hopeful in 2021 we can create a program to give away weekends to families that would otherwise be unable to afford the getaway.

How can our readers further follow you on social media?

Readers can join my modest but strong following of ~300 @courtneymlevy on Instagram. They can also follow my work at courtneylevy.com.

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