Level Up Your Listing: From Setbacks to Success in Real Estate

This week I am diving into my recent experience at the Level Up Your Listing Summit, an event that brought together powerhouse professionals in the short-term rental and real estate investment space.

I just returned from a four-day trip to Phoenix, Arizona, where I attended this incredible event hosted by Natalie Palmer and Tatianna Taylor-Tait. These two women are industry leaders—one a designer, the other a coach and podcast host—both with successful short-term rental businesses.

Why Level Up Your Listing?

The summit is designed to help short-term rental owners maximize their listings and elevate their businesses. However, the event wasn’t just about short-term rentals; it also featured experts from various areas of real estate investing. If you’re wondering why I attended, let me remind you—I own a short-term rental in Kentucky, co-host another in Virginia, and previously operated one in North Carolina before selling it for a $100K profit.

With six years of experience as an Airbnb Superhost, the conference immediately piqued my interest. Not only was it relevant to my role as a host, but it also aligned with my recent pivot in Brand & Market, where I now focus on branding and marketing strategies for realtors and short-term rental owners. I jumped in, booked my ticket, and prepared for an experience that turned out to be far more impactful than I could have imagined.

Taking the Leap

I discovered the summit only six weeks before attending, though it had been announced nine months prior. Typically, I hesitate with last-minute decisions, but something about this event pulled me in. Without overthinking, I told my husband, “I have to go.” So, I did. I booked my ticket, my flight, and my Airbnb, all on a gut feeling that this was the right move.

From the moment I arrived, I knew I had made the right decision. Walking into the welcome party on the first night, I felt nervous—I didn’t know a single person. But I reminded myself that all I needed was 30 seconds of courage to introduce myself. After that, conversations would flow naturally. And they did.

By the end of the conference, I had a solid group of friends, many of whom I’m now in a group chat with. We’re already sharing property listings, discussing branding strategies, and exchanging real estate insights. The networking alone made the trip worth it, but the summit had so much more to offer.

Embracing Confidence

At the start of the year, I chose confidence as my word of the year. After experiencing setbacks in Kentucky, my belief in myself and my decisions had been shaken. If you want to hear the full story, I cover it in Episode 3 of the podcast. The move to Kentucky didn’t go as planned, and while I tried to frame it as a learning experience, the reality is that it felt like failure.

But attending Level Up Your Listing was my first tangible action toward rebuilding my confidence. I showed up alone, without prior connections, and put myself out there. One of my first conversations was with Sophia from Somerled Designs, a summit sponsor. She was incredibly welcoming, and I’ll never forget her kindness. That moment reinforced that I was exactly where I needed to be.

I had set a goal to introduce myself to Natalie and Tatiana, the event hosts. While I didn’t get the opportunity to speak with Tatiana due to how busy she was, I did manage to introduce myself to Natalie. As the event was winding down and vendors were packing up, I walked up to her and said:

“Hey, my name is Ali. I wanted to introduce myself and thank you for putting on this amazing event. I really resonated with your opening presentation.”

Then, in a bold moment of declaration, I added:

“Mark my words—I will be on your Rising Star panel next year.”

The 2021 or 2022 version of me would never have had the confidence to say something like that. The craziest part? I don’t even have a concrete plan for how I’ll make it happen. But I will make it happen.

Natalie’s response? She immediately took out her phone and asked for my Instagram handle. I’m now on her radar. That moment felt surreal—almost like an out-of-body experience—but I love that I had the confidence to claim my future success.

The Rising Stars Panel

On the third day of the summit, I experienced another defining moment. I hadn’t paid much attention to the schedule beforehand, so I was surprised to see an agenda item called the Rising Stars Panel. Natalie and Tatiana had been closely tracking past attendees’ progress, and this panel was their way of celebrating those who had made significant strides in their businesses. The catch? The panelists had no idea they’d been selected until the moment they were called on stage.

The four panelists had inspiring stories of resilience and growth. And there was still more to learn. The conference wasn’t just about strategy—it was about mindset, resilience, and showing up for yourself.

The Power of Bold Moves and Transformative Lessons

One of the most fascinating stories shared at the event was about a woman who identified a critical gap in the short-term rental market and turned it into a thriving business. She specializes in setting up short-term rentals in just seven days. If a designer has already created the concept and selected the furniture, she steps in to execute the vision—installing every design element and furnishing the space efficiently. The speed and precision of her work are remarkable, and her ability to scale her business threefold in just one year is nothing short of inspiring.

Similarly, another rising star in the industry faced significant challenges while co-hosting properties. Initially working under a real estate brokerage, she quickly realized that the firm was taking a significant portion of her earnings. When she decided to leave, she was met with contractual roadblocks, preventing her from taking clients with her. Undeterred, she rebuilt her business—not just once, but twice—before finally stepping out on her own for good. Now, having rebuilt her business three times over, she stands stronger and more successful than ever.

The Ripple Effect of a Powerful Event

A recurring theme among many attendees was how transformative this event had been for them. Several individuals shared their experiences from previous years, highlighting how they had felt overwhelmed, managing client onboarding and Airbnb messages even while attending. Fast forward to today, and their businesses have grown to the point where they could be fully present at the event, a testament to the effectiveness of the strategies they had learned in past years.

This ripple effect was especially meaningful for the event hosts, Natalie and Tatiana. As someone who has co-founded an event before, I deeply understand the immense effort required to pull something like this off. Having previously hosted an event with 30 women, witnessing an event that successfully brought together 300 attendees was awe-inspiring. The impact of such gatherings extends far beyond the event itself—it influences careers, confidence, and long-term business trajectories.

Learning from the Best: Seth and Tori Bolt

One of the most impactful presentations at the event came from Seth and Tori Bolt, the powerhouse couple behind Bolt Farm. They have built a $32 million business featuring luxury treehouses, mirrored cabins, and high-end glamping experiences in Tennessee. Their journey, however, was far from smooth.

Before establishing their thriving business, they faced a massive setback in Charleston, South Carolina. After investing heavily in luxury treehouses, local regulations changed, making it impossible for them to operate their rentals. As Seth put it:

“I had commercial property that had no commercial value.”

Hearing this struck an emotional chord with me. I nearly teared up in the audience because I, too, have felt the deep frustration of investing time, money, and passion into a project only to have external factors derail it. Up until that moment, I had only seen the success story of Bolt Farm—I had no idea about the struggles that preceded it.

Betting on Yourself: The $1 Million Pre-Sale

Determined to keep their dream alive, Seth and Tori discovered a mountain property in Tennessee for $250,000. But they had already lost so much money in Charleston that they couldn’t secure a bank loan for the purchase.

That’s when Seth decided to take a bold risk.

Before even owning the property, he pre-sold $1 million in reservations in under a month—proving to the bank that the demand was real. His original goal had been $500,000, but they blew past that number, reinforcing the power of believing in their vision and taking strategic action.

The key takeaway? Success is a poor teacher.

This phrase resonated with me and many others at the event. It made me reflect on my own experiences—particularly my time in Kentucky. If everything had gone smoothly there, I might have been overly confident without truly understanding the depth of what it takes to succeed. But failure? Failure teaches you everything.

Embracing the Lessons of Failure

Kentucky taught me a lot, but up until now, I haven’t sat down to fully process those lessons. I often say, “I learned so much in Kentucky,” but could I list out exactly what I learned? I’m not sure.

That’s why, inspired by Seth and Tori’s talk, I’ve decided to take the time to document everything I gained from that experience—beyond just real estate knowledge and zoning laws. I need to recognize how Kentucky shaped me on a personal level. Because that experience changed me. And sometimes, the biggest growth happens in the hardest moments.

One of the most impactful conversations I had was with Tori Bolt. After hearing about her journey and how she regained trust and confidence in herself, I asked her directly how she managed to do it. Her response was simple but powerful: prayer.

She encouraged me to lean into my faith, and it struck a chord. While in Kentucky, during one of the most challenging times in my life, I had already taken steps back toward my faith. When everything seemed to be falling apart, it was the only thing that gave me peace. And yet, hearing Tori’s words made me realize I had only taken a step—I hadn’t fully embraced it. That conversation pushed me to reconsider how I looked at my experience in Kentucky, not just as a lesson in real estate and business but as a personal transformation.

Building a Business from the Ground Up: Isaac French’s Story

Another speaker who left a lasting impression on me was Isaac French, the owner and co-founder of Live Oak Lake, a micro resort in Texas. His story resonated with so many of us in the room because it wasn’t just about success—it was about perseverance.

Live Oak Lake is a stunning property, built on a man-made lake on a five-acre lot outside of Waco. It consists of seven beautifully designed short-term rentals, each scattered around the property. One of its most unique features is a shipping container pool, a design element that immediately caught my attention.

But the journey to bring this vision to life wasn’t easy.

When Isaac started, he was working as a bookkeeper, earning a modest $60,000 a year—not exactly the income that makes banks eager to hand out multimillion-dollar loans. But when he found the perfect piece of land, he knew. He could see the potential, and he was determined to do whatever it took to bring his dream to reality.

He faced rejection after rejection from banks that wouldn’t finance his project. It wasn’t until he secured the support of his family—giving them equity in exchange for co-signing—that he finally obtained the funding he needed. The challenges didn’t stop there. The construction process was filled with setbacks, but Isaac and his team pushed through. Finally, after overcoming every hurdle, Live Oak Lake was complete.

And then, just as they prepared to welcome guests, Airbnb removed them from the platform without explanation.

Turning Setbacks into Strength

Isaac’s story took an unexpected turn, and his experience was a stark reminder that even when you do everything right, external forces can shake your foundation. With Airbnb cutting off his main avenue for bookings, he was faced with a critical decision: panic or pivot.

He chose to pivot.

Instead of relying on Airbnb, he doubled down on marketing his property directly. He invested in high-quality branding, storytelling, and leveraging social media to generate bookings. He built a brand that went beyond just listing on a third-party platform—he created an experience that people sought out.

Hearing this, I couldn’t help but reflect on my own experiences. The setbacks I’ve faced, the plans that didn’t go as expected, and the moments of self-doubt—they’ve all been teaching moments. Success, as Isaac and Seth Bolt both emphasized, is a poor teacher. It’s through the challenges, the pivots, and the resilience that we grow.

Isaac’s story reminded me that we’re never truly stuck. There’s always another way forward if we’re willing to adapt, learn, and trust in our vision.

Relearning to Trust My Intuition

Isaac’s story struck a nerve. Over the last few years, I had transitioned from making bold, instinctual decisions to relying solely on spreadsheets, numbers, and logical strategies. This shift happened after my Kentucky experience, which felt like a failure. I lost confidence in myself and my ability to make the right decisions.

However, Isaac’s journey reminded me of something I had lost: the importance of intuition. Numbers and logic matter, but they shouldn’t override gut feelings and creativity. That realization alone made attending this summit worth it.

The Unexpected Influence of a Book

My journey to rediscovering my confidence took an unexpected turn when I picked up a book called Alchemy. This book, which explores the “dark magic” in branding and business, caught my attention at the summit. Intrigued by its bold title and premise, I decided to buy it along with another book they had been meaning to read, Unreasonable Hospitality.

On the plane ride home, I began reading Alchemy. Contrary to expectations, it was the book that captivated me the most. It presented an idea that sometimes rational, logical decisions don’t always yield the best results. The author provided an example of a charity’s donation campaign, where the most logical envelope (one that promised a tax write-off) had the worst response, while a more aesthetically appealing envelope received the highest donations. This example reinforced the idea that people don’t always make decisions based on logic; emotional and intuitive responses often guide their choices.

Reinforcing the Need for Creativity and Vulnerability

This book, along with the messages shared by the speakers at the summit, reinforced my growing realization: success isn’t always about rigid strategies and numbers. It’s about embracing creativity, intuition, and the willingness to take risks.

Throughout the event, one recurring theme emerged—telling your story. Despite the fear of vulnerability, the entrepreneur recognized the power in sharing their journey, especially the struggles I had faced in Kentucky. While the experience was difficult, I realized that telling my story authentically could help others and bring value to the community.

I acknowledged that, for years, they had been hesitant to share my challenges, opting instead to portray a polished, professional image. But now, I felt a sense of relief in being able to tell my story from a place of confidence and learning, rather than from a place of failure.

Natalie shared her own vulnerability. She discussed how, despite coaching women on short-term rental success and hosting a podcast, she struggled with feeling like a fraud. This resonated deeply with me, as I had experienced similar thoughts and emotions. It was a powerful reminder that even those who seem confident in the public eye can be fighting their own battles behind the scenes.

A Call to Action for Entrepreneurs

Embrace vulnerability, trust your instincts, and not be afraid to share your stories—no matter how messy or imperfect they may seem. Whether you’re navigating the world of short-term rentals, real estate, or any other business venture, remember that setbacks and detours are part of the journey. By trusting yourself, staying open to opportunities, and continuing to learn, you’ll find your path to success.

This journey of self-discovery and entrepreneurial growth is just beginning, and it’s exciting to think about where it will lead. So, mark your calendars for the next Level Up Your Listing Summit and get ready for the next chapter in building your dream brand and business.