What if your real estate business was designed to serve your life — not run it? In this episode, we chat with Fouad Bazzi, a former banker who left the corporate world to build a thriving short-term rental business centered around freedom, family, and purpose. He shares how he scaled his operations, mentors the next generation (including his own kids), and shifted from chasing work-life balance to creating true work-life unity. This isn’t just about real estate — it’s about building a values-dri...
Jul 01, 2025•44 min•Season 1Ep. 260
What if your next real estate deal could help you eliminate capital gains taxes—while building a thriving short-term rental business? In this episode, tax strategist Ashley Tison dives into the powerful world of Opportunity Zones and how investors can use them to unlock huge tax advantages. These zones aren't just distressed areas—they include beachfront properties, university towns, and booming urban districts. Ashley explains how to transform a property in an Opportunity Zone, count even furni...
Jun 24, 2025•34 min•Season 1Ep. 259
What does it take to turn a small real estate side hustle into a global corporate housing empire? In this episode, we sit down with Gary Brown and his son Ken Brown of Furnished Quarters to explore their incredible journey from NYC real estate investors to international leaders in corporate housing. With roots in their family’s furniture business and a knack for strategic growth, this father-and-son duo has helped shape the company’s expansion from a few furnished apartments in Manhattan to a gl...
Jun 17, 2025•33 min•Season 1Ep. 258
What does it take to grow from managing one small rental to overseeing 40+ short-term properties in just seven years? In this episode, we sit down with Alex Steeg, a short-term rental entrepreneur who's built a thriving business across Boston’s North Shore. His journey is nothing short of inspiring—from starting with a modest two-family property to managing a diverse and growing portfolio. Alex shares how his early career in residential advising unexpectedly prepared him for the world of propert...
Jun 10, 2025•56 min•Season 1Ep. 257
Want to turn your vacation rental into an unforgettable adventure that guests can’t stop talking about? In this episode of the SmartStay Show, we sit down with Rachel DeSantis — the mastermind behind QR Clue, a groundbreaking in-home escape game that transforms ordinary short-term rentals into immersive, puzzle-filled experiences! Imagine your guests stepping into a thrilling story where they solve clever puzzles, uncover hidden clues, and win prizes — all through simple, strategically placed QR...
Jun 03, 2025•29 min•Season 1Ep. 256
Feeling “equity rich” but still cash strapped? You’re not alone—and there’s a smarter way to break free. In this eye-opening episode, We sit down with Certified Financial Planner Alan Franks to explore how real estate investors can unlock hidden capital, boost returns, and build lasting wealth. Alan shares powerful strategies for using tools like home equity lines of credit and securities-based lending to access cash without selling off valuable assets. He also sheds light on how the post-COVID ...
May 27, 2025•44 min•Season 1Ep. 255
What happens when a frustrated Airbnb host builds a tool to solve his own problem—and ends up launching one of the most influential platforms in short-term rentals? In this episode, we sit down with Pierre-Camille Hamana, CEO and founder of Hospitable, to explore his surprising journey from law school dropout to tech entrepreneur. What began as a simple solution to automate guest messaging for his own rental has grown into a powerhouse property management platform supporting tens of thousands of...
May 20, 2025•47 min•Season 1Ep. 254
What Happens When Your Airbnb Becomes a Disaster? Join us as we sit down with Andy Gurczak, a seasoned public adjuster and new short-term rental owner, to explore the often-overlooked world of insurance claims for vacation rentals. In this eye-opening episode, Andy reveals insider tips on protecting your property and why your standard homeowner's insurance policy might not have your back when you're hosting on platforms like Airbnb. From how one plumber's report can make or break a claim, to the...
May 13, 2025•39 min•Season 1Ep. 253
Did you know your short-term rental could be a powerful tax-saving machine? In this episode, We sit down with Sean Graham—CPA, real estate investor, and cost segregation expert—to uncover how vacation rental owners can legally slash their tax bills using smart depreciation strategies. From bonus depreciation and the short-term rental loophole to material participation rules, Sean breaks down complex tax concepts in a way that actually makes sense (yes, really!). You'll learn how the IRS actually...
May 06, 2025•41 min•Season 1Ep. 252
Are you ready to find your next cash-flowing short-term rental property — and actually know it’s a winner before you buy? In this episode, We sit down with John Bianchi, the self-proclaimed "Airbnb Data Guy," who's helped uncover over 200 profitable STR properties. John pulls back the curtain on how to spot the best markets, why understanding local regulations is critical, and how effective marketing can make or break your rental’s success. You'll learn John's two-step method for market selectio...
Apr 29, 2025•49 min•Season 1Ep. 251
Are you putting all your hosting eggs in the Airbnb basket? What if there's a smarter way to grow your short-term rental business? In this eye-opening episode, we sit down with Mark Simpson, founder of Boostly and one of the world’s top experts in direct booking strategies. From running a family farm stay to becoming a global authority on short-term rental marketing, Mark’s journey is as inspiring as it is informative. Discover why relying solely on one platform can be a risky move—and how you c...
Apr 22, 2025•43 min•Season 1Ep. 250
Are you leaving money on the table with your short-term rental? In this episode, We sit down with CPA and tax strategist Anne Gannon to uncover the often-overlooked financial advantages of real estate investing. Anne simplifies complex tax topics and reveals how savvy investors use short-term rentals not just for income—but to build long-term wealth. From depreciation strategies to smart tax planning, you'll learn how to make the most of your property and use the tax code to your advantage. Whet...
Apr 15, 2025•40 min•Season 1Ep. 249
"What if your vacation rental came with VIP treatment?" Dive into the world of luxury short-term rentals with Kevin Duran, founder of JKW Vacation Club. In this episode, we explore a game-changing approach to vacation stays—one that goes beyond traditional Airbnb bookings. Kevin shares how his innovative membership model offers travelers a full concierge experience, including airport shuttles, grocery delivery, and exclusive local experiences. For property owners, JKW provides a powerful marketi...
Apr 08, 2025•30 min•Season 1Ep. 248
Is Your Short-Term Rental Truly Welcoming to All Guests? In this must-listen episode, we sit down with Mrs. Schneider, an expert who understands the real challenges travelers with disabilities face. They uncover practical, budget-friendly ways to make your rental more accessible—like installing lever door handles, modifying bathrooms, and making small yet impactful changes. With nearly 70 million Americans living with disabilities, creating an inclusive space isn’t just the right thing to do—it’...
Apr 01, 2025•40 min•Season 1Ep. 248
Would You Quit Your 9-to-5 to Build a Short-Term Rental Empire? Payton Cummings did exactly that—leaving behind a steady paycheck to scale a thriving 17-property short-term rental business! In this episode, she shares her journey from corporate consulting to full-time entrepreneurship, the mindset shifts that made it possible, and how community and strategy helped her think bigger. If you're dreaming of turning your side hustle into a sustainable business, this episode is packed with real insigh...
Mar 25, 2025•35 min
Ever wondered if one spontaneous decision could completely change your career? That’s exactly what happened to Jayla Siciliano. While on vacation, she crunched the numbers on a short-term rental, saw its potential, and the next day, put in an offer on her first property. In this episode of SmartStay Show, Jayla takes us through her journey from that impulsive purchase to building a thriving short-term rental business across multiple states. We dive into the challenges of managing properties remo...
Mar 18, 2025•35 min•Season 1Ep. 245
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 colors, eye-catching murals, and Instagrammable moments that make listings pop. Whether you're a new hos...
Mar 11, 2025•31 min
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 world of short-term rentals. As experienced guests, they dive into what makes a great host, the importance...
Mar 04, 2025•1 hr
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 rentals in Bartlett, New Hampshire: Summit Vista, a condo with breathtaking views, and Lift House, a sough...
Feb 25, 2025•56 min
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 style, responds like you (yes, even with emojis! 😎), and frees up your time. Hosts with 1-10 listings get...
Feb 18, 2025•34 min•Season 1Ep. 241
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 decisions. David shares insider tips on leveraging your property’s equity and why guest experience is more crit...
Feb 11, 2025•36 min•Season 1Ep. 240
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 secrets for success. Plus, we explore how his martial arts background has shaped his mindset for resilience...
Feb 04, 2025•43 min•Season 1Ep. 239
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 booking confirmations to review requests, we share a 5-step strategy to keep your guests informed an...
Jan 28, 2025•37 min•Season 1Ep. 238
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 Pettyjohn, the co-founder of Proper Insurance, to unpack why short-term rental insurance is so crucial -...
Jan 23, 2025•42 min•Season 1Ep. 236
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 thriving hospitality brand. We dive into how Generation Z’s desire for connection inspired his appro...
Jan 21, 2025•42 min•Season 1Ep. 237
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 discuss her unique approach to creating unforgettable guest experiences, from curated book collections and v...
Jan 07, 2025•37 min•Season 1Ep. 235
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 importance of staying positive, adapting quickly, and creating consistent content—even when it doesn’t yie...
Jan 02, 2025•48 min•Season 1Ep. 234
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 deliver a seamless stay. From reducing guest packing stress to offering promo codes and affiliate opportun...
Dec 30, 2024•31 min•Season 1Ep. 233
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 innovative tools to real-world strategies for maximizing revenue, we cover everything you need to know abou...
Dec 23, 2024•43 min•Season 1Ep. 232
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, empowered his local team, and mastered the art of delivering unforgettable guest experiences. Plus, he re...
Dec 17, 2024•48 min•Season 1Ep. 231
