EP 210: Why Your Instagram Isn’t Converting (and How to Fix It)

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.

Are you leaving thousands of dollars in bookings on the table because your website has no opt-in? In this episode of Branded and Booked, I walk you through the exact funnel we set up for Cabins on the Cumberland that grew our email list to over 1,100 potential guests—people who have never stayed with us but are now primed to book. You’ll learn: Why simply having a direct booking site isn’t enough How to use pop-ups, giveaways, and promo codes to collect guest data The 5-email sequence we use to convert subscribers into paying guests How we’ve leveraged QR codes, ads, and social media to drive traffic The results we’ve already seen: $5,000 in bookings directly tied to this funnel Marketing doesn’t have to be complicated. With the right opt-in strategy, you can build a list of warm leads that generates revenue for you month after month. 📲 Ready to stop losing leads and start converting browsers into bookings? Hit play and I’ll show you exactly how we did it. ✨ Let’s stay connected: → DM me @theweberco or follow @hostedbythewebers → Visit theweberco.com or hostedbythewebers.com for more resources → Hop into my free Facebook group: STR, Boutique Hotel, Airbnb Hosts: Branding & Marketing Tips

A question I was asked recently stopped me in my tracks: “Steph, where does your willpower come from?” It made me reflect on my story—and here’s what I realized: you don’t need everything perfectly lined up to create the life and business you want. I didn’t have financial support for college. I didn’t have a mic for 200+ podcast episodes. I didn’t have a clear, linear path into entrepreneurship. But I showed up anyway. In this episode, I’m sharing the real side of that journey: ➡️ How my family’s financial crisis shaped the way I work and lead ➡️ What self-funding college taught me about grit and clarity ➡️ Why defining your “why” matters more than a perfect setup ➡️ How I navigate the overlap of being a mom, daughter, and entrepreneur ➡️ The boundaries I’ve set to keep family and health first If you’ve ever felt like you can’t start until you “have it all together,” this episode is proof you already have what you need. Whether you DIY your Instagram or hand it off entirely, you’ll leave knowing exactly where to focus so your time (and budget) on the platform actually pays off. ✨ Let’s stay connected: → DM me @theweberco or follow @hostedbythewebers → Visit theweberco.com or hostedbythewebers.com for more resources → Hop into my free Facebook group: STR, Boutique Hotel, Airbnb Hosts: Branding & Marketing Tips  

If you run a boutique hotel, micro resort, short-term rental, or property management company, your Instagram can lead to bookings — but only if you’re using it strategically. In this episode, I’m sharing why most hospitality brands miss the mark and exactly how to change that. We’ll cover: The one account setup mistake that instantly splits your audience (and how to fix it) Why your “pretty pictures” might actually be hurting your bookings The secret ingredient missing from most hospitality Instagram strategies A simple shift that turns passive scrollers into active inquirers How to make Instagram’s evolving features work for you — not against you The overlooked partnership that can fast-track your results in weeks, not years What to expect when you commit to a real strategy (and how long it takes to see traction) Whether you DIY your Instagram or hand it off entirely, you’ll leave knowing exactly where to focus so your time (and budget) on the platform actually pays off. ✨ Let’s stay connected: → DM me @theweberco or follow @hostedbythewebers → Visit theweberco.com or hostedbythewebers.com for more resources → Hop into my free Facebook group: STR, Boutique Hotel, Airbnb Hosts: Branding & Marketing Tips  

If you've ever wondered what co-hosting really looks like — the wins, the hard lessons, and everything in between — this is the episode for you. I'm pulling back the curtain on how we've grown our boutique co-hosting business, the boundaries we’ve had to draw, and the challenges that have shaped the way we operate today. Here’s what I cover in this episode: The difference between co-hosting and traditional property management Why slow growth with the right properties is the goal What I look for in new properties (and red flags I now avoid) The absolute hardest part of this business (cleaning, anyone?) Why documenting SOPs is non-negotiable — and how I finally got mine together The surprising way I landed some of our best clients What new co-hosts must get clear on before saying yes to anyone If you’re thinking about stepping into the co-hosting world — or already in it and feeling the weight of it all — you’re not alone. This one’s for you. ✨ Let’s stay connected: → DM me @theweberco or follow @hostedbythewebers → Visit theweberco.com or hostedbythewebers.com for more resources → Hop into my free Facebook group: STR, Boutique Hotel, Airbnb Hosts: Branding & Marketing Tips  

Let’s be honest—building a co-hosting business sounds easier than it is. You think: I’ve got systems, I’ve got listings…now where are the bookings? Or worse—you get the bookings and then spend your nights cleaning up after guests who clearly missed the “no parties” line in your house rules. In today’s episode, I’m sitting down with Punith Upadhya, who went from managing two properties to twelve in under six months—and not by working more, but by becoming the version of himself who could lead at that level. We’re talking about: What it really takes to grow a co-hosting business from the ground up The wild guest story that forced Punith to overhaul his entire vetting system How to train your team to follow their gut (yes, really) Why your business growth will never outpace your self-image Tactical mindset habits that actually move the needle—without the fluff Whether you're deep in the weeds of short-term rental ops or dreaming about scaling without working 60-hour weeks, this convo is full of the perspective shift you didn’t know you needed. LINKS & RESOURCES: ➡️Connect with Punith on LinkedIn: Punith Upadhya ➡️Follow me on IG: @theweberco ➡️Learn more at: theweberco.com ➡️Join my free Facebook Group: STR, Boutique Hotel, Airbnb Hosts: Branding & Marketing Tips

In this special solo episode, I get personal and share a raw behind-the-scenes look at where my heart, head, and business are at right now. From influencer beginnings in 2016 to a (game-changing!) pivot into coaching and consulting in 2020, and then again into the world of short-term rentals—this episode takes you through the honest evolution of what it means to build a business and a life that’s in true alignment. I open up about: Why I walked away from chasing arbitrary revenue goals The “two-year shift” cycle that always signals a big move How selling our first STR created more opportunity, not less Our family’s dream to hit the road for a year of camper life What it looks like to build and scale two businesses with intention Letting go of what success should look like—and rewriting it your way This is one of those episodes that’s less about strategy and more about soul. If you’ve ever felt the pressure to hit milestones that don’t align with your actual dreams, this one’s for you. Love this episode?: Follow along for more real-time updates: @theweberco.  Curious about STR branding and marketing support? Visit theweberco.com Join the free Facebook community for STR owners: Branding & Bookings for STR Hosts

If you’re still doing everything yourself in your short-term rental business, this episode is the sign you need to stop. I sat down with Marisa Grover—a systems + operations expert for STR owners—and we’re diving deep into the exact ways you can streamline, delegate, and actually get your time back. Whether you’re overwhelmed with guest communication, hiring cleaners, or just tired of being in your inbox 24/7… this one’s for you. Inside the episode, we cover: ✅ The first systems you must have in place (even if you're just getting started) ✅ Tools and automations Marisa recommends for saving hours each week ✅ How to decide what to keep doing yourself vs. what to outsource ✅ The mindset shift every owner needs to go from burnout → balance ✅ Real-world examples of STR owners getting out of the weeds If you're dreaming of running your rental like a real business—not just a second job—this episode will give you the next right steps. 🎧 Tune in now and start building systems that work for you.  

In this episode of Branded and Booked, I’m pulling back the curtain on our biggest project to date—Cabins on the Cumberland. I’ve been getting two questions over and over again: 1️⃣ “What would you do differently?” 2️⃣ “Would you ever do this again?” Spoiler alert: Yes, I would. But there are definitely things I’d change next time. I’m walking you through: The origin story of how this nine-acre riverfront development came to life (yes, it started with a Facebook post from my brow girl) The deal structure, bank process, and why we chose partners over raising capital What I would 100% change about the timeline, build order, and amenity placement Why sweat equity mattered, and how we managed roles, logistics, and full-on furniture delivery runs My honest take on whether I’d go new build or renovation for the next big idea What’s next (RV parks, campgrounds, glamping?? 👀) Whether you’re dreaming about developing a vacation rental community or knee-deep in one already, this episode will help you think more strategically—especially if you're planning to bring in partners or build from scratch. We’ve learned a LOT over the past year and a half, and we’re this close to wrapping the final phase. August 2025, let’s go. Have questions about building, partnerships, or STR strategy? DM me on Instagram @theweberco or visit theweberco.com to learn how we help vacation rental owners turn their vision into a brand that books.  And don’t forget to join my free Facebook group to STR, Boutique Hotel, Airbnb Hosts: Branding & Marketing Tips!