Behind the Stays

Latest Episodes:

He’s a Doctor by Day, a Twin Girl Dad at Night, and an STR Entrepreneur In-Between Jun 14, 2022

Show notes

In just a moment, you’ll meet Billy Chu — owner of The Blue Bungalow, a chic escape in Palm Springs, California.

Billy and his wife Becky are both doctors who live in Los Angeles and parents to young twin girls.

A couple of years ago, Billy and Becky joined an online community of medical professionals who invest in real estate in order to learn more from their peers about the industry.

In early 2021 they stepped into the longer-term rental game by purchasing a couple small multifamily properties.

But the couple really wanted to try their hand at short term rentals and had been eyeing properties in Palm Springs.

Here was the problem — getting into the short term rental game in the fall of 2021 when the real estate market was going bananas seemed all but impossible.

But after consuming dozens of hours worth of STR podcasts, losing out on multiple bids, and almost throwing in the towel, they discovered the home which they now call theirs.

Tune in to hear the story behind how Billy and Becky bought a 4 bed, 3 bath property 5 minutes from downtown Palm Springs and transformed it into The Blue Bungalow.

Book your stay at The Blue Bungalow

Book your stay at The Salty Saguaro

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

Guesty For Hosts allows short-term rental hosts to manage listings from Airbnb, VRBO, and Booking.com in one calendar and send a series of automated messages before, during, and after their stay. The platform also has features that help you manage cleanings, build a custom booking website, and so much more. Start your 14 day free trial today — no credit card, set up fee, or commitment required — and cancel anytime if you don't love it. While getting started, use the discount code “SPONSTAYNEOUS” for 20% off of your first year." Behind the Stays is brought to you each week by Sponstayneous — a free, biweekly newsletter that brings subscribers the best last-minute deals and upcoming steals on Airbnb. You can subscribe, for free, at www.sponstayneous.com

314,000 People Applied for Airbnb’s Live Anywhere Contest — And They Won. Meet the Family Traveling the World and Living Full-Time on Airbnb. Jun 07, 2022

Show notes

Meet Stephanie Hays and Peter Woolcock — winners of Airbnb’s Live Anywhere contest.

Last summer, Airbnb announced that they were looking for 12 individuals who’d be willing to live full-time via stays booked on their platform for a year — and over 314,000 applicants from all around the world applied for this once in a lifetime opportunity.

One of the 12 selected was Stephanie Hays. Stephanie and her husband Peter are no strangers to travel — in fact the couple first met each other in a bar in Shanghai!

Since then, they’ve traveled to more than 70 countries and lived abroad on a number of occasions.

Most recently, Steph and Pete were living in Chattanooga, Tennessee along with their toddler son, Hays. When she heard about the contest something told Stephanie that she just had to throw her hat into the ring.

And, well, that something was right.

Tune in to hear the incredible story behind what this young family has learned after 9 months of living around the globe on Airbnb.

You can follow their travels on Instagram here

You can watch their travel vlogs on YouTube here

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

He’s An Accountant, Artist, and Airbnb Superhost — Meet Isaac French the Creator of Live Oak Lake Jun 03, 2022

Show notes

Meet Isaac French, the creator of Live Oak Lake, a collection of seven stunning cabins nestled around a small lake in Waco, Texas.

Isaac is what you might call a curious creator. He was homeschooled growing up and his parents enabled him the freedom to pursue a plethora of interests — from art, to architecture, and accounting to entrepreneurship.

Isaac comes from a family of entrepreneurs and learned a lot about business, architectural design, and general contracting from his grandfather who built luxury homes all across the state of Texas.

And it was this influence of his grandfather’s, in part, that emboldened Isaac to purchase an overgrown, 5 acre plot of land just outside of Waco, Texas and transform it into an Insta-worthy vacation destination.

Tune in to hear the remarkable story of how Isaac brought Live Oak Lake to life.

Book your stay at Live Oak Lake.

Follow Live Oak Lake on Instagram.

Follow Isaac on Twitter.

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

He Lost His Job During COVID — So He Watched 200 Hours of YouTube Videos And Then Went All in on STRs (And Twitter) May 31, 2022

Show notes

In just a moment you’ll meet Taylor Jones, Head of Acquisition at Superhost Labs.

Taylor was working in sales when COVID hit. A few weeks after the world shut down, Taylor’s job was put on a two-month pause and he knew he had to start looking for a new frontier.

Taylor had always dreamed of getting into real estate but had never quite known where to start. With newfound time on his hands, and with nowhere to go, he began Googling.

After watching more than 200 hrs of YouTube videos, streaming a plethora of STR podcasts, and reading through dozens and dozens of blog articles, Taylor finally pulled the trigger on his first-ever short-term-rental.

And while he didn’t know it at the time, this decision would ultimately upon up an entirely new career trajectory for Taylor.

Tune in to hear the story behind how Taylor Jones became the Head of Acquisition at Superhost Labs, a short-term-rental investment startup, and became one of the leading voices on all things STRs on Twitter @MrJonesSTRs.

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

Why These Mission-Driven Entrepreneurs Built an Airbnb in Virginia Wine Country May 24, 2022

Show notes

In just a moment, you will meet Katrina Kuhn and Kathy and Sayres Dudley — the dynamic trio who brought to life The Dwelling Place, a special, peaceful escape in Radford, Virginia.

Kathy was the 12th child in her family and was born on the land that would become Iron Heart Vineyard in Southwestern Virginia.

Kathy and Sayres met in college, married young, and have two sons.

Today, Kathy and Sayres run an executive recruiting firm that specializes in the real estate space, but that’s only half of their story.

The Dudleys have always had a heart for mission-driven entrepreneurship, and Kathy is the founder of four nonprofit charities and ministries, including Imani Bridges, an organization whose mission is to connect Christians from different denominations around the world to use their gifts, talents, and resources to become agents of transformation.

Tune in to hear the incredible story of how and why Kathy and Sayres felt compelled to purchase a home in Southwestern Virginia and with the help of their co-host Katrina, transform it into a serene escape for the world to enjoy.

Book your stay at The Dwelling Place

Purchase Kathy's book, Bridges: Transforming Communities Together

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

How They Used Human-Centered Design to Build a Scandinavian Villa in Asheville May 17, 2022

Show notes

In just a moment you’ll meet Hillary and Jason DeMeo — the creators of the IROX ONE, a Scandinavian modern retreat in Asheville, North Carolina.

Hillary and Jason are serial entrepreneurs.

A few years ago, the couple left their respective day jobs to go all in on an idea they had dreamed about for years.

And that idea was to start We Are Curio — a creative studio built for explorers and innovators.

Hillary and Jason have consulted with incredible brands like Disney, NASA, the Orlando Magic, and Chick-fil-A within the context of We Are Curio, but the couple always dreamed of expanding their work into the hospitality space.

Tune in to hear the remarkable story of why this dynamic duo built the Irox Living brand and how they brought their first property, the IROX ONE to life.

Book your stay at IROX ONE

Discover Irox Living's Website

Follow Irox Living on Instagram

Learn More About We Are Curio

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

How They Knew It Was Time to Go All In — And Just Get The Lake House May 14, 2022

Show notes

In just a moment, you’ll meet Megan and Darrin — the creators of the Lakeview Hilltop, a coastal-chic cottage on Claytor Lake in Radford, Virginia.

Originally from the California Bay Area, and a graphic designer by trade, Megan has always had an awareness of the role space plays in inspiring new ideas and perspectives.

Darrin, who grew up in the Southwestern Virginia area, had always dreamed of having a lake house. But with two young kids and demanding jobs the idea of acquiring a vacation home in this season of life seemed untenable.

But then COVID hit. And within a matter of months, a charming home that overlooked one of Virginia’s most beautiful, and somewhat undiscovered lakes became available.

Tune in to hear the story behind how Megan and Darrin acquired the home which they now call Lakeview Hilltop and brought it to life.

Book Your Stay at the Lakeview Hilltop

Follow Megan and Darrin on Instagram

Visit the Lakeview Hilltop Website

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

He’s An Actor By Day and Super Airbnb Host by Night — Meet the Creator of Airstream Island Apr 13, 2022

Show notes

In just a moment you’ll meet Andrew Hunter — the creator of Airstream Island, a mid-century, tropical hideaway in Atlanta, Georgia.

Andrew is an actor. He will never forget the first time his mother took him to see Fiddler on the Roof. He was transfixed by the characters in the show, but more bewildered by the fact that you could make money pretending to be someone you weren’t!

Fast forward a couple of decades and Andrew is pursuing his acting dream by day and Instagram influencing at night to help pay the bills. But after he meets the love of his life — and proposes to her just two months later — Andrew realizes that in order to continue his acting dream, he’s going to need some supplemental income to support his family.

And that’s when the idea that would ultimately become Airstream Island was born.

Tune in to hear the story behind how Andrew transformed his backyard into a tropical escape and how he grew it to become one of Atlanta’s top-rated Airbnbs.

Book your stay at Airstream Island

Follow Airstream Island on Instagram

Follow Andrew Hunter on Instagram

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

It’s 11:32 pm on a Thursday night and you wake up in a panic. You forgot to send your guests the custom lockbox combination for your Airbnb, and you missed the 17 messages they sent saying they couldn’t get in because you enabled “sleep mode” on your iPhone — you know, to try and cut down on screen time before bed and all. After apologizing profusely and sending them a bottle of bubbly — in hopes they won’t leave you a 1-star review — you think to yourself, “how do other hosts stay on top of guest communications?" The answer? They use Guesty For Hosts — an easy to use rental management platform. With features like Automated Messages that send important communications to guests at the exact right times…you'll never have to jeopardize your beauty sleep again. Guesty For Hosts allows short-term rental hosts to manage listings from Airbnb, VRBO, and Booking.com in one calendar and send a series of automated messages before, during, and after their stay. The platform also has features that help you manage cleanings, build a custom booking website, and so much more. Start your 14 day free trial today — no credit card, set up fee, or commitment required — and cancel anytime if you don't love it. While getting started, use the discount code “SPONSTAYNEOUS” for 20% off of your first year." Behind the Stays is brought to you each week by Sponstayneous — a free, biweekly newsletter that brings subscribers the best last-minute deals and upcoming steals on Airbnb. You can subscribe, for free, at www.sponstayneous.com

He’s Worked at Fairmont, Sonder, and Airbnb — Now He’s Pioneering The Next Big Thing in Hospitality Apr 06, 2022

Show notes

In just a moment you’ll meet Ryan Killeen — General Manager of The Annex Hotel.

You might call Ryan a child of the hospitality industry. He grew up traveling the world with his mom who worked in the luxury hotel space, and had the privilege of encountering a diverse set of cultures and experiences all around the world.

Ryan studied hotel management in college, and while in school, he started cleaning bathrooms and making beds with the housekeeping team at the Fairmont Pacific Rim, which was considered Vancouver’s definitive luxury hotel.

His hard work paid off, and when an opportunity to join the opening team in Dubai at Fairmont the Palm arose, Ryan took it!

After a couple of years, Ryan became interested in the budding space of short-term rentals, so he took jobs at both Sonder and Airbnb.

But Ryan has always been entrepreneurial so when a new opportunity to join a hospitality start up came his way, he took it.

Tune in to hear the story behind The Annex — a new hospitality concept marrying the best of boutique hotels, Airbnb and cutting edge technology that Ryan and his team are developing.

Book Your Stay at The Annex Hotel Here.
Connect with Ryan on LinkedIn Here.

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

They Left It All Behind to Build a Luxury Micro-Resort in Highlands, North Carolina: The Story of Flat Mountain Farm Mar 30, 2022

Show notes

Meet Margaret Shutze — the creator and owner of Flat Mountain Farm, a luxury escape and events venue in the Appalachian Mountains of Highlands, North Carolina.

Margaret has helped design some of the world’s most incredible luxury hotels working on projects for The Ritz Carlton, Belmond, Waldorf Astoria, and the Four Seasons.

And it was her love for design and hospitality that inspired her and her husband Chris to take a risk and build a couple of Airbnb’s and a micro-events venue on the 3 acre lot they lived on in Colorado.

To their surprise, it was a hit! So much so that they began to dream of something even bigger…

Tune in to hear the story behind how Margaret and Chris bought a magical, rustic, 28-acre plot of land and transformed it into a haven that they call Flat Mountain Farm.

Book your stay at Flat Mountain Farm

Follow Flat Mountain Farm on Instagram

This week's episode is brought to you Guesty for Hosts — the bestie of top-rated Airbnb hosts.

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