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Founder

Director of Cleaning

Area Manager

Platform Manager

Area Manager

Area Manager

Area Manager

Sales Associate

Marketing Manager

JD Dempsey, Founder
From a young age, I loved the idea of sharing new experiences with the people I care about. This meant trips to new places like California with my younger brother and sister, driving the Pacific Coast Highway from campsite to campsite in a rented convertible, spending the last of our money on gas and s’mores, surfing in Hawaii with old friends, and random hikes in Colorado with new friends.
The problem that plagued me was my office job. I knew if I was spending 50 weeks a year at the office, I was not spending enough time with my friends and family living through the vast experiences life has to offer. Fueled by a desire for passive income, I accidentally stumbled into Airbnb by renting out a spare bedroom in the first home I purchased. I quickly learned hospitality suited me; I easily connected with every guest, and some even became long-time friends.
That’s when the need to start Live Free clicked. On one hand, I could ensure guests had memorable experiences during their travels with friends and family. On the other, I could help my friends and family buy some of their time back by handling their real estate guest experiences, leveraging my love for hospitality.
This was not always the case. For the first few homes I tried other property managers. I quickly learned that property managers rarely have full alignment with the homeowners. Most property managers focus on volume, profit, and hidden fees, because they have never been owners. At Live Free, scaling focuses on amplifying the magic of the guest and owner experience. We are owners and optimize for maximum owner revenue through the guest experience. How can we make a guest’s stay awesome with a unique home design, more fun amenities, and best-in-class customer service interactions? How can property owners gain the most confidence that their guests are over the moon, their properties are well maintained, and the owners themselves can live free with extra income and no worries?
My engagement was at none other than a vibey desert Airbnb in Joshua Tree with my family and friends, filled with Airbnb experiences during the day and campfire convos under the stars at night. The hosts’ thoughtful design, hospitality, and recommendations made it possible for us to create lifetime memories. When a guest books with Live Free, hoping to create memorable experiences with their loved ones, the mission becomes personal. The Live Free team works to ensure guests create positive, lifelong memories.
We don't just manage; we curate. Every property is handpicked, meticulously maintained, and optimized as a Legacy asset to ensure a 5-star guarantee.
From booking to checkout, our dedicated Area Managers provide 24/7 white-glove support. You aren't just a guest; you are part of the Live Free inner circle.
We set the benchmark for luxury. Whether it's a modern lodge or a romantic hideaway, every space is equipped with premium essentials that exceed global hospitality standards.
Integrity and passion for the Poconos drive our growth. We operate with total transparency, transforming properties into high-performing experiences.