15 Minute call: $60

30 Minute call: $110

60 Minute call: $200

Short Term Rental Expert

Jen Gladysz

About Jen Gladysz

Jenn Gladysz brings a wealth of diverse experiences to the short-term rental industry, blending a background in the military, arts, and high-pressure service business. Originally from New York, Jenn’s journey began with a desire for adventure, leading her to join the Army, where she spent three years working on Army Watercraft—a unique role that taught her resilience, adaptability, and teamwork. After her time in the military, she pursued her passion for culture and creativity, earning a degree in Art, Culture, and Museum Studies from New York University.

Jenn’s career path took a turn from the nonprofit world when she founded and built the largest and highest-rated pet care business in Brooklyn. Over 15 years, she developed a deep understanding of customer service, attention to detail, and creating exceptional client experiences—skills that have translated seamlessly into managing short-term rentals.

In 2020, Jenn sold her business and hit the road with her family, spending a year traveling across the U.S. in a camper. It was during this time that she fell in love with the stark beauty and tranquility of Joshua Tree. Deciding to make it home, Jenn channeled her entrepreneurial spirit into investing in and setting up short-term rentals. She has since become an expert in curating exceptional spaces and optimizing their performance, combining her eye for design, operational expertise, and deep understanding of what travelers are looking for.

Today, Jenn is dedicated to providing guests with unforgettable stays that showcase the magic of the desert, blending thoughtful design, seamless hospitality, and a connection to the area. Her varied experiences uniquely equip her to help others navigate the short-term rental industry, whether by managing properties or consulting on how to create profitable and welcoming spaces.


  • Short-Term Rental Setup and Design: Expertise in curating inviting, functional, and aesthetically pleasing spaces tailored to the short-term rental market.

  • Investment Strategy: Skilled in identifying profitable short-term rental opportunities and maximizing property potential.

  • Operational Excellence: Proficient in managing day-to-day operations, ensuring seamless guest experiences and efficient property management.

  • Hospitality and Guest Experience: Focused on creating personalized, memorable stays that foster positive reviews and repeat bookings.

  • Customer Service: Over 20 years of experience delivering exceptional service and building strong client relationships.

Areas of Expertise

  • Marketing and Optimization: Knowledgeable in pricing strategies, listing optimization, and leveraging platforms to increase bookings and revenue.

  • Problem-Solving and Adaptability: Developed resilience and quick-thinking skills through experience and high-pressure entrepreneurial ventures.

  • Community Connection: Passionate about promoting the unique beauty and culture of Joshua Tree to enhance guest stays.

  • Consulting and Mentorship: Offers guidance to new and experienced investors on setting up, managing, and scaling short-term rental businesses.


  • Founder of Cocoon: Built and scaled Cocoon, a boutique vacation rental management company in Joshua Tree, known for its thoughtfully designed properties and exceptional guest experiences.

  • Largest Pet Care Business in Brooklyn: Founded and grew Brooklyn’s highest-rated pet care company, serving thousands of clients over 15 years before successfully selling the business.

  • Military Service: Served three years in the U.S. Army working on Army Watercraft, gaining invaluable skills in leadership, teamwork, and problem-solving.

  • Degree from NYU: Earned a degree in Art, Culture, and Museum Studies from New York University, showcasing a lifelong passion for creativity and design.

  • Desert Host and Advocate: Established a reputation as a trusted and knowledgeable host, providing exceptional stays that highlight the unique beauty of the Joshua Tree area.

  • National Road Trip Adventure: traveled the country in a camper for a year, gaining firsthand experience in hospitality and understanding diverse travel needs.

  • Short-Term Rental Expert: Successfully invested in and set up multiple profitable and beautifully designed short-term rentals, becoming a recognized expert in the industry.

Notable Achievements


Mentorship Focus

Jenn is an excellent communicator and coach. She will help you with identifying profitable short-term rental markets and evaluating property potential based on location, demand, and competition. She can help guide mentees in choosing the right property to meet their financial and lifestyle goals, with an eye for both aesthetics and functionality. Jenn Offers her mentees expertise in creating unique, guest-friendly spaces that stand out in a crowded market and rafting compelling property listings with professional photography, engaging descriptions, and strategic pricing. She has Developed streamlined processes for guest communication, cleaning, and maintenance to ensure efficiency and guest satisfaction as well as knowing the best way to implement dynamic pricing strategies and leverage analytics to maximize occupancy and income. Jenn is excellent with Brand Development and can coach her mentees on building a recognizable and trustworthy brand that attracts repeat guests and grows their reputation. In short term rentals, a great guest experience is paramount and Jenn will teach you how to deliver exceptional hospitality to drive positive reviews, repeat bookings, and word-of-mouth referrals.