Winthrope Wellington is educating the diaspora about living & investing in Jamaica

May 13, 2023  -Pretty soon, Winthrope Wellington will have to start waking up at 4 am. The Jamaican sun takes no prisoners, and with the summer months approaching, Wellington, who is better known as “Throp”, is determined to outpace the heat. Every day, the 39-year-old head of Throp Media squeezes in a yoga routine and a run. He credits this practice of regular running for helping him establish discipline and the determined mindset he brings to all avenues of his life.

Journey to Jamaica

There’s a theme of motion throughout Wellington’s story. Born and raised in New York City, he witnessed firsthand his father’s entrepreneurial spirit through both his thriving NYC-based taxi company and Travelers Beach Resort, which sits on the seven-mile beach in Negril, Jamaica.

Initially not content to follow in the family business, a young Wellington majored in finance and management at the University of Albany, where he made strides to reach the top of his field. He soon qualified for a second-round interview for a position at one of the leading investment groups, Morgan Stanley.

Caught up in a whirlwind, Wellington recalls the furious and fast pace of city life took its toll. Slamming espressos, the pressure to find a job, balancing a social life, the anxiety of sending applications, the seemingly endless and rigorous interviews, were all a part of regular life. “I had my moment of truth,” Wellington explains. “I asked myself why I was doing this.” He needed to slow down.

Adjusting to Life in Jamaica

In 2006, he moved to his father’s native country, Jamaica, and began assisting with the Travelers Beach Resort. “Not a lot of thought was put into the decision,” he admits, “But it seemed like the best opportunity for me and my life from a long-term perspective.”

It would be easy to assume that what came next was an immediate love affair with his new island home. After all, to date, along with executive roles at his family-owned hotel, Wellington has also held the position of Negril chapter chairman for the Jamaica Hotel & Tourist Association, and is the founder of Throp Media. All of these jobs are about celebrating the potential and wonder of Jamaica.

“Moving to Jamaica was a rough transition,” he freely admits. “I was trying to stick a square peg into a round hole.” He says there was a real sensory and cultural overload on top of learning the hotel business on the fly. Homesick, Wellington would fly back to New York every month, racking up an unsustainable travel expense. He was so out of touch with his surroundings that he didn’t realize he was living in paradise. “There was a period of, say, two to three years without going to the beach or going in the water,” he laughs, “and I live on the beach!”

To fall in love with the country, he learned to see it through the eyes of others. Friends would visit or move to Jamaica and he would marvel at how at peace they were. He traveled around the island taking in everywhere from dense urban Kingston to serene, remote Treasure Beach. Along with his two younger brothers, he took over the operations of Travelers Beach Resort, providing another vantage point for what the island could do for visitors and permanent migrants alike.

“I realized this immense sense of gratefulness and gratitude,” recalls Wellington. He’s convinced Jamaica is not just special, but will become a wealthy island. “Man, I feel like I got in on Microsoft in the seventies,” he chuckles.

Founding Throp Media

In 2017, his youngest brother, Wingate Wellington, took over every aspect of running the resort. Under his stewardship Travelers is thriving, earning rave reviews from visitors and guests. While Winthrope Wellingston remains a managing director at the resort, he suddenly came into a surplus of free time. His first plan was to become a travel vlogger, documenting his fitness journey on a quest to compete in the six major marathons across the world. However, he hit his first snag. “I discovered very quickly that nobody cared about my running,” he laughs. On top of that, traveling costs quickly proved to be prohibitive.

So, he recalibrated. Instead of showing his journey around the world, he would showcase Jamaica, especially Negril, his adopted home. Now instead of leaving the island, he is going to do all he can to bring people to the island. On his Youtube channel simply called “Throp,” he hosts a series of interviews with notable Jamaicans and foreigners who have invested in Jamaica. Through a combination of compelling guests, high production values, and prolific output – sometimes releasing three interviews in a week – Wellington has managed to maintain a growing and passionate community he affectionately calls Throppers.

Throp-X was the natural next step for his eager community, excited about investing and networking, and an affable host willing and able to put it all together. “I used the community to canvas different topics and questions,” he explains. “I wanted to bring together these people the community already knew about, and have this parasocial relationship with.” Throp-X allows the community to see a podcast in person, and to interact with the experts they’ve come to know through Wellington’s videos.

The annual event takes place in Negril at where else but the Travelers Beach Resort. It’s possible to get a packaged deal that includes lunch and dinner, residential and commercial real estate tours, panel discussions, and more. For Throppers who can’t make the trip, a virtual ticket is available for $150, providing complete remote access to the five-day event.

The event’s panel discussions are diverse and some surprising, with gregarious speakers sharing riveting insights into various disciplines, bucking what you might expect from a conference focused on entrepreneurship and investment. Particular standouts include “Overcoming Bad Mind in Business” and “Cautionary Tales from a Jamaican Real Estate Lawyer.”

While several videos of the last event are already online, some are still making their way to the channel, Wellington notes.

Words of Wisdom

Despite managing a production company and organizing annual events, Wellington still dreams about the prestigious Six Star Medal for runners. “I could not be here with my business and my channel without running,” he reflects. “It has taught me so much about myself.” He remembers discovering the qualification times for the Tokyo marathon, one of the Six Major marathons. For the men’s full marathon, the time was, and remains, under 2 hours and 32 minutes. The maximum number of entrants is 50 split between 25 men and 25 women. “This isn’t fair,” he remembers thinking in 2016. “I started pointing my finger outwards.” Today, he can hit under the qualifying time before breakfast.

“Never put limitations on what you can do and what you can achieve,” he advises. He believes Throp Media can go international, and what is going to stop him? Like his running and the country that has adopted him, he believes Throp Media has untapped potential ready to flow to the surface.