What if the next wave of real estate outperformance isn’t driven by location alone — but by experience? In this episode, we sit down with Caden Weatherly, founder of Creator Hospitality, to unpack how immersive, design-forward travel stays are reshaping the investment landscape. From themed micro-resorts to highly curated short-term rentals, Caden shares how creating memorable guest experiences can translate into premium pricing power, stronger occupancy, and compelling investor returns.
We explore the economics behind experiential hospitality, how underwriting differs from traditional multifamily or commercial assets, and what passive investors should evaluate before entering this niche. If you’re curious about where branding, hospitality, and real estate intersect — and how differentiated assets can create both impact and income — this conversation offers a forward-looking perspective on turning unique travel experiences into big returns.
Episode Highlights Here:
Brett
Before we jump into this episode, I want to invite you to join our community to help you become a better steward scale to billions and ultimately give more or all of it away. All I want
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Thank you so much for subscribing. It means the world to me. Welcome to the build it to billions podcast where we got successful entrepreneurs and investors on their journey from millions to billions. We leave the key to scaling and compounding your wealth and life starts every single day with the mindset and practice of stewardship over ownership and applying billionaire biblical principles. Our ultimate goal is to help you scale and compound, compound your wealth and life so you can give more all of it away to help MVPs, the most vulnerable people. My name is Brett Swarts, and every episode, we’re joined by some of the world’s best millionaires, billionaires and entrepreneurs, and they share their secrets, wisdom and insights with us, so we can all compound our wealth and life and make a bigger impact. Hey, I’m sorry about our next guest. He’s out of the Great State of North Carolina. He’s the managing partner of creator hospitality fund, and he leads both the strategic direction investing oversight of the firm. He’s responsible for assembling a team of top tier industry leaders to bring the fund’s vision to life, which is curating an innovative portfolio that fuses creative design with discipline execution. I want you to think like the most amazing cool like Airbnb experiences that you’ve never, maybe seen before, and that’s actually what the topic we’re talking about today, which is next gen of hospitality. Investors, please welcome the show with me. Mr. Caden. Weatherly, Caden, how we doing?
Caden
Doing great. Brett, thanks for having me.
Brett
Absolutely. If our listeners get tonight for the first time, would you give us a little more about your story and your current focus?
Caden
Yeah. So, my story kind of starts off with doing photography and videography right out of high school, getting to travel around a lot with different musicians or athlete tours, and getting just to really immerse myself in the travel industry. Also growing up, I was fortunate enough to travel with my family a lot too. And so, travel has always been like a
key pillar in my life. And interestingly enough, I wasn’t expecting to get into real estate, but when I was a kid in high school, I was constantly drawing out floor plans for houses or just other kind of designs. So, looking back, looking back now, it’s kind of like a funny full circle moment where I get to include travel and design into my career now. So going from travel related content creation and documentary work, then started going into property management, managing a property in Park City, Utah that’s in the top 10% of properties on the platform, not just in Park City. And from there was kind of getting, you know, a little bit more involved in the real estate space and started seeing more and more just the unique experiential properties were the ones that were making the most amount of money. And decided to put together a team of people that are already the experts in this space and have a fund that kind of brings this institutional level into the arena.
Brett
This is so cool, by the way, everyone’s got to go to creator hospitality. Calm. Createdhospitality.com. You’re going to see some of the properties that Caden is in the team have put
together. And it’s, you know, like you need to see it to really experience this. It’s pretty remarkable. I feel like one of these I’m looking at Caden is like the Shire, like, are you taking
me to my hobbit roots here is, that is, I don’t know where this is, at hotel, to give it, bring this to life right away. So, people can start to start to see a vision as they’re listening or
watching this.
Caden
Yeah, absolutely. So, depending on the property that you’ll see listed on the website, some of them are owned by our advisors or the Investment Committee, or by partners that we’re going to be collaborating with. And so, you’ll see a lot of examples of properties that are already like within, let’s say just the portfolio or the experience of the team, not necessarily within the fund. The fund is about to launch. And then there’s additional photos in there that kind of give examples of more context that are not related to us, but kind of some of these examples, like that Shire themed one. The Hobbit house is owned by one of our advisors, Christy Wolf, and she is just one of the legends in the space of hospitality, experiential Airbnb. She goes out and hand builds these. And whether it’s the tree house resort in or, sorry, a tree house and Hawaii or a firehouse or fire lookout teamed Wow, fire lookout tower themed Airbnb and Idaho pirate ship themed Airbnb the hub or the Shire Esque Hobbit home. They’re just she’s just really well-known within the space.
Brett
And so, if you like this little, short clip of the interview I just did, click over here to watch the full interview. And please don’t forget to subscribe. Thanks so much, everybody.
Watch the episode here:
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About Caden Weatherly
Caden Weatherly is a real estate entrepreneur and hospitality investor focused on building high-performing experiential travel properties. As the founder of Creator Hospitality, he specializes in acquiring and developing unique, design-forward stays that blend immersive guest experiences with strong investment fundamentals. His approach centers on identifying emerging travel trends, leveraging short-term rental data, and creating properties that command premium nightly rates through thoughtful branding and storytelling.
With a background rooted in creative entrepreneurship and media, Caden brings a marketing-driven perspective to hospitality real estate — understanding that today’s travelers are seeking memorable, shareable experiences rather than standard accommodations. By combining operational excellence with experiential design, he works to deliver compelling risk-adjusted returns for investors while elevating the guest experience in niche hospitality markets.
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