The Short Term Rental Playmaker

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 for the #1 luxury short-term rental management company in Central Texas - managing 60+ luxury short-term rental properties across Austin and San Antonio.

In addition to his role at FSVHR, Ryan became a coach and consultant for STR Secrets, the leading short-term rental business coaching program, where he helped operators overcome self-limiting beliefs and build profitable, lifestyle-driven STR businesses. 

Today, Ryan continues to coach and mentor new short-term rental operators, share insights as a thought leader in the space, and prioritize a life designed around freedom, impact, and balance.

To get in touch with Ryan visit his website - https://www.ryan-leake.com/

Or book him for a one hour 1 on 1 consulting session at - https://www.ryan-leake.com/contact

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. This ongoing education, combined with his operational experience, allows Lance to guide investors in identifying properties with strong performance potential, reducing risk, and building long-term value through strategic short-term rental investments.

BOOK A CALL WITH LANCE - https://www.savvy.realty/lancewolfe

[email protected]  |  (772) 631-2886 

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 STR operators buzzing. Whether you're a self-managing host, a co-host scaling your portfolio, or an investor looking to streamline operations, this episode is packed with insights that could transform the way you manage your properties.

In this episode we cover:

How Hospitable started and the vision behind it
The new VRBO API connection and what it means for your listings
How AI is being built into the platform to save you time and money
What's coming next and why serious STR operators should be paying attention
If you're not using Hospitable yet, this episode might just change that.

🔗 Learn more about Hospitable at hospitable.com

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 within the short-term rental industry that did not exist: short-term rental safety. With this passion and expertise, Justin built the Breezeway Safety Program and plays a pivotal role in helping property managers and owners uphold safety standards at their rentals.

If you want to know more about Breezeway visit https://www.breezeway.io/ or call 857-600-2799. 

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 in touch with Jeff, go to his website https://strhomefinancing.com/ or call him at 817-984-5481.

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 the STR market. That experience creates a great perspective and strong belief that the hidden treasure of Jacksonville holds incredible, untapped potential for investors to build their wealth and portfolios.

This is a city filled with culture, rivers, intercoastal waterways, charming neighborhoods, pristine beaches and even a countryside--that most investors have yet to discover. With downtown revitalization happening now, new businesses emerging, world-class healthcare systems expanding and the PGA tour spotlight, demand is rising quickly. And what investor doesn't want to be ahead of the game with early access to Jacksonville's growth and expansion? 

Dashia wants to form a lifelong partnership with her investors, while making the process seamless from start to finish. There are only a handful of cities that offer this level of potential for STRs and Jacksonville is one of them. The window of opportunity is still open-- and with Dashia guiding the way, you can build lasting wealth in a market that's just beginning to be discovered!

To get in touch with Dashia email [email protected]  or call (904) 625-0546