EP 244: Building Businesses, Raising Kids & Going on the Road for a Year
Release Date: 05/21/2026
EP 250: How Our Micro-Resort Grew Revenue 76% (And What It Really Took)
Branded & Booked
For the first time, I'm pulling back the curtain on what our first full peak season actually looked like at Cabins on the Cumberland. There are so many conversations online about buying boutique hotels, building micro resorts, and creating passive income, but very few people are willing to talk about the numbers behind the scenes. In this episode, I'm sharing ours. I break down our June and July performance year over year, where our ADR and occupancy landed, how a completed guest experience changed everything, and why branding, revenue management, direct bookings, and thoughtful hospitality...
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EP 249: The Difference Between a Nice Hotel and a Booked-Out One with Courtney Petrovich
Branded & Booked
What separates a hotel that's simply beautiful from one that guests can't stop booking? In this episode, I sit down with hospitality designer Courtney Petrovich, founder of Deanery Designs, to talk about the role design really plays in the success of a hospitality brand. We dive into why boutique hotel design is so much more than selecting furniture and finishes, how thoughtful design can help attract investors before a project is even built, and the operational decisions that can save owners time and money for years to come. We also talk about the shift we're seeing as more short-term rental...
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EP 248: Our First Weeks Living in an RV + A New Way to Bring Your Brand to Life
Branded & Booked
We're officially recording our first podcast episode from the camper, and after more than two weeks on the road, it's safe to say this adventure has already taught us more than we expected. In this episode, I'm sharing an honest behind-the-scenes look at what it's been like transitioning into full-time RV life with our family. From unexpected truck delays and finding a long-term tenant for our home to exploring South Dakota's national parks, navigating tiny living with two little boys, and discovering just how much lifestyle freedom entrepreneurship can create, this episode is a candid update...
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EP 247: How They Reached 70% Direct Bookings (And Why Most Hosts Are Asking the Wrong Question) with Rose Tipka
Branded & Booked
Everyone wants more direct bookings. But what if the question isn't "How do I get more direct bookings?" What if the real question is, "How do I build a business that guests want to book from directly?" In this episode of Branded & Booked, I sit down with Rose Taika, founder of Your Family's Place, a vacation rental company in Ohio's Amish Country that generates roughly 70% of its bookings through its own website. Rose is a homeschooling mom of six, a best-selling author, and a hospitality entrepreneur who has built a portfolio of family-focused vacation rentals by thinking differently...
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EP 246: How 29% of Our Bookings Generated 43% of Our Revenue
Branded & Booked
In this episode of Branded & Booked, I'm pulling back the curtain on the real booking and revenue numbers from May at Cabins on the Cumberland. If you've ever wondered whether investing in direct bookings is actually worth it, this episode provides the proof. I break down exactly where our bookings came from, how much revenue each channel generated, and why direct bookings continue to outperform Airbnb when it comes to profitability. I also share the pricing strategies, marketing tactics, and guest experience considerations that have helped us grow direct bookings into a meaningful part of...
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EP 245: The Hospitality Industry Is About to Split in Two (And Most Hosts Aren’t Ready) with Gil Chan
Branded & Booked
I genuinely think the hospitality industry is entering one of the biggest shifts we’ve seen in years — and the hosts who survive over the next 3–5 years are going to think very differently than the ones who thrived during the Airbnb gold rush. In this episode, I sat down with Gil Chan, founder of Crafted Stays, to talk about where hospitality is headed, how AI is changing the way guests search for stays, and why branding and direct bookings matter more than ever moving forward. We talked about why relying completely on Airbnb is becoming increasingly risky, how AI tools like ChatGPT are...
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EP 244: Building Businesses, Raising Kids & Going on the Road for a Year
Branded & Booked
We’re about 30 days away from leaving for a year-long camper trip with our boys… and honestly? Life feels a little chaotic right now. In this episode of Branded & Booked, I’m sharing a very real behind-the-scenes update on what’s been happening as we prepare to leave “normal life” for a completely different season. From our disastrous first RV test trip to truck issues throwing a wrench into our plans, packing up our house, balancing explosive business growth, and preparing for Collin to leave his six-figure job… there’s been a lot happening all at once. This episode is...
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EP 243: The Legal Mistakes STR Owners Keep Making with Katie Johnson
Branded & Booked
Most short-term rental owners spend all their time thinking about branding, bookings, design, amenities, and guest experience… But almost no one talks about the legal side of this business until something goes wrong. In this episode, I sat down with STR attorney, host, and co-host Katie Johnson to talk about the legal mistakes we see owners and property managers making all the time and honestly, some of these are way more common than they should be. We talk about LLCs, insurance, rental agreements, safety compliance, co-hosting contracts, operating agreements, capital raising, and what...
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EP 242: What Virgin Voyages & Coachella Understand About Influencer Marketing That Most Brands Don’t
Branded & Booked
Influencer marketing is not just about getting pretty content. It’s about creating a moment people want to be part of. In this episode of Branded and Booked, I’m breaking down what boutique hotels, micro resorts, and short-term rental brands can learn from companies like Virgin Voyages, 818, COMFRT, and Colorescience when it comes to using creators in a way that actually drives attention, demand, and revenue. Because the brands doing this well are not treating influencer marketing like an afterthought. They are building entire experiences around it. I’m sharing why Virgin Voyages’...
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EP 141: What No One Is Telling You About AI in Hospitality
Branded & Booked
I feel like everywhere I turn right now, someone is talking about AI…how fast it is, how efficient it is, how it can replace entire roles on your team. And while I do think there’s a place for it (and we’re absolutely exploring that on the operations side of our businesses), I’ve had this growing tension around how it’s being used in marketing… especially in hospitality. Because here’s the reality I can’t ignore: so much content is starting to sound the same. Same captions, same emails, same listing language. And when everything feels templated and mass-produced, we lose the...
info_outlineWe’re about 30 days away from leaving for a year-long camper trip with our boys… and honestly? Life feels a little chaotic right now.
In this episode of Branded & Booked, I’m sharing a very real behind-the-scenes update on what’s been happening as we prepare to leave “normal life” for a completely different season. From our disastrous first RV test trip to truck issues throwing a wrench into our plans, packing up our house, balancing explosive business growth, and preparing for Collin to leave his six-figure job… there’s been a lot happening all at once.
This episode is honest, messy, vulnerable, funny at times, and probably one of the most personal conversations I’ve shared in a while. We talk about entrepreneurship, lifestyle freedom, risk, pressure, intuition, parenting, and what it actually looks like when you start building a life outside the version everyone expects you to live.
Because the truth is… I don’t think entrepreneurship is just about making more money anymore. I think it’s about creating a life you genuinely want to wake up inside of.
If you’ve ever questioned whether you’re building a business… or building a life you actually want to live, this episode is for you.
Follow along on the journey:
Instagram: @theweberco
Personal adventures + camper life: @lifewiththewebers
Work with us: theweberco.com