The Short Term Rental Playmaker

Today Joe is joined by Nicole & Wilson Rattler the real estate team behind Heavenly Shores! 

Nicole & Wilson are a husband and wife real estate team that got into the field based on there passion for real estate and love for investment properties where families can come and create lasting memories for years to come.

They fell in love with the Emerald Coast the first time when they visited many years ago. They loved it so much that it became their home. That passion has inspired them to help others do the same. They each have d...

Today Joe talks about conferences. With so many different ones, even Joe's own conference coming up soon in Palm Beach, what do you get out of them? Should you go to one? What are the long term benefits of a conference with other renters and sellers? Joe talks you through it all and gives you what you need to know to see if conferences are the right place for you and your money. If you have any questions leave them in the comments and we will be back next week for another amazing episode!

Today Joe is joined by Jeremy Holden. Jeremy was born and raised in the New York Area. He attended Bentley University graduating in 2020 with a degree in Finance. Soon after, Jeremy moved to Scottsdale to pursue a career in real estate. He acquired his first investment in 2020 and quickly growing his portfolio to its current state. In 2021, Jeremy obtained his real estate license and joined Realty One Group. His background in finance coupled with his strong communication skills, position Jeremy's clients for success. In 2022, Jeremy won Phoenix's Rising Agent of the Year. Outside of real estate, Jeremy is an...

Today Joe comes on for a solo podcast. He shares his experiences over the last four years of being in the Short Term Rental space and some things he has learned along the way.

Things have gotten more crazy and busy over the years, so Joe has taken some time to look at his business and make some changes to make things run more smoothly and effectively.

Take a look at your business and see if anything that Joe mentions today on the podcast could be modified to fit your needs. Thank you so much...

This week Brad and Mo Crawford return to the new Short Term Rental Playmaker Podcast, after having a fantastic leap since we last spoke to them. 

Since their last appearance on the show things have certainly changed. They added many more retail properties to their lists, have gained a tremendous amount of experience, and are here to share that experience with you.

Thank you so much to Brad and Mo for coming back onto the show and for never stopping their growth in the rental market.

Today Joe is joined by Tanya Rooney. Tanya is a real estate proprietor, podcast host, author, and coach, helping entrepreneurs build scalable momentum by creating communities that are centered around growth, education, and authentic networking. As the owner of BAFS Real Estate and Yay You’re Here Properties in her home state of Minnesota, Tanya has spent the last 15 years building her own career, as well as coaching others, on the foundation of resourcefulness and connection with others. Her philosophy is that no one can win alone, and this stands as the cornerstone of her Tribe Builders brand. Most ne...

In this episode, Joe sits down with Jodie Odlin — and amazing Host who built and remotely runs a 15-property short-term rental portfolio in the small English town of Tetbury, and the founder of Hospitable Hosts, a global book series and community built to raise the standard of hospitality in short-term rentals. Jodie shares how Hospitable Hosts grew out of pandemic-era conversations into a multi-volume bestselling book series (now spanning multiple editions, including a Couples Edition and a Sisterhood Edition) featuring real stories from real hosts, and why she believes putting guests first is a business strategy, not just a ni...

Today Joe interviews Michael O'Connell, the founder of Happy Guest. Happy Guest is a guest management software that empowers Airbnb hosts and short‑term rental managers to deliver memorable, professional guest experiences for every stay, every time. Through thoughtful automation, every interaction feels warm, human, and completely seamless—all leading to a happy guest.

Mike came from Turno, the #1 housekeeping platform in short-term rentals, where he learned exactly which operational problems break most hosts. Then he founded Happy Guest with his friends.

At Happy Guest, Mike is creating an operational backbone — a system that takes the ch...

In today's solo episode, Joe talks about how to build and then manage generational wealth for your family. One thing that a large portion of the wealthiest people have or invest in is Real Estate. Real Estate is one of the best ways to build generational wealth, allowing fundamental growth that can continue to expand as you invest more into it. 

Joe lays down the foundation to get you started down the path and gives you information to help you succeed. If you have any questions please leave them down below and we will see you next w...

In today's solo episode, Joe breaks goes into detail about buying your first Short Term Rental. Analysis paralysis is a huge problem when it comes to selecting and then moving forward on your first rental. 

Joe gives you some examples and then explains how he overcame it to be where he is today. If you have any questions about today's topic please leave a comment down below and we will be back next week for another amazing episode.

Ryan Bakke began his career at Deloitte, the world’s largest accounting firm, where he specialized in Investment Management Taxation and led tax technology initiatives for some of the largest global investment banks. That experience gave him a front-row seat to how the wealthy strategically leverage the tax code to their advantage.

Today, Ryan is the founder of Tax Strategy 365, where we help real estate investors reduce taxes and build generational wealth through proactive, strategic planning. What started as a solo practice has grown into a platform where he has acquired multiple CPA firms—and is actively expa...

Michael Dinwiddie, founder of Hospitality HQ, built his business from day one for freedom — off his phone, and present with his family. In this episode, he shares how that mindset led to Rental Mind, his new software helping STR hosts stay organized and buy back their time. We dig into the chaos most hosts don't realize is eating their hours, and how Rental Mind turns that chaos into simple systems. Michael also gets real about what it actually takes to step back from day-to-day operations without things falling apart. If you're a host who feels owned by your rental bu...

Today's episode marks the 100th episode that Joe has done, bringing the audience information, great guests, and amazing stories. Across these two years Joe has never missed a week and always seeks to bring you the knowledge and confidence to start and meet your own goals with in the short term rental space.

Today Joe also has huge announcement. Tune in to see what that is and get a look at the next season of the Short Term Rental Playmaker Podcast. As always if you have any questions leave them in the comments below and we will...

Today Joe takes a look back at the year as a whole. With the Summer season about to end within the next few weeks, we take a look at a few cases studies and the overall successes of many different venues.

Joe breaks down what worked, what he saw so far over this year, what comes next and so much more. If you have any questions please comment them down below and we will see you back next week!

Today Joe talks to Leah Yuhasz. Leah is a local investor, property manager and long-time resident of Florida's beautiful Emerald Coast. Where she has lived for over 9 years, but her connection to this coastline goes back even further. She grew up vacationing here and always dreamed of owning her own piece of paradise.
 
Today, she not only lives and raises her family on this fast-paced island in Florida, She also run a hands on short term rental management company from Destin - 30A - PCB. These homes aren't just income generators ---theyre legacy properties just like you a...

Today Joe talks about luxury, luxe and what it really means to become an Airbnb Luxe destination. An Airbnb Luxe is the platform’s ultra-premium tier, featuring extraordinary, professionally designed homes that pass a rigorous 300-point inspection. Every booking in this category includes a dedicated 24/7 "trip designer" who acts as a bespoke concierge to arrange private chefs, airport transfers, and customized local experiences.

Joe breaks that down and what you can do to help your rentals on the path to that Luxe status.

If you have any questions please leave a comment down below and we...

Today Joe talks about being in the heart of the Summer Season. New rentals coming in, the heat, maintenance issues, rental burn out and much more. Joe breaks it all down and what you can do to take steps to prevent it or get in front of it.

If you have any questions please leave a comment down below and we will be back next week with another amazing episode!

Today Joe welcomes back Melissa Young with the Savvy STR agent team. Melissa was a guest on the show back when it was called Cohost Coach where she talked about herself, what she does, bringing her experience into the real estate side of things. Today she returns to talk to Joe about investing in the Midwest. With so much prime real estate, the benefits far outweigh anything else. Melissa and Joe break it down today on this addition of the Short Term Rental Playmaker Podcast.

Melissa Young is a St. Louis short-term rental Realtor, Airbnb real estate...

Today Joe is joined by Beth Turner. Beth is the founder and CEO of Simpli Host, an all-in-one property management software platform. Designed specifically for hands-on, short-term rental hosts (such as Airbnb or VRBO), the platform helps individuals juggle day-to-day tasks, unified messaging, team management, and property maintenance.

Simpli Host consolidates those operations by allowing hosts to manage everything in one central place, eliminating the constant anxiety of wondering if a cleaner showed up or if the hot tub was working. Key features of Simpli Host include Centralized Messaging, Smart Integrations, Task Automation, Policy Enforcement and much...

Today Joe talks about that problem guest. It's peak season right now and business is great. All your rentals are booked full and the summer is looking bright, but then you have that one problem guest. How do you deal with them? What are steps you can take to resolve the issues they are having or fix them before they even become issues?

Joe will answer all these and more, talking about what has worked for him in the past and going into detail on the steps you can take to be successful, even when dealing with...

Today Joe is joined by one of the best cleaning and handyman in Panama City Beach, Katie Elder. Katie started with just a single condo a week and with her husband turned it into a well oiled machine working with many different crews and now service 28 units. They work along side many other families to keep everything looking amazing to help both the Host and the Guests have an amazing stay at each and every one of their units.

Katie fights through the misconceptions that all you need is a cleaner or a handyman and your property...

Every day you're not using AI in your STR business is a day you're leaving time and money on the table. The operators winning right now aren't working harder — they're working smarter, and tools like Claude are a big reason why.

In this episode, Joe sits down with Bill Faeth and Chris Wharton to talk about how AI is transforming the short-term rental industry. Bill, Chris, and their team are actively building powerful AI skills inside Claude that are helping hosts and co-hosts automate tasks, cut overhead, and streamline operations in ways that used to require an en...

Today Joe gets to sit down with Tyler Coon. Tyler Coon is the CEO and founder of Savvy Realty. Tyler has been focused exclusively on short term rental investment real estate since 2019. Based in Asheville, North Carolina, Savvy STR Agents is a dynamic real estate team with expansion agents across the country who are devoted to aiding investors in acquiring lucrative STR properties. Tyler has successfully expanded the team's presence to cover Florida, the Carolinas, Kentucky, the Smoky Mountains, Myrtle Beach, Southern California, and Washington, D.C., with plans for further growth. Tyler is committed to strategically aligning his...

Today Joe talks to Ryan Leake who two years ago started from scratch and today manages 60+ luxury short-term rental properties, and has coached dozens of early-stage operators as they signed their next clients, built their first real systems, and gained traction in their own management businesses.

Ryan Leake, originally from Mill Valley, CA, moved to Austin, TX in 2023, where he left corporate America and founded Host Del Casa, a short-term rental management company. 

After successfully building the business, Host Del Casa merged with Five Star Vacation Home Rentals (FSVHR), where Ryan is now a Partner f...

Today Joe talks checking to see where you are at in terms of rentals and how well things went your 1st quarter of 2026. He talks about things you should be looking for, what you should be looking forward too, and how you can enter into the 2nd quarter of 2026 with a gameplan that works.

If you have any questions please let them in the comments below, thank you and see you all next week!

Today Joe talks to Brian Wilfong, a real estate investor with decades of experience and knowledge in the space. The two talk about Brian's experience getting into real estate investing in the beginning, how his experiences shaped his life path, and all the things he learned along the way. 

We will be back next week for another amazing show. If you have any questions please leave them down below in the comments!

Today Joe talks to STR Savvy Agent Lance Wolfe about the space and treasure coast rental properties. Lance Wolfe is a Florida real estate professional specializing in short-term rental (STR) investment properties along the state’s coastal markets, from Satellite Beach to Jupiter. As an active STR owner and founder of Wolfe Vacation Rentals, a boutique co-hosting and consulting company, Lance brings hands-on experience in property management, pricing strategy, and guest experience optimization to every client engagement.

He is also a member of the Build Short-Term Rental Wealth Inner Circle, an advanced investor education and networking group. Th...

Today Joe does a solo podcast to talk about Knowing Your Why. Why did you choose this business? Why do you want to do this? Why did Joe start this business. Knowing your why can lead to a more successful outlook overall. Understanding your goals, the meaning behind each step can lead you down your path of success, and it all starts by asking a simple, Why?

Please comment down below if you have any questions and we will see you next week!

What if the property management system you've been using — or overlooking — is quietly becoming the most powerful tool in the short-term rental industry?

In this episode, Joe sits down with Pierre Camille Hamana, co-founder of Hospitable, to unpack how one of the STR industry's most beloved platforms got its start and where it's headed next. From its humble beginnings to a full-featured property management system trusted by thousands of hosts worldwide, Hospitable has never stopped evolving.

Pierre pulls back the curtain on the new VRBO API integration, game-changing AI features, and the product roadmap that has...

Today Joe talks to Justin Ford with Breezeway. Safety and Awareness are two things that every short term rental needs to keep in mind at all times, the safety of your guests is paramount so they can enjoy the time they spend with you and no one knows that better than Justin Ford.

Justin is an International Short-Term Rental Safety Expert and the Director of Safety & Certification at Breezeway. After 13 years as a vacation rental Property Manager, 15 years as a firefighter, and four years in the US Coast Guard, Justin combined his experiences to create a niche...

Today Joe talks about what is happening in the industry right now, what you can do to capitalize, and the things you need to look out for. He talks about successful ideas and ventures as well as putting yourself in a position to be successful this year. If you have any questions please comment down below and we will see you guys next week with another great guest! 

Today Joe talks to Jeff Chisum with STR Home Financing. Jeff is one of the best in the industry for Loans and Financing within the rental space. He specializes in 10% down financing for vacation homes/STR properties in all 50 States. We have options from fully qualifying to bank statement loans. Additionally we have DSCR loans that are very STR friendly.

Joe talks to him about loans, the best types and times for each of them, the process, and just his general advice when looking into purchasing a Vacation Home Rental.

If you want to get...

Today Joe talks to Savvy STR Agent Dashia LoCoco. They go through what got her started in the business, how she is doing now, and her outlook at the future. 

Dashia LoCoco is a licensed Florida Realtor and registered critical care nurse who brings a holistic approach to life and real estate investing. She calls on her precision, foresight and trusted network of local STR experts to create smooth, hands-off deals and properties that perform for her investors. Through her years as a traveling nurse, living across the U.S., she's seen city after city surge in t...

Today Joe talks to Tom Ackley, Owner at Getaway and Stay. Tom has maintained a level of excellence that awarded him with the short term secret investor of the month honor. The two talk about Tom's experience, passions and of course Getaway and Stay. 

Getaway and Stay offers top-tier vacation rentals in stunning locations such as the Smoky Mountains, Door County, Green Bay, Gulf Shores and Cody. Each destination provides a unique mix of natural beauty and local attractions, ensuring a memorable getaway. Whether you’re looking for a cozy mountain cabin, a luxurious beach house, or a c...

Today Joe talks about a vital piece of the Short Term Rental Playmaker playbook, Calendar Management. What you can do throughout Spring Break and into Summer to maximize your profits, properties and more. If you have any questions please leave a comment down below and we will catch you in the next episode!

This week Joe brings on a dear friend, Harshad Lalan. Harshad and his wife Ishita are the creative minds and passionate entrepreneurs behind two thriving ventures: 5Seasonshomestays and Ishita Interiors. This dynamic couple combines their love for design and hospitality to create exceptional experiences, both in the spaces they design and the homes they host.

Harshad Lalan brings a strategic and hands-on approach to both businesses, ensuring that every project and guest experience is handled with the utmost care and precision. His expertise in management and customer service is the backbone of 5Seasonshomestays, where guests enjoy personalized...

In this episode of the Short-Term Rental Playmaker Podcast, I sit down with Ryan Duffy and Shae Duffy, a powerhouse couple who are redefining what short-term rentals can look like in the Greater Branson area, specifically Omaha.

Ryan and Shae aren’t just buying properties—they’re building and developing unique, experience-driven homes designed to stand out in a crowded market. From breathtaking Ozark views to creative builds like their container home, their portfolio proves that design and intentionality matter.

But what makes their story truly powerful is the sacrifice behind the success.

At one...

In this episode of the Short-Term Rental Playmaker Podcast, I sit down with Steve Resnick, a featured author in Hospitable Hosts Couples Edition, whose journey is a masterclass in scaling with intention.

Steve started just like many hosts—owning three short-term rentals in the Ocean City area. But instead of stopping at ownership, he saw an opportunity to build something bigger. Today, Steve runs a property management company overseeing 80+ short-term rental properties called HeavenlyRez, helping other owners maximize performance while building a sustainable, systems-driven business.

We dive into how Steve made the leap from owner to...

In this special episode of the Short-Term Rental Playmaker Podcast, I’m switching seats and sitting down with my wife, Jen Rohne, to share our story—the real one behind the business, the brand, and the growth.

From sharing an office and figuring things out as we went, to designing and setting up short-term rentals, co-hosting properties, and building a hospitality business together, this episode is all about the big leaps we took—personally and professionally.

We talk openly about how we leaned into each other’s strengths, navigated uncertainty, and made intentional decisions that allowed...

In this episode of the Short-Term Rental Playmaker Podcast, Joe sits down with Kerri Gibson and Phillipe Gibson, the powerhouse couple behind Châlets Hygge.

Based in Quebec, Canada, Kerri and Phillipe have intentionally built a hospitality portfolio that blends thoughtful design, guest experience, and strategic growth. What started as a small short-term rental operation has grown into 6 beautifully curated STRs, and most recently, the acquisition of a 17-unit boutique hotel—a massive leap that required a completely different mindset and operational approach.

They also share insights from being featured contributors in the upcoming book Hos...