Behind the Stays

Meet Justin and Shaun — the creators of The Chal-A Frame , a beautifully curated escape nestled between the Stratton and Mt. Snow ski areas in Vermont. Justin and Shaun are both architects.  They were roommates in college and have been close friends ever since. One day while hanging out with the rest of their crew, Justin and Shaun got really excited about the possibility of having a place in the...

About the Episode: Meet Melissa Hessney Masters — the founder of Tanglebloom and the creator of the Tanglebloom Cabin .  Melissa has always been creative.  Growing up in the fingerlakes region of New York,  she found herself mesmerized by natural beauty — whether it be wildflowers or waterfalls, Melissa was transfixed by the innate purity of the natural world.  She started her first business when...

Meet Connor Gross — an entrepreneur in his mid-twenties who is currently focused on building a portfolio of self-storage units across the state of Texas. Connor graduated from Northeastern University in 2020.  As a part of a co-op program at Northeastern, he was able to spend a semester building his first start-up, Cardly , with his co-founder Giovanni, which was a snazzy looking credit card holde...

In just a moment, you’ll meet Natalie Palmer — an Airbnb Ambassador, a 17x superhost, and the creator and host of the popular No Vacancy podcast.  Natalie was never really sure what she wanted to do when she “grew up”...but she was always quick to say “yes” when opportunities to step outside of her comfort-zone surfaced.  So, after spending a couple of months learning about short-term rental inves...

Meet Alexis and Skeeter — the creators of The Kingdom A-Frame, a quintessential New England escape in Burke, Vermont.  Alexis and Skeeter love mountain biking and have traveled to Northeastern Vermont to traverse the Kingdom Trails for years!  These trails are known as the crown jewel of East Coast mountain biking. Alexis and Skeeter have three dogs and struggled to find an Airbnb that both allowe...

Meet Damian Sheridan, founder of The Book Direct and Scale Rentals Shows — a couple of the leading events for short-term rental hosts and property managers interested in building their direct booking strategies. Growing up, Damian wanted to be a professional footballer…but, he quickly learned that in addition to passion for the game, you needed the skill as well! Years later while working at a tra...

Meet Janice Smith, the creator of the Cozy Rock Cabin ( @cozyrockcabin ), a 750 square-foot cabin on 3 acres of wooded land in Freeport, Maine. Janice has always had a knack for project management — and this skill has served her well as she led an ed-tech startup, launched her own video production agency, and brought not one, not two, but three cozy Airbnbs to life.  Now Janice has used instagram...

Meet Sara Roitman,  the creator of Field and Lake , a new collective of boutique vacation rentals on the shores of Lake Michigan. Sara is an attorney by trade and lives in Chicago with her beautiful family.  A few years back, Sara and her husband had purchased a vacation home on Lake Michigan so that they could escape from the city with the kids for long weekends and a couple of weeks each summer....

Meet Ethan Abitz — one of the OG Airbnb Instagram Influencers. Ethan first started using Instagram in high school to promote an apparel line he started. This was when Instagram let you upload a photo and select from just a handful of filters before posting your shot — no stories, reels, etc. In college, Ethan thought he wanted to work on Wall Street. He was interested in finance and investing and...

Meet Spenser and Marcy Kernea, the creators of the Retreat at Fall Branch Falls , a pristinely crafted escape in Georgia’s Blue Ridge Mountains.  Spenser has always been a big dreamer.  And while Marcy is fond of big ideas herself, she often has to counterbalance Spenser’s idealism with just a smidge of realism. Spenser once had this grand idea of opening up an authentic Italian gelateria in Tenne...

In just a moment you’ll meet Jamie Lane , Vice President of Research at AirDNA . After spending a decade at CBRE, one of the country’s largest American commercial real estate services and investment firm, Jamie was itching for a change…   He had always loved the hospitality space, and the short-term rental space in particular, so when he got a call from Scott Shatford the founder of AirDNA about j...

Meet Emir Dukic, founder and CEO of Rabbu. Rabbu helps investors find and manage short-term rentals.   Emir started working in tech via a cold email.  He reached out to the founder of Kick, which was a social network dedicated to talking about all things soccer, asking if he could help the company grow in any way. He started volunteering for the company, was eventually hired, and then worked his w...

In just a moment you’ll  meet Evan Dolgow, Head of Predictive Hospitality at Jarvis ML.  Jarvis ML was founded by the guys over at Google who built the machine learning platforms powering Google Ads and Payments.  Evan and his team have a vision of democratizing the data and technology that OTAs have and making these tools and insights accessible to short-term and vacation-rental hosts in order to...

Meet Lauren and Cam Green, the founders of The Fort Treehouse Company — Canada’s premier luxury treehouse company. Cam and Lauren met at summer camp.  They were a part of the same friend group for more than 15 years before they started dating, but once they did, it was clear that they were a perfect match. Both Lauren and Cam are quite entrepreneurial.  Lauren tends to have the big ideas and Cam i...

Meet Ali Nichols — Co-Founder of Getaway . Getaway is on a mission to make vacation rental real estate accessible to the next generations  of investors and to reimagine travel memberships by allowing investors to stay in the premier homes they own.  Ali has been interested in real estate since she was a young child.  She’d come home on Sunday mornings after church and circle listings in the newspa...

Meet Heather Davis, the creator of the Stone City Treehouse in Hardwick, Vermont. Heather grew up in New York but always had great affinity for the Green Mountain State — so much so that her only criteria for where to go to college was that it had to be in Vermont.  In 2012 Heather started renting her home on Airbnb in order to help pay the bills. Being a single mom with two teenagers in Vermont w...

Meet Daniel Rusteen.  Daniel is the self-proclaimed “world’s best at Airbnb.” And before you laugh or roll your eyes, he’s got a pretty solid case for why this title is fitting.  Daniel worked at Airbnb for several years, launched his own Airbnb property management business, is building his own collection of luxe Airbnbs, has a plethora of courses, tools, and resources he’s developed for Airbnb ho...

Meet Nate Ritter — founder of Room Steals, a travel membership that provides customers with incredible deals on hotel rooms. Nate is a technology executive who has started, bought, and sold companies and who has also consulted for companies like Microsoft and Land Rover. Fun fact — Nate also popularized the use of the hashtag on Twitter…pretty cool, huh?  In this episode, we talk about: Where the...

Meet Bryce Garcia.  Bryce works in sales for a SaaS company by day and is building his own collection of STRs by night. When Bryce’s mom found out he had bought a condo in Austin,  site unseen, during the middle of the pandemic, and planned to live in one room and rent out the other on Airbnb she thought he had gone NUTS. But when Bryce made enough money over one holiday weekend to pay his mortgag...

Meet Jon Kreye — an award-winning Airbnb and VRBO photographer. Growing up, you’d often find Jon in the backyard snapping photos of trees, flowers, and wildlife — he has always been moved by the beauty nature offers.  Jon dreamed of being able to do photography full-time, but was sober to the fact that making it as a full-time photographer is super difficult. One day, while traveling in Minnesota,...

In just a moment you’ll meet Joel Holland , CEO of Harvest Hosts —  an RV membership program that allows travelers to stay overnight at unique locations around the country including farms, wineries, breweries, and more. Joel is what you might call a creative hustler.  As a young teenager, you could either find him selling DVDs and books on eBay or out and about shooting video.   Joel loved capturi...

Meet Tyann Marcink  — the Queen of Guest Experience at Touch Stay , a digital guidebook platform for short-term and vacation rental hosts.  Tyann has a knack for charting her own path. She’s a resilient creative who owns 2 rental management brands and has been active in the vacation rental industry since 2007. Discover Tyann’s hot takes about the future of the hospitality industry, hear the story...

Meet Marcus Rader — Founder and CEO of Hostaway .  Marcus grew up in Finland.  He was quite a curious kid, but struggled to develop any lasting hobbies as he was easily distracted. After flying for the first time as a six year old, Marcus’ dream was to become a pilot.  Something about being at 30,000 feet was inspirational and invigorating.  Sadly, Marcus was diagnosed with epilepsy just a few yea...

Meet Marc Hostovsky, Founder and CEO of Minoan —  a customizable, curated retail platform for short-term rental hosts.  Marc is a self-proclaimed boutique geek and is passionate about the future of retail.  After spending nearly 6 years working at Jet.com and then Walmart (acquired Jet.com), he quickly realized that the best product experiences don't happen on screens or shelves, they happen in re...

In just a moment you’ll meet Heather Bien and Adam Shapiro, the creators of Rosehill Cottage — a charming river house on the Rappahannock River in Virginia.  Heather works in marketing at a tech start-up by day and runs her lifestyle and travel blog by night, and Adam works for the federal government.   While the couple lives in Washington DC, they thoroughly enjoy weekend escapes from the city. ...