From corporate finance to education equity, Nick Freeman didn’t take the expected path.
At 26, with an MBA and master’s in finance in hand, he walked away from the corporate world and stepped into Chicago Public Schools. What he saw there (school closures, resource disparities, and the weight of systemic inequity) reshaped his career and his calling.
Today, Nick is the Co-founder and Chief Growth Officer of Innovare, where he works at the intersection of education leadership, edtech, and AI-powered tools. His team helps schools turn real-time data into action reducing administrative burden, streamlining school improvement planning, and giving educators time back to focus on what matters most: relationships.
But this conversation goes beyond technology.
Raised on Chicago’s South Side in Hyde Park, Nick grew up watching his parents run a neighborhood baseball league for twenty-five years out of their basement. They didn’t build it for profit. They built it for community. That example shaped how he thinks about leadership, trust, and responsibility.
In this episode, Nick speaks candidly about being a Black founder in venture capital spaces where less than one percent of funding goes to leaders who look like him. He reflects on mental health, the pressure of representation, and the power of removing the mask: rejecting code-switching and leading in your authentic voice.
This is a conversation about education reform, authentic leadership, community-driven innovation, and what it takes to stand firm in your values while building something that lasts.
If you care about equity in schools, AI in education, or leading without shrinking who you are, this one’s for you.
Chapters:
00:40 👋🏾 From Finance to a Quarter-Life Pivot: Nick’s Journey into Education
03:44 🏡 Baseball, Basement Offices, and Growing Up in Hyde Park
07:21 🏫 What School Closures and Inequity Look Like Up Close
24:27 🤝 Co-Founding Innovare: Building with Community at the Center
26:29 💰 Venture Capital, Representation, and Not All Money Is Good Money
28:11 🧭 Removing the Mask: Authentic Leadership and Code-Switching
34:31 🤖 AI in Education: Saving Educators Time to Focus on Relationships
41:52 🔭 Legacy, Family, and Building Something That Lasts
Connect with Nick Freeman on LinkedIn and explore Innovare’s work to see how data, technology, and authentic leadership can help drive equity in education.
Episode 81
