Behind the Stays

Meet Michael Romanowicz, the founder and CEO of DEN Outdoors .  Mike is a software designer by trade, but has always had a love for the natural world. So, when he wasn’t busy leading the product team at Conductor, which was a content marketing platform owned by WeWork, Mike was tinkering with some designs for a minimalist, beautiful cabin he could build in the woods one day. After sharing his desi...

Meet Chase Charifa, the creator of the Lightfoot Cabin — a cozy, unique escape nestled in the foothills of Big Bear Mountain in Southern California.  A few years ago, Chase and his wife April started a production studio as a side hustle.  The couple regretted not having a videographer at their wedding and this inspired them to start their own studio to shoot weddings and events. In doing research...

Welcome to another Marketing Mondays on the Behind the Stays podcast feed! In this episode we chat ALL about SEO and how Airbnb hosts can leverage the power of great keyword research to increase their organic rankings on Google.  In today's lesson we share a lot of screenshots and data...so...you MAY wish to WATCH this episode on YouTube, which you can do here: Stream Marketing Mondays on YouTube...

Meet Brooke Pfautz , founder and CEO of Vintory — a sales and marketing platform exclusively dedicated to helping professional vacation rental managers and short-term rental entrepreneurs grow their inventory.  Brooke built one of the largest mortgage banking firms in the DC Metro Area, but when the financial crisis of 2008 hit, Brooke began to reconsider what it was he wanted to do with his life....

Welcome to Marketing Mondays — a new, weekly segment on the Behind the Stays podcast that covers specific marketing strategies and tactics that Airbnb hosts and hospitality entrepreneurs can immediately use to promote their stays.    On this second episode of this new Behind the Stays segment, Zach covers: Why you should build a website for your Airbnb even if you don't have a direct booking site...

Meet Levi Kelly — a creator whose cabin tour videos have garnered nearly 80 millions views on YouTube. Growing up, Levi used to goof around and shoot funny videos with his buddies and then edit them on the iMovie app on his phone. In high school he realized that shooting and editing video was more than just a hobby of his…it felt like something he was destined to do. After successfully landing a f...

Meet Whitney and Andrew Bradberry, the creators of the Front Range A-Frame in Bailey, Colorado, just an hour outside of Denver.  Whitney is a freelancer marketer by trade, and her husband Andrew is a firefighter paramedic.  Given their non-traditional jobs, the couple has always enjoyed tinkering on creative projects together. Whitney’s father loved Colorado and it’s because of him that she fell i...

Welcome to Marketing Mondays — a new, weekly segment on the Behind the Stays podcast that covers specific marketing strategies and tactics that Airbnb hosts and hospitality entrepreneurs can immediately use to promote their stays.  On the first episode of this new Behind the Stays segment, Zach covers: Why you should work with creators A framework for how to discern who to work with and how to wor...

Meet Emily South — the creator of The Appalachian A-Frame in Sugar Grove, North Carolina just 20 minutes outside of downtown Boone. Emily and her husband John are entrepreneurs.  Emily is a yoga instructor and John owns and runs a production studio. Given their non-traditional career paths, Emily and John don’t have some of the benefits one might expect from a 9-5 such as a 401k match or stock opt...

Meet Jamie Kraus, the creator of Chestnut Hill — a beautiful appointed home located 5 minutes from Main Street in Breckenridge, Colorado.  Jamie and her husband have three young adult sons and live in the great state of Texas.  Growing up, Jamie would vacation in the Colorado mountains with her family and dreamed of one day owning a home in Breckenridge. A few years ago, Jamie was diagnosed with b...

Meet Chris Broomfield, the creator of Evergreen Cabins — one of Instagram’s favorite collections of luxurious cabin rentals in the Adirondacks. Growing up, Chris loved to tinker. At the age of 14 he started building picnic tables and bar stools with his next door neighbor that he’d sell to local patrons. It was at this young age that Chris realized he wanted to work for himself…that he wanted to b...

Meet Tiffany Lund — the creator of The Havarti Haus , an accessible, Scandinavian-style retreat in the White Mountains of New Hampshire, opening in late 2023. Tiffany and her family love to go on adventures — the outdoors has always been a place of restoration and reinvigoration for them. Tiffany and her husband Jim have an incredible son named Morty.  Morty, like his parents, loves the outdoors. ...

Meet Mike Iannetta, better known as Mike Will Travel, a YouTube creator and hospitality marketing specialist. Mike started his first business at the age of 17.  He raised $5,000 on Kickstarter to start what he thought would be the next big board shorts brand. Now, the clothing line didn’t quite pan out, but it solidified for Mike that he wanted to spend his career starting and running his own busi...

Meet John Andrew Entwistle, Founder and CEO of Wander, one of the most exciting startups in the travel and hospitality space today.  John Andrew had a non-traditional schooling experience.  He started and ran a game server company when he was just 13 years old, so focusing on homework wasn’t a high priority.  In high school, John Andrew and his father agreed that an online option would be best for...

Meet Ty and Mary, the creators of The Northwoods A-Frame and Tiny Cabins near Itasca State Park in northern Minnesota.  Ty and Mary both have demanding jobs – Ty is an architect and Mary a nurse. So, in October 2020, after months of lockdown, the couple was in dire need of a getaway. Mary had been following an A-Frame on Instagram for a few months and decided to plan their getaway around when the...

Meet Addie Wales, the creator of The Ely Cabin Collective — a boutique collection of Airbnbs near The Boundary Waters Canoe Area Wilderness in Minnesota.  Growing up, Addie always wanted to be an entrepreneur. She remembers pitching her first business to her dad as a 10 year old which was for an ice cream shop where the roof of the shop was shaped like an ice cream cone!  In the fall of 2020, Addi...

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...