The year is 1997. Jeff Talmadge sits hunched over the keyboard of a gray desktop computer, waiting for a dial-up connection to come alive. He is inspired, having just attended a seminar in which Bill Gates described the growing digital phenomenon of interactive websites. Typing furiously, Jeff envisions an interactive site that he and his wife, Joan, can use to advertise their summer home to potential tenants. And not just their house, Joan also began to interest other owners. It completes the last line of code, finalizing the domain: weneedvacation.com.
Long before self-booking sites and travel apps existed, WeNeedaVacation.com (WNAV). The rental listings site is the brainchild of the Talmadges, who, when buying a vacation home on Cape Cod, were eager to rent it out in the summer and enjoy it out of season. Jeff saw the potential for a website where renters could see photos, prices, and schedules, as well as certain amenities such as “walk to beach,” “outdoor shower,” and “air conditioning,” and then send simply an email to the owner to express interest. It seems obvious now, but it was a completely new concept back then. “Our main competitor was the classified section of the Boston Globe,” Joan recalled of that time. “When I was calling owners to see if they would be interested in listing on our site, I had to overcome a lot of skepticism.”
Joan and Jeff say they’ve grown their business the way they do most things, deliberately and thoughtfully. A former software engineer, Jeff has maintained the site, adding new listings and features to the site to meet growing demand. A full-time writer and editor, Joan prospected for new clients and tenants whenever she could. She started writing tutorials with tips and tools to share with other owners.
The business eventually grew enough that they needed to hire a few employees to work alongside them in their home office in Wellesley. Bringing in more staff, they opened an office in Cape Town. Today, their team of two is now a team of 14, including their son and COO, Jim Reese. The site hosts nearly 4,000 listings on Cape Cod, Martha’s Vineyard and Nantucket, a handful of which are the original listings from 25 years ago. Jeff and Joan pulled their own property off the site this year alone, having moved full-time to where it all started.
When asked what sets them apart from larger self-booking sites, Joan’s answer is simple: a personal touch. “We are local. We know the Cape and the Islands. We have the expertise to help owners in ways that larger sites can’t,” she explains. “We do a lot of labor, especially with the new owners. We know what it is.
WNAV’s subscription model not only provides digital marketing and advertising services, but also training and consulting, the Talmadges say. They advise owners on how to provide what they believe to be the best possible experience for their guests through one-on-one consultations, webinars and workshops. They say they let owners manage their own listings, but are ready to answer any questions. They advise their landlords to “treat your tenants like you would treat friends who come over for the weekend. This goes a long way towards establishing a positive relationship. In many cases, these families have a week in the summer to take their vacation.
WNAV’s highly tactile business model has become particularly prominent in recent years. They have seen an increase in the number of new registrants renting not a second home but their primary residence. As the cost of living continues to soar, some residents choose to leave their own homes during the summer months to supplement their income. Coincidentally, Joan has seen demand for private home rentals rise steadily since 2020 as COVID sent holidaymakers looking for alternatives. “They felt safer renting a private house rather than staying in hotels. They didn’t have to wait in line or wear a mask. They could invite a closed circle of friends and family, cook at home and enjoy Cape Town’s natural outdoor spaces,” says Joan. “They could have a great vacation without fear. It brings new people into the market.
This increased demand from owners and vacationers keeps WNAV and their business partners very busy. The website connects small businesses to curation services for homeowners: real estate agents, photographers, property managers, cleaners, caterers, car rentals, and more. In a region fueled by hospitality and tourism, dot-coms have become a key part of the economy.
The Talmadges appreciate how special Cape Cod has been for their family and business. Their Orleans home sits along the National Seashore and overlooks Pleasant Bay. They revel in the incredible environment they now enjoy every day since moving. Their daughter and her family have also moved to Cape Town, further clarifying the importance of preserving the natural beauty that surrounds them. “As I focus on what kind of planet my generation will leave to my seven grandchildren, I worry and know I need to do more,” Jeff tells the website.
This passion for preserving the environment led them to create a green initiative in 2019, incorporating real-world practices into their business. Through the initiative, WNAV says they provide guidance for homeowners to implement climate-friendly practices, including energy from renewable sources, eco-friendly cleaning products, energy-efficient appliances energy, electric vehicle chargers and free filtered water for guests (to reduce plastic bottle waste). They’ve added a green flag to the search criteria on their site, encouraging tenants to follow similar green practices and generally broadening awareness of how we can each make positive changes for the climate.
Despite rapid advances in digital marketing and ever-increasing competition, they say WNAV continues to thrive. When asked how they lasted for so long, Joan replied, “We realized the importance of keeping up. You have to evolve, or you fail,” says Joan. “Our son Jim was a computer science student, so he took on the role of bringing our site into the modern age. He helped us realize the changes we needed to make.
Speaking of their particular niche, “We started when the internet was in its infancy and we were in the right place at the right time. Being local, we are fortunate to have extremely knowledgeable and dedicated staff, many of whom are vacation rental owners themselves!
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