Booked Solid Show - Short Term Rental Podcast

"You never want to compete on price. You want to compete on experience." — Brianna Amigo

In 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 Amigo

• Instagram: @briannamichelleinteriors
• Website: 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 Wicks

When 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 Wicks

Website: wellandgoodpro.com
Instagram: @wellandgoodpro
LinkedIn: 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.co
• Website: theolivejar.co
• Quiz: What’s Driving Your Bookings?
• Summit Blog: Level Up Your Listing
• Book 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 Couch

Connect 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: [email protected]

🔗 Instagram (Personal): @jaytullrich

🔗 LinkedIn: Jay Ulrich

🔗 Instagram (HostBuddy): @hostbuddy_ai

In this episode of Booked Solid, Amy Corbett reveals how she’s transforming quirky spaces like vintage train cars and grain bins, into sought-after escapes. Discover how her brand, All Belong Co., is redefining what it means to be a host by creating inclusive, unforgettable experiences that go beyond the ordinary. From harnessing niche communities to building direct bookings that aren't dependent on Airbnb, Amy’s journey is all about breaking the mold and making guests feel truly at home. If you're ready to take your STR game to the next level with bold, one-of-a-kind stays, this episode is for you!

🌐 Connect with Amy Corbett

• Email: [email protected]
• Phone: (434) 515-1045
• Website: allbelong.co

🌐 Follow All Belong Co

• Instagram: @allbelong.co
• Facebook: All Belong Co
• LinkedIn: All Belong Co
• YouTube: All Belong Co

Jamey King is a Senior Marketing Executive at eviivo, where he brings deep expertise from years in the vacation rental and short-term accommodation industry. With a background that includes leadership roles at Sony Electronics, VRMA, PointCentral, and Safely, Jamey has shaped strategies in business development, partnerships, and marketing across the board. Now based in Indiana, he leads efforts to grow eviivo’s brand awareness and bridge its presence across European and U.S. markets.

In this episode of Booked Solid, Jamey shares his approach to building a thriving STR business through strategy, consistency, and intentionality

Connect with Jamey King

📧 Email: [email protected]
📱 Phone: 317-629-6100
🌐 Website: www.eviivo.com

Follow eviivo on Socials
🌟 Facebook
🐦 Twitter
📸 Instagram
🔗 LinkedIn
📺 YouTube

Recently, I had the pleasure of being interviewed by Avery Carl on The Short Term Show. This interview was even more special because Avery and her team were kind enough to agree to a crossover episode for Booked Solid to spotlight direct booking strategies and tools that help STR hosts take control of their business.

We discussed a topic near and dear to my heart: building sustainable, long-term success through direct bookings. While we covered a lot, I want to share a few takeaways that I think will especially resonate with hosts.

Building a Direct Booking Site in 15 Minutes. Here’s How...

🗓️ Let's talk about your property! Book a call with me today, ⁠here⁠

When it comes to growing a short-term rental business, many operators rely on online travel agencies (OTAs) or job boards. But Owen Johnson, took a different route through Direct Bookings.

In this episode of Booked Solid, Gil dives into Owen's unconventional approach to direct bookings, where the focus is on building systems and loyalty that don’t depend on third-party platforms. Owen shares his journey of growing a thriving remote team, mastering pricing automation, and crafting a seamless guest experience that keeps customers coming back for more.

🌐 Connect with Owen Johnson

📧 Email: ⁠[email protected]⁠
📞 Phone: (425) 516-7928
📸 IG: ⁠@northwestpads⁠
🌐 Website: ⁠www.nwpads.com

When most people think about real estate agents, they picture the transaction — the showing, the contract, the close. But for Tyler Coon, it’s just the beginning.

On this episode of Booked Solid, Gil sits down with Tyler, founder of Savvy Realty, a nationwide real estate team laser-focused on helping investors buy (and succeed with) short-term rentals. What sets Tyler apart isn’t just his knowledge of STR markets or his deep portfolio of investor clients — it’s how he turns a real estate purchase into a launchpad for long-term profitability.

This conversation goes beyond the sale — into operations, trust-building, design strategy, and the critical role of direct bookings from day one.

🌐 Connect with Tyler Coon

• 📍 Savvy STR Agents on Facebook

• 📸 @savvy.realty on Instagram

• 👤 Tyler Coon on Facebook

• 📧 Email: [email protected]