This past August, in recognition of Black Philanthropy Month and the global call to honor the theme of Sankofa — a West African principle that urges us to “go back and get it” — we proudly welcomed the next class of Gamechangers: Black philanthropic leaders and bold collaborators shaping the future through innovation, generosity, and trust.
play_arrow
Holly Rachel is a Nashville-based entrepreneur and tech executive driven by a passion for innovation, inclusion, and community. As Executive Director of Fisk University’s Darrell S. Freeman Sr. Incubation and Innovation Center, she helps cultivate the next generation of diverse entrepreneurs and business leaders. Holly is also the co-founder of Rachel + Winfree Consulting and serves as President of the Blacks In Technology Nashville chapter. With a background as a forensic scientist at the Tennessee Bureau of Investigation and a master’s degree in chemistry from Vanderbilt University, she brings a rare blend of analytical expertise and community-minded leadership to everything she does.
Tell us your story. (Your journey, your work, or what brought you to where you are today.)
I came to Nashville in 2009 for graduate school and never really left. After working for a while, I started a small tech consulting business, Rachel Lerner Free Consulting, which introduced me to Nashville’s small business community. That experience opened my eyes to both the potential and the gaps in resources available to small business owners, especially in minority communities. When the opportunity came to help create the Freeman Center, I wrote the proposal and later stepped into the executive director role. It felt like the perfect way to build something meaningful that could fill those gaps and give small businesses the tools they need to grow and thrive.
Name a person, tradition, or community value from your past that guides how you give or serve today.
I can’t name just one person … it’s really the sum of the people I’ve met along the way. I’ve learned from great leaders, and I’ve also learned from those who fell short. Both have shaped how I show up for the community and how I envision the Freeman Center’s role. Every experience, good and bad, helps guide what I want this work to stand for.
Sankofa teaches us to look back so we can move forward. If you could speak to your younger self or to future generations of Black gamechangers, what lesson or moment from your past would you share?
I’d tell them and my younger self that it’s okay to do things differently. In fact, it’s better to do things that no one else is doing. Don’t be afraid to stand alone in your idea or your approach. That’s how innovation happens, and that’s how you create real change in the community.
The parable of the talents teaches us to grow and share what we’ve been given. How have you used your gifts — whether time, talent, or resources — to make an impact in your community?
No matter where I’ve worked, a for-profit or nonprofit, the common thread has always been community. My focus has been on identifying the needs around me and figuring out where I can fill the gaps. For the past 10 to 15 years, my work has really been about using my skills and experience to build what I want to see in the world and help others improve their lives along the way.
How have you seen Black generosity and community investment show up in ways that might not always be recognized as philanthropy?
That’s one of the things I love most about working with the Black and minority communities — people show up. They give their time, their knowledge, their services, and their support without hesitation. It’s not always about writing a check. Sometimes, it’s the volunteering, mentoring, and showing up for one another that makes the biggest impact. That’s philanthropy, too, even if it doesn’t always get recognized that way.
How do you define “being a Gamechanger” in collaborative efforts or philanthropy?
To me, being a Gamechanger means doing things differently and bringing something new, fresh, and bold to the table. It’s about challenging the norm and collaborating with others who are also unafraid to do things their own way.
What wisdom or encouragement would you share with someone in Nashville who’s just beginning their journey here locally as a philanthropist or community leader?
Show up. Join the ecosystem. Get to know the people and the work already happening around you. That can mean attending meetups, fundraisers, or conferences; anywhere you can connect and learn. Once you understand the landscape, you can see where your strengths fit and how to collaborate to build on what’s already working.
What are you curious about, excited to see unfold, and/or looking forward to initiating over the next year?
Lately, I’ve been focused on how minority founders can use technology to strengthen their businesses. There’s a digital divide that goes beyond just having devices or Wi-Fi — it’s also about understanding how to use technology to be more efficient and reach further. I’m really excited to explore new tools, new ideas, and new ways to help our business owners close that gap and take their work to the next level.
Black Philanthropy Month: Sankofa Now!
The past holds the key to our future. As we navigate growing challenges, we must draw strength from those who came before us. For this year’s Black Philanthropy Month recognition, we must:
- Remember our philanthropic roots, built on collective care and community-driven investment.
- Reclaim our power to shape the future, ensuring Black-led change is not just recognized but sustained.
- Rise by reinvesting in our people, our movements, and our solutions, because the future of Black philanthropy (and all humanity) depends on what we do today.
A thriving Black community benefits everyone. The fight for equity, opportunity, and justice strengthens our collective future, creating a world where all can prosper. Black philanthropy has always been a catalyst for change. In a time when progress is at risk, we need all hands on deck.
