In this episode of Where Should I Invest, I’m thrilled to introduce my new co-host, Kelly Casimiro!

Kelly’s journey is incredible. She went from having zero real estate experience to building a thriving midterm rental business, all while managing a full-time job and family life. And now? She’s thinking even bigger with her eyes set on hotel ownership in 2025.





From mindset to tough tenant lessons to bold hospitality goals, Kelly shares how she’s turning vision into freedom and why I’m so excited to have her join me on the show.

Let’s dive in!
In this episode, you will be able to learn about:

* How Kelly went from zero real estate experience to building a midterm rental business while working full-time and raising a family
* The mindset, routines, and time management strategies that help her juggle it all, including time-blocking and using a virtual assistant
* A behind-the-scenes look at a tough tenant situation that shifted her entire investment strategy
* Why she’s pivoting from managing multiple rentals to pursuing hotel ownership in 2025 and how she plans to make it happen
* The role of mentorship, continuous learning, and infinite banking in building long-term financial freedom


Kelly Casimiro is a real estate investor, midterm rental host, and full-time working mom who’s on a mission to design a life of freedom and purpose. With no prior background in real estate, Kelly entered the investing world through sheer grit, mindset work, and strategic action, quickly building a successful midterm rental portfolio while balancing a demanding job and family life.

Her journey is proof that you don’t need to “have it all figured out” to start. Through time-blocking, systems, and smart delegation, Kelly has mastered the art of doing more with less and she’s not stopping anytime soon. Her latest goal? Acquire and revitalize a hotel in 2025.

Kelly is passionate about hospitality, financial literacy, and creating experiences that go beyond four walls. She’s a powerful example of what’s possible when you combine vision, structure, and the willingness to pivot. As the new co-host of Where Should I Invest, Kelly brings fresh perspective, practical insights, and real talk to every conversation.
Contact Kelly Casimiro here:
Instagram: https://www.instagram.com/kelly_casimiro/
Website: https://cazerhomes.holidayfuture.com/
LinkedIn: https://www.linkedin.com/in/kelly-casimiro/
This episode has been brought to you in part by:
Dalia Barsoum, Streetwise Mortgages – https://streetwisemortgages.com
US Properties – https://www.usproperties.ca
Mid Term Rentals – https://midtermrentalproperties.com
Inspire Beach Resort – https://inspirebeachresort.com
Jamil Rahemtula – https://jamilrahemtula.com

Do you need help or ideas for your own real estate investing business?
Reach out and let us support your journey at Back to Episodes