Cocktails With… – Jamaica Observer

Leah Hollingsworth

HOLLINGSWORTH, CEO, Isle & Co

 

Style Observer (SO): How would you describe yourself in a few words?

Leah Hollingsworth (LH): I would describe myself as passionate, disciplined, and layered.

SO: When did you first realise hospitality was your calling?

LH: I’ve always been a people person, but it was through my first internship. I worked at a hotel and took on many roles — front desk, housekeeping, food and beverage — and saw first-hand how my job affects guest experience, and committed myself to that in different disciplines.

SO: What did your years as sales manager with Marriott International teach you about excellence?

LH: Working with Marriott International, and the Luxury Group specifically, taught me that excellence is the standard, and you never fall below it. Good enough never is. Set your standards so high that excellence is your baseline. I apply that to both my personal and professional life.

SO: Was there a defining moment that made you decide it was time to build something of your own?

LH: Yes. I celebrated 10 years with Marriott in May and, while grateful for the experience, I felt a shift to follow my own passions after garnering that experience [and turning it] into something that could contribute to Jamaica’s growing hospitality landscape.

 

SO: What has been the biggest leap of faith in this transition?

LH: Trusting in myself enough to step into entrepreneurship fully. A comfort zone is a beautiful place, but nothing ever grows there.

 

SO: Tell us about your new hospitality company Isle & Co. What gap are you hoping to fill?

LH: Luxury today is about convenience. People are busier than ever, and they want trusted professionals to handle the details. Isle & Co is a hospitality concierge service that prepares properties for the people who will experience them.

As Jamaica’s real estate and hospitality sectors continue to grow, there’s often a gap between completing a property and having it truly guest-ready. Isle & Co bridges that gap through hospitality research, logistics, and execution, with a full launch planned for this fall.

 

SO: What can clients expect that feels uniquely ‘you’?

LH: Attention to detail, discretion, and a personalised experience. I approach every project as if it were my own. Clients can expect clear communication, thoughtful execution, and someone who’s genuinely invested in getting every detail right.

 

SO: What does luxury hospitality mean in today’s market?

LH: Luxury hospitality is no longer defined by price tag, but by experience. Beautiful design matters, but so do the thoughtful details, seamless execution, and genuine care that make a space feel welcoming from the moment someone walks through the door.

 

SO: What advice do you wish someone had given you early in your career?

LH: 1) Every single experience will shape you

2) Celebrate your successes and failures. Both take great courage.

 

SO: Having worked in hospitality, you’ve experienced some incredible destinations. Which place has stayed with you most, and why?

LH: Jamaica Inn, by far! Not just for the beautiful landscape, but for the warmth and familial aspect. That’s what makes for a memorable experience.

SO: What’s one hotel experience that completely raised your standards?

LH: The Baccarat Hotel in NYC. The modern elegance, class, and details… I have yet to experience anything like it.

 

SO: What’s still on your travel bucket list?

LH: Italy, for the food. Africa, for the history and culture.

 

SO: Your personal style is very polished. How would you describe your aesthetic?

LH: Feminine with a touch of drama. I love strong silhouettes and statement pieces, balanced with a classic bag.

 

SO: What’s your beauty or wellness non-negotiable?

LH: Eight hours of sleep, hydration, and most importantly, minimal stress.

SO: What does your perfect day off look like?

LH: A slow morning with tea and The Golden Girls, a good workout, exploring somewhere new, and ending the day with laughter and a glass of wine.

SO: Share with us the title of the last book you read.

LH: The Surrender Experiment: My Journey Into Life’s Perfection by Michael A Singer.

SO: What’s the one fragrance/make-up item you can’t leave the house without this summer?

LH: Tom Ford Soleil Neige Body Oil.

SO: Luxury resort or boutique hotel?

LH: Boutique.

 

SO: Planner or spontaneous?

LH: Planner.

 

SO: Closet full of handbags or closet full of shoes?

LH: Handbags.

 

SO: Rolex or Cartier?

LH: Cartier.

 

SO: Morning workouts or evening wind-downs?

LH: Morning workouts to start the day right.

SO: Beach, mountains or city escapes?

LH: City escapes.

 

SO: Finally, what’s your personal credo?

LH: In the words of Shabba Ranks: Willpower, strong mind, and ability. To me, that’s approaching life with determination, resilience, and belief in yourself. Those qualities, together with faith and integrity, can carry you through almost anything.