Turning a Single Airbnb into an 8-Property Hospitality Brand
Dear Valentine started small and scaled faster than founder Melissa Shelton anticipated — thanks to obsessive financial planning and one major business-plan pivot.
Author Novo
Melissa Shelton had a vision: Build a boutique hospitality company in New Orleans by renovating historic houses, partnering with luxury design brands to outfit the properties like showhouses, and grow a portfolio of unique destinations coveted by guests. In 2020, the concept was just an idea, but six years later, is a fast-growing operation running eight properties across the city, generating more than $1 million in annual revenue.
Shelton, a former executive at a luxury furniture brand, knew a thing or two about design — but scaling a hospitality business was new territory. During the early days of Covid lockdown, Shelton and her husband were living in New York but purchased a property in New Orleans, Shelton’s hometown. She tells Novo how, over four years, she took the business from idea to open, tracking every lesson and pivot along the way.
2020: Take a leap of faith — but have a backup plan
“Whenever I make a major decision I always come up with several backup plans in case something doesn’t go as expected — any real estate investor will tell you, you always need an exit strategy. When we bought the property in 2020, plan A was always to turn it into what it is, but that came with a lot of requirements. Am I going to quit my job? Are we going to move back here? As a backup, we knew it would be very easy to just turn it into a rental property.”
2021: Start generating some money — fast
“Our no. 1 priority was to make the house pay for itself. We painted, updated some fixtures and let it coast on Airbnb until we were certain that we were going to develop it into a larger company, which would require a full renovation. And I wanted that historic renovation to be a part of our story, really integrated into the hospitality element.”
2022: Learn what you don’t know
“I listened meticulously and religiously, every day for at least a year, to the Bigger Pockets podcast about real estate investing. I joined a coaching group with a short-term renting investor, and I built a network of people who were doing work similar to what I was doing, so I had a dial-a-friend support system. When I hit a roadblock, I could at least pick up the phone.”
May 2023: Accept if and when your business plan should evolve
“My plan had always been to buy a property, renovate it, and make it available for rent. We were pitching Toulouse Street Millworks as a partner, wanting them to do all our custom millwork. They loved the concept, and told us they’d just bought another historic property that they were trying to figure out what to do with. Would we want to develop it into a Dear Valentine property, where they were the owner but we operated the company, brand, and guest messaging?
This ended up being our pivot: I’ve since added seven properties to my portfolio without having to put capital toward them. One of our newest properties we just opened, several millions of dollars have been invested, and I have not had to pay for that development cost. This helped us scale quickly while bootstrapped — in just two years we’ve done over a million dollars in revenue with eight properties that are branded and presented to the public as Dear Valentine. It’s not important who owns them. I’d love to build up owned properties someday, but this shows proof of concept.”
June 2023: File the paperwork and make it official
“We were formalizing our relationship with this partner to turn their property into a Dear Valentine property, and we needed to get this off the ground. So Dear Valentine became an LLC, and each project is centered around two parts: development and design consulting; and operations and management.”
Sept. 2023: Perfect your pitch
“We started pitching brands about being a partner in this showhouse and historic renovation program, with help and support from a PR firm. For example, a national brand might donate product in exchange for photography, which can be very expensive for a construction materials company. For smaller brands, we would ask for a discount on products to showcase them in the home, as an experiential opportunity to get the product in the hands of luxury guests who are design-focused.”
Early 2024: Craft a how-to-quit-my-job strategy
“I had an exit strategy from corporate, a living document that I kept. Back in 2021, it started as more of a sanity plan. By summer 2023, it got really granular. I held onto my job for so long because we needed to fund the business. We took on all the marketing and supply investments, and I was using credit card promotions for six months at a time to help cover those costs. As we got closer, it got more granular in financial planning as we prepared for one income to end and another to begin.”
May 2024: Quit!
“There was definitely a desire on both sides to end the relationship at that point. It felt really good, like a natural sunsetting.”
August 2024: Open the doors
“The house we operate for that first investor was the first to open to guests, and we’ve grown from there. Last year we had over 500 reservations, and in May we welcomed 95 guests for Jazz Fest weekend alone.”
