We caught up with the brilliant and insightful Caroline Ramos a few weeks ago and have shared our conversation below.
Caroline, thanks for taking the time to share your stories with us today Everyone has crazy stuff happen to them, but often small business owners and creatives, artists and others who are doing something off the beaten path are hit with things (positive or negative) that are so out there, so unpredictable and unexpected. Can you share a crazy story from your journey?
Embarking on the entrepreneurial journey with Host & Keep, a vacation rental management firm based in South Florida, has been an odyssey filled with remarkable highs and some truly unexpected situations. When I founded Host & Keep, my vision was to create a seamless, stress-free experience for both property owners and guests, ensuring that every stay was memorable for the right reasons. The path has been rewarding, a testament to resilience, innovation, and the importance of exceptional customer service. Yet, amidst the success stories and glowing guest reviews, there have been incidents so bizarre they’ve tested our resolve and capabilities in ways I could never have imagined.
One such incident involved a guest, whom we’ll call Anna, who was staying at one of our premium properties. Anna had ventured out to explore the nightlife and ended up meeting a man who claimed to be the owner of the nightclub they were at. He drove a flashy Ferrari and had all the trappings of wealth and success. Charmed and swept up in the moment, Anna invited him back to her vacation rental. The following morning, she awoke to a scene straight out of a nightmare: her belongings, including her passport, were gone, and so was the man. With a flight scheduled for the next day, panic set in. Our team at Host & Keep immediately sprang into action, assisting Anna in filing a police report and liaising with the embassy to ensure she received the necessary documentation to return home safely. This incident underscored the unpredictability of hosting and the critical need for rapid, compassionate responses to guest crises.
Another unforgettable challenge involved a property owner, Mr. Lopez, who was unaware that he had fallen behind on both his mortgage and utility payments. The oversight led to all services being cut off and a notice of delinquency affixed to the front door, all during a guest’s stay. The situation was dire, with the potential to not only disrupt the guest’s experience but also damage our reputation. Understanding the gravity of the situation, our team worked tirelessly to resolve the financial discrepancies. Mr. Lopez, a foreigner and traveling at the time, was relieved to have our support in navigating the complexities of managing his property remotely. We reassured the guest of their safety and ensured that their stay would not be further affected, offering compensation for the inconvenience. This incident highlighted the importance of meticulous financial oversight and the value of having a dedicated property management team to avert potential crises.
These experiences, while challenging, have been instrumental in shaping the ethos of Host & Keep. They’ve taught us the importance of preparedness, the art of crisis management, and the value of empathy. As a CEO, these stories are reminders of the unpredictable nature of the vacation rental industry and the resilience required to navigate it successfully. They’ve reinforced my belief in the importance of building a team that’s not only skilled in property management but also in handling the unforeseen with grace and efficiency. The journey of entrepreneurship is unpredictable, but with each challenge comes the opportunity to learn, grow, and further our mission to provide exceptional experiences for our clients and guests alike.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
As Caroline Ramos, the CEO of Host & Keep, my journey into the vacation rental management industry was born from a blend of passion for hospitality and an entrepreneurial spirit that thrives on creating meaningful experiences. Before founding Host & Keep, I spent years in the corporate hospitality sector, where I honed my skills in customer service, property management, and business strategy. However, I always felt drawn to the idea of building a company that could offer a more personalized, attentive service to both property owners and guests. The leap into entrepreneurship was driven by a desire to fill a gap in the market for high-quality, reliable vacation rental management that prioritized customer satisfaction and property owner peace of mind.
At Host & Keep, we specialize in managing an array of vacation properties, ensuring they are not only well-maintained but also generating optimal revenue for our clients. Our services span from marketing properties on leading rental platforms to handling guest communications, maintenance, and everything in between. What sets us apart is our commitment to creating exceptional guest experiences while maximizing owner returns. We utilize a data-driven approach to pricing and marketing, along with a deep understanding of local tourism trends, to ensure our properties stand out in a crowded market.
The problems we solve for our clients are multifaceted. For property owners, the challenge of managing a vacation rental while juggling personal responsibilities or living abroad can be overwhelming. Host & Keep alleviates this stress by offering a comprehensive management solution that covers every aspect of the rental process. For guests, the challenge lies in finding a rental that meets their expectations in terms of quality, reliability, and service. We bridge this gap by ensuring all our properties are not just accommodations, but destinations that offer memorable experiences.
What I am most proud of is the culture we’ve built at Host & Keep, one that values integrity, excellence, and empathy. These values are reflected in the way we interact with both clients and guests, and in the positive feedback and repeat business we receive. Our ability to navigate unforeseen challenges, such as the incidents I’ve shared, demonstrates our team’s commitment to going above and beyond for our clients.
For potential clients, followers, and fans, I want you to know that Host & Keep is more than just a vacation rental management company. We are your partners in creating unforgettable experiences, whether you’re a property owner looking to maximize your investment or a traveler seeking the perfect getaway. Our dedication to innovation, quality service, and creating lasting memories sets us apart in the industry. With Host & Keep, you’re not just investing in a service; you’re joining a community that values excellence, connection, and memorable experiences above all else.
Can you tell us about a time you’ve had to pivot?
A pivotal moment that stands out in my career—and indeed, the trajectory of the company—occurred during the early stages of the global pandemic in 2020. Like many in the hospitality and vacation rental industry, Host & Keep faced an unprecedented crisis as travel ground to a halt, bookings were canceled en masse, and the future of global tourism became uncertain overnight. This period tested not only our resilience but also our ability to adapt and innovate under pressure.
Pre-pandemic, our business model was heavily reliant on international travelers and short-term bookings, which had served us well up to that point. However, with borders closing and stay-at-home orders in place, it became clear that we needed to rethink our strategy if we were to survive the tumultuous period ahead. The pivot we chose was multifaceted and required a rapid shift in our approach to property management and marketing.
Firstly, we shifted our target market from international travelers to locals seeking safe getaways within their own country or region. We recognized that, while people might not be traveling abroad, the desire for change of scenery and a break from the monotony of lockdown life was stronger than ever. To appeal to this new demographic, we tailored our marketing strategies to highlight the benefits of local vacations, or “staycations,” emphasizing the safety, convenience, and affordability of our properties.
Secondly, we diversified our offerings to include longer-term stays. With more people working remotely and schools moving to online formats, there was a growing demand for rentals that could serve as temporary homes or remote offices. We quickly adapted our properties to cater to these needs, installing high-speed internet, creating dedicated workspaces, and offering flexible booking options to accommodate longer stays.
This pivot was not without its challenges. It required a significant overhaul of our operational procedures, marketing strategies, and customer service approach. We had to negotiate with property owners, many of whom were concerned about the shift away from the traditional vacation rental model. Additionally, implementing rigorous cleaning and safety protocols to meet public health guidelines was paramount to reassuring guests and owners alike.
The result of this pivot was transformative. Not only did we manage to keep our doors open during a time when many in the industry were struggling, but we also discovered new markets and revenue streams that have since become a staple of our business model. This experience taught us the importance of agility in business, the value of listening to and anticipating the needs of our customers, and the power of innovation in the face of adversity.
Reflecting on this period, I am immensely proud of the way our team rallied together to navigate the challenges. It reinforced my belief in the importance of flexibility, creativity, and resilience in both business and life. This pivot was not just a survival tactic; it was a profound learning opportunity that has shaped the way we approach challenges and opportunities at Host & Keep. It’s a testament to the idea that, even in the most difficult of times, there are opportunities to evolve and emerge stronger.
We’d love to hear a story of resilience from your journey.
Certainly. Reflecting on my journey as Caroline Ramos, CEO of Host & Keep, a story that vividly illustrates resilience occurred during the company’s infancy. Launching a vacation rental management firm was filled with excitement and promise, but the path was far from smooth. A particular instance that stands out and tested our resilience involved a severe natural disaster—a hurricane—that hit one of the regions where we managed several properties.
This hurricane was unprecedented in its ferocity, causing widespread destruction across the area. Several of the properties under our management sustained significant damage. Roofs were torn off, windows shattered, and interiors flooded. It was a devastating blow, not just to the physical assets we managed but also to our brand reputation and trust with property owners and guests. The timing couldn’t have been worse; we were still establishing ourselves in the market, and this disaster threatened to undermine all the hard work and progress we had made.
The immediate aftermath was chaotic and stressful. Property owners were understandably distraught, guests had to be relocated or refunded, and the future looked uncertain. The easiest path might have been to retreat, to cut our losses and reconsider the viability of the business. However, retreating was not in our ethos. Instead, we chose to face the challenge head-on, demonstrating the resilience that would come to define Host & Keep.
Our response to this crisis involved several key actions. First, we prioritized open and honest communication with both property owners and guests. We provided regular updates on the situation, outlining the steps we were taking to address the damage and restore operations. Transparency and empathy in our communications helped to maintain trust during this critical time.
Second, we mobilized a rapid response team to assess and repair the damage to properties. This involved not just fixing the physical damage but also ensuring that each property was safe and welcoming for future guests. We worked tirelessly, often in challenging conditions, to bring properties back to their pre-disaster state or better.
Lastly, we learned from the incident and implemented new strategies to mitigate future risks. This included investing in more robust disaster preparedness and recovery plans, enhancing our property inspection processes, and establishing stronger partnerships with local contractors and emergency services.
The resilience we showed in the face of this disaster became a turning point for Host & Keep. Not only did we manage to recover and rebuild, but we also emerged stronger and more prepared for future challenges. This experience reinforced the importance of resilience, adaptability, and leadership in crisis situations. It was a testament to our team’s commitment to our clients and to each other, highlighting that even in the darkest times, perseverance and unity can lead to growth and strengthening of bonds.
This story of resilience has since become a foundational narrative for Host & Keep, embodying our commitment to overcoming obstacles, no matter how daunting. It has shaped our company culture, inspiring a sense of determination and optimism that drives us forward, even in the face of adversity.
Contact Info:
- Website: www.hostandkeep.com
- Instagram: https://www.instagram.com/hostandkeep/
- Facebook: https://www.facebook.com/HOSTANDKEEP
- Linkedin: https://www.linkedin.com/company/host-and-keep-vacation-rental-investments-management/?viewAsMember=true
- Youtube: https://www.youtube.com/@hostandkeep