EP 208: How to Train Your Team to Think Like You (and Trust Their Gut) with Punith Upadhya

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!

Why Influencer Marketing Still Works—But Only If You Do It Right Influencer marketing isn’t dead—it’s just misunderstood. In this episode, you’ll get the 411 on what’s working (and what’s not) when it comes to influencer strategy for boutique hotels, short-term rentals, and hospitality brands. You’ll also hear behind-the-scenes stories from recent campaigns (including one that turned a $0 stay into $7,000 in bookings), red flags to watch for, and the mindset shift owners need to make before diving in. If you’ve been burned by bad influencer experiences or feel overwhelmed by where to start, this is your permission slip to rethink the strategy—and do it the right way. What You’ll Learn: Why influencer marketing is not just about pretty photos and free stays The exact deliverables Steph includes in her influencer campaigns Metrics that actually matter (spoiler: it’s not likes) A $7K case study that proves influencer ROI Two influencer red flags you need to watch out for Why your organic content has to be dialed in first What makes an influencer pitch an instant yes—or a hard pass Bottom line: Influencer marketing works—but not if you hand over a free stay and call it strategy. Resources Mentioned: Want us to run your influencer campaigns or help you build your strategy from the ground up? DM “INFLUENCER” on Instagram @theweberco and we’ll send you the details.  Love this episode? Join my free →  Facebook Group to keep the conversation going!

This week on Branded and Booked, I’m sharing how Cabins on the Cumberland (our micro-resort) brought in 50% direct bookings in May—and the exact strategy behind it. Even while the property is still under construction, we created a marketing plan powered by storytelling, strategy, and a whole lot of intention. In this episode, you’ll learn: Why content is just one part of a bigger marketing picture How pairing SEO with storytelling builds long-term visibility The 3 C’s of marketing you need to revisit ASAP What to offer instead of a basic newsletter to grow your list Why collecting phone numbers matters (even if you’re not texting yet) How to prep during the slow season so you’re fully booked in the busy one What to keep in mind about partnering with local businesses ✨ If you're trying to grow a direct booking strategy that actually works, this one’s for you. DM me the word “INFO” at @theweberco on Instagram to learn more about how I can help you build a brand that books and a marketing strategy that converts.  Love this episode? Join my free →  Facebook Group to keep the conversation going!

Airbnb’s latest updates aren’t just platform tweaks—they’re a strategic move to keep hosts (and their guests) locked into Airbnb. From limiting outside links in communication to discouraging direct bookings, these changes could seriously impact how you grow YOUR business, build guest relationships, and maintain control over your brand. In this episode, I’m breaking down what the changes mean, why they’re a potential threat to independent hosts, and most importantly, how to stay in control of your brand, your business, and your bookings. Whether you’re new to hosting or own multiple properties, this episode will help you take ownership of your short-term rental brand, so you’re not just building someone else’s platform. What You’ll Learn: ✅ What’s changing on the Airbnb platform ✅ Why relying solely on the platform is riskier than ever ✅ How to capture your guests’ information while they’re at your property ✅ How to build a guest pipeline you actually own (hello, email list + direct booking!) ✅ The key marketing assets every STR host needs to future-proof their business Resources Mentioned: 🔗 Read Airbnb’s Policy Updates → HERE📲 Connect with me on Instagram → @theweberco🎙️ Love this episode? Join my free →  Facebook Group to keep the conversation going!  

In today’s episode of Branded & Booked, I’m handing the mic to three incredible short-term rental business owners who went through my last round of STR Marketing Bootcamp—April, Cathleen, and Jess. Each of them has a different business model, different challenges, and different results, and you’ll hear firsthand how this 12-week live coaching program helped them build a powerful brand and marketing system that leads to more direct bookings and increased guest loyalty. What You’ll Learn in This Episode: ✔️ Why relying only on OTAs (Airbnb, Vrbo) limits your business growth ✔️ How these STR pros built a renowned brand and systemized their marketing ✔️ The behind-the-scenes of an STR lifestyle photoshoot (and why it matters!) ✔️ Real results from real business owners who made the shift to direct bookings 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 ✨ Cathleen – Discovered in Travels 📍 Poconos, Pennsylvania | Short-term rental business & travel experiences 🔗 Follow along: @discoveredintravels | www.discoveredintravels.com ✨ Jess – Wander North | Northern Michigan Vacation Rentals 📍 Traverse City, MI | Real estate expert specializing in STR investments 🔗 Follow along: @wander.north.rentals | www.wandernorthrentals.com/links Resources & Links Mentioned 🔥 Want to learn more about STR Marketing Bootcamp? Join the waitlist → here📲 Connect with me on Instagram → @theweberco🎙️ Love this episode? Join my free →  Facebook Group to keep the conversation going!  

Be honest: Have you ever said “Oh, I own an Airbnb,” when asked what you do? Now imagine the difference between that and saying something like “I run a short-term destination for young couples.”. The difference? Branding. In this episode, we dive into what makes an Airbnb (or any business) go from just another option to a must-experience destination. Because let’s be real—every industry is saturated, and standing out isn’t about being the best; it’s about creating a feeling that guests fall in love with. What You’ll Learn in This Episode: ✨ How to turn your Airbnb into a raving guest magnet ✨ Why a brand is more than a logo—it’s an emotion ✨ What branding is NOT (and why most hosts get it wrong) ✨ The key to making guests feel transported—not just accommodated ✨ The ultimate way to differentiate in a crowded market This episode will change how you think about standing out in a competitive space. Because when you build a brand people connect with, they won’t just stay once—they’ll keep coming back. Steph on Instagram: @theweberco and @hostedbythewebers. And don’t forget: Join our Free Community >>HERE.  

Some short-term rentals offer a place to stay, but some create an unforgettable experience… The Asheville Affair offers a trip guests will never forget. In this episode, we’re taking you behind the scenes of how we designed, branded, and launched a short-term rental built for bachelor and bachelorette groups—and how you can apply these strategies to make your own rental stand out. You’ll learn: ✔️ The strategy behind designing a space that stays booked (it’s more than just good decor) ✔️ How we crafted an experience-first brand that attracts high-value guests ✔️ Key lessons from launching a rental that commands premium pricing If you want to move beyond generic listings and create a rental that’s the only choice for your ideal guests, this episode is packed with insights you can use. 🎉 FREE Workshop! 🎉 Want to go deeper? DM me the word ‘workshop’ on Instagram, and I’ll send you access to an exclusive free training inside my Facebook group >>HERE!