Founded in York, Maine in 1983, Maureen Regan and her daughter Jennifer Thibodeau are leading the way with high quality service for homeowners, guests, and their community.

 

How did you decide to start Seaside Vacation Rentals?

Maureen Regan (MR): I came to York, Maine, in 1981 from NYC where I sold surgical supplies. I was recovering from cancer. I fell in love with the area and felt I needed to make a lifestyle choice, so I took various part-time jobs—one of which was working with the York Harbor Inn and the other with a real estate company that was struggling. I saw a need for a vacation rental company and started my company after leaving the real estate company.

 

Where did the name originate?

MR: The name was originally Regan Real Estate and Rentals. We still have a separate company called Regan Real Estate (RRE).

Jen Thibodeau (JT): As the business began to grow, and we were getting inquiries about rentals for kayaks, party tents, and everything in between, we had a family meeting and decided to make Seaside Vacation Rentals a new company separate from RRE. We have kept the real estate company because it generates business through our guests and homeowners who are looking for their second home or selling.

 

What were some of the early successes and challenges?

MR: The real estate market was really crazy in the early 1980s. It was booming in our area. All the real estate companies in this area had a few rentals but much preferred doing sales. I asked them for their rentals, and they just gave them to me. Of course, they regretted it when the real estate bubble burst in the mid- to late 1980s!

Also, there were two people who did rentals (one from a general store and one from a souvenir gift shop) who both retired and were happy to give me all their rentals! It seems crazy when looking at this today. The challenges were that many of the properties we took on were not well maintained, and everyone who was renting properties was doing it differently. For example, exit cleaning was asked of the guests, but it was never checked. The elderly couple who rented from the general store actually gave people their money back if it rained all week during their vacation stay. Imagine my surprise when the first family came to me expecting that!

 

Maureen, you wrote a fantastic book titled The Rental Game: Winning with a Professional Vacation Rental Team. What motivated you to write the book and what did you learn in the process?

MR: It was a very impulsive decision. I went to a bookstore looking for a book on vacation rentals for a new homeowner, and all I could find was a series of books written by someone who bad-mouthed management companies and said how easy it was to do the renting yourself. I thought this was ridiculous because I knew how hard we all worked and the value we added to the process. So I decided to write the book, The Rental Game: Winning with a Professional Vacation Rental Team. Primarily, I learned that it was a whole lot harder than I thought it would be and took a whole lot more time than originally planned. But I also interviewed and learned a lot more about vacation rental management from meetings with industry leaders—all of whom were incredibly generous with their time and information.

 

Are you looking at writing another book?

MR: Yes, I have started thinking of another book dealing with the history and key people who have changed this industry over the years.

 

When and why did Jen take the leap and join the company?

JT: When my mother started the business, I began working on projects, such as our printed catalogues, booking properties, and cleaning in the summer. When we opened up a position for a reservationist, because I was only interested in helping out from time to time, one of my best friends enthusiastically interviewed and got the job. It wasn’t until years later, after having worked in other industries and for other people, that I decided to return to Seaside full-time (and permanently). I chose to return after having realized that I really did enjoy all those family conversations revolving around Seaside and that the industry itself was so fun, challenging, and rewarding that I wanted to be part of the evolution of vacation rentals—and work with my mother, of course!

 

What differentiates Seaside from your competitors?

MR: Most of our competitors are still real estate companies with a sideline of renting.

JT: There are a few who are doing a lot of rentals but have not kept up with trends, like online booking, 24/7 maintenance, and cleaning services. Also, we are committed to providing the best service possible to our guests and homeowners, resulting in return rental rates of over 60 percent.

 

Since 1983, a lot has changed in the vacation rental industry. How do you work together to address advancements and issues while keeping your core values?

MR: Having two and now three generations working in the business helps us keep up with advancements in technology and keep those old-fashioned customer service ideals. Our multi-generation family mirrors who are guests are, so when Jen’s millennial children talk about the importance of social media or adventure vacationing, we listen. Being a part of VRMA has also helped us tremendously to keep on the cutting edge of what is happening.

We saw early on that doing the right thing paid off in the long run even if it wasn’t always easy. One of the first years we were in business, we had an owner who canceled all his rentals at the beginning of the season. We hustled and found everyone a new place, except for one holdout who didn’t want to move even though our policy was to upgrade every one of those folks. Finally, we found just the right house on the water, which he accepted and cost us a bundle. It was difficult for us, but he and his family came back to rent with us for over twenty years after that.

JT: One of the main reasons we developed a new position within Seaside—homeowner liaison—and beefed up our customer service was a direct result of the implementation of the Internet. As more and more communications moved online, our owners were initially flustered and scared, and guests felt neglected. Even today, we have some homeowners and guests who prefer to be called, rather than emailed, who we send holiday greeting cards to and accept cookies from in the mail.

 

You are heavily involved in the community and in the industry. What motivated you to become so involved, and how has your commitment to the community and the industry benefited your business?

MR: Since the beginning, we have always been involved. I think the motivation probably came from my mom, Annette, who helped with the business in the very beginning. She would bring big pitchers of lemonade to the volunteers at the information center and always attended every chamber event. We still are very involved. Jen is on the board of our regional group, the Maine Beaches Association, which is composed of seven seacoast chambers, and she just stepped down from the presidency of the York chamber. I served on these as well at one point, and I am currently serving as president at the Vacation Rental Management Association (VRMA). The bottom line is that these are our neighbors, colleagues, and friends, and by being involved we are all working together for the betterment of our community and industry.

JT: Also, with our connections, we have more knowledge of what is going on in the area (to share with our guests through our concierge), we get a bird’s-eye view of the state’s marketing plans, we obtain information regarding statistics and trends within our state and nationally, and we make new connections that are infinitely helpful.

MR: And when a potential customer of ours goes to one of those connections looking to rent his or her vacation home or find a weekly rental, we are that customer’s first source of referral. It’s a nice feeling.

 

As we celebrate Mother’s Day, what have you learned from each other and about working with family?

MR: I feel immensely fortunate to be working with my daughter, Jen. We can laugh, enjoy each other’s company, and share a hug when the day is not going so well. I also look forward to Jack and Aidan, my grandchildren, working more and more in the company.

JT: They’ve been coming to work after school for a few hours now that our season is beginning to rev up, and it is wonderful for both Mom and me to witness them being part of this business and the industry too. I have to say that I couldn’t have asked for a better mentor. In all the years of working together, traveling for work together, and pushing each other to be the best we can be—as well as the business—we have cultivated a relationship that we couldn’t have dreamed of.

 

What advice do you have for other companies working closely with family members?

MR: I would say don’t try to force your children into the business or into a particular management slot. Let them find their way and do what they love within the company if they choose to work with you. Don’t expect it always to be perfect. The big downside is that every family gathering is a company board meeting.

JT: It is important for me to have some clarity and comfort with the distinction between my “Seaside” mom and my regular mom. We respect each other’s ideas and knowledge, we give each other space when it’s needed, and most important, we can see each other as valuable and viable business partners. This has created a harmonious relationship at work for us—most all of the time.

 

What trends and opportunities are you seeing in vacation rentals today?

MR: Trends I see are the greater acceptance of the vacationing public to use vacation rental homes, the homogenization of the industry, the buying up of small vacation rental companies by large companies—often with no vacation rental experience—and much more.

Opportunities are also great. I think that those small companies who focus on core values while incorporating newer ideas in travel and still hang on to what makes them unique have a great potential right now to stand out in a business that is becoming increasingly more mainstream and cookie cutter. Trample that cookie cutter, and be proud of what makes your company different and cool!

JT: I see the world expanding. People are traveling more and discovering neighborhoods and exploring towns. They are traveling closer to home or just venturing outside of what they never really considered before in planning a vacation. I see immense growth with the building and buying of properties, specifically catering to this industry. I see the uniqueness of this industry eroding somewhat, but I know that there are many opportunities that are bound to reveal themselves soon—looking forward to it!