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

Can Last-Minute Bookings Actually Boost Your STR Revenue? Last-minute bookings aren’t just a backup plan anymore—they’re becoming a key revenue strategy for short-term rental hosts. In this episode, we sit down with Alex Alioto, co-founder of Whimstay, about how shifting traveler behavior—especially among Gen Z and millennials—is reshaping the way hosts think about occupancy, pricing, and calendar...

What does it really take to break free from the 9-to-5 and build a thriving short-term rental business? In this episode, We sit down with Jake Martin, a former corporate professional who left the security of his W2 job to chase a different kind of success—one built on freedom, flexibility, and financial independence. Jake opens up about the real story behind his transition: the fears, the failures...

What if you could run a thriving real estate business from anywhere in the world—without ever setting foot in most of your properties? In this episode, we sit down with Adrienne Green, a savvy real estate investor who turned house hacking into a passport for full-time travel with her family. She shares how she built rock-solid systems, empowered virtual assistants, and mastered the art of delegati...

What does it take to turn a remote West Texas ghost town into an Instagram-worthy short-term rental experience? In this episode, discover how a former NYC creative director brought his branding expertise to the desert to create the cinematic Ghost Town Casitas. Learn how storytelling, design, and photography come together to craft rentals that offer more than just a stay—they deliver an unforgetta...

Ever wondered what it really takes to leave your 9–5 and build a successful short-term rental business on Cape Cod? 🌊🏡 In this episode, we sit down with Matt Cutler, who made the bold leap from a traditional W2 career to creating a thriving STR operation in one of New England’s most iconic vacation destinations. Matt pulls back the curtain on the emotional and financial realities of leaving corp...

What does it take to walk away from a high-paying corporate job and build a 50+ property short-term rental empire? In this episode, I sit down with real estate investor and coach Matt McCall Stillman, along with attorney and legal expert Rory Gill, for a powerful conversation about what it really takes to succeed in the short-term rental world. We dive into Matt’s journey—how he went from corporat...

Ever wonder what it really takes to pack up your life, move to a new city, and build a short-term rental business from scratch? In this episode, We sat down with my friend Chachi Horgan — a former real estate agent from Maine who took a leap, moved to Florida, and built Roam Ready Vacation Rentals, scaling to 11 properties in less than two years. We talk about everything — the mindset it took to s...

Can a side hustle built on friendship and a love of travel become something bigger? Join Jason Muth, Rory Gill, and Ethan Sobel as they share the real story behind Prideaway Stays , their co-hosting venture in Provincetown. From a family dream of owning a Cape home to building a guest-first rental brand, this episode dives into the heart of short-term rental hosting. Discover how they scaled their...

What if your best-performing Airbnb was sitting just a mile away—and you almost missed it? In this episode, we talk with Jeremy Beland, a real estate investor who made the leap from wholesaling to building a killer short-term rental portfolio in Port St. Lucie, Florida. He shares how one overlooked pocket became home to his top-performing property—and why hyper-local strategy matters more than mos...

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 t...

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 u...

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-s...

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 s...

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 so...

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 le...

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 h...

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...

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 com...

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 mark...

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 inspirin...

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 plan...

"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, g...

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...

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 dream...

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 sho...