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

💡 What if there’s a way to slash your tax bill while building real estate wealth —without buying a single new property? In this episode, we turn the spotlight on one of the most powerful, yet often overlooked, wealth-building tools for investors: tax strategy . Eric Oliver of Maven Cost Segregation to break down, in plain English, how cost segregation and 100% bonus depreciation can dramatically...

💡 Tired of losing revenue to Airbnb and Vrbo? What if you could connect directly with guests and keep more of your profits? Today, we sit down with Eric Goldreyer , CEO and founder of Savvy , to explore the future of direct bookings in vacation rentals. Eric shares how Savvy’s book-direct marketplace empowers property managers to connect travelers straight to professionally managed properties—oft...

What happens when a lifelong teacher realizes the classroom isn’t the only place she can make an impact? Today we sit down with Colleen Coale , co-founder of Hurford Place Hospitality, to unpack her journey from elementary school teacher to running 90% of a fast-growing short-term rental management company in Pennsylvania’s Pocono Mountains. Colleen shares the mindset shift that moved her from “I’...

What if the smartest move in real estate isn’t buying more… but selling at the right time? In this episode, we do something most investors avoid — we talk honestly about letting go . They share the real reasons behind their decision to sell one of their short-term rental properties and unpack the uncomfortable questions every investor eventually faces but rarely discusses. Joined by their friend a...

Ever wondered what makes a short-term rental truly unforgettable? Some hosts swear by bold color schemes, while others lean into quirky themes, but what really drives bookings and keeps guests coming back? Today, we sit down with renowned designers Bri West and Jordan McDonough here on SmartStay Show to explore the art and strategy of standout short-term rental design. Discover how bold color, ima...

What actually makes one short-term rental crush it… while another barely books? Today we sit down with Kenny Bedwell, a former data analyst turned short-term rental expert, to unpack what truly separates top-performing properties from the rest. We talk about why blending in is the fastest way to lose (and why your rental needs its own “Impossible Whopper”-style edge), how Kenny’s investment strate...

What does it really take to build a short-term rental business that supports the life you want? Today we sit down with special guest Dan Rivers from Synergy Stays as they unpack the real motivation behind Dan’s journey, from real estate sales to revenue management expert, all driven by the goal of creating a truly mobile lifestyle. In this episode, Dan shares practical pricing strategies, why list...

What does it really take to stay ahead as short-term rentals and property management continue to evolve? In this episode, we sit down with Pierre-Camille Hamana , CEO of Hospitable , for a candid conversation about where the hospitality industry is headed and what hosts need to be thinking about right now. We dive into real-world strategies around automating guest communication, using dynamic pric...

Can intentional design actually boost your short-term rental profits? Find out in this week’s episode featuring Vacation Rental Design Strategist Erica Dike . We dive into why the most successful rentals combine eye-catching style with smart strategies for ROI . Erica shares her journey from student Airbnb host to expert designer, offering actionable tips for balancing personal taste with guest ap...

Is going solo really the best way to scale a short-term rental business—or can the right partnership take you further, faster? In this episode, we sit down with Evan Davison and Evan Montgomery to unpack what actually happens when two ambitious operators decide to merge their short-term rental businesses. We talk openly about dividing roles using the visionary and integrator model, building trust,...

What does it really take to scale a short-term rental business, and when does “more” stop meaning “better”? In this episode, we sit down with Blake and Jeremy from Cribs Consulting, the powerhouse duo behind one of Austin’s most respected short-term rental operations. We dig into their journey from managing just three Airbnbs to nearly a hundred properties, and the surprising decision to intention...

What really makes a short-term rental unforgettable—and consistently five-star worthy? In this episode, we sit down with Allegra Muzzillo—editor-turned-designer, superhost, and one of the sharpest minds in STR design—to uncover the secrets behind creating guest-ready spaces that truly stand out. Allegra shares her fascinating journey from the fast-paced world of NYC publishing to crafting beautifu...

How do you turn a rustic flower farm into the Northeast's most enchanting glamping experience? On this episode, I step into the heart of the Vermont woods to chat with the incredible Melissa Hessney Masters , the creative force behind Tangle Bloom . This conversation is all about transformation: how Melissa took a rustic flower farm and her deeply imaginative spirit and turned it into one of t...

Ever wonder what it really takes to walk away from a steady W2 and reinvent your life in real estate and short-term rentals? In this episode, host Jason Muth sits down with Jeremy De Grasse for an honest, inside look at how they each stepped out of corporate careers and built thriving businesses in the stunning Adirondacks. Together, they dive into the lessons learned the hard way, the juggling ac...

What happens when a pro athlete walks away from the game and builds an entirely new kind of success? In this episode, I had an in-depth conversation with former MLS goalkeeper Spencer Richey to explore his remarkable transition from the world of professional soccer to thriving real estate entrepreneur . Spencer shares the pivotal mindset shift that allowed him to step away from sports, the courage...

Ever wondered what it really takes to make a vacation rental truly pet-friendly—and profitable? 🐾 In this episode, we sit down with John Bradford and Mike Shytle from Petscreening to unpack the world of pet screening and what it means for both hosts and guests. We dive into how hosts can build trust with pet-loving travelers while navigating the practical and legal challenges that come with allow...

What happens when an ice cream shop owner decides to reinvent hospitality in the heart of bourbon country? 🍨🥃 In this episode, we sit down with Andrew Llewellyn , the creative force behind some of Louisville’s most exciting group-focused short-term rentals. From transforming forgotten commercial buildings into stylish hangout destinations to curating unforgettable experiences for bachelor partie...

Ever wondered what it takes to leave a tech career and build a thriving short-term rental business? In this episode, Morgan Steir joins me to share his journey from tech sales to managing a successful lakeside cabin in New Hampshire. Hear his honest insights on self-managing rentals, launching a home services franchise, and mastering everything from guest experience to vendor challenges. A must-li...

What makes some short-term rental listings instantly irresistible while others get scrolled past? 🎥 Join us and real estate photographer Kaylee DeCollibus as we dive into the secret sauce of standout listings — professional photos! Discover how eye-catching imagery goes beyond first impressions to shape guest experience, drive bookings, and capture a property’s true vibe. From creative staging to...

In this episode, we sit down with Ben Koons from Keystone Bookkeepers to unpack the unique challenges of managing finances in the short-term rental world. From early days of DIY spreadsheets to implementing professional systems, they explore what it takes to build scalable, stress-free bookkeeping practices for growing portfolios. Jason and Ben also break down Airbnb’s new fee structure, share pra...

What if the key to short-term rental success isn’t just location, but insight? In this episode, we sit down with Jamie Lane, Chief Economist at AirDNA, for a masterclass on data-driven investing in the STR space. From his roots as a self-proclaimed “data nerd” to becoming a hands-on host himself, Jamie shares how powerful analytics and real-world experience intersect to shape smarter investment st...

What happens when an ICU nurse brings his heart for care into the world of short-term rentals? In this episode, we sit down with Jeremy Rosen, who’s turned his passion for helping people into a thriving business managing over 20 properties—all while still working hospital shifts. He shares how compassion, clear systems, and smart tech have helped him scale without losing the personal touch. From b...

Is the future of hosting all about midterm rentals? In this episode, we chat with Katie Lyon from Furnished Finder to uncover why midterm stays are gaining major traction—and why they’re no longer just for travel nurses. From contractors and relocating families to corporate nomads, a whole new wave of guests is looking for furnished, flexible housing options. Katie shares real-world strategies to...

Ever wonder how a beachfront condo in Provincetown could become a gold mine? In this episode, we sit down with Kareem Sanjaghi—Prideaway Stays’ very first client—to hear how he went from mortgage officer to full-time musician and savvy real estate investor. Kareem shares the story behind his short-term rental success, the importance of location in the Cape Cod market, and the ups and downs of mana...

What if one tool could organize your entire short-term rental business—and actually give you your time back? In this episode, we sit down with hospitality veteran turned systems expert Michael Dinwiddie to talk about the real-world challenges of managing short-term rentals and how the right systems can transform your operation from chaos to calm. Michael shares how he uses Notion as a “second brai...