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...

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 A...

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...

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 p...

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, s...

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,...

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...

If you've ever answered a guest message at the dinner table… in the middle of a family moment… or felt like you're "on" 24/7 in your hosting business… this episode is for you. In this episode, I'm joined again by Marissa Grover, and we're getting really honest about what it actually looks like to grow a co-hosting or property management business without the right support in place. We talk about th...

Peak season is here, and I know a lot of you are gearing up the same way you always have… watching your calendar, adjusting pricing, and hoping the algorithm works in your favor. But in this episode of Branded & Booked, I'm challenging that entire approach. Because the biggest shift you can make right now isn't tactical, it's foundational. You're not just managing listings. You're building a busin...

A hot tub is not your strategy. Neither is a game room. Or a pickleball court. Or checking every box on Airbnb. In this episode of Branded & Booked, I'm calling out one of the biggest mistakes short-term rental owners are making right now: confusing amenities with strategy. Because here's the truth… Amenities might help you compete, but they are not what positions your brand. And if your entire ma...

Want more direct bookings… fast? Not from chasing trends. Not from posting more on Instagram. But from leveraging what you already have. In this episode of Branded & Booked , Steph breaks down the number one strategy that will drive direct bookings in the next 30 days: email marketing. And before you roll your eyes… this isn't about sending a "newsletter." This is about building a system that capt...

$100K in bookings in the first 60 days. Not from luck. Not from "just listing it on Airbnb." But from building something intentionally different. In this episode of  Branded and Booked , Steph sits down with  Yash Bhatt  to break down what happens when you approach your short-term rental like a hospitality brand instead of just an investment. After launching their property,  Altitude 22 , in Decem...

Influencer marketing is one of the most polarizing topics in the short-term rental industry. Some hosts swear by it. Others say it's a complete waste of time. In this episode, I'm sharing what influencer marketing has actually looked like for our clients... and the results it's produced when it's done strategically. We're talking about a boutique hotel campaign that generated a  3.7x ROI , and ano...

What happens when you take an underperforming boutique hotel… and completely reimagine it? In this episode, I'm joined by former client Andrés Pérez, co-owner of The Iceberg Tahoe, and we're breaking down the story behind transforming what was once the Avalon Lodge in South Lake Tahoe. Andres spent nearly a decade working at Google before transitioning into real estate investing. Like many investo...

You don't have a marketing problem. You have a branding problem. I know that might sound bold, but after dozens of strategy calls with short-term rental owners and boutique hotel founders, I can tell you this with confidence: most marketing issues are actually brand clarity issues. As we head into peak season, so many of you are thinking about ads, influencers, social posts, email campaigns, SEO....

Colin and I just spent two nights at Bolt Farm Treehouse and I'll be honest… I can't turn the hospitality side of my brain off. If you're in the short-term rental or boutique hotel world, you already know their story. It's talked about a lot. But this episode isn't about the hype. It's about what it actually feels like to check in as a guest at a high-end brand everyone admires. What surprised me....

Let's talk about something that feels personal… but is actually wildly strategic. Naming your short-term rental or micro resort sounds fun (and it is!), but more importantly... it's positioning. It's perception. It's your first marketing asset. And I see so many owners starting with the name before they've ever gotten clear on their guest, their brand messaging, or the experience they're actually...

I need you to hear this story. A stay-at-home mom with a traveling husband hit a breaking point with suburban life and said, "If I'm doing this, I might as well be at the beach." Her husband agreed to buying a beach house only if it made financial sense. So she made it work. Ninety days later, they closed on their first short-term rental on the coast of North Carolina. It performed not because she...

The moment a guest opens your door, you're no longer just a real estate investor, you're running a hospitality business.   In this episode, I'm sitting down with my friend Katie to talk about something a lot of hosts say they care about, but don't always know how to execute: true hospitality. Katie spent years in global PR and communications for brands like W Hotels, Ritz-Carlton, Le Méridien, and...

In this episode, I'm talking honestly about wealth, real estate, and the parts of the journey that usually get left out online. The "we went from nothing to millions" stories can make it feel like you're behind, when in reality, a lot of those results were shaped by timing, market conditions, and decisions that can't be duplicated today. Colin and I walk through our actual financial path, from stu...

In this episode, I'm breaking down the real ROI of marketing for boutique hotels, micro resorts, and short-term rental owners, and I'm doing it with actual numbers, not fluffy marketing talk. One of the biggest questions I hear from owners is, "What's my ROI on marketing?" And the truth is, most hospitality businesses are looking at marketing the wrong way. It's not an expense you justify month to...

In this episode, I'm diving into why personal branding in 2026 is no longer optional, especially if you're in boutique hospitality. If you're building short-term rentals, a co-hosting or property management business, a boutique hotel, or a micro resort, your personal brand is becoming one of the biggest drivers of trust, connection, and bookings. We talk through what a personal brand actually is (...

We're kicking off 2026 with a decision that has nothing to do with quarterly goals and everything to do with the kind of life we want to live. In this episode, I'm pulling back the curtain on why our family is planning a full year of camper life — how the idea started, what finally pushed us to commit, and why this felt like a now-or-never moment. I share a glimpse into the planning process, the r...

This final episode of Branded and Booked is a year-end reflection on what I outgrew in 2025 and what I'm intentionally carrying into 2026. I talk about finishing a 12-cabin micro-resort and what it really feels like to build something big when the risk is real and personal. I share lessons from growing The Weber Co. and Hosted by the Webers, including getting clearer on alignment, pricing our expe...

It's done. Cabins on the Cumberland is officially complete. In this episode, I'm sharing what it really took to build a 12-cabin micro resort with an event venue, game center, and year-round amenities — from construction milestones and financing lessons to direct bookings, full buyouts, and what's next. We talk through: How the build unfolded over 2.5 years What I'd do differently with underwritin...