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ChooseHappiness

Autobiography of Sheldon James
Hospitality Leader | Entrepreneur | Cultural Advocate | Connector of the Caribbean

My name is Sheldon James, and my life’s work sits at the intersection of hospitality, trade, and culture—driven by a deep belief in the transformative power of connection, service, and purposeful enterprise.

I am the Director and Sales Manager of Choose To Be Happy Vacation Rentals and Property Management Services, where I oversee a dynamic and growing portfolio of short-term rental properties across Kingston and St. Ann, Jamaica. Through Choose To Be Happy, I’ve built a trusted brand rooted in guest satisfaction, operational excellence, and meaningful partnerships. Whether welcoming families, digital nomads, or returning diaspora, my team and I create experiences that feel like home—infused with Jamaican warmth, professionalism, and style.

Beyond hospitality, I am the Proprietor of BuySmart Solutions Group, a wholesale and logistics company with operations in Kingston, Montego Bay, and Havana, Cuba. BuySmart specializes in import/export, market development, and supply chain innovation for the Caribbean. I’m particularly proud of our efforts to support BIPOC entrepreneurs, small retailers, and regional wholesalers through fair trade access and business incubation. One of our signature ventures is the Jamaica Logistics Zone (JLZ)—a government-recognized Special Economic Zone (SEZ) that promotes economic growth through tax incentives, bonded warehousing, and cross-border investment.

But business is only part of my story.

I am also the Founder of the Sheldon Lee Foundation: Cuban Art Without Borders, a cultural initiative dedicated to preserving and promoting Caribbean creative expression—especially from coastal and Afro-descendant communities. Through the foundation, I am curating a rare and growing collection of contemporary Cuban and Caribbean art, supporting underrepresented voices, and elevating the region's cultural identity in global forums.

At heart, I am a connector and builder—of people, systems, and opportunities. I work across borders with humility and ambition, driven by a long-term vision of a more inclusive, prosperous, and culturally confident Caribbean. My career has taught me, "People are my greatest resource" and that sustainable impact comes from aligned partnerships, shared values, and the courage to innovate.

Whether I’m closing a property deal, launching a trade route, mentoring a young entrepreneur, or collecting a piece of art from a Cuban studio, I do so with the same intention: to uplift, to connect, and to leave something meaningful behind.
Birthday
September 7
Website
http://www.choosetobehappytoo.com
Location
Kingston, Jamaica
Company Name
Choose To Be Happy, LLC
Your Expertise
Real Estate: Other
What Books from MJ DeMarco Have You Read
  1. The Millionaire Fastlane
Gender
Male
Do you Already Own a Business?
I have a profit generating business ($251k-500k)
Occupation
Director & Sales Manager

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  3. 10

    Location Award! ($10)

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