
12 minute read
Keys To The Kingdom
HEATHER PLAMPIN NEARLY LOST IT ALL … THEN HIT THE GROUND RUNNING WITH A SHORT-TERM RENTALS BUSINESS THAT TODAY MANAGES A PORTFOLIO OF 80 PROPERTIES AND TURNS OVER UPWARDS OF $16 MILLION.
HER SECRET? A BIT OF LUCK, PLENTY OF PERSISTENCE, AND A WHOLE LOT OF HOUSE CLEANING.
TWO decades ago, Florida entrepreneur Heather Plampin had a flourishing home renovation company. Then came the 2008 housing crisis, and almost overnight her Sarasota business collapsed. “I found myself reeling from the effects of the recession on both a professional and personal level,” she says. “Homeowners and contractors were unable to pay the debts to me for jobs completed. I was holding a large portfolio of homes that were intended to be ‘flipped’, but investors and homebuyers were falling off left and right. It seemed as if overnight I ran out of funds and credit to support my business and my livelihood. I found myself broke, going through a divorce, and trying desperately to save my own home.”
Plampin found whatever jobs she could at the time, which were menial in comparison to her earnings as a business owner. She was unable to make mortgage payments and slowly went into foreclosure. Eventually the bank asked her to no longer send partial payments as they would not accept them. “I had never endured such a process or the emotional turmoil that followed. I was forced to hire an attorney and file for Chapter 13 bankruptcy and to protect my home under the Homestead Act,” she says.
At that time, the mortgage industry was completely backed up, as were the courts. Delays in cases were so prevalent banks were paying owners to stay in their homes and to maintain the grounds and pools. “Even my own foreclosure case was dismissed because the defense attorney for the bank that owned my loan went bankrupt,” says Plampin. “My foreclosure case was later renewed by the bank through another attorney.”

Sarasota began looking like a ghost town. Friends and colleagues were abandoning their homes and moving up north with family. “My father, Roger Van Wie – who was also in the real estate business and greatly affected by the housing crisis – lost everything, including his own marriage, all the while battling throat cancer. He began to run out of money not soon after me, and desperate to find a means to afford the only asset he had left, his primary residence on Siesta Key, he began to explore the notion of vacation rentals, a seemingly up-and-coming lucrative rental market that allowed for outsized revenue in comparison to long-term rentals.”
After speaking with the one and only vacation rental management company on the Key, he found himself turned away for not having a pool. “We thought how strange it was to be shunned for not having a pool!” says Plampin. “He decided that if no company would be willing to take on his home for the lack of one amenity, then he would simply do it himself. My father is a highly analytical, research junkie who loves a good challenge.” He decided he would place his home on the one-and-only vacation rental listing site at the time, VRBO, a precursor to AirBnB. “Roger hosted his first guest in 2009. The listing was a huge success, and he began generating good income to pay the bills.”
Plampin was still working odds and ends jobs, but started helping him on the side. “I would clean the homes for the guest arrivals, meet the guests in person and show them the nuances of the home. My father and I together would go over our hospitality strategy to ensure guests would rebook with us.” In her own state of personal despair, she found those moments brought her great joy. “I found myself spending more and more time helping my father with the business infrastructure. He had an amazing vision that I knew I could implement and build into existence. He wanted to not only help himself, but other neighbors who also wanted to salvage their homes.” Ultimately, he created the business model for The Cottages on the Key, Inc.


The Cottages On The Key
“As homeowners decided to join the portfolio,” says Plampin, “I found myself moving away from my day jobs, and spending more time helping my father. Eventually, we decided it was best I made the leap, and for me to come on board full time. Roger and I were official business partners, with a family owned and operated business located on Siesta Key.” Her personal life also began to look up. “I had a new love interest that was getting serious, and my foreclosure process was taking a turn for the better with the ability to restructure my debt under Chapter 13.”
Father and daughter decided to expand their portfolio of homes to the mainland, where Plampin’s personal home was located. “I wanted to put it on the rental program and see if it would rent. I placed it on VRBO at a very high rate, hoping to give me some time to find a place to live with my new beau in the interim. I will never forget I put my home on the market in August, and it was immediately booked for September, a shocking rental to receive for Florida’s market as a new listing! That’s when it got real.”
Plampin found a beautiful three-bedroom home just down the street, and all three moved in. “It was a crazy time – me, my boyfriend and my father, living together with all our pets. It was how we supported each other through the rough times. We were able to save so much money in doing so. At this point, my home was successfully rented as a vacation home, my Chapter 13 foreclosure was approved, and I had five years to pay off all of my debts.”
The Cottages on the Key began expanding at an extremely fast pace… now guests who were coming into town were seeking investment opportunities in real estate, taking advantage of the low buy in entry points, and creating second and third homes under the newest vacation travel trend – a vacation rental home, managed by professional rental managers to generate outsized revenue for their personal retirement plan. It was a pure success that has boasted over 25% revenue growth year over year. “And here I sit 15 years later,” says Plampin, “with my private home completely paid off, and my company on track to do $16M in revenue this year. My father recently sold his home on Siesta Key at the peak of the market, and has grown his private retirement portfolio of homes. He is also finally able to enjoy semi-retirement and live healthy and happy with his beloved chihuahua, Mocha!”

All Points North
At 45 years old, Plampin has successfully transformed her initial desperation into a thriving enterprise. Add to that, she has recently embarked on what she believes could become an even larger venture by expanding her model nationwide. After over a decade of cultivating her businesses organically, she emphasizes that her growth mindset for both The Cottages and the new venture, The Compass Collection, is driven not solely by revenue targets, but by a sense of calling.
“I aim for every guest to experience complete happiness in every possible way,” says Plampin. “One thing I was such a stickler for at the very beginning is the level of cleanliness. I myself am a self-proclaimed cleaning fanatic, and when my father started renting his home, I thoroughly enjoyed being responsible for cleaning after a guest’s departure and ensuring it was spectacular for the next guest. I wanted everything to be in pristine condition and in its perfect place. Nothing was missing. I knew from listening to other guest’s previous stories (there were no online reviews back then) that one of the major downfalls our competitors exhibited was lack of cleanliness.”

Guests who stayed with her company shared nightmare stories about their experiences. “You can imagine that staying in someone else’s personal home back then was totally avant garde! So that meant that guests didn’t really expect too much. It was commonplace for guests to bring their own cleaning supplies, sheets, and pillows. Owner’s closets were usually still full of hanging clothes and personal effects could be found in drawers and on shelves. I knew how disheveled this could make a home appear, along with no real industry cleaning standards. So I set out to create those standards for our company.” Soon, the cleaning work grew too large for Plampin to handle on a turnover day (when one guest checks out and another checks in the same day.) “I decided we needed to hire outside cleaning vendors but that I would need to provide them a checklist to ensure they cleaned to the level that I felt represented our company’s standards.”
That simple checklist evolved into a cleaning and inspection system that is still in existence today, and which Plampin calls the “CottageClean” standard. “Now hundreds of our cleaners have been trained in these best practices to ensure we maintain our brand standard every single day. While there were no industry standards, our guests were surprised to come into our homes where there were no personal effects, there was room for their belongings, and the cleaning was verified and checked by inspectors.”
Guests were also quite surprised that they had immediate access to the business owner, and Plampin made sure she didn’t miss a single call. “I would straight out ask them on their first night whether they were satisfied with the level of service or should I send the cleaner back out immediately? They were simply astounded that I was even in the same town as them when I called!” Back then, most owner operators lived in different areas of the world, and were hard to reach. It certainly was not typical to reach a manager that was merely minutes away and ready to drop everything to help guests with an issue.

“And so, the truest form of our reputation was born. We were known for being the vacation rental company that had boots on the ground, and superior cleaning services. It later separated us heavily from other competitors, simply because we hired only the best cleaners and we paid top dollar for their services. They were gold to us and we treated them as such. They deserved it. They were the ambassadors that held the outcome of our guest’s first impressions.”
Recently, Plampin launched The Compass Collection to manage luxury vacation rentals remotely. The company utilizes The Cottages’ refined processes and systems, developed over 15 years, to handle everything for homeowners except on-site maintenance tasks like fixing leaky faucets or broken garage doors. The Compass Collection aims to collaborate with vacation homeowners nationwide, spanning from Park City, Utah, to Nashville, and even to the Hamptons in New York.
The Compass Collection differentiates itself from other vacation rental management companies through its attention to detail and experience. “I think that stems from my desire to help owners achieve their goals,” says Plampin. “The uniqueness with TCC is that while it is a new start up, it is built from the ground up, through its mother company, The Cottages on the Key, with over 15 years of industry experience. As I said before, when I initially started in my endeavors with my father, short-term vacation rental homes were simply an avant-garde travel trend as opposed to the traditional hotel stay.

“When I was building our business from scratch, I didn’t have a ‘manual’ or a book of SOP’s to guide me, and I certainly didn’t have access to the technology that the industry has created today. It simply didn’t exist. But today, those tools and resources are prolific in our now multi-billion dollar industry, having created millions of jobs that never existed before.” Yet it comes with a price and mostly makes these tools cost prohibitive to smaller players with one or two homes, or perhaps a B&B or boutique hotel owner. “I think about that every day and have wondered how I can pay it forward? I was, afterall, an owner in need of help myself, floundering between jobs, trying to make ends meet and going through foreclosure and bankruptcy. I was a good person, just going through a rough time with everyone else. How much better could I have done with access to such great resources had they existed? So why should I not provide that same level of service to others in need now?”
“We essentially have grown to a size where we feel that we should share our resources, knowledge and commitment to hospitality to like minded individuals… and individuals is the key word here. The sales pitch for The Compass Collection is that we provide revenue management along with sales and marketing on behalf of the owner so that they can focus on asset preservation and the guest experience. We’ll give you a dedicated team that is specialized to you, and your portfolio, regardless of its size. Let us leverage our growth and our access to technology to help you succeed. There’s no other company out there that will give you access to systems and resources that will empower you, and allow you to control your own destiny. There’s no other company out there that will literally build you the infrastructure you need to manage your assets, and give you the manual you need to play the game and win.”
