Booked Solid Show - Short Term Rental Podcast

In this episode of Booked Solid, Garrett Brown—BiggerPockets Short-Term Rental Expert and founder of Cameron Ranch Glamping—shares how he turned a single house into a land-hacked luxury retreat business. Using a blend of creative hospitality, structured site analysis, and marketing systems built on influencer content, Garrett achieved a remarkable 76% direct booking rate. He walks us through his strategy, mistakes, wins, and advice for hosts aiming to move beyond Airbnb dependency.🔗 Connect with Garrett​Instagram: @GarrettBrownRE​YouTube: BiggerStays by BiggerPockets​Email: garrettbrown@biggerpockets.com

“It’s not about how much you make—it’s about how much you keep.” At just 25 years old, Chad Harker is building a high-cash-flow STR portfolio in Edmonton using real estate acquisitions, direct booking strategies, and custom-built AI systems to scale—without burning out.In this episode, Chad shares how he house-hacked his way into the industry, scaled using BRRR-style methods, and now automates his business with tech tools like HostBuddy and custom GPTs. Whether you're just getting started or scaling fast, Chad’s no-fluff approach to growth, guest retention, and profitability will shift your mindset—and give you real tools to work with.🎧 Listen in to learn how to:Turn one property into a self-funded portfolioBuild repeat guest systems that feel like five-star diningUse AI and SOPs to streamline operationsGrow your brand while keeping more of what you earn📲 Connect with ChadIG – Business: @ecoescapes780IG – Personal: @chad_harker780

“When you're doing something hard, it's supposed to feel hard… but know that you're on the right path.”Skyler knows firsthand: building a direct‑booking short‑term rental business from the ground up is not easy, but it can be extraordinary. In this week’s episode of the Booked Solid Show, Skyler shares how he and his wife, Maddie, went from furnishing arbitrage properties in San Diego to launching investor-backed, luxury wellness retreats in Upstate New York—complete with custom saunas, cold plunges, and bridal‑ready properties. You’ll learn their scrappy strategies, brand‑building secrets, and how they’re leaning into a book club community to fuel expansion—without losing balance.Connect with Skyler hereEmail: skyler@fortheloveofupstate.com | madi@fortheloveofupstate.comInstagram: @skylerandmadiTikTok: @madiandskylerSTR Book Club IG: @thestrbookclub

a 🛠️ “Design isn’t just about what it looks like—it’s about what it earns.”Our guest is Ishita Lalan, founder of Ishita Interiors and architectural designer behind over 150 short-term rental transformations across the country. From $500,000 gut-renovations to quick-turn landscape upgrades, Ishita approaches every STR with the mindset of an investor and the precision of an architect.This episode is for the host who’s ready to stop “furnishing a unit” and start building a direct booking brand. Whether you’re managing your first property or optimizing your tenth, Ishita breaks down the key frameworks behind design decisions that pay off—financially and emotionally—for your guests and your business.You’ll leave this episode thinking differently about your layouts, your finishes, and even your photos—because design, when done right, isn’t decoration. It’s strategy. Let’s get into it!🔁 Connect with IshitaInstagram: @ishita.interiorsWebsite: www.ishitainteriors.comFacebook: Ishita Nagda Lalan

Kenny Bedwell, CEO of STR Insights and a short-term rental investor, shares his innovative approach to increasing direct bookings by marketing local experiences over just the properties. He discusses effective lead generation strategies that build trust with potential guests, emphasizing the importance of community engagement and curated content. Kenny also delves into the delicate balance of entrepreneurship and family life, revealing insights on managing time and leveraging social media to boost profitability while maintaining personal commitments.

"You never want to compete on price. You want to compete on experience." — Brianna AmigoIn the world of short-term rentals, one thing is clear: good design isn’t just pretty—it’s profitable. On this episode of Booked Solid, Gil sat down with Brianna Amigo, founder of Brianna Michelle Interiors, to uncover how design directly impacts bookings, guest experience, and your bottom line. From her marketing roots to transforming over 300 properties nationwide, Brianna is leading a movement where curated spaces and outdoor amenities aren’t luxuries—they’re expectations.👤 Connect with Brianna AmigoInstagram: @briannamichelleinteriorsWebsite: briannamichelleinteriors.com

"One man's trash is another's treasure. We all have our things we obsess over. If we were all doing the same things, we’d have major problems." – Jonathan WicksWhen Jonathan Wicks launched Well & Good Professional Services, he wasn’t just starting another cleaning company — he was reimagining how professionalism and consistency in vacation rental servicing can elevate the entire guest experience. In this episode of the Booked Solid Show, Jonathan shares his journey from being a Chicago-based host with a lake house to leading a national STR servicing company built on hospitality-grade standards.🔗 Connect with Jonathan WicksWebsite: wellandgoodpro.comInstagram: @wellandgoodproLinkedIn: Well & Good Pro

Dawn LaMattina Asher is the founder and creative director of The Olive Jar, an experiential marketing studio focused on vacation rental design, amenities, and media content creation for visionary hosts. With 20 years of experience in experiential storytelling across entertainment media, hospitality, and brand marketing, Dawn helps hosts transform ordinary stays into unforgettable guest experiences that foster loyalty and connection."Experiential marketing builds brand loyalty." That’s the powerful truth Dawn shares in this value-packed conversation. More than good design or amenities, what your guests feel during their stay creates lasting emotional bonds with your brand. We dive deep into what makes a stay memorable and how those emotional experiences convert into direct bookings and repeat guests📲 Follow Dawn Here:Instagram: @theolivejar.coWebsite: theolivejar.coQuiz: What’s Driving Your Bookings?Summit Blog: Level Up Your ListingBook a Discovery Call

On this episode of the Booked Solid Show, Gil is joined by Kim Herrlein, the Chief Leisure Officer of Purveyors of Leisure. Kim is a short-term rental operator who has mastered the art of large group travel through beautifully designed estate properties in California's Coachella Valley. She recently expanded her hospitality vision by launching The Fainting Couch, a boutique hotel in Northern California’s wine country. In this episode, Kim shares her journey from real estate investor to STR operator, and now a boutique hotelier, with a focus on curating seamless, luxurious experiences for her guests.Whether it's hosting multi-family gatherings at her spacious estates or redefining boutique hospitality with a contactless model, Kim's approach is rooted in understanding her ideal guest avatar and crafting an unforgettable stay. She also dives into her strategies for direct bookings, guest nurturing, and her belief in elevating hospitality through thoughtful design and personalized service.Visit Purveyors of Leisure | Visit The Fainting CouchConnect with Kim here:🌐 Facebook - Purveyors of Leisure📸 Instagram - Purveyors of Leisure📸 Instagram - The Fainting Couch🌐 Facebook - The Fainting Couch Hotel

In this episode of the Booked Solid Show, we sit down with Jay Ulrich, CEO and Co-Founder of HostBuddy AI, the platform that’s shaking up the short-term rental industry. Jay is a property manager turned tech innovator, known for transforming his 50-unit portfolio in San Diego into a blueprint for smarter, more resilient hosting.With a deep understanding of the challenges hosts face from OTA over-reliance to endless guest messaging, Jay built HostBuddy AI to give hosts real control over their business. His approach blends laser-focused niche strategy with cutting-edge AI to boost direct bookings, streamline operations, and enhance guest experiences.Whether you’re a solo host or scaling a full-blown STR empire, Jay’s insights will change how you think about tech, hospitality, and growth. This episode is your backstage pass to the future of property management one where hosts call the shots.📲 Connect with Jay Ulrich:📞 Phone: (240) 357-6127📧 Email: jay@hostbuddy.ai🔗 Instagram (Personal): @jaytullrich🔗 LinkedIn: Jay Ulrich🔗 Instagram (HostBuddy): @hostbuddy_ai