Behind the Stays

Latest Episodes:

How to Verticalize the $100 Billion Short-Term Rental Industry — A Chat with the Founder and CEO of Wander Jan 17, 2023

Show notes

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 him as it’d allow him the opportunity to continue to pursue his projects and build companies.

In this episode of Behind the Stays, John Andrew talks about:

-being raised by a single dad

- how he started and grew his second company Coder

- what it was like being a Thiel Fellow

- and, of course, the past, present and future of Wander — a company on a missions to verticalize the 100B+ short-term rental industry with a network of smart vacation homes in inspiring places that guests can control from their phones.

Discover Wander

Follow John Andrew on Twitter

This episode is brought to you by our friends at AirDNA.

I receive questions ALL the time from listeners who want to get started in STR investing and or who want to scale their portfolio on what resources I recommend they tap into.

Here are three reasons I always recommend an AirDNA subscription:

1. AirDNA offers the most accurate data platform in the industry and is trusted by small- and large-scale investors across the globe.

2. Their easy-to-use tools unlock access to millions of data points on any property, anywhere, so you can start your journey to financial freedom with confidence.

3. You can even enter any address in the world to find out how much it’d earn as a vacation rental — how cool is that?

If you’re interested in getting into the STR game or taking your game a bit more seriously, I’ve got some exciting news for you.

AirDNA is giving Behind the Stays listeners 20% off their first 3 months of any MarketMinder subscription or an additional 20% off any annual MarketMinder subscription.

Use the discount code BTS20 at checkout!

Behind the Stays Subscriber Survey — please take 5 minutes to complete this survey so that we know how we can make the show even better!

About the Show

Behind the Stays is brought to you twice a 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.

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

They Booked an A-Frame They Follow on Instagram — And It Inspired Them to Build Their Own. Jan 13, 2023

Show notes

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 home had availability.

Upon their arrival, Ty and Mary were met with such a deep peace that they began dreaming about what it would take to create something of their own so that they might share this serenity with others.

Tune in to hear how Ty and Mary designed, built, and branded an A-Frame and a couple of Tiny Cabins that they call Northwoods.

Book Your Stay at Northwoods

Follow Northwoods on Instagram

This episode is brought to you by our friends at The Host Co.

The Host Co. enables short-term rental host to build their own storefronts and offer amenities like late night snacks, massages, fresh flowers, grocery delivery, in-home shopping and much more.

The Host Co. makes it easy for guest to augment their stay with the products and services they need and makes it easy for STR hosts to make up to an additional $10k in ancillary revenue on each rental.

Hosts keep 93% of all sales and The Host Co. takes care of guest receipts, sales tax and payouts to you and vendors.

Create your free store today by visiting TheHost.co and be sure to tell the team their that you heard about them from Behind the Stays!

And, for a limited time, Behind the Stays listeners will get $30 back on their first sale when you use the discount code BTS30 at check out!

Behind the Stays Subscriber Survey — please take 5 minutes to complete this survey so that we know how we can make the show even better!

About the Show

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

How to Build an Off-Grid Airbnb and a Unique Hospitality Brand — The Story of the Ely Cabin Collective Jan 10, 2023

Show notes

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, Addie got a call from her uncle about a 40 acre plot of land that was for sale which included a charming, but quite dilapidated, log cabin.

Addie and her husband Ben made the 4-hour drive from the Twin Cities to explore the opportunity further and, while they didn’t know it at the time, this trip up north would be the start of a remarkable adventure.

Tune in to hear the inspiring story of how Addie transformed that dilapidated cabin into the Ely Log Cabin and how this renovation inspired the launch of The Ely Cabin Collective.

Book a Stay at The Ely Cabin Collective

Follow The Ely Cabin Collective on Instagram

Follow The Ely Log Cabin on Instagram

This episode is brought to you by our friends at AirDNA.

I receive questions ALL the time from listeners who want to get started in STR investing and or who want to scale their portfolio on what resources I recommend they tap into.

Here are three reasons I always recommend an AirDNA subscription:

1. AirDNA offers the most accurate data platform in the industry and is trusted by small- and large-scale investors across the globe.

2. Their easy-to-use tools unlock access to millions of data points on any property, anywhere, so you can start your journey to financial freedom with confidence.

3. You can even enter any address in the world to find out how much it’d earn as a vacation rental — how cool is that?

If you’re interested in getting into the STR game or taking your game a bit more seriously, I’ve got some exciting news for you.

AirDNA is giving Behind the Stays listeners 20% off their first 3 months of any MarketMinder subscription or an additional 20% off any annual MarketMinder subscription.

Use the discount code BTS20 at checkout!

Behind the Stays Subscriber Survey — please take 5 minutes to complete this survey so that we know how we can make the show even better!

About the Show

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

3 Guys, 2 Acres, 1 Bar, and No Builder — This is The Story of The Chal-A Vermont. Jan 06, 2023

Show notes

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 mountains where they could host their friends and families on long-weekends.

Justin began scrolling through Zillow listings every night looking for plots of land in Vermont that might work for the guys to build their dream getaway on.

Tune in to hear the fun story of how Justin and Shaun found their land, how they collaborated on designing the A-Frame, what they did when they had to fire their builder halfway through the project, and the role Instagram has played in helping them book their first guests.

Alright, without further ado, get ready to meet Justin and Shaun.

Stay at The Chal-A Frame

Follow The Chat-A Frame on Instagram

This episode is brought to you by our friends at The Host Co.

The Host Co. enables short-term rental host to build their own storefronts and offer amenities like late night snacks, massages, fresh flowers, grocery delivery, in-home shopping and much more.

Hosts keep 93% of all sales and The Host Co. takes care of guest receipts, sales tax and payouts to you and vendors.

Create your free store today by visiting TheHost.co and be sure to tell the team their that you heard about them from Behind the Stays!

And, for a limited time, Behind the Stays listeners will get $30 back on their first sale when you use the discount code BTS30 at check out!

Behind the Stays Subscriber Survey — please take 5 minutes to complete this survey so that we know how we can make the show even better!

About the Show

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

How a Flower Farmer Built Vermont’s Most Wish-Listed Airbnb — The Story of The Tanglebloom Cabin Jan 03, 2023

Show notes

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 she was in high school, selling hand-sewn clothes on the internet and in the parking lots of Phish concerts.

And while she couldn’t have guessed it then, this was the first stepping stone in her journey to become a flower farmer and short-term-rental entrepreneur.

Tune in to hear the enthralling story of how Melissa brought her wedding and event flower business, Tanglebloom, as well as Vermont’s most wish-listed Airbnb, to life.

Book a Stay at the Tanglebloom Cabin

Follow the Tanglebloom Cabin on Instagram

Follow Melissa on Instagram

This episode is brought to you by our friends at AirDNA.

I receive questions ALL the time from listeners who want to get started in STR investing and or who want to scale their portfolio on what resources I recommend they tap into.

Here are three reasons I always recommend an AirDNA subscription:

1. AirDNA offers the most accurate data platform in the industry and is trusted by small- and large-scale investors across the globe.

2. Their easy-to-use tools unlock access to millions of data points on any property, anywhere, so you can start your journey to financial freedom with confidence.

3. You can even enter any address in the world to find out how much it’d earn as a vacation rental — how cool is that?

If you’re interested in getting into the STR game or taking your game a bit more seriously, I’ve got some exciting news for you.

AirDNA is giving Behind the Stays listeners 20% off their first 3 months of any MarketMinder subscription or an additional 20% off any annual MarketMinder subscription.

Use the discount code BTS20 at checkout!

Behind the Stays Subscriber Survey — please take 5 minutes to complete this survey so that we know how we can make the show even better!

About the Show

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

Confessions of a 25-Year-Old Real Estate Investor and Internet Entrepreneur — Meet Connor Gross Dec 27, 2022

Show notes

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 holder that attaches to the back of your iPhone.

After selling the start-up in early 2020, Connor began learning about real estate investing. While the idea of investing in a short-term rental was attractive, in Connor’s mind, being responsible for a place where folks actually lived or vacationed was a bit too much of a headache. So, he decided to start with self-storage.

Tune in to an energetic, idea-producing conversation where Connor and I discuss:

How he convinced the host of a luxury Airbnb villa in Bali to let him stay in their home for free
How he founded, built, and sold his first e-commerce company
Why you’re never too young or too old to start your entrepreneurial journey
Connor’s hot takes on the future of travel and hospitality after living out of a suitcase for 2 years and traveling to more than 30 countries.

This episode of Behind the Stays is brought to you by our friends at Touch Stay.

Touch Stay enables hosts to build beautiful, digital guidebooks in a matter of minutes… And enhances the guest experience by packaging your recommendations for coffee, wine bars, artisan bakeries, and Michelin star restaurants in a single online location. Guests can access everything through a simple link — and yes, it works WITHOUT a wifi connection. Touch Stay allows you to customize your guidebook to match your brand — pick the colors, fonts, and images that best align with your STR. Learn more about a plethora of other features they have, and start your free trail at touchstay.com/bts(as in, Behind the Stays). If you liked this episode, you're going to love some of our other recent conversations: How She Built an Insta-Famous Airbnb — The Story Behind the Cozy Rock Cabin. She Left Her Law Career to Become a Hospitality Entrepreneur — Meet the Creator of Field and Lake How They’re Building Canada’s Premier Luxury Treehouse Company

About the Show

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

Why Building Your Network as a Hospitality Entrepreneur is So Critical Dec 20, 2022

Show notes

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 investing and hosting, Natalie asked her parents if she could try her hand out at turning their family’s vacation home in the mountains into an Airbnb.

While skeptical, they agreed to give her a shot…and within one ski season, they had made enough to pay the mortgage on the home for the entire year!

This early win inspired Natalie to further immerse herself in learning everything she could about how to deliver an exceptional guest experience while also growing a profitable business.

Natalie and I discuss the power of networking and why more hosts should participate in STR industry events, frameworks for how to structure your time as a hospitality entrepreneur, and why she’s throwing a women’s only STR hospitality event in Scottsdale, Arizona called the “Level Up Your Listing Summit.”

You’ll learn more about this event towards the end of the interview but I want to highly encourage all the ladies tuning into today’s chat to check out Natalie’s event.

Natalie is also giving all Behind the Stays listeners a 10% discount when they use the code BTS10 at check out. Learn more about the Level Up Your Listing Summit here.

Follow Natalie on Instagram

Stream the No Vacancy Podcast

This episode of Behind the Stays is brought to you by our friends at Touch Stay.

Touch Stay enables hosts to build beautiful, digital guidebooks in a matter of minutes… And enhances the guest experience by packaging your recommendations for coffee, wine bars, artisan bakeries, and Michelin star restaurants in a single online location. Guests can access everything through a simple link — and yes, it works WITHOUT a wifi connection. Touch Stay allows you to customize your guidebook to match your brand — pick the colors, fonts, and images that best align with your STR. Learn more about a plethora of other features they have, and start your free trail at touchstay.com/bts(as in, Behind the Stays). If you liked this episode, you're going to love some of our other recent conversations: How She Built an Insta-Famous Airbnb — The Story Behind the Cozy Rock Cabin. She Left Her Law Career to Become a Hospitality Entrepreneur — Meet the Creator of Field and Lake From Serving in Afghanistan to Hosting on Airbnb: Meet the Founders of Seasons‘ Yield Farm

About the Show

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

How an Instagram Post Landed Their Airbnb in Vogue — Meet the Creators of The Kingdom A-Frame Dec 13, 2022

Show notes

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 allowed dogs and offered an inspirational aesthetic.

After doing some back-of-the-napkin math, the couple realized that, given the frequency of their travels to Burke, they might actually be better off buying a place then continuing to book stays on Airbnb.

Tune in to hear the fun story of:

How Alexis and Skeeter found and refurbished The Kingdom A-Frame
How an instagram post landed their A-Frame in Vogue
How they’ve balanced increasing their nightly rate (as their insta-fame has grown) with their original mission of creating a beautiful, accessible, and unique escape for all

Follow The Kingdom A-Frame on Instagram

Book Your Stay at The Kingdom A-Frame

This episode of Behind the Stays is brought to you by our friends at Touch Stay.

Touch Stay enables hosts to build beautiful, digital guidebooks in a matter of minutes… And enhances the guest experience by packaging your recommendations for coffee, wine bars, artisan bakeries, and Michelin star restaurants in a single online location. Guests can access everything through a simple link — and yes, it works WITHOUT a wifi connection. Touch Stay allows you to customize your guidebook to match your brand — pick the colors, fonts, and images that best align with your STR. Learn more about a plethora of other features they have, and start your free trail at touchstay.com/bts (as in, Behind the Stays). If you liked this episode, you're going to love some of our other recent conversations: How She Built an Insta-Famous Airbnb — The Story Behind the Cozy Rock Cabin. She Left Her Law Career to Become a Hospitality Entrepreneur — Meet the Creator of Field and Lake From Serving in Afghanistan to Hosting on Airbnb: Meet the Founders of Seasons‘ Yield Farm

About the Show

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

How to Increase Your Airbnb’s Ranking on Google (And Other Musings on Direct Booking Strategies) Dec 06, 2022

Show notes

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 travel agency, Damian developed an affinity for Search Engine Optimization — also known as SEO.

The idea that, with the right set of strategies and tactics, you could rank #1 on Google for a term like “best vacation rentals in Miami” fascinated him…and before too long he became something of an expert in SEO!

Tune in to hear the motivational story of how Damian parlayed his SEO skills into a full-time gig and what inspired him to build a collection of niche, in-person events for hosts and operators interested in growing their direct bookings.

Connect with Damian on LinkedIn

Learn More the Book Direct Show

Learn More about the Scale Rentals Show

Rate and Review this Episode on Apple Podcasts

Subscribe to Sponstayneous

This episode of Behind the Stays is brought to you by our friends at Touch Stay.

About the Show

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.

How She Built an Insta-Famous Airbnb — The Story Behind the Cozy Rock Cabin. Nov 29, 2022

Show notes

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 to promote all of her homes, but one in particular, the Cozy Rock Cabin, has become what some might call “insta-famous” having garnered over 70k followers.

Tune in to hear the moving story of why Janice wanted an Airbnb in Freeport, how she DM’d the creator of The Raven House — one of the OG insta-worthy cabins — and convinced him to help her develop the plans of her own cabin, and her theory on why Jimmy Kimmel follows the Cozy Rock Cabin on Instagram.

Book Your Stay at the Cozy Rock Cabin

Follow the Cozy Rock Cabin on Instagram

Rate and Review this Episode on Apple Podcasts

Subscribe to Sponstayneous

This episode of Behind the Stays is brought to you by our friends at Touch Stay.

About the Show

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.