Entrepreneur grows company over 730% in just a year

A few years ago Courtney Schomburg, 37, took a look at her life and decided the life she had built in St. Louis with her family wasn’t part of her future. 

In partnership with her mom, Schomburg owned and ran INhance IT Staging Home for over 13 years. It became a multimillion-dollar business. They decided to sell it to an employee after creating vision boards one night and everyone in the family had living at the beach as part of their vision. While it was a tough decision, it was the right one for them to make, she says. Especially for Schomburg, who had decorating and designing vacation homes as part of her board. 

Growing a business substantially is just something Schomburg does. One standout example: Sales at her vacation rental home management company, Sarasota-based Pink Pineapple Properties, topped out at $30,000 in 2020. In 2021 that figure grew 733.33%, to $250,000. And she’s expecting to double that in 2022. And by adding properties, concierge services and increasing the nightly price of stays, she might just be able to do it.

So what’s Schomburg's secret to owning two successful businesses? Creating a cohesive business plan, having the right people in place and growing at a rate she could handle. 

Pink Pineapple Properties is a one-stop shop for clients. With Schomburg’s real estate license and design background, investors can purchase a home, with Schomburg serving as a broker, and then have it designed and maintained — all by Pink Pineapple. The biggest home sale she's brokered a deal for while working for an investor, so far, was a $1.5 million house on Holmes Beach in Bradenton. This model is particularly lucrative for clients who live out of state but want to invest in the scorching-hot Florida market. 

The strategy to include real estate services stems from a shift of the original business plan. “Since we’ve done that, it’s opened a whole new world,” she says. That’s what contributed to the boom in clients, by creating a specific niche for Schomburg to tackle. She says most real estate agents don’t have design experience while most designers don’t have real estate knowledge. So Schomburg is the best of both worlds. 

In 2019, she and her husband Jon Schomburg, 37, purchased their first Pink Pineapple home while still living in St. Louis, to get the business going. Then the pandemic took hold in 2020. With it being a relatively new company, Schomburg says they had to roll with the punches. “We lost every booking I had worked so hard for,” she says.

She instead focused her attention on the one vacation home they did have, and looked for mid-term renters rather than short term. 

Then, finally, on the other side of the pandemic, people started to venture out a bit more. In less than a year, Pink Pineapple surged from one to 12 properties. 

How does one handle that kind of growth? “Day by day,” Schomburg quips. 

But really, the husband-wife duo set up back-end systems to help automate some of the processes. Now, Jon does most of the back-end tasks while Courtney is able to focus on the design and maintenance of each property. “We make a great team,” she says. 

The Pink Pineapple team itself has grown to four employees. That includes the husband-wife duo, an onsite handyman and an assistant. Courtney's hopeful the firm can hire four more, for a total of eight employees by the end of the year. 

Schomburg, facing a classic entrepreneurial challenge, is especially focused on finding someone who can replace her so she can focus on growing the business, by finding more investors and ensuring the Pink Pineapple standard of comfort meets high-end design. 

The best experience she’s had with the company was with a vacation home named the Hollywood House: the homeowners told her to do whatever she wanted, as long as she included some color. 

“It turned out fabulous,” she says. “That was one of the first times I was able to spread my wings and show my talent.” 

Of course, now that she’s proven herself, most of the clients let her have free range with the design. 

“You know you’re at a Pink Pineapple house because of how comfortable you are,” she says. The goal is to make sure guests are comfortable with high-end furnishings. Each guest stay is complete with a handwritten ‘welcome’ note, hand-painted sand bottles and a signature pink pineapple. 

One of the more important details Schomburg includes is the Airbnb Superhost status she earned. At first, it wasn’t that difficult because she was only managing a single property. “Now that we own 12 properties, it’s a lot harder to keep the Superhost status,” she says. 

And it’s liable to get a whole lot more difficult with the company’s future plans. Schomburg hopes to  add 10 more properties to the portfolio. That's one reason why the future for Pink Pineapple looks bright, Schomburg says. “There are so many investors who want to own a piece of paradise.”