SPOTLIGHT When I started Windsor Group LLC, my focus was simple: build something meaningful, create opportunity, and deliver excellence. What I didn’t fully realize at the time was that entrepreneurship would become one of the most powerful vehicles for impact in my life—not just economically, but in how I give back. Business ownership didn’t just give me a platform to grow revenue; it gave me the ability to be intentional about where that success flows. Over time, giving back stopped being something we did occasionally—it became part of who we are. It became a responsibility. In 2025, Windsor Group LLC proudly continued our commitment to impactful and intentional corporate giving. For the third consecutive year, we were named to the Washington Business Journal’s list of Top Corporate Philanthropists in the Greater Washington, DC region—an honor that reflects our focus on aligning business growth with community investment. Our outreach focused on organizations that help close the gap between what communities need and what is available through traditional systems. That gap is real—and for many, it’s where hope either grows or disappears. We continued our work with the Code of Support Foundation, helping provide coordinated care and resources to veterans and their families— communities that I feel deeply connected to, both personally and professionally. We supported the Sallie Eaton Benevolence Foundation, increasing our contribution from 50 to 100 Thanksgiving meals for families facing food insecurity during a time of rising job loss. We invested in the Williams Franklin Foundation, supporting HBCU students pursuing careers in business and entrepreneurship, because representation and access matter. We partnered with the Women Veterans Interactive Foundation to support women who have served our country but still face barriers to housing, health, and economic stability. And through organizations like Agape Love in Action and the Black Art Today Foundation, we supported both immediate needs and cultural expression—because community is not just about survival, it’s also about identity and voice. But as Windsor has grown, my thinking has evolved. I’ve started to ask a different question: What does it mean to give in a way that outlives the company itself? Because the truth is, businesses don’t last forever. At some point, Windsor Group will no longer exist in its current form. And when that day comes, I don’t want our impact to end with it. Legacy, to me, is about continuity. It’s about building something that keeps working long after you’ve stepped away. That means thinking beyond corporate giving and toward personal commitment. It means creating structures—whether through foundations, partnerships, or longterm investments—that ensure the causes I care about continue to be supported for years to come. It also means being clear about what matters most. For me, that includes supporting veterans and military families, because I understand their journey. It includes investing in people who look like me—creating access, opportunity, and pathways that may not have existed otherwise. And it includes addressing food insecurity, because no family should have to choose between basic needs and dignity. If business ownership taught me anything, it’s that we all have the ability to make things happen. The question is: what are we choosing to build that will last? Windsor Group has allowed me to give in ways I never imagined. But the next chapter is about ensuring that giving doesn’t depend on the business—it becomes part of the legacy. Because at the end of the day, success isn’t just measured by what you build. It’s measured by what you leave behind. DIEDRE WINDSOR is the founder and CEO of Windsor Group LLC and a member of the Enterprising Women Advisory Board and the Enterprising Women Foundation’s Entrepreneurs of Purpose program. She was a recipient of the Enterprising Women of the Year Award, and mentors and supports the Young Enterprising Women Program. Connect with her at www.windsorgroup-llc.com. Diedre Windsor Windsor Group LLC Leaving a legacy that outlives the business enterprising Women 97
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