We were lucky to catch up with Lindsey Pleasant recently and have shared our conversation below.

Lindsey, thanks for joining us, excited to have you contributing your stories and insights. Are you happier as a business owner? Do you sometimes think about what it would be like to just have a regular job?

As a business owner, I appreciate the flexibility that allows me to spend more time with my family, but I sometimes miss the structure of a traditional job. Working in hospitality and property management can be challenging because the work is continuous and often goes unrecognized. Balancing work and family life is something I think about often, and while I enjoy the independence of running my own business, I occasionally wonder what it would be like to have a regular job.

The last time this happened was not too long ago when a long-time client did not approve of our price increase, and another client was upset over a very small change to pricing the property. We have been investing more into marketing, improving the guest experience, and fine-tuning our processes to maximize returns for our clients. But in that moment, it felt like those efforts weren’t being recognized. It was frustrating because we know the value we bring and the expertise we offer, yet it felt like some clients didn’t trust the process or see the bigger picture.

I remember sitting at my desk after those conversations, staring at my inbox filled with more questions, more requests, and more fires to put out. It was one of those days where I thought, “Wouldn’t it be nice to have a regular job where I clock in, do my work, and clock out without carrying the weight of every decision?” The pressure of constantly justifying our worth and proving our strategy works can be exhausting. But then I remind myself why we do this—why we push through these tough moments. We’ve built something meaningful, something that delivers real results, and most of our clients do trust us. It’s just hard when a few don’t, and in those moments, it’s easy to question everything.

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

I got into this business during a transitional period in my career. After leaving the mergers and acquisitions and real estate industry, I found myself in between jobs and coming out of a bad work environment. I knew I wanted to work for myself—not just to have the freedom to make my own rules, but because I wanted to be the kind of boss I never had. I had experienced firsthand what it was like to work under leadership that wasn’t supportive, and I believed that being a good boss—one who values and respects their team—would lead to higher employee retention and a stronger business.

Of course, learning how to be that kind of leader didn’t come easily. It was a lot of trial and error. In the beginning, I was too lenient, and unfortunately, some people took advantage of that. But through those challenges, I learned how to set boundaries, build a team that aligns with my vision, and create a work culture rooted in both accountability and support.

Despite the ups and downs, one thing remained constant—I’ve always loved real estate. That passion is what kept me going and ultimately led me to build a business that blends real estate with hospitality and design. Our business focuses on helping property owners turn their homes into successful short-term rentals. We handle everything from marketing, pricing strategy, and guest experience to design improvements that enhance a property’s appeal. We don’t just list a home and hope for the best—we take a hands-on approach to ensure that each property is positioned for success. This includes professional photography, strategic pricing adjustments based on market trends, and high-touch guest communication to maintain excellent reviews and repeat bookings.

One of the biggest challenges we solve for our clients is helping them see the full potential of their property. Many homeowners don’t realize how small changes—like updated furnishings, better linens, or a more thoughtful layout—can significantly impact their revenue. We guide them through this process, making sure their investment is protected while also creating an exceptional experience for guests.

What truly sets us apart from our competitors is that we genuinely care about our guests and their experience. Unlike most property managers who have limited availability or take a more hands-off approach, we are here for our guests almost all hours of the day. Whether it’s a late-night check-in question, a special request, or an urgent issue that needs immediate attention, we prioritize responsiveness and hospitality. We don’t just manage properties—we create experiences, and that level of service is what keeps guests coming back and properties performing at their best. Our hands-on approach ensures that both guests and property owners feel supported, which is something you don’t always find in this industry.

I’m most proud of the fact that we’ve built a business that prioritizes quality over quantity. We’re selective about the properties we take on because we want to maintain a high standard, and we genuinely care about the success of our clients. It’s incredibly rewarding to see a property go from being just another home to becoming a sought-after vacation rental that guests rave about.

For potential clients, I want them to know that we are more than just a management company—we are partners in making their property a success. We bring experience, strategy, and a genuine passion for what we do. If you’re looking for someone who understands not just the numbers but also the nuances of guest experience, design, and long-term investment strategy, we are the right team to work with.

How did you build your audience on social media?

I had a background in marketing before starting this business—I was the Director of Marketing in my previous job, where I helped multiple industries with their marketing strategies. That experience gave me a strong foundation in understanding how to market specific industries because every industry has a different audience, demographic, and platform strategy. When I started this business, I took on all the marketing myself, which allowed me to shape our brand and messaging from the ground up.

One of the biggest challenges was figuring out how to tailor marketing strategies that I had seen work globally to a much smaller, niche market like Round Top. It’s a unique place—small but with a distinct draw for visitors. I had to focus on showcasing not just the properties we managed but also the overall experience of being here. We built our audience by creating credibility online, staying consistent, and, most importantly, developing a reputation that people wanted to follow. It took about four years before we started seeing a real return on our marketing efforts, and over time, we’ve expanded into new avenues we weren’t utilizing before.

For anyone just starting out with social media, my biggest piece of advice is to be persistent. You won’t see results overnight—especially in industries like ours, where relationships matter just as much as online presence. It takes time to build trust, both digitally and in person. A lot of people assume that if they just spend money on ads, they’ll immediately see returns, but it doesn’t work that way. You have to put in the effort, be consistent with your messaging, and genuinely connect with your audience. Over time, those efforts compound, and you’ll start to see the impact of your work.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

There isn’t one single book or resource that shaped my entire management and entrepreneurial philosophy—it’s been more of a collection of experiences, trial and error, and learning from both successes and failures. However, one book that had a profound impact on me is Unreasonable Hospitality by Will Guidara. It completely changed the way I think about guest experience and service. The idea of going above and beyond in unexpected ways—of making people feel truly valued—resonates deeply with how I approach my business. In an industry where personal touches make all the difference, this book reinforced my belief that exceptional hospitality isn’t just about meeting expectations but about exceeding them in ways that create lasting impressions.

Beyond books, one of the most valuable resources for me has been getting involved in hosting groups and attending conferences with property managers from all over the world. There really aren’t many people in Central Texas who understand property management at the level that we do. While there are plenty of people managing Airbnbs, many don’t share the same mindset when it comes to Unreasonable Hospitality—going above and beyond for guests and truly treating it as a professional business. In fact, there are far more people managing short-term rentals casually rather than professionally. Because of that, I had to seek out my resources from out of state, learning from people who operate at a much larger scale. That outside perspective has been invaluable in shaping how we run our business and continue to elevate the guest experience.

At the end of the day, nothing replaces real-world experience, but surrounding yourself with like-minded professionals and continuously learning from the best in the industry has been a game-changer for me. It has allowed me to refine our approach, stay ahead of industry trends, and ensure that we are always providing the highest level of service to both our guests and property owners.

Contact Info:

• Website: https://hostievacationrentals.com/
• Instagram: https://www.instagram.com/hostievacationrentals/
• Facebook: https://www.facebook.com/hostievacationrentals
• Linkedin: https://www.linkedin.com/in/lindsey-pleasant-0697b274/

Image Credits

ellen rene photography