Being built to last does not mean remaining the same. In fact, longevity demands the opposite. It requires the ability to evolve, innovate, withstand difficult seasons and continually prepare for what comes next. That is true for businesses, and it is equally true for YEA.

Over the past 20 years, Jamaica’s entrepreneurial landscape has changed considerably. The challenges facing today’s entrepreneur are different, the opportunities are greater and technology has changed what is possible. YEA must therefore continue to evolve alongside the entrepreneurs we serve.

As President, I am particularly proud that as we honour our history, we are also positioning YEA for its next chapter. Our focus remains on building the whole entrepreneur, strengthening our members commercially while supporting their professional and personal development. Through mentorship, capacity building, advocacy, strategic partnerships, market access and meaningful connections, we want YEA to remain a place where entrepreneurs do not simply start businesses, but build enterprises capable of lasting.

Twenty years reminds us that entrepreneurship is never a solo journey. YEA has been a community of connection, support and opportunity for generations of Jamaican entrepreneurs, and our responsibility is to ensure that legacy continues.

Over the next twelve months, we will celebrate the people and stories that built YEA, honouring our founders, past presidents and entrepreneurs, while creating new opportunities for those coming behind us. Look out for a year of reflection, recognition and new beginnings as we celebrate where we have been and boldly shape where we are going.

Being surrounded by other business owners gave him access to experiences, advice, relationships and lessons that would have been much harder to acquire in isolation. “In business, we make mistakes. I have had my fair share along the way. Some were expensive. Some cost time I did not get back,” he reflected.

The value of an entrepreneurial community, he says, is that someone else may already have faced the problem you are trying to solve. “It is often cheaper to learn from someone else’s mistake than to make your own.” In that sense, Pairman did not simply help build YEA. YEA helped to build the entrepreneur he became.

If he were starting again, Pairman says he would spend less time asking, “What business should I start?” and more time asking, “What problem can I solve exceptionally well?” He would stay closer to customers, measure results rather than activity and establish a stronger voice within his industry much earlier. Social media, podcasts, panels, articles and industry forums now give entrepreneurs opportunities to demonstrate expertise and build credibility that did not exist in the same way when YEA began. Pairman believes sharing knowledge rarely diminishes competitive advantage. Instead, credibility can turn strangers into clients, clients into relationships and relationships into opportunities.

Despite the challenges entrepreneurs still face, including access to capital, bureaucracy and the cost of doing business, Pairman is optimistic about Jamaica’s entrepreneurial future.

Technology has lowered barriers to entry. Social media has widened access to customers. E-commerce has transformed distribution. Artificial intelligence is giving small businesses capabilities that once demanded considerably more money and manpower.

His challenge to Jamaican entrepreneurs is therefore to think beyond simply creating businesses that employ their founders. He wants to see more enterprises that scale, employ others, export, embrace technology, solve meaningful problems and create wealth beyond the person who started them.

Pairman also believes success should increase an entrepreneur’s willingness to give back, not postpone it. Mentoring, volunteering and helping other entrepreneurs, he argues, should be part of the journey itself.

Twenty years after becoming YEA’s first President, Pairman does not describe himself as having arrived. He describes himself as still learning, questioning assumptions and seeing opportunities he could not have imagined two decades ago.

For Ledford, that connection between fashion and identity is central to the brand. CAW’s own positioning captures it simply: this is more than fashion. It is identity.

That makes New York a particularly fitting market. The city is home to one of the world’s most influential fashion industries and one of the largest concentrations of Jamaicans and Caribbean nationals outside the region. For CAW, that creates both a commercial and cultural opportunity.

At the same time, the brand has the opportunity to reach consumers who may have no Jamaican connection but are attracted to distinctive design, craftsmanship and the message of confidence behind the product. That dual appeal is important.

Ledford has built CAW around the idea that women should feel comfortable showing up boldly and authentically. The Confident Authentic Woman is therefore not merely the company’s name. It represents the woman the brand is designed to serve.

The expansion also comes at a time when women-owned businesses continue to play a significant role in the global economy. CAW enters that environment as both a woman-led enterprise and a distinctly Caribbean brand.

The move is therefore more than expansion. It is the export of identity, confidence and culture. The challenge will be to scale while preserving the authenticity that makes CAW distinctive. For Ledford, however, being authentically Jamaican is not a limitation. It is part of the brand’s international advantage.

Questions about profitability, cash flow, expansion and the strength of internal systems, she believes, can fundamentally change how an entrepreneur manages a business.

The journey has not been without challenges. McGaw-Smith has had to navigate client acquisition, staffing, systems development, growth and the challenge of building an organisation capable of functioning beyond its founder. One of her biggest lessons is that sustainability requires more than technical competence.

By 2021, McGaw & Company had expanded its team, moved into a larger office, and secured major engagements. McGaw-Smith was named YEA Young Entrepreneur of the Year, while the firm was recognised among the top performers in the Scotiabank Vision Achiever Programme.

Her elevation to Public Accountant brings McGaw-Smith full circle, returning her to auditing, which formed part of the foundation of her career. It also allows McGaw & Company to expand its services to include audit and assurance.

For MSMEs, she believes the lesson is clear: do not wait until financing, investment, a contract or regulatory requirement arises before getting your financial house in order.

Over 40 entrepreneurs were challenged to think differently about funding and business readiness as the Young Entrepreneurs Association of Jamaica marked World Entrepreneurs Day on August 21, 2026, with the staging of Cash In on Change.

The special entrepreneurship-focused session was pushed by YEA in collaboration with NexxSTEPP Lifelong Educational Services and the U.S. Embassy-supported Catalyst Circle programme. The event formed part of YEA’s broader strategy to improve access to funding and other opportunities for entrepreneurs, while strengthening their capacity to successfully pursue those opportunities.

The interactive session explored funding, business readiness, social impact and the importance of entrepreneurs being able to clearly communicate the value that their businesses create.

It culminated in a pitching competition, with Dr Julian McKoy Davis emerging as the winner of the $10,000 cash prize.

For YEA, Cash In on Change also reflected a deliberate effort to broaden the financing conversation beyond traditional commercial loans.

Entrepreneurs today can potentially access resources through grants, equity investment, pitch competitions, corporate partnerships, development financing, social impact funding and other non-traditional sources.

The challenge is not only knowing that these opportunities exist, but understanding what funders require and being able to demonstrate that the business is capable of responsibly using the resources it receives. That is why YEA is increasingly linking its access to finance agenda with capacity building, mentorship, networks and practical business support.

YEA President Cordell Williams said access to funding must go hand in hand with readiness. While YEA continues to connect entrepreneurs to financing opportunities, she stressed that businesses must also be able to present credible financials, demonstrate a viable market and clearly explain how funding will support growth.

The wider message of Cash In on Change was simple: funding matters, but so do readiness, strong systems, credible financials, networks, social impact and the ability to communicate value.

The Young Entrepreneurs Association of Jamaica and the Embassy of Colombia in Jamaica are deepening discussions aimed at creating practical opportunities for Jamaican entrepreneurs to build relationships, strengthen their capacity and explore the Colombian market.

That developing relationship was given a cultural expression on August 27, 2026, when YEA partnered with the Colombian Embassy and the UCC Business Development and Consulting Institute (BDCI) to stage Entrepreneur Movie Night at the UCC Lecture Theatre in Kingston. The evening featured a special screening of the Colombian film La Suprema, and brought entrepreneurs and business stakeholders together around entrepreneurship, international market access and cultural exchange.

The event emerged from discussions between YEA and the Embassy which began in early July. Those conversations have been progressively identifying various opportunities for collaboration with the intention of ultimately capturing and executing the agreed initiatives under a Memorandum of Understanding.

YEA President Cordell Williams said the relationship could help Jamaican entrepreneurs better understand the Colombian market while creating access to useful networks and opportunities.

The staging of Entrepreneur Movie Night at UCC also signalled the continued strengthening of YEA’s longstanding relationship with the university’s Business Development and Consulting Institute. The two organisations have previously collaborated through consultancy and capacity-building initiatives, and the event created another opportunity to bring their entrepreneur networks together.

UCC BDCI representative Tennille Howell-Hussey said the collaboration reflected the institution’s continued interest in supporting entrepreneurial growth.

The programme itself reflected that progression, with UCC BDCI addressing Building Entrepreneurial Capacity Through Strategic Partnership, YEA focusing on From Capacity Building to Market Access: Creating More Opportunities for Entrepreneurs, and the Colombian Embassy highlighting Colombia as a gateway for entrepreneurship, trade and business collaboration.

Among the strategies shared were understanding how to dress for one’s body type, identifying timeless pieces that can be worn in multiple ways, learning how to maximise an existing wardrobe on a budget and using styling, accessories and skincare to create a polished professional image.

Turner also encouraged participants to shop more strategically by selecting versatile pieces that can transition between meetings, networking events and other professional engagements.

The event was supported by Krystal Cameron Designs, Skin By Indie, Perkup Coffee and Aunty Beryl’s Catering, with the participating businesses also benefiting from exposure to the entrepreneur audience.

Beyond the learning session, Dress for Success created a relaxed environment for entrepreneurs to network, build relationships and shop, allowing YEA to combine capacity building with direct support for entrepreneur-owned businesses.

Following the success of YEA’s Young Entrepreneurs Success Series: Protect Your Business Before You Pitch in June, delivered with the Jamaica Intellectual Property Office and facilitated by JIPO Executive Director Lilyclaire Bellamy, the Young Entrepreneurs Association of Jamaica is supporting wider MSME participation in the World Intellectual Property Organization’s (WIPO) Scaled Up Intellectual Property Management Clinic in Jamaica.

The WIPO-led initiative, supported by JIPO and other business development partners, builds on basic IP protection by helping entrepreneurs identify, manage and leverage intangible assets such as brands, designs, technology, content, processes and know-how for commercialisation, competitiveness and market expansion.

Selected enterprises will receive expert training, mentoring and tailored guidance in areas including trademarks, licensing, contracts, internationalisation and risk management.

YEA President Cordell Williams notes that YEA welcomes the expanded approach because while entrepreneurs must protect their intellectual property, they must also understand how to turn those assets into business value.

The programme is open to businesses across sectors including technology, creative industries, manufacturing, food and beverage, agriculture, tourism, fashion, health and consumer goods.