Specialists in Rental Property Management at Venture Out
Venture Out Property Solutions was born from a desire to provide homeowners with better options for managing and renting their Venture Out homes or lots.
In 2022 our founder, Marcelo Papalardo, a homeowner at Venture Out, encountered underwhelming results with the on-site realtor, and no alternatives that met his needs so he decided to manage his own rentals, using trusted local expert Ruby Shipley as his property manager.
With a background in customer service and technology, Marcelo worked closely with Ruby to perfect the guest experience and rental management process applying continuous improvement, innovation, and the use of advanced technology.
Venture Out Property Solutions was born in 2024, when Ruby and Marcelo decided to join forces to cater to Ruby's customers were looking to outsource the complete rental management experience. Through her company, Fussy Flamingoes, Ruby provided the Property Management and Cleaning Services, and Marcelo enabled Fussy Flamingoes to provide a turnkey solution by providing the technology and reporting functionalities required for a 100% turnkey experience for homeowners.
In 2025, Jessica Smith, successful owner of Jessica Smith's Amazing Cleaning and Ruby's mentee joined forces with us, a planned move which was accelerated due to Ruby's unfortunate passing.
Our Commitment:
We are committed to helping homeowners achieve the best financial returns, by providing an optimized, turnkey guest experience, omni-channel sales and marketing of your property, and ensuring guests enjoy memorable, hassle-free stays. We rent your property under your rules, and take care of it like it's our own.
Whether you’re:
A homeowner seeking better returns and peace of mind,
An investor looking for a seamless, turnkey rental solution, or
A guest dreaming of an unforgettable vacation,
We’re here to deliver beyond expectations.
People and Processes: The Key to Our Success
At the heart of our rental management success is a simple but powerful formula: exceptional people and efficient processes. Our team, Jessica Smith and Marcelo Papalardo, proud Venture Out owners—brings years of experience and a deep connection to the community. Their leadership and vision ensure that every detail is handled with precision and care.
What sets us apart is our commitment to working with local talent. We proudly contract local residents, many of them fellow Venture Out homeowners, to deliver unparalleled service. Their firsthand knowledge of the community and dedication to excellence create a seamless experience for homeowners and guests alike.
Rentals Property Management & Cleaning Services
Owner of Jessica Smith's Amazing Cleaning LLC
Licensed Property Manager.
Owner at Venture Out, year-round resident.
10+ years specializing in cleaning services in the Lower Keys.
5+ years actively managing properties and marketing rentals of Venture Out Properties.
Long-time resident with deep roots in the Community.
Mentored by Ruby Shipley.
Technology Management & Financial Administration Enabler
Owner of Venture Out Property Solutions LLC
Venture Out Owner , seasonal resident.
20+ years managing services businesses and customer service to top corporations worldwide.
10+ years developing software based solutions to optimize customer service and services delivery.
2+ years developing a Venture Out specific rental management process, supported by technology systems.
Active member of the Venture Out Community.
Ruby Shipley †
Founder of our partnership model, mentor and inspiration
Owner of Fussy Flamingoes, LLC - Honorary Partner
Owner at Venture Out, year-round resident
20+ years leading cleaning operations and customer service operations in the Washington DC area for large corporations
5+ years involved in managing rentals and cleanings at Venture Out
Active member of the Venture Out Community.