We recently connected with Stephen Witt and have shared our conversation below.

Alright, Stephen thanks for taking the time to share your stories and insights with us today. Risk taking is something we’re really interested in and we’d love to hear the story of a risk you’ve taken.

My journey began at the prestigious Old Edwards Inn, the largest Relais & Châteaux resort in the world, nestled in the heart of Highlands, North Carolina. I was given an extraordinary opportunity: to become the face of VIP stays at their exclusive estates, including Fairview House, Hutchinson House, Piermont Cottage, and Terrace on Main. It was a blank canvas—an invitation to create an unforgettable guest experience without much guidance or precedent.

I took on the challenge headfirst, collaborating with the marketing team to design a comprehensive menu of bespoke services. They shared a few initial ideas, like hosting a movie night on the lawn or curating chef experiences. But I envisioned more than just standard amenities. I saw an opportunity to redefine luxury hospitality. I expanded on those concepts, transforming them into immersive, high-end experiences that became the hallmark of VIP stays at Old Edwards.

This all unfolded in the middle of the pandemic, a time when space and privacy became the ultimate luxuries. Highlands, North Carolina, experienced an unprecedented travel boom in 2020, and we were consistently at full occupancy through 2022. My program was thriving, becoming a cornerstone of the estate’s appeal. But then, a major shift occurred. Due to the program’s overwhelming success, Old Edwards decided to pull their internal staff from supporting my initiative. It wasn’t because the program lacked merit; rather, other departments couldn’t spare their employees, who were earning additional income by working with me on their days off.

I was faced with a dilemma. Suddenly, my access to over 700 employees vanished, and my carefully crafted program seemed doomed. I could no longer rely on in-house staff for massages, chef services, or chauffeur experiences. But instead of giving up, I adapted. I began contracting every service externally—licensed massage therapists, private chefs, chauffeurs—each meticulously vetted to uphold the high standards I had set. Where I couldn’t hire, I stepped in myself, handling every other detail to ensure an exceptional guest experience.

I thought it would be the end of the program, but to my surprise, it worked. I had found a way to make it successful independently. That’s when the idea for The Highlands Concierge was born. For nearly three years, I sat on this concept, refining it in my mind, until I finally took the leap and launched my own luxury concierge service.

The Highlands Concierge wasn’t just a business venture; it was the embodiment of everything I had learned about hospitality, creativity, and resilience. It was about delivering more than just services—it was about curating experiences that became cherished memories. That vision, combined with the perseverance to see it through, is what continues to drive The Highlands Concierge today.

I knew that launching The Highlands Concierge would require more than just ambition—I needed a deeper understanding of the local network and a broader experience beyond the insulated world of Old Edwards Inn. To achieve this, I made a strategic move in June 2022 by joining Highlander Mountain House as the Operations Director. My role encompassed overseeing every facet of the hotel’s daily operations, from the front desk and reservations to maintenance and housekeeping. It was the perfect environment to learn the inner workings of a boutique hotel from the ground up.

But just as I was finding my footing, an unexpected challenge was thrown my way. The owner acquired another property—a 14-room boutique hotel in town—right before the July 4th weekend. It came with its own set of hurdles: no housekeeping staff, no laundry facilities, and 100% occupancy due to the post-pandemic travel surge. I suddenly found myself responsible for two hotels, each with unique demands and no existing infrastructure to support them.

It was baptism by fire. In just two weeks, I built laundry and housekeeping departments from scratch, ensuring the new hotel passed all inspections without compromising the high standards of the already-renowned Highlander Mountain House on Main Street. I worked tirelessly, putting in nearly 90 hours per week to cover callouts and maintain exceptional service at both properties.

This period was grueling, but it was also transformative. Managing two bustling hotels, one with a full-service restaurant offering breakfast, lunch, and dinner, felt like earning a master’s degree in hospitality management. It was overwhelming, exhausting, and yet, it prepared me for the next step. After about eight months, I realized that to bring The Highlands Concierge to life, I needed a role that would give me the flexibility and breathing room to launch my own business.

When I decided to leave, I did so with respect and transparency, giving ample notice. The owner pleaded with me to stay, even offering a significant cash advance as an incentive. But my vision for The Highlands Concierge was clear, and I knew I needed to pivot strategically to make it a reality. I chose to work part-time at a local florist on Main Street and as a staging manager for a multimillion-dollar realtor. These roles weren’t full-time and sometimes required very few hours, which meant I began dipping into my savings to fund my business dreams.

By the time I officially launched The Highlands Concierge in May 2023, my bank account was $500 in the red. It was a sink-or-swim moment. I had spent the first six months of the year meticulously crafting my website, ensuring every detail reflected the luxury and bespoke experiences I intended to offer. When I finally went live, I secured my first client just one month later, in June 2023. From that point on, it was like catching lightning in a bottle—new clients were rolling in nearly every two weeks.

I was flying by the seat of my pants, learning how to manage rapid growth on the go. But it was exhilarating. The challenges, the sleepless nights, the financial risks—they were all part of building something that was authentically mine. The Highlands Concierge wasn’t just a business; it was the culmination of every lesson, every hardship, and every dream I had nurtured along the way.

By August 2023, The Highlands Concierge had reached a pivotal milestone—I secured a prestigious client, Big Billy Cabin, a historic log cabin built in 1929 by the renowned Joe Webb. This property became a cornerstone of my portfolio and is still under my management today. At this point, I was overseeing three luxury rental properties scattered across the Highlands-Cashiers Plateau, each meticulously maintained with a perfect record of five-star ratings. Not a single review fell below this standard, a testament to my obsession with housekeeping excellence and attention to detail.

My approach to luxury property management goes beyond aesthetics. While staging is crucial for creating an inviting atmosphere, maintaining that look requires a deep understanding of high-end housekeeping. It’s the most challenging aspect to master in any property management business, but it’s also what sets The Highlands Concierge apart. Every pillow is perfectly fluffed, every room immaculately cleaned, and every amenity thoughtfully curated to enhance the guest experience.

Since I am not a licensed realtor in North Carolina, I can’t technically call myself a property manager. Instead, I identify as a Cabin Manager, providing concierge services not only to the homeowners but also to the guests of these short-term rentals. In many ways, I’m pioneering a new niche in the industry—one where a concierge can serve as a co-host on platforms like Airbnb and VRBO, manage guest communications, and oversee all operational aspects, except the financial transactions, which remain the homeowner’s responsibility.

This innovative approach hasn’t gone unnoticed. Some real estate companies are less than thrilled with my success, but I have no intention of becoming a realtor. My priority is clear: safeguarding my clients’ properties and enhancing the guest experience, not selling homes. This unique focus has allowed me to build a reputation based solely on service excellence, transparency, and unwavering commitment to my clients.

Today, I proudly hold 116 consecutive five-star reviews across Airbnb, VRBO, and Google. It’s surreal to see how far The Highlands Concierge has come, but this success is no accident. I’ve developed a meticulous system to ensure flawless guest experiences, along with a strategic plan to turn around any unexpected issues. This method has proven effective every single time.

Unlike many in the industry, I refuse to rely on automated messaging. Every communication is crafted personally, ensuring each guest feels valued and heard. It’s about building a genuine connection, one message at a time. This dedication is reflected in our company motto: “Above and Beyond for Every Single Interaction.”

The Highlands Concierge is on a mission to redefine luxury travel in Highlands and Cashiers, North Carolina. Our properties surpass the amenities offered by the world’s top resorts, delivering a level of bespoke service and attention to detail that is truly unparalleled. Nothing else compares, and I’m just getting started.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

What Sets Us Apart:
One of the key differentiators of The Highlands Concierge is my innovative marketing strategy, which not only showcases our exclusive properties but also ensures full compliance with North Carolina’s stringent real estate laws. Since I am not a licensed realtor in North Carolina, I navigated the legal landscape with the help of a real estate lawyer to find compliant and creative ways to promote our properties. North Carolina’s real estate regulations are among the most complex in the nation, requiring a nuanced approach to marketing short-term rentals.

To adhere to these laws, I strategically partnered with external marketing firms that use their booking platforms to showcase the properties. This allows me to display the homes without violating any regulations related to property listings, as my services are always attached to any social media post. This strategic partnership not only keeps The Highlands Concierge compliant but also enhances our visibility across multiple platforms, driving more direct bookings.

I have discovered a deep passion and natural talent for marketing and branding. I personally handle every aspect of our digital presence—from website design and social media management to branding and content creation. Each post, reel, and story is crafted with a strategic purpose, highlighting the unique charm and luxury of our properties while reinforcing our brand identity.

I am constantly experimenting with new marketing techniques. For example, my approach to social media reels is inspired by trends in satellite radio—using the latest top-charting songs to enhance engagement and maximize reach. This instinctive trendspotting has already yielded impressive results, with some posts reaching over 18,000 views. People have even asked me if I’ve hired a professional social media team because of the polished, engaging nature of my reels, but it’s all me—every creative idea, late-night edit, and strategic post.

From designing logos for individual properties to curating themed decor and experiences, I handle every detail to ensure a cohesive and luxurious brand identity. I take immense pride in creating visually stunning content that not only captivates potential guests but also tells a story of elegance and exclusivity. My goal is to not just market properties but to create a narrative of luxury living that resonates with discerning travelers.

I am not just following trends—I am setting them. My unique blend of creative marketing and strategic legal compliance sets The Highlands Concierge apart from every other property management or concierge service in the region. By pioneering a new role in the industry as a Cabin Manager, I am demonstrating how concierge services can be innovative, compliant, and exceptionally successful.

As the proprietor and lead Airbnb Concierge of The Highlands Concierge, I wear many hats—from business strategist and marketing guru to customer service expert and creative director. My hands-on approach and personal involvement in every aspect of the business are what make The Highlands Concierge more than just a service—it’s a luxury experience that reflects my vision, passion, and commitment to excellence.

By blending innovative marketing, strategic legal navigation, and unmatched creativity, The Highlands Concierge isn’t just competing in the luxury travel market—we’re redefining it.

Industry and Services:
The Highlands Concierge operates within the luxury hospitality and short-term rental management industry, specializing in high-end concierge services for vacation rentals and second homeowners in Highlands and Cashiers, North Carolina. We provide an all-encompassing suite of services, including:
• Airbnb Concierge: Personalized guest experiences for short-term rentals, including curated local experiences, private chef services, and in-home spa treatments.
• Cabin Management: Comprehensive property care and maintenance for second homeowners, ensuring homes are impeccably maintained and ready for arrival at any time.
• Airbnb Staging: Expertly designed interiors that enhance guest appeal while maintaining the charm and uniqueness of each property.

The Highlands Concierge is redefining luxury travel by pioneering a new industry role: the Cabin Manager. Unlike traditional property managers or realtors, we focus solely on safeguarding our clients’ homes and delivering unparalleled guest experiences. Our commitment to excellence is evident through:
• Bespoke Experiences: We curate unique, high-end experiences that rival the offerings of world-class resorts. From private helicopter tours with exotic car chauffeurs to exclusive in-home spa treatments, our services are meticulously designed to create unforgettable memories.
• Exceptional Attention to Detail: Every property under our care maintains a flawless record of 115 consecutive five-star reviews on Airbnb, VRBO, and Google. This achievement stems from an obsessive commitment to housekeeping excellence and a personalized approach to guest communication.
• Personalized Guest Communication: We don’t use automated messages. Every interaction is customized to ensure guests feel genuinely welcomed and valued, embodying our motto: “Above and Beyond for Every Single Interaction.”
• Exclusive Portfolio and Experiences: We manage a portfolio of historic cabins and luxury cottages, each offering unique, bespoke amenities that exceed the standards of any luxury resort. Our curated experiences, such as chef dinners with custom tablescapes and themed decor, set us apart in the luxury hospitality space.
• Pioneering a New Industry Role: As a Cabin Manager, I bridge the gap between traditional property management and luxury concierge services. This innovative approach allows us to focus entirely on enhancing guest experiences and maintaining property security, without the conflicts of interest associated with real estate sales.

By combining personalized luxury with operational excellence, The Highlands Concierge is not just managing properties—we are curating experiences and setting new standards in the world of luxury travel.

Can you share one of your favorite marketing or sales stories?

Yes, there was a significant marketing risk I faced last spring that tested every aspect of my problem-solving skills and perseverance. It involved a Private Chef experience for eight guests at Big Billy Cabin, meticulously planned months in advance. This was highly unusual since I typically receive requests for Chef experiences with less than 24 hours’ notice, which I genuinely enjoy. It’s one of the aspects that sets The Highlands Concierge apart—our agility and ability to execute luxurious last-minute experiences flawlessly.

But this one was different. I had ample time to plan, which included curating a beautifully themed tablescape to complement the menu. The design was centered around a pink and blue theme, with stunning Versace and Royal Cauldon bone china—blue plates for the gentlemen and pink plates for the ladies. I had envisioned a vibrant, floral tablescape to tie everything together. However, as the event day arrived, everything started to go wrong.

Obstacle 1: The Florist Canceled

On the morning of the event, the florist informed me that they couldn’t provide any flowers. I had to think quickly. With no time to spare, I dashed to a local nursery and improvised by purchasing live plants, choosing lush blooms that could capture the vibrant elegance I had envisioned. I created a unique mix of tropical foliage and pink and blue hydrangeas that perfectly matched the china. The result was stunning—a breathtakingly beautiful and unconventional tablescape that received rave reviews. It was a risk that could have easily fallen flat, but necessity and creativity prevailed.

Obstacle 2: The Chef Never Showed Up

Just when I thought I had conquered the day’s challenges, the unthinkable happened—the Chef never showed up and was already paid with a 50% deposit. I was in shock. My entire business model is built on delivering flawless, luxury experiences, and the thought of canceling wasn’t an option. I had six hours to come up with a solution. Panic set in, but then I remembered that I grew up in a culinary household; my mother was a chef who owned restaurants around the world. Although I had never wanted to pursue cooking professionally, I realized I had the skills and knowledge to pull it off. Reluctantly, I decided to step in as the Chef myself.

With the clock ticking, I raced to the grocery store to buy all the necessary ingredients. In my flustered state, I forgot a few key items, including olive oil and vanilla extract for the homemade Godiva lava cakes that were the highlight of the dessert menu. While the French onion soup was broiling to perfection, I dashed to a nearby restaurant, leaving the server to manage the kitchen alone—a decision I made only because I trusted my instincts and knew exactly how long the soup needed under the broiler.

The server was incredibly nervous, and in a desperate attempt to maintain the illusion of a professional Chef experience, I initially asked him to pretend to be the Chef. But his nerves got the best of him, and I had no choice but to take center stage. The irony wasn’t lost on me—when selling this experience, I had confidently assured the client, “If you see me in the kitchen, there’s a huge problem.” I now realize that I had unintentionally jinxed myself.

Despite every obstacle, the dinner went off without a hitch. The guests never suspected the chaos that had unfolded behind the scenes. In fact, they raved about the food and the beautifully curated tablescape. It was the most nerve-wracking experience of my career, but also the most rewarding.

This event could have been a disaster. If anything had gone wrong, my reputation for delivering flawless luxury experiences would have taken a hit. But instead, it became a testament to The Highlands Concierge’s unwavering commitment to excellence and my personal determination to always exceed expectations, no matter the odds.

This experience taught me that sometimes the biggest risks yield the greatest rewards. It solidified my belief in my ability to adapt and innovate, even under the most challenging circumstances. It also redefined my approach to marketing. I now emphasize our resilience, creativity, and the extraordinary lengths we go to ensure every guest experience is flawless.

This is what sets The Highlands Concierge apart—not just our luxury offerings, but our unrelenting pursuit of perfection, even when the odds are stacked against us.

Any insights you can share with us about how you built up your social media presence?

How I Built My Social Media Presence

When I first launched The Highlands Concierge, I knew that building a strong social media presence was crucial for reaching my target audience of luxury travelers and second homeowners. I began by focusing my efforts on Facebook, where I quickly grew an engaged audience. However, my rapid growth didn’t come without challenges.

Due to North Carolina’s stringent real estate regulations, I faced numerous challenges on Facebook. Competitors or others in the industry began reporting my business page, accusing me of violating rules—even though I meticulously followed the law. To this day, I still face these attacks, but Facebook (Meta) doesn’t disclose who is behind the reports. The situation escalated in 2023 when my personal Facebook account, which I had since 2009 and contained a decade’s worth of photos and memories, was deleted. This was a devastating setback, but it also became a turning point.

The issue was that losing my personal account meant losing control of my business page. I spent over 24 hours nonstop navigating Meta’s complex recovery system to regain access. It was a grueling process, but I learned how to safeguard my social media presence against future disruptions. I also sought legal counsel to ensure I was compliant with North Carolina’s real estate advertising laws. It turns out that I had inadvertently stumbled into a gray area where the line between property management and real estate representation is thin. With the guidance of a real estate attorney, I found compliant ways to market my services while strategically partnering with booking platforms and always including my concierge services in every post.

Once the legal battles were under control, I went back to what I love most—content creation. I focused on showcasing the unique experiences and luxury services The Highlands Concierge offers, creatively integrating my services with stunning property visuals. I didn’t just post photos; I told stories. I highlighted the narratives behind each property, the bespoke experiences, and the meticulous attention to detail that set my brand apart. This approach resonated deeply with my audience, and within the first year, I grew the account to over 500 followers organically on Facebook.

While Facebook was growing steadily, my Instagram presence was initially lacking. It wasn’t until my first Christmas in business that I decided to dive into the world of reels. At first, I used an editing software to craft high-quality videos. I genuinely loved the creative process and quickly realized that reels were a game-changer for engagement. Eventually, I transitioned to using my phone for a more streamlined and spontaneous approach, allowing me to post in real-time.

My Instagram began gaining traction and eventually surpassed Facebook in popularity. People started noticing, even my own family pointed out my natural talent for marketing. They often joked that I should have gone to college for marketing. Honestly, if I could go back, I would pursue a degree in marketing because I genuinely love the strategic and creative process of building a brand’s digital presence.

I realized early on that content creation isn’t just about posting beautiful photos—it’s about crafting a narrative and connecting emotionally with your audience. I developed a strategic approach that involves:
• Themes and Branding: Every post aligns with the luxury and bespoke identity of The Highlands Concierge. From logo designs to color schemes, everything is cohesive and intentional.
• Fast-Paced, Engaging Videos: I create short, fast-paced videos that are visually stimulating and tailored to capture the attention of luxury travelers. This approach keeps my audience engaged and coming back for more.
• Trending Audio and Virality: I draw inspiration from satellite radio, paying attention to trending songs. If a track catches my attention, I incorporate it into my reels, staying ahead of social media trends and maximizing engagement. This has led to several posts going viral, with some reaching over 18,000 views organically.
• Target Audience and Ad Boosting: I am strategic about boosting posts, carefully selecting target audiences that align with my luxury clientele. My goal is to reach a potential viewership of at least 6,000,000, ensuring my content resonates with the right audience.

Advice on Building a Social Media Presence
1. Understand Your Brand and Audience: Know who you are and who you’re trying to reach. Authenticity resonates, and consistency builds trust.
2. Stay Agile and Creative: Don’t be afraid to experiment with new formats or ideas. Social media is constantly evolving—embrace the change.
3. Master the Algorithm: Pay attention to trends, optimize your posting times, and engage with your audience consistently.
4. Never Underestimate Legal Compliance: Especially in regulated industries, ensure you are fully compliant. Seek legal counsel if necessary.
5. Perseverance is Key: There will be setbacks—whether it’s losing accounts or facing industry pushback. Stay resilient, adapt, and keep pushing forward.

Today, my Instagram is thriving, and my unique approach to reels has set a new standard for luxury concierge services on social media. But I’m just getting started. My goal is to set new trends and continue to grow my digital presence, potentially even going viral with the right strategy.

Building The Highlands Concierge’s social media presence wasn’t just about gaining followers—it was about building a community of loyal clients and followers who resonate with my brand’s story and vision. It’s about turning challenges into opportunities and letting creativity lead the way.

Contact Info:

• Website: https://www.thehighlandsconcierge.com
• Instagram: https://www.instagram.com/thehighlandsconcierge
• Facebook: https://www.facebook.com/thehighlandsconcierge.com
• Linkedin: https://www.linkedin.com/in/thehighlandsconcierge
• Other: https://maps.app.goo.gl/9R7d7U8zisNyHqvN7?g_st=com.google.maps.preview.copy

Image Credits

Ashley Lee Photography