The Short Term Rental Playmaker
The ins and outs of vacation rental property management and how to grow your cohost/property management business.
Episodes
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 abo...
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 R...
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 h...
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 experienc...
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 additio...
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 ...
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 cen...
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.
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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 skill...
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 presenc...
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 Ca...
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 prop...
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 y...
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...
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 vacatio...
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!
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