Meet Jenn Gladysz

We were lucky to catch up with Jenn Gladysz recently and have shared our conversation below.

Jenn, so many exciting things to discuss, we can’t wait. Thanks for joining us and we appreciate you sharing your wisdom with our readers. So, maybe we can start by discussing optimism and where your optimism comes from?

I’ve always been an optimist. I focus on the good and what’s working, while staying realistic about challenges and areas that need improvement. I’m a natural problem solver—I enjoy untangling issues and finding the best way forward. This approach keeps me feeling positive, even when faced with tough situations. I believe that with the right mindset and teamwork, most problems can be solved.

As a property manager, being both optimistic and a problem solver is essential. Issues in need of creative solutions pop up all the time, often right before check in, and we need to figure out quick solutions. It helps to genuinely enjoy the process and feel confident that you can make things happen.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

I started Cocoon, a boutique vacation rental management company in Joshua Tree, to offer something special – a warm yet professional hosting experience. I saw a real need for a fresh approach in the vacation rental management space.

Many other companies are either too cold and corporate or too casual and unprofessional. We offer the right blend of personal service with professional standards. The best part of vacation rentals is that personal connection between the guest, the host and the destination. Our job is to foster that connection. Our goal is for our guests to have a transformative stay. The desert is a special place to introduce to our guests and we feel very grateful for the opportunity.

We’re also dedicated to supporting the local community and businesses and providing guests with authentic, memorable experiences, which include add-ons like sound baths, cacao ceremonies, private chefs, guided hikes, stargazing tours and more. We’re more than just a stay!

We handpick unique properties that really capture the essence of desert living. We’re growing our portfolio carefully, ensuring each home meets our high standards.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

I have to laugh when I look back at the experiences I’ve had that have led me to vacation home property management.

I spent three years in the Army, which taught me attention to detail. When in training, if you wanted a weekend pass, your room had to pass inpection. I learned to make a bed perfectly, clean the bathroom until it sparkled and to stage everything in its place.

I also come from an arts background and studied at NYU, this taught me a lot about design and colors, This artistic sensibility complements my military experience.

And for fifteen years, I operated my own dog walking business in Brooklyn. While people often envision me strolling city streets with a pack of dogs—which is how it began—by the time I sold the company, we had become Brooklyn’s largest and highest-rated dog walking service. We boasted two offices, four managers, and a team of fifty employees. This entrepreneurial journey taught me how to run a business effectively, establish efficient procedures, scale operations, and manage a 24/7, 365-day-a-year enterprise—much like vacation property management.

This eclectic blend of experiences has equipped me with a wide range of skills necessary to successfully operate Cocoon. For others who are just starting out on their journey, I would say to learn from the opportunities you have, you never know where they might take you.

Any advice for folks feeling overwhelmed?

I’m so fortunate to live in an area where, when I’m feeling overwhelmed, I can go out into the desert, find some true quiet and just step away for a time to reset and just breathe. I find that a few minutes (or hours) out in the desert allows me to refocus, prioritize and adjust so I’m not feeling overwhelmed. I recommend taking some time in your quiet place… and finding some time to visit the desert.

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