The Short Term Rental Playmaker
The ins and outs of vacation rental property management and how to grow your cohost/property management business.
Episodes
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!
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...
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 pro...
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...
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 bus...
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 ...
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 ...
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