Level Up Your Listing Summit 2026 Recap: The Connections, Education, and Mindset Shifts That Made This Year So Impactful

Some events you attend for the education. Others are about networking. And sometimes you go because you have a gut feeling you’re supposed to be there.

The Level Up Your Listing Summit is one of those events. After attending the Level Up Your Listing Summit 2026, I left with new connections, fresh ideas, and a completely different perspective on where the short-term rental industry is heading.

If you’re new here, Level Up Your Listing Summit is a short-term rental conference co-founded by Natalie Palmer and Tatiana Taylor-Tait. The event is designed primarily for women in hospitality, but anyone in the short-term rental space can benefit. Owners, co-hosts, designers, property managers, and hospitality entrepreneurs all attend.

Over the last four years, the event has grown into something really special. One thing I appreciate most is how the organizers listen to feedback and improve the conference each year.

This was my second year attending, and I noticed a difference right away. Last year focused heavily on design. This year shifted toward investing, financing, and long-term business strategy. As someone growing in this industry and exploring what’s next, that change felt incredibly timely.

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Why the Level Up Your Listing Summit 2026 Hit Differently

One of the biggest changes this year was the addition of breakout rooms.

Instead of staying in one room all day, attendees could choose sessions that matched their goals and interests.

Heather and I attended together this year, which made the format even better. When two sessions happened at the same time, we divided and conquered. One of us attended one room while the other went to another. Later we compared notes and shared the highlights.

The educational content also felt stronger and more varied this year. Speakers focused on investing, capital raising, creative financing, and portfolio diversification. The conversations went far beyond simply owning short-term rentals.

Natalie Palmer’s own business pivot helped shape the programming. She is transitioning from coaching to raising capital for a brand called For the Love of Upstate. She and the founding team shared insights about capital raising that were especially valuable.

That information felt timely as Heather and I explore the next phase of our real estate investment journey.

Several lenders also attended the summit. One specialized in creative financing for both single-family rentals and larger hospitality projects like boutique hotels or micro-resorts. Stephanie Zenzos also spoke about diversifying investments and building retirement strategies as entrepreneurs.

Overall, the summit felt more mature this year. The topics reflected where many operators are heading next.

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How Level Up Changed My Business Trajectory

If you listened to my recap of Level Up Your Listing 2025, you already know how much that event impacted my business.

Last year I arrived feeling stuck. At the time we owned Kentucky and the Commonwealth. I was also co-hosting my mother-in-law’s property, The Homestead at Cunningham Creek in Virginia. Emotionally, I felt drained. I honestly thought we might sell Kentucky before the end of the year.

I bought my ticket only a few weeks before the summit. It was a last-minute decision.

I saw an Instagram ad and told Caleb, “I think I need to be in this room.” He supported the idea immediately.

At the time, I didn’t know anyone attending. I hadn’t followed Natalie or Tatiana before. Still, something told me I needed to go.

That one decision changed everything.

During the summit, I met an incredible group of women. One of those women was Heather. We stayed connected throughout the year and kept each other accountable. Our friendship grew quickly.

By the end of 2025, Heather helped me underwrite Luna. This year we attended Level Up together.

Moments like that remind me what can happen when you get in the right room.

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The Community Is Still the Best Part

The education at Level Up is excellent. Still, the community remains the most powerful part of the event.

Speakers deliver incredible insights. The content is extremely valuable. Yet the relationships built in the room often matter even more.

This year I reconnected with people I met last year. I also met several collaborators in person for the first time.

Those connections made the experience even more meaningful.

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Catching Up with Matt Sanderson from STRIQ

One of those connections was Matt Sanderson, co-founder of STRIQ.

If you haven’t heard of it before, STRIQ is an investing tool for short-term rental buyers. The easiest way to explain it is that it functions similarly to Zillow, but specifically for STR investments.

The platform pulls listings from MLS feeds and evaluates their potential as short-term rentals. It compares data from similar properties and estimates performance.

Listings appear in different colors. Red signals a weak investment. Yellow suggests further review. Green indicates a strong opportunity.

That is the simplified explanation, but it shows how powerful the tool can be.

Matt and his wife returned this year as sponsors. It was great catching up and hearing about their next version of the platform. STRIQ 2.0 will include more AI-driven features and deeper analysis tools.

They are clearly building something valuable for investors in this industry.

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Meeting Brianna Amigo in Person

Another highlight was finally meeting Brianna Amigo of Brianna Michele Interiors.

I first discovered Brianna at Level Up last year when she spoke on a design panel. When we purchased Luna, she was already on my shortlist of designers to contact.

We ultimately hired her, and the experience has been incredible.

If you listened to our podcast episode together, you already know how much creativity and intention she brought to Luna. Seeing her in person after months of collaboration felt special.

Brianna returned this year to speak on another design panel. During one audience question, she shared a real-life example of executing a client’s vision. That example happened to be Luna.

That moment felt very full circle.

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Spending Time with a Client in Real Life

Another meaningful part of the summit was spending time with my client Alexis, the owner of Victoria House Sevierville.

We are currently building her direct booking website and managing social media for the property. Meeting in person allowed me to understand the story behind the brand even better.

Victoria House Sevierville is an incredible project. Alexis’s family has owned the home for over one hundred years. Multiple generations lived there over time. At one point it operated as a boarding house.

Today Alexis is restoring the property and transforming it into a boutique hospitality experience. The home now includes five themed suites, each inspired by family history or Tennessee culture.

Every conversation with Alexis reveals another layer of the brand story. Hearing those details in person helped me understand the vision much more deeply.

As a brand strategist, those moments matter.

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One of the Most Memorable Presentations: AI in Hospitality

One session completely captured the room’s attention: Brian Hatcher’s presentation on AI.

Brian, founder of Hatch Capital, attended last year as a guest. This year he returned as a presenter.

During his session he explained how different AI tools can support hospitality businesses. Each platform has unique strengths. Some tools excel at creative work. Others specialize in analysis, automation, or communication.

Brian connected these tools to real operations tasks. AI can support pricing strategy, guest communication, market research, and workflow management.

He planned a live demo showing how AI could analyze an Airbnb listing. The tool would evaluate comps, adjust pricing, and identify opportunities for improvement. Unfortunately the platform temporarily went down during the session.

Even without the demo, the presentation was incredibly impactful.

Many attendees said the session alone made the trip worthwhile.

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How AI Could Change Short-Term Rental Operations

Brian also shared how he is building AI agents that can support short-term rental businesses around the clock.

These tools do not replace owners. Instead, they function as intelligent assistants that help analyze data and automate repetitive tasks.

AI can help monitor market pricing, respond to guest messages, and suggest pricing changes in real time. It can also organize information and generate follow-up communications.

Hearing those possibilities was fascinating.

I have already experienced how dynamic pricing tools improve performance. Before attending Level Up last year, I manually set seasonal rates. Later I adopted PriceLabs and saw major improvements.

Now we are exploring how AI-assisted pricing could take optimization even further.

The technology continues to evolve quickly, and hospitality operators are beginning to adopt it.

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Key Takeaways from Level Up Your Listing Summit 2026

Several other speakers delivered valuable insights throughout the summit.

Federico Zimmerman from RevFactor discussed revenue management strategies. Katie Johnson from STR Law provided guidance on legal compliance and short-term rental regulations. Ben Wolff shared marketing strategies for experiential hospitality properties.

One of Ben’s ideas stood out.

He explained that successful properties build demand long before guests plan a trip. The goal is to reach travelers while they casually scroll social media. A unique property might catch their attention and inspire them to save the listing or send it to a friend.

By the time they plan travel, the property already sits at the top of their mind.

Rob Abasolo also spoke about operations and scaling hospitality businesses. His co-founder Bridget from Funkit Interiors joined the design panel. Their companies combine operational strategy with creative design.

Together they demonstrate how hospitality brands can balance function and aesthetics.

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The Mindset Takeaways I Didn’t Expect

I expected strong education and networking from this summit.

What I did not expect was the mindset work.

Historically, mindset conversations were not something I focused on. Over the last few months, however, I have started exploring personal growth and understanding how I approach work and relationships.

Two ideas from the summit stayed with me.

The first idea was simple.

You can just do things.

One designer shared this perspective during a panel discussion. Her point was that nobody begins as an expert. Every successful professional once started without experience.

If you want to design properties, start designing. If you want to launch a podcast, start recording. If you want to pursue a bigger project, begin before you feel fully qualified.

The second lesson came from Rob Abasolo.

His advice was to “punch a hole in the wall.”

The phrase is both literal and symbolic. When something feels intimidating, the hardest step is the first one. Once you begin, there is no turning back.

Momentum builds naturally from there.

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The Full-Circle Moment I’ll Never Forget

Then came the moment I still can’t quite believe.

Last year, at the end of the summit, I introduced myself to Natalie Palmer.

During that conversation I said something bold.

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

At the time it felt like an out-of-body moment. Still, I said it out loud.

And this year it happened.

I was named a Rising Star in the hospitality industry at Level Up Your Listing Summit 2026.

The organizers called me on stage and presented an engraved crystal award. I joined three other incredible women who were also recognized for their work over the past year.

The moment felt incredibly humbling.

Much of my work happens quietly behind a computer screen. I spend hours building brands, creating websites, and recording podcast episodes.

Being recognized by a community that shaped my journey meant a lot.

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My Advice If You Want to Be in Rooms Like This

At the end of the Rising Star panel, we were asked to share advice for others.

My answer was simple.

Say it out loud.

Speak the dream out loud. Share the goal. Talk about the project you want to build.

When you say those things publicly, you open the door for collaboration and support. The right people may hear you and step in to help.

That is exactly what happened for me.

I spoke a bold goal out loud last year. Then I kept showing up and doing the work.

Eventually the goal became reality.

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Why You Should Attend the Level Up Your Listing Summit

If I had to summarize this year’s summit in one sentence, it would be this:

A lot can change in a year when you keep showing up.

Level Up Your Listing continues to be one of the most impactful events in the short-term rental industry. The education is valuable, but the relationships and encouragement matter just as much.

If you are building something in hospitality, there is room for you in that room.

And if you see me there next year, come say hi.