EP 141: What No One Is Telling You About AI in Hospitality

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 very thing that actually drives bookings, connection. This episode is me unpacking that in real time. The good, the bad, and honestly… the ugly of what I'm already seeing happen as more people lean on AI without a real strategy behind it. I talk through where I think AI actually makes a lot of sense (like supporting your team, reducing burnout, streamlining backend systems), but also where I think we need to be really careful. Because if your brand isn't clear, if your messaging isn't rooted in a real guest experience, AI is only going to amplify what's already broken. More content isn't the answer. Better, more intentional content is. We also get into what this means for trust. Because at the end of the day, hospitality is human. It's how your guest feels before they book, during their stay, and after they leave. And if your marketing starts to feel robotic, overly polished, or disconnected from reality, you're not just missing bookings… you're eroding trust. That's a much bigger problem. My hope with this episode is that it challenges you a little bit. Not to avoid AI, but to use it differently. As a tool, not the strategy. To double down on your story, your perspective, your brand voice… the things AI can't replicate. Because the brands that are going to win in this next season are the ones that feel real. If you want support building a brand and marketing strategy that actually converts to direct bookings, you can connect with us at theweberco.com. And if you're not already, come hang out with me on Instagram. I'm always sharing more behind the scenes there.

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 the chaos so many hosts are living in… the constant notifications, the pressure to always be available, and the reality that this business is anything but passive when you're doing it alone. Marissa shares her story of scaling to 30 properties while juggling motherhood and nonstop operations, and the moment that changed everything for her… responding to a guest message while in labor. That experience forced her to take a hard look at what she had built and ask, "Is this actually the life I wanted?" From there, we dive into what shifted, how she started building a team, and why hiring earlier would have changed everything. We also break down what it really looks like to hire your first VA… when you're actually ready, what to delegate first, and the different ways you can hire depending on your budget and comfort level. We talk about the mindset shift from seeing team members as an expense to seeing them as an investment, and how the right support can actually increase your income while giving you your time back. Finally, we get into systems… why they feel overwhelming, why most people avoid them, and how they're actually the key to creating the freedom everyone is chasing in this industry. If you've been feeling stretched thin, stuck in the day-to-day, or unsure how to take the next step, this conversation will give you both the perspective and the practical starting points you need. If this episode resonated with you, I'd love to hear from you. Come connect with me on Instagram @theweberco or visit theweberco.com to learn more about how we can support you in building a brand and marketing strategy that actually works for your business. And if you want to connect with Marissa, you can find her on Instagram @marisa.grover, where she shares more about systems, operations, and building a business that supports your life… not the other way around.

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 business. And if your strategy starts and ends with OTAs, you're building it on borrowed land. Inside this episode, I walk through the mindset shift that separates hosts who stay stuck in the cycle of price tweaking and platform dependency from those who actually build something scalable and sustainable. I share what it looks like to step out of obsessing over Airbnb performance and into building a brand, an audience, and a direct booking ecosystem that gives you real control. I also pull back the curtain on what this has looked like at Cabins on the Cumberland, including hitting nearly 50% direct bookings on one cabin and outperforming market ADR before even experiencing a full peak season with the full property complete. Not as a highlight reel, but as proof of what happens when you commit to long-term strategy over short-term wins. You'll start to see why the real risk isn't seasonality or competition, it's building something you don't actually own. And what becomes possible when you shift your focus to branding, marketing, and guest experience in a way that compounds over time. Because the goal isn't just to fill your calendar this season. It's to build a brand, a system, and a business that keeps it full. If you're ready to stop relying on OTAs and start building a brand that drives direct bookings, you can learn more about working with us at theweberco.com. And if you want hands-on support building your brand, marketing strategy, and direct booking systems, our agency offers both done-for-you services and consulting to help you get there.

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 marketing strategy is built on what you have instead of how it makes people feel, you're going to stay stuck competing on price, copying competitors, and relying on OTAs to fill your calendar. Inside this episode, I'm breaking down what actually drives bookings in today's market, and it's not more "stuff." It's clear positioning, intentional storytelling, and a branded guest experience that creates real emotional connection. I walk through why "box checking" is hurting your bookings more than helping, how to turn your features into experiences your guests actually remember, and what it really takes to stand out in a saturated STR market. You'll also start to see why competing on price is a race to the bottom, and what it looks like to step out of it by building a brand people trust and come back to. Because the goal isn't just to get booked. It's to build a brand people choose, return to, and are willing to pay more for. If you've been adding amenities, tweaking your listing, and still not seeing the traction you want, this episode will completely shift how you think about your strategy. Ready to go deeper? STR Marketing Simplified kicked off today, April 7, but you can still join me. We're diving into how to build a brand that drives direct bookings, increases guest loyalty, and gives you more control over your business without relying on OTAs. Save your seat here: https://www.theweberco.com/str-marketing-simplified

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 captures attention, nurtures trust, and converts guests when they're actually ready to book. Because the truth is, most short-term rental owners are either not collecting emails at all… or they're collecting them and doing nothing with them. And that's exactly why they're stuck relying on OTAs. In this episode, Steph walks through what's actually working right now when it comes to email marketing and how to implement it in a way that leads to real results quickly. We break down why email is often dismissed in this industry, why that mindset is costing hosts bookings, and what it looks like to use email as a true revenue-driving channel instead of an afterthought. You'll learn why consistency matters more than perfection, why templates alone won't convert, and why your messaging needs to actually connect if you want to see results. We also dive into the exact funnels you need to have in place. From capturing potential guests through strategic opt-ins… To re-engaging past guests who already know and love your brand… To building automated sequences that keep you top of mind long after someone leaves your site… Because here's what most hosts miss: Guests don't always book the first time they find you. But if you're not staying in front of them… someone else is. This episode will show you how to fix that. If you've been relying on OTAs, struggling to see traction with your marketing, or feeling like your website traffic isn't converting, this is the piece you're missing. If you're ready to stop guessing and start building a marketing system that actually drives bookings… Save your seat for STR Marketing Simplified here:https://www.theweberco.com/str-marketing-simplified From April 7–9, we're diving into the marketing strategies that lead to more bookings, increase guest loyalty, and give you more control over your STR business. We'll cover how to build a profitable STR brand, the email marketing strategies that convert to bookings, how to make social media work without posting every day, and the truth about influencer marketing for short-term rentals. The workshop is free, but spots are limited.

$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 December 2025, Yash shares that they secured over $100,000 in bookings within the first 60 days and are now on track to exceed $200,000 in their first year, outperforming their original goal of $175,000. Yash walks through his journey from real estate investing into short-term rentals, starting with converting a Scottsdale home into an STR, then taking on a full gut renovation in Sedona, and eventually building Altitude 22 in Maine as a fully realized, design-forward, brand-led property. Throughout the conversation, it becomes clear that these results didn't come from following the standard STR playbook—but from intentionally doing things differently. We dive into why design is not just aesthetic but directly impacts performance, why doing things the standard way leads to average results, why being local does not make operations easier, and why systems matter more than most hosts realize. Yash shares how the biggest shift came from moving out of an investor mindset and into an operator mindset, where every decision is made through the lens of guest experience. From what guests see when they sit in the hot tub, to how the home flows from space to space, to what the first five minutes of the stay feel like—every detail was designed with intention. And that's exactly what's reflected in their bookings. Yash shares that every guest who has booked so far fits their exact ideal guest avatar and recognizes the level of thought that went into the experience. We also break down what experiential hospitality actually means. Not just adding more amenities—but creating moments that don't show up on a spreadsheet, yet completely change how a guest feels in your space. From custom lighting in the theater room… To guided amenity cards… To thoughtful details like white noise machines and full-size cribs… These are the things that build trust, drive better reviews, and ultimately lead to stronger long-term performance. If you've been focused on optimizing your listing but feel like something is still missing, this episode will show you exactly what that is. If you're a short-term rental owner trying to figure out where your marketing efforts should actually go, I'm breaking it all down inside my free 3-day workshop, STR Marketing Simplified. From April 7–9, we're diving into the marketing strategies that lead to more bookings, increase guest loyalty, and give you more control over your STR business. We'll cover how to build a profitable STR brand, the email marketing strategies that convert to bookings, how to make social media work without posting every day, and the truth about influencer marketing for short-term rentals. Save your seat here: https://www.theweberco.com/str-marketing-simplified The workshop is free, but spots are limited. Connect with Steph: theweberco.com, @theweberco Follow Altitude 22: altitude22maine.com, @altitude22main

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 another property that went from zero direct bookings to 45% direct bookings after implementing the right marketing foundations and influencer partnerships. But those results didn't happen because someone posted a pretty Reel. They happened because the strategy behind the scenes was built intentionally. In this episode, I walk through the real process behind sourcing influencers, structuring partnerships, negotiating deliverables, and actually tracking results... from website traffic to email subscribers to bookings. Because influencer marketing is not just about exposure. It's about bringing the right audience into your ecosystem and having the systems in place to convert that attention into real bookings over time. If you're a short-term rental owner trying to figure out where your marketing efforts should actually go, I'm breaking it all down inside my free 3-day workshop, STR Marketing Simplified. From April 7–9, we're diving into the marketing strategies that lead to more bookings, increase guest loyalty, and give you more control over your STR business. We'll cover how to build a profitable STR brand, the email marketing strategies that convert to bookings, how to make social media work without posting every day, and the truth about influencer marketing for short-term rentals. Save your seat: theweberco.com/str-marketing-simplified Connect with Steph: @theweberco Learn more about The Weber Co.: theweberco.com

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 investors, he started with long-term rentals, then moved into short-term rentals. But eventually he realized something a lot of people in this industry are starting to discover. Scaling single properties is hard. The margins are tighter than people on Instagram make them seem, interest rates change the math, and building a real hospitality business requires something more strategic than just buying one property after another. That realization is what led Andres and his team into the boutique hotel space. In this conversation, we walk through the entire journey of acquiring the property that would eventually become The Iceberg Tahoe. From building broker relationships that led to an off-market opportunity, to negotiating seller financing, raising investor capital, and renovating a 20-room hotel in just 90 days. But the transformation didn't stop at the renovation. The property had outdated branding, weak reviews, and no real identity that matched the experience Andres wanted to create. Instead of trying to polish what was already there, they made the decision to start fresh. That's where the branding work came in. Together we built the strategy behind The Iceberg Tahoe. A name designed to be memorable, iconic, and deeply tied to the Tahoe experience. A brand story rooted in mystery, discovery, and the idea that there's always more beneath the surface. Because branding is not just about making something look better. It's about creating a story people want to be part of. It's about giving a property an identity that guests remember, talk about, and come back to. It's about positioning a business so that marketing actually works. And the early results are already showing up. Just a few months after launch, The Iceberg Tahoe has already seen strong early revenue and is generating a meaningful percentage of direct bookings. Even more interesting, the branding has created real excitement among investors and stakeholders who now feel emotionally connected to the project they helped bring to life. This episode is a behind-the-scenes look at what happens when branding, strategy, and hospitality vision all come together. If you've ever wondered what it actually takes to reposition a property, launch a boutique hotel, or build a hospitality brand that stands out in a crowded market, this conversation is packed with insight. Let's get into it. Connect with Andrés and The Iceberg Tahoe: @theicebergtahoe Connect with Steph: @theweberco Apply to work with us: theweberco.com 

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. And yes, marketing matters. But if the foundation underneath it isn't solid, none of it will convert the way you want it to. In this episode, I break down the real relationship between branding and marketing and why you cannot have one without the other. Branding is not your logo. It's not your color palette. It's not a Canva mood board. Branding is the emotional connection. It's the lifestyle you're selling. It's the reason someone chooses you instead of another property in the same market. It's where trust is built. It's where loyalty is formed. Marketing, on the other hand, is the action. It's how you distribute that brand into the world. It's social media, email, Pinterest, YouTube, OTAs, paid ads. But without brand clarity, marketing becomes posting and praying. It becomes throwing spaghetti at the wall and hoping something sticks. And that's where so many owners get stuck. In this conversation, I walk you through exactly how we approach brand strategy inside our agency. From developing deeply specific audience avatars to crafting mission, vision, core values, positioning, tagline, differentiators, guest experience design, and even the first ten minutes of a stay. Because when branding is dialed in, marketing gets easier. Clearer. More consistent. More profitable. We also talk about the rise of AI in hospitality and why human-centered storytelling matters now more than ever. Hospitality is built on emotion. If your brand doesn't make people feel something, your marketing will struggle to convert. The biggest takeaway? Everything in branding informs marketing. Every email. Every caption. Every touchpoint. Every piece of signage on your property. If you're frustrated that your direct bookings aren't growing the way you hoped, this episode will help you diagnose whether the issue is truly marketing… or if it's time to strengthen the brand foundation underneath it. And if you're ready to build a brand that actually fuels your marketing, you'll want to listen all the way through. Let's get into it. Connect with Steph: @theweberco Apply to work with us: theweberco.com

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. What impressed me. What made me pause. Because here's the truth: not everything was perfect. There was a last-minute room switch. An "all-inclusive" experience that wasn't fully inclusive for dietary needs. A few small design and communication hiccups. And yet… it still worked. We still left feeling connected. Rested. Thought about. Why? Because the welcome was strong. The intention was clear. The storytelling was emotional. From the curated in-room upgrades to the cocktail hour experience to the way they invited guests into something bigger than just a place to sleep, there were so many moments that reminded me what hospitality is actually about. In this episode, I break down: ➡️What they did exceptionally well ➡️Where clarity and alignment could have been stronger ➡️What "all-inclusive" really needs to mean ➡️How guest flow impacts shared spaces like wellness areas ➡️Why appealing to all five senses changes everything And the biggest takeaway? Your property does not have to be flawless to be unforgettable. Excellence isn't perfection. It's thoughtfulness. It's alignment. It's making sure the experience you promise is the experience your guest actually walks into. If you're building a micro-resort, refining your STR, or dreaming about something bigger, this one will challenge you in the best way. Let's get into it. Connect with Steph: @theweberco Apply to work with us: theweberco.com