EP 222: Short-Term Rental Investing: What I'd Do Differently Now

If I were starting over in short-term rentals today, I wouldn't rush into the first deal just to say I owned one — and I definitely wouldn't invest where everyone else is telling you to. In this episode, I'm walking you through our real journey: buying our first STR, building a six-figure co-hosting business, and realizing pretty quickly what wasn't the right long-term play for us. We talk about market selection, cash flow vs. equity, why I'd avoid certain oversaturated markets now, and what I wish I had understood sooner about renovations, contracts, and boundaries. If you're in the "should we buy?" or "what's our next move?" phase — or you're thinking bigger than single-family STRs — this episode will help you slow down and make smarter, more intentional decisions. We cover: The investing choices I'd change if I started over Why market selection matters more than ever Cash flow vs. long-term equity (and how I think about it now) What co-hosting actually looks like behind the scenes Why we're focused on micro resorts and boutique hotels moving forward Connect with me: 📸 @theweberco 🌐 theweberco.com

2026 is not the year to play it safe — and it's definitely not the year to keep relying on Airbnb alone. In this episode of Branded and Booked, I break down what I see coming next for short-term rentals, boutique hotels, micro-resorts, and the investors behind them — and why branding, direct strategy, and personal visibility are no longer optional. From platform changes and rising fees to the growing gap between checkbox amenities and truly curated guest experiences, this conversation is a wake-up call for hosts who want longevity, leverage, and real brand value. In this episode, we cover: Why more investors are shifting away from single-family STRs and toward boutique hotels, micro-resorts, and larger experiential projects The real cost of relying solely on Airbnb — and why 2026 is the year direct booking strategies become essential Why design alone isn't enough (and what real brand strategy actually includes) How brand clarity directly impacts the guests you attract — and the problems you avoid The rise of personal branding for hosts, operators, and real estate investors with bigger visions What it actually looks like to leverage your personal brand to attract partners, clients, and opportunities Why the guest experience gap is widening — and how curated rituals, storytelling, and intentional touchpoints win The evolution of influencer marketing (no more random trades, ever) Why hospitality brands are becoming media brands — and how content now drives demand How strong branding and marketing directly increase the exit value of your properties Connect with me: 📸 @theweberco🌐 theweberco.com

2025 has been one of the biggest years of growth I've ever had — across three hospitality businesses, inside my personal life, and in the direction I'm heading for 2026. I'm breaking down what worked, what stretched me, and what I'm changing moving forward. I walk through each business — The Weber Co., Hosted by the Webers, and Cabins on the Cumberland — and share the real numbers, the mindset shifts, the growing pains, and the wins. I also open up about the conversations Colin and I have been having about our boys, school, where we want to live, and why "camper life" is the plan for next year. If you're building something big, navigating pivots, or trying to figure out how to scale without losing yourself in the process… this one's for you. Connect with me: 📸 @theweberco🌐 theweberco.com  If this episode was helpful, I'd love you to leave a 5-star review and share it with another business owner who's ready to take control of their business and bookings.

In this bite-sized solo episode, I'm breaking down the insane results we've helped our client, Tremont Lodge, achieve since partnering in spring 2025. From stock photos and low engagement to over $40,000 in tracked direct bookings, you'll hear exactly how an integrated marketing strategy — blending social media, email, influencer collaborations, and automation — completely transformed their results. I'll walk you through the story from the very beginning: where Tremont was when they came to us, the first steps we took to revamp their brand presence, and how each piece of the strategy now works together to drive measurable growth. What You'll Learn How we turned uninspired, stock-driven content into a story-driven brand experience that connects The 3 C's we use with every client: Content, Conversations, and Collaborations The power of ManyChat funnels and promo codes for tracking real ROI on organic content How influencer partnerships drove more than $16K in direct bookings — and how to choose the right creators for your season Why timing matters for influencer stays and how to shift focus in slower seasons Ways to integrate organic, paid, and email marketing so they all amplify one another Key Takeaways If you're a boutique hotel, short-term rental, or small business wondering how to actually track what's working in your organic marketing — this episode gives you the blueprint. From codes to lead funnels, I'll show you exactly how to build a strategy that drives bookings, builds your list, and grows your brand all year long. Connect with me: 📸 @theweberco 🌐 theweberco.com  If this episode was helpful, I'd love you to leave a 5-star review and share it with another business owner who's ready to take control of their business and bookings.

Three years ago, it was enough for your Airbnb to have cute décor and a decent location. Today? The game has changed. In this episode, Steph sits down with Jordan, co-founder of Somerled Designs, to talk about what it really takes to compete in the 2025 short-term rental market. You'll learn how Somerled has scaled from a college-friend side hustle to 50+ design projects per month, why they pair market research with creative interiors, and how their signature approach—"where strategy meets design"—helps investors turn underperforming listings into high-return assets. Whether you're investing in a new property or trying to breathe life into an existing one, this conversation will completely shift how you think about design, guest experience, and ROI. Connect with Somerled Designs Website: somerleddesigns.comInstagram: somerled.designs Connect with Steph Website: theweberco.com Instagram: @theweberco  

You don't have to stay stuck on the OTA hamster wheel. 👏 In this episode, I'm pulling back the curtain on real short-term rental owners who decided enough was enough—and took control of their marketing. You'll hear from five amazing hosts who implemented the exact strategies I teach inside STR Marketing Bootcamp and saw direct booking results they didn't think were possible: ✨ Kathleen in the Poconos, who clarified her guest avatar (big groups celebrating milestones) and used content pillars to launch a direct booking site. ✨ April in Lake Tahoe, who leaned into lifestyle photography and a referral-only model to position her co-hosting business as exclusive. ✨ Debra in Blue Ridge, GA, who branded her cabins as the dog-devoted stays and booked three guests through her site in the very first week of email funnels. ✨ Jess in Northern Michigan, who turned a great visual brand into a marketing system with email and social—without burning out. ✨ Nolan, who grew from a Caribbean villa to a boutique hotel in Utah, using story-driven marketing to book his biggest stay yet: over $30K. 👉 Every single one of them started with the same foundation: STR Marketing Bootcamp. If you're ready to: Nail your guest avatar so your content actually attracts the right people Build a direct booking engine with email marketing that works while you sleep Position your brand so guests happily pay more …then Bootcamp is where you need to be. ⚠️ Doors close October 1. Don't wait. Join us here: https://www.theweberco.com/str-marketing-bootcamp    Meet Today's Guests & Connect With Them ✨ April – Modern Mountain Vacations 📍 Lake Tahoe, CA & NV | Boutique STR consulting & co-hosting business 🔗 Follow along: @modernmountainvacations | www.modernmountainvacations.com ✨ Kathleen – Discovered in Travels 📍 Poconos, Pennsylvania | Short-term rental business & travel experiences 🔗 Follow along: @discoveredintravels | www.discoveredintravels.com ✨ Jess – Wander North Rentals 📍 Traverse City, MI | Real estate expert specializing in STR investments 🔗 Follow along: @wander.north.rentals | www.wandernorthrentals.com/links ✨ Debra – Shiny Apple Cabins 📍 Blue Ridge, GA | Dog-friendly mountain view & creekside cabins with private dog park 🔗 Follow along: shinyapplecabins.com | Instagram: @shinyapplecabins ✨ Nolan – Caribbean Vista + Boutique Hotel 📍 Roatán, Honduras & Southern Utah | Luxury villa + boutique hotel co-hosting 🔗 Follow along: @caribbeanvista

Don't forget — STR Marketing Simplified kicks off today (Sept 23–25)! It's a free 3-day workshop where I'll walk you through how to rely less on OTAs and build a marketing system that works. Save your seat here (or catch the replays if you can't make it live). 👉 Save your seat here! Are direct bookings just a trend… or the future of your short-term rental business? In this episode of Branded and Booked, I'm diving into one of the most important conversations I've had with STR hosts over the last two years: should you go all in on a direct booking strategy, and if so, when? Airbnb isn't going anywhere, but the constant policy and fee changes remind us that we don't own that platform. What we can own is our brand, our guest relationships, and a marketing strategy that brings in more control and more revenue. Here's what I cover in this episode: Why direct bookings aren't just a passing trend The shift I'm seeing with Airbnb policies in 2025 and how it impacts us as hosts When to start your direct booking strategy (hint: the best time is today) The key marketing levers that actually move the needle — SEO, email marketing, and yes, social media when it makes sense Real-life examples of how I've approached direct bookings with my own properties This conversation is packed with clarity and action steps so you can move forward with confidence. Resources & Links: Reserve your spot in the STR Marketing Simplified Workshop (Sept 23–25) → Register here! Follow me on Instagram for more tips and behind-the-scenes: @theweberco If you enjoyed this episode, leave a quick review and share your favorite takeaway! I can't wait to see you inside!

If you've ever wondered how to make social media actually work for your short-term rental, boutique hotel, or micro resort—this episode is for you. I'm breaking down my 3 C's of Marketing on Social Media Strategy that I've been teaching since 2020. These tried-and-true pillars have helped businesses across industries grow their brands, book more clients, and build genuine connections. In this episode, you'll learn: How to develop a content strategy rooted in your brand stories and guest experience. Why conversations (and engagement funnels like ManyChat) are essential to boost visibility and track bookings. How to approach collaborations and influencer marketing in a way that actually drives results. I'm also shareing real client examples, proven strategies, and practical ways you can implement the 3 C's in your own business right now. And if you're ready to go deeper? Be sure to save your seat for my free 3-day workshop, STR Marketing Simplified, happening September 23–25. I'll walk you through these strategies in even more detail, plus give you examples and tools you can apply immediately. A replay will be available for a limited time, but you'll get the most out of being there live. 👉 Save your seat here! Resources & Links: Reserve your spot in the STR Marketing Simplified Workshop (Sept 23–25) → Register here! Follow me on Instagram for more tips and behind-the-scenes: @theweberco If you enjoyed this episode, leave a quick review and share your favorite takeaway!  

Are you running yourself ragged trying to market your short-term rentals… and still not seeing results? You're not alone. In today's episode of Branded and Booked, I'm digging into the top two mistakes I see STR hosts make with their marketing—mistakes that cost you time, money, and bookings. Here's what we cover: Why splitting your attention across multiple property accounts and brands is actually holding you back The difference between "spaghetti marketing" and strategy (and how to stop wasting energy) The two non-negotiables every STR owner needs in place before worrying about social media How a streamlined brand and direct booking setup can put thousands back in your pocket each year 🎉 And don't forget: I'm hosting STR Marketing Simplified, a free 3-day workshop happening September 23–25. If you're ready to build a brand that stands out and a direct booking strategy that actually works, grab your spot HERE. Replay will be available if you can't join live. Follow along on Instagram @theweberco for more tools, strategies, and behind-the-scenes of how we're building guest-first brands in the STR space.

Airbnb just announced another major policy change — and hosts on Facebook are losing it. But here's the truth: panicking won't protect your business. Strategy will. In this episode, I'm breaking down: ➡️ What the new Airbnb host fee structure actually means ➡️ The simple pricing adjustment we're making right now to protect revenue ➡️ Why direct bookings must be part of your growth plan (and the exact first steps I'd take) ➡️ How email + SMS marketing is the lowest-hanging fruit you're probably ignoring ➡️ The role social media and ads play when you're ready to scale At the end of the day, we are entrepreneurs — which means we stay solution-oriented. These platform changes aren't the end of your business. They're the nudge you need to take more control of your bookings, your brand, and your bottom line. 🎙️ Plus: I'm hosting a free 3-day live workshop, STR Marketing Simplified, starting September 23. We'll dig into brand foundations, the marketing strategies that actually drive direct bookings, and how to stop building your business at the mercy of Airbnb's rules. 👉 Save your seat here: https://www.theweberco.com/str-marketing-simplified Follow along on Instagram @theweberco for more tools, strategies, and behind-the-scenes of how we're building guest-first brands in the STR space.