Building a Data-Driven, Personal, and Community-Centric Rental Business

In this episode of the Hospitable Hosts podcast, we welcome Cathleen Cataldo, Founder of Discovered in Travels. It’s a boutique, family-run vacation rental management and consulting company helping property owners in the Poconos maximize revenue while delivering memorable guest experiences.

In the episode, Cathleen shares how she got into STR management and how she applies her corporate trend-forecasting experience in the fashion and beauty world to the short-term rental industry, helping her stay ahead of the competition. She explains how being a boutique, family-led business allows them to treat each home they manage as their own and provide a personalized experience for both homeowners and guests.      

Press Play now to discover how Cathleen and her mom transformed their passion for travel and hospitality into a full-service property management business and how they use technology to operate more efficiently.

Do you prefer to read the highlights? We’ve got a summary of the key takeaways below.

How Cathleen Got into STR Management

Cathleen says her background is in the beauty and fashion industry, and she spent over a decade working in corporate roles in the heart of Manhattan as a fashion trend forecaster.

Back in 2023, Cathleen’s family decided to build their first short-term rental, so she set out to learn how to manage it.  “And I realized that so much of my trend forecasting experience, I could apply to this industry, and I fell absolutely in love with it. And now it's what I do full-time.”

Cathleen shares how analyzing consumer insight data helps her predict what guests will want before they even ask for it. She was doing this when she worked in the beauty and fashion industry with multi-million-dollar brands that had to decide which products to invest in and create 2 to 5 years in advance.

“I apply the same methodology by studying guest patterns, looking at lifestyle, behavioral, environmental, and economic shifts. I notice those repeat patterns and decipher which ones are here to stay that we can invest in long-term to future-proof our listings and get ahead of the competition,” Cathleen explains.

Importance of Branding

At Discovered in Travels, they approach each vacation rental as a brand. Cathleen emphasizes that branding goes far beyond just a logo and colors. For short-term rentals, it's all about defining your target guest persona, understanding their needs and preferences, and building experiences for them.

“You want to have a pretty logo and colors to make it look professional and polished. But then you need to decide what type of family we want to bring in. Do you want to bring in young millennials, Gen-Z families just getting started, and families with infants? Or are you trying to bring in that multi-generational family with grandparents and parents, and maybe those older grown children in their twenties? The products that you put in the home, how you create the experience, how you decide that home is going to look are very different for those two separate groups of families.”

Why Family-Run Matters

Cathleen points out that having a boutique, family-run company is their biggest selling point when she’s speaking to potential property management clients. It allows them to treat every home like their own. “We are currently managing eight properties, one of which we own as a family, and it just allows us to have more attention to the details,” Cathleen says.

“We're able to problem solve a little bit faster because there aren’t all these different chains of command. We're also able to offer a high-touch experience for the homeowners and the guests that the bigger property management companies simply can't because their focus is systems and scaling, which is awesome, but they don't have the time to focus on the personalization the same way we do. So for us, it's important to build relationships with the guests so that they come back again.”

Using Technology

Cathleen says they use technology to help automate repetitive tasks. She notes that Hospitable has been with them since day one, when they had only one property.

“There were so many different things within Hospitable that just allowed us to scale a little bit faster, even though we are still so small. Like, for example, the rental agreement automation in Hospitable that is something that we recently implemented.” Cathleen says that in many communities, they are required to collect specific information from guests, and Hospitable helps them with that so they don’t have to track down guests who aren't filling it out.  

“Now, it's so nice to have that automated with Hospitable, where if they don't fill it out when booking,there are automated messages a day, three days, and seven days after that get the guests to fill out that information.”