SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

What makes a short-term rental truly unforgettable? In this episode of SmartStayShow , we uncover the secrets behind top-performing vacation rentals with Mark Lumpkin, sales director at STRCRIBS . From bachelorette-themed escapes in Nashville to hidden speakeasies and glow-in-the-dark mini-golf , Mark shares expert tips on designing spaces that attract guests—and boost revenue. We dive into bold c...

Ever wondered what it’s like to live as a digital nomad, staying in over 30 short-term rentals around the world? In this exciting episode of the Smart Stay Show , we sit down with Eric and Marissa Dingler , a family that sold most of their possessions and turned their home into a life of adventure. From Costa Rica to Liverpool, the Dinglers share their incredible journey and insights into the worl...

Can You Build a Thriving Short-Term Rental Business While Working Full-Time? In this episode, we sit down with Jim McGowan , a seasoned sales professional who has successfully built a profitable short-term rental portfolio—all while maintaining his full-time job! Jim takes us through his journey, from an early misstep in fractional ownership to fully owning and managing two stunning vacation renta...

Can AI Handle Guest Communication Better Than You? In this episode of The Smart Stay Show , we sit down with Jay Ulrich , CEO and co-founder of HostBuddy.ai , to explore how AI is revolutionizing short-term rental management. Jay, a former civil engineer turned short-term rental host, shares his journey from scaling Select Stays to 40 units to developing an AI-powered platform that learns your sty...

Can hard money lending and short-term rentals be the ultimate power duo? In this episode of The Smart Stay Show , We sit down with David Little , co-founder of Crown Capital Resources , to explore how savvy investors are using short-term rentals as a game-changing exit strategy. We dig into DSCR loans, the Burr method for vacation rentals, and how tools like AirDNA are influencing lending decision...

How did one property cover an entire mortgage—and spark a 30-property empire? In this episode of the Smart Stay Show , We sit down with Islam Elgarhi , a short-term rental investor and entrepreneur, to uncover how he turned a chance discovery into a thriving business. From scaling his portfolio with smart systems to creating an AI tool that helps hosts tackle unfair reviews, Islam shares his secre...

Ever wonder why some hosts seem to always get glowing reviews while others struggle? In this episode of the Smart Stay Show , I’m joined by my business partners Alex Steeg and Kory Himmer to dive into the game-changing power of proactive communication in short-term rental hosting. We break down how setting clear expectations upfront can prevent negative reviews and enhance guest satisfaction. From...

Ever Dealt With a Water Damaged Rental Property? This Could Save You Thousands. As short-term rental owners, Rory and I have seen it all - from the good, the bad, to the downright disastrous. One fateful night, we got that dreaded 2am call about a water damaged property, and let me tell you, it was a nightmare.  But what happened next is the real story. In this episode, we sit down with Darren Pet...

Ever wondered how hostels are redefining the travel experience? In this episode, I sit down with Nate St Cyr , the visionary co-founder of Malama Capital and Howzit Hostels, to uncover how he’s revolutionizing the traditional hostel concept. From daily pancake breakfasts and Margarita nights to crafting a vibrant, community-driven atmosphere, Nate shares his journey of turning a simple idea into a...

What happens when a passion for design meets the wild beauty of Joshua Tree?   In this episode, Rory Gill and I sit down with Dre Shapiro , a designer whose journey into short-term rentals is as inspiring as it is unexpected. Dre fell in love with a vacation rental in Joshua Tree, turned it into her own, and transformed it into a guest favorite through her incredible design sensibilities. We discu...

Ready to learn from one of the top short-term rental experts in the game? In this episode of the Smart Stay Show , we’re joined by Garrett Brown , the resident expert at Bigger Pockets, who shares his journey from hospitality to real estate success. Garrett reveals how his background in hotels and restaurants shaped his approach to managing multiple short-term rentals. He also talks about the impo...

Ever wondered how to transform your short-term rental into a family-friendly haven ? In the latest episode of the Smart Stay Show , Rory and I sit down with Fran Maier , CEO of Baby Quip, to explore how providing essential baby and toddler gear can elevate the guest experience. Fran shares her journey as a host-turned-innovator and how Baby Quip helps families travel light while ensuring hosts del...

What if you could reduce your reliance on OTAs, save money, and build a loyal guest base—all while maintaining complete control over your short-term rental business? That’s exactly what we’re exploring in this episode of The SmartStay Show ! Rory Gill and I sit down with Abby Grous , the Senior Product Manager of Direct at Hospitable, to unpack the power of direct bookings. From Hospitable’s innov...

Ready to take your short-term rental business to the next level? In this episode of the Smart Stay Podcast , Rory Gill and I chat with Punith Upadhya , the mastermind CEO of Moon Gaze Stays , who’s figured out how to run a world-class short-term rental operation from hundreds of miles away ! Puneet pulls back the curtain on his game-changing strategies, including how he’s built seamless systems, e...

In this episode of the Smart Stay Show , I sit down with Christina Melander , the founder of Knotty Pine Design and a talented short-term rental host, to discuss how she creates memorable guest experiences with a blend of budget-conscious, authentic design. Christina shares her insights on crafting distinctive, fantasy-driven vibes that stand out on listings and leave a lasting impression. We dive...

In this episode of The Smart Stay Show , we’re diving into the critical role of signage in short-term rentals. From the must-have Wi-Fi sign to rules about smoking, plumbing, and pets, this episode is packed with practical advice to help you create a seamless guest experience. We’ll discuss how to balance necessary information with tasteful design, avoid the pitfalls of overwhelming guests, and ev...

In this episode, we’re joined by the brilliant Justin Miller , co-founder of Showplace and a true trailblazer in hospitality design. Justin brings a wealth of experience to the table, having co-founded Pillow, a groundbreaking property management tech platform, and now leading Showplace, where he helps rental owners and investors create spaces that leave a lasting impression. Justin’s journey is a...

In this episode, We dive into the crucial role of location in short-term rental success. From being close to key attractions like beaches and national parks to considering the charm of quieter residential neighborhoods, I’ll walk you through the factors that can make or break your rental’s performance. I also share my experiences hosting in Provincetown, Massachusetts, and offer practical tips for...

In this episode, I’m joined by Jarrett Chouinard , the founder of Stellar Retreats , who shares his inspiring journey into the short-term rental world. Starting with just one arbitrage unit in Connecticut, Jarrett has grown his business into a thriving operation spanning multiple properties in New York, Rhode Island, and beyond. We’ll dive into his experiences with the challenges of the arbitrage...

In this episode, we’re thrilled to sit down with Brent Hieggelke, the visionary founder of Trustr, a groundbreaking platform redefining the short-term rental experience.  Brent brings decades of experience in the vacation rental world, and together, we dive into how Trustr taps into the power of social networks to create trusted, more personal guest-host connections. Say goodbye to renting to tota...

In this episode, we explore the intersection of travel, content creation, and short-term rental marketing with special guest Jordan Kahana, founder of Stayamo. As the lines between work and vacation blur, today’s creators are reimagining how destinations are experienced and showcased. Jordan explains how Stayamo connects properties with creators, making it easier for hosts to collaborate with stor...

Ever wondered what it’s like to live in a house full of entrepreneurs all driven to succeed? Meet Jesse Ray, the mind behind the "Growth House" concept, where like-minded professionals live, learn, and grow together under one roof. In this episode, Jesse Ray shares his journey from corporate America to real estate investing and the game-changing decision that sparked his success: building a commun...

Have you ever wondered if the skills you’ve developed in your day job could translate into a thriving business? Meet Mike Stone—a former corporate attorney who transformed his career, channeling his expertise into building a successful short- and medium-term rental empire. Mike’s journey began with an ambitious leap from the legal world into vacation rentals, and his success speaks to the power of...

Today, we're thrilled to welcome Andrew Rodriguez, the co-owner of Stay Booked, a full-service short-term rental management company. Andrew and his wife, Lindsay, have built an impressive portfolio of larger, unique vacation homes in sought-after destinations like the Poconos.  What sets Andrew and his team apart is their unwavering commitment to quality over quantity. From the moment a guest lays...

In today’s episode, I’m excited to introduce you to a truly inspiring figure in the vacation rental industry, Rose Tipka. Rose isn't just a successful short-term rental host; she's a homeschooling mom of six who's managed to build a multi-million-dollar portfolio while maintaining an admirable work-life balance. Her journey into vacation rentals started unexpectedly when her husband purchased thei...