NEW York native Winthrope “Throp” Wellington grew up witnessing his father’s remarkable entrepreneurial ventures. His father’s thriving taxi company, Winthrop Car Service, and Travellers Beach Resort, nestled along the pristine seven-mile beach in Negril, served as vivid examples of entrepreneurial spirit.

Initially, Throp chose to forge a different path, majoring in finance and management at the University of Albany. Driven by ambition, he aspired to climb the corporate ladder, eventually securing a second-round interview for a coveted position at the prestigious investment firm Morgan Stanley.

Today, Throp is a Jamaica-centric YouTuber who has amassed 36,000 subscribers known as the Throppers. This community is built up of diaspora and non-Jamaican nationals who are fascinated about investing and living in Jamaica. Through various interviews and discussions with expats and repats who have made Jamaica their home, Throp conceptualised the Throp-X conference which will be hosted for the second time on November 13-17 in Negril.

We sat down to talk to Throp about his journey.

Q: You had a great opportunity to have a thriving finance career in New York, why did you decide to move to Jamaica?

A: In 2006, I made a life-changing decision to relocate to Jamaica to join my family’s hotel business. I honestly didn’t put much thought into it. My final thought process of my senior year of college was, “why am I running around and trying to join this rat race when I can join my own family’s business”. A month after my college graduation, I worked under my dad’s tutelage for four years, eventually becoming the general manager for the hotel. After that, I decided to go to business school to get my MBA in entrepreneurship from Babson College. After graduating from Babson and moving back to Jamaica, my dad retired and handed the keys of the hotel over to me and my two brothers. During this period I also became the chapter chairman of the Negril chapter of the Jamaica Hotel & Tourist Association (JHTA) and eventually was elected to the executive board of the JHTA which I served on for one year. After my brother finished business school he took over the leadership of Travellers. Shortly after, I founded Throp Media, with the shared purpose of celebrating the beauty and potential of Jamaica.

Q: When and why did you decide to launch the Throp YouTube channel?

A: In 2018, my initial goal was to become a travel vlogger, documenting my fitness journey and a quest to compete in the world’s six major marathons. However, I quickly found out that no one cared about my travels or my running. I eventually decided to use my unique experience of being born and raised in NY and then moving to Jamaica as a way to show others that if I can do it, so can they. I then began interviewing others who have made the journey, showing that if they can do it, so can you. I have proudly cultivated a growing and passionate community affectionately referred to as “Throppers”. The community came up with this nomenclature, not me.

Q: The Throp-X investment conference is targeted towards people who are interested in investing and moving to Jamaica. What inspired you to conceptualise this?

A: It was the Throp community that came up with the idea. Initially, they wanted to do a meet-up in Jamaica just to meet me but I wanted to see how I could offer more value than just meeting me. So I thought the best way was to bring the content they love so much into real life. Over months we discussed different ideas together on my livestreams and we came up with the concept. We even came up with the name of the conference together.

A particular highlight of the conference is the exclusive real estate tour, providing participants with an up-close look at the diverse residential and commercial offerings in the Negril region.

Q: What are people expected to learn and gain from Throp-X?

A: I’m going to be hosting expert panels alongside Amashika Lorne, where attendees will learn first-hand the processes of purchasing real estate, building and developing properties, and financing projects, as well as an exclusive real estate tour where you can explore Negril’s residential and commercial offerings. We will also have wealth management experts making presentations for those looking to have a greater understanding of Jamaica’s equity markets.