May 28, 2026 – The Metro South Chamber of Commerce hosted its 35th Annual Small Business & Entrepreneur of the Year Awards Luncheon, bringing together business leaders, educators, and public officials to celebrate outstanding achievement in small business and entrepreneurship across the region. The event additionally highlighted the importance of workforce readiness and education-to-career alignment as key drivers of long-term economic growth in Metro South.
The program focused heavily on workforce readiness and the need to better prepare students for real-world employment opportunities. A central theme of the discussion was the expansion of career-connected learning through new Advanced Placement course offerings, including AP Business with Personal Finance and AP Cybersecurity. These initiatives, developed in partnership with the U.S. Chamber of Commerce and College Board, are designed to strengthen the pipeline between education and industry by equipping students with practical skills that translate directly into today’s workforce. Learn more – Addressing the Readiness Gap: Preparing Students for Today’s Workforce. With 84% of employers saying grads aren’t workforce-ready, the U.S. Chamber of Commerce and the College Board are launching new AP courses to equip students with business essential knowledge.
Speakers included Eric Paley, Secretary of the Massachusetts Executive Office of Economic Development, who spoke about the Commonwealth’s economic development strategy and the importance of building a strong talent pipeline to support continued business growth. Clare Bertrand, Executive Director of Career Strategy & Employer Partnerships at the College Board, emphasized the role of education in preparing students with career-relevant skills and expanding access to coursework that aligns with workforce needs. Keegan Shepardson, Massachusetts District Director for the U.S. Small Business Administration, shared updates on SBA resources available to small businesses, including access to capital, technical assistance, and programs that support entrepreneurs at every stage of growth. Together, the speakers reinforced the importance of aligning education, workforce development, and small business support to strengthen the regional economy.
🏆 Entrepreneur of the Year: Mother’s Daughter Juice + Wellness Bar
Chandra Gouldrup is a visionary entrepreneur bringing fresh energy and purpose to Brockton through her farm-to-table juice and wellness concept. As the founder of a new juice and wellness bar, Gouldrup has created a space rooted in health, accessibility, and community connection. Her business emphasizes fresh, locally sourced ingredients and nutrient-rich offerings designed to promote wellness while supporting regional agriculture. Driven by a passion for holistic health and economic revitalization, Gouldrup chose Brockton as the home for her venture, investing in the city’s continued growth and vibrancy. Her establishment goes beyond a traditional juice bar—serving as a welcoming hub where residents can gather, recharge, and learn about healthier lifestyle choices. Through curated menu options, educational touchpoints, and a focus on quality, she is helping to make wellness more approachable and inclusive. Gouldrup’s entrepreneurial journey reflects both resilience and purpose. By combining business innovation with a commitment to community impact, she exemplifies the spirit of entrepreneurship in Metro South. Her work not only introduces a valuable new amenity to Brockton but also contributes to a broader movement toward healthier, more connected communities.
🏆 Small Business of the Year: Vineyard Farm
Vineyard Farm, located in West Bridgewater, Massachusetts, is a growing agricultural destination founded by Elio Silva. Since opening in 2023, the 74-acre, family-operated farm has become a valued part of the local food system, offering fresh produce, prepared foods, and a welcoming, community-focused farm market experience. A standout feature is Vineyard Farm’s popular seasonal corn maze, which draws visitors from across Metro South and beyond. Alongside pick-your-own produce, farm animals, and seasonal events, the farm provides an engaging, family-friendly environment that connects people to agriculture and the origins of their food. Silva has demonstrated strong vision and investment, committing $2.4 million to expand operations, including a new multi-use agricultural facility that will support production, retail, and agritourism. The project will create jobs, strengthen local food access, and enhance year-round programming. Silva’s journey from Brazil to business owner reflects perseverance and entrepreneurial spirit. Vineyard Farm stands as a model small business; blending innovation, agriculture, and community impact while creating a vibrant destination for the region.
The 35th Annual Small Business & Entrepreneur of the Year Awards Luncheon underscored the strength and diversity of Metro South’s business community, while highlighting the importance of preparing the next generation for workforce success. With a focus on education, economic development, and entrepreneurship, the program reinforced the Chamber’s ongoing commitment to fostering growth, collaboration, and opportunity across the region.
View more photos on flickr! Photos courtesy of Rich Morgan Photography.
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