I spent my 26th birthday in my favorite way—traveling. At the time, I was living in Medellín, Colombia, but on December 1, 2023, I found myself back on Oahu. Almost a year after I had embarked on a global walkabout, I returned to the island to sell a car I had kept there, catch some waves, and reconnect with friends. That evening, I found myself at Himalayan Kitchen, sharing curry and mai tais with a friend—someone that I didn’t know at the time would soon become my business partner. As we swapped stories about life and business, I had no idea that this casual dinner would set the stage for my next major venture: a move across the world, a new chapter in real estate and hospitality, and a chance to build something meaningful.
The Leap of Faith
To fully appreciate the significance of that evening, let’s rewind a few years to where the story really began. In 2022, I dropped out of college and moved to Hawaii. I walked away from a traditional path in investment banking to chase a half-formed dream: pursue a relationship, start a business, and learn how to surf. Two of those things went well—I launched my first business, a Jeep rental company, and I became a solidly mediocre surfer.
Along the way, I met Bryan, the same friend I shared my birthday dinner with. He had responded to a post I made in a real estate forum, and we became fast friends and surf buddies. Hawaii was everything I hoped for, but after a year, the relationship I moved for fizzled. With nothing tying me down, I automated my Jeep business and booked a one-way ticket to Bali. That decision kicked off a year-and-a-half-long adventure across three continents.
A Global Classroom in Hospitality
That trip was nothing short of cinematic. I dirt biked up Mount Batur, partied on remote beaches in Sumba, rode out a typhoon on a boat in the Philippines, and developed an obsession with artisanal coffee in Medellín. I learned to kite surf at Lake Calima and played cowboy in the mountains of Park City. I even found myself shooting content with models in Indonesia and touring cacao farms in Colombia. Every destination felt like a new chapter in an epic movie, and I savored every second of it.
What I didn’t realize at the time was that I wasn’t just collecting memories—I was gathering firsthand knowledge of what makes an experience unforgettable. Whether I was staying in a jungle bungalow or a luxury beach villa, I saw the same common thread: the best stays weren’t about extravagant amenities but about thoughtful touches, seamless service, and a sense of adventure. Time and again, I found myself thinking, This is what life’s about.
The Lightbulb Moment
By the end of 2023, I had everything I could have wanted—except a clear path forward. Professional vacationer isn’t exactly a job title you find on LinkedIn. That’s where fate intervened. During that December dinner, Bryan shared how he had been running a successful real estate brokerage on Oahu with our future business partner, Jacky. As an investor-friendly agent, Bryan was hard at work helping clients purchase vacation rental properties. But he noticed a troubling trend: too many owners were receiving subpar service from their property managers. He floated the idea of launching a vacation rental management company—one that prioritized exceptional service for both guests and property owners.
It was a lightbulb moment for me. A career centered around creating the kind of experiences that make life worth living? Sign me up.
Building Island Stays
Three months later, after a whirlwind farewell tour of South America, I packed my bags and returned to Oahu. Together, we launched Island Stays Hawaii, the property management division of Halepuna Real Estate Hawaii. From day one, it felt like the culmination of everything I had learned.
Our team clicked from the start. Jacky, a master of all things legal, compliance, and accounting, ensures that our property owners can confidently navigate Hawaii’s highly regulated short-term rental market. Bryan, with his sterling reputation and background in luxury hospitality, brought deep industry insights and a built-in client base of property owners who trusted his expertise. And then there’s me—a year older, a little wiser, and fueled by the lessons I gained from my travels. I wake up every day excited to provide our guests with stays that aren’t just accommodations but memories in the making.
Why We Do What We Do
At Island Stays, we understand that a perfect stay in a magical location can be transformative. It’s not just about having a beautiful unit with great amenities—it’s about curating an experience where guests feel seen, cared for, and free to create their own stories. I know what it feels like to wake up in a place that takes your breath away, to sip coffee on a balcony overlooking the ocean, and to laugh with friends after a day of adventure. That’s the kind of magic we aim to deliver to every guest who stays with us.