HBCU Founders Accelerator Spring 2025 Cohort Spotlight: Meet Aaron Mitchom from OurFreedom.ai
This Spring, we launched the fourth cohort of the HBCU Founders Accelerator Program. Over the next several weeks, we’ll be shining a spotlight on the remarkable founders and their entrepreneurial journeys. First up, meet Aaron Mitchom from OurFreedom.AI.
Can you tell us a little about your background and what inspired your entrepreneurial journey?
My entrepreneurial spark ignited at Morehouse College when Robert F. Smith, CEO of Vista Equity Partners, paid off our class's student loans and challenged us to pay his generosity forward by creating positive impact in our communities. After developing skills at Bank of America's Technology, Media & Telecom group, I wanted to tackle problems close to my heart. Growing up with family members cycling through incarceration, I saw firsthand how tough it was to stay connected. A real eye-opener came when my grandmother shared that she was still paying off her 1963 home loan because she kept helping family with prison expenses, including sky-high communication costs. That conversation hit home; here was an industry stuck in the dark ages where families like mine suffered unnecessarily. With my Morehouse education and finance background, I launched OurFreedom.ai to transform prison communications and keep families connected affordably.
What problem is your startup solving and what inspired you to tackle this issue?
OurFreedom.ai is addressing the substantial challenges in prison communication today. Growing up with a family impacted by incarceration, I witnessed firsthand the struggle with expensive calls, complicated mail systems, and the emotional toll of limited connection. The industry remains largely unchanged, with two companies controlling 80% of the market through kickback-driven contracts that squeeze every penny from families already stretched thin. So we built an all-in-one platform that transforms the experience. We're reimagining prison communication with crystal clear calls, innovative voice messaging that lets families share moments exactly when they happen rather than waiting for calls, and an integrated mail system that makes sharing photos and letters efficient and reliable. Even in states now offering free calls, our platform adds value by providing immediate voice messaging and dependable mail services that traditional providers charge premium rates for. Our comprehensive communication hub bypasses traditional contracts to offer a user-friendly way for families to maintain meaningful connections during separation.
What have been some of the biggest challenges you have faced while building your startup, and how did you overcome them?
Building OurFreedom.ai has presented significant challenges. Our biggest hurdle has been disrupting an industry where two established companies have dominated for decades, a formidable task that required innovative thinking. We tackled this by completely rethinking the approach; why fight the giants directly when we could create something entirely new? So we built our platform to work independently of those restrictive contracts while still keeping all the necessary security measures. Another challenge is building trust with families who've been burned before. We've addressed this by partnering with organizations already trusted in the community and designing our entire user experience based on direct feedback from the families we serve.
What has been your proudest moment so far?
My proudest moments come from speaking with families who have incarcerated loved ones. This industry has been exploited for decades, yet few outside those affected realize what's happening. We're building solutions for those often forgotten by society, and their reactions show immediate impact. We regularly attend events hosted by RocNation, Fortune Society, Defy Ventures, Trinity Church, and Tech:NYC to stay connected with our customers. When these families hear that someone understands their challenges firsthand, you see hope and gratitude in their expressions. They feel seen, perhaps for the first time in their difficult journey. You can hear what our customers think in the Love Behind Walls podcast episode, where I speak with women whose husbands are incarcerated. These interactions reaffirm our mission. Creating technology that reconnects families and restores dignity to a process that has stripped it away for so long drives our team daily.
Where do you see your company in 5 years and how do you see it impacting your community?
In five years, OurFreedom.ai won't just be a company; we'll be the go-to communication lifeline for millions of families touched by incarceration across the country. I see us expanding beyond our current offerings to become a comprehensive support system, with solid data showing how our platform helps reduce recidivism and smooths the reentry process. We'll have built partnerships with supportive services to address the whole spectrum of challenges families face. The real win, though? Communities will feel the ripple effects: stronger family bonds during separation, less financial drain on vulnerable households, and better outcomes when people return home with support networks intact. I'm particularly excited about how we'll have shifted expectations, making affordable, dignified communication during incarceration the norm, not the exception. By proving there's a better way that works for everyone, we'll have pushed the entire industry to level up their game. That's the legacy I'm working toward!
What led you to become interested in Nex Cubed? What resources do you believe will be most helpful?
What led me to Nex Cubed was their exceptional commitment to HBCU founders during a time when the funding landscape for Black entrepreneurs is particularly challenging. Only 0.4% of all funding went to startups with Black founders last year, the lowest share in years and down more than two-thirds from just three years ago. Nex Cubed's unwavering dedication to supporting founders like me when we need it most initially drew me to the program. The advisor network has proven incredibly valuable, connecting us with experienced leaders who understand both the justice tech space and enterprise SaaS models. Their guidance has helped us refine our go-to-market strategy as we prepare for wider launch. Nex Cubed's mission to create a world where all founders have equal opportunities and access to support, resources, and capital within an inclusive and diverse startup ecosystem perfectly aligns with what we're building at OurFreedom.ai.
What is the most valuable lesson you have learned as a startup founder so far?
The most valuable lesson I've learned is to take all feedback with a grain of salt. If you implement every suggestion, you can lose focus on what truly needs to be done, sometimes even changing things back and forth. Nobody knows your company better than you do. Another crucial lesson: don't be afraid to ask for help. I've been amazed by how many people are willing to support when you simply ask. Being vocal about your needs can yield surprising results. By clearly communicating what we need, we've secured discounts, accessed innovative solutions, received invitations to strategic events, and more. The entrepreneurial community is genuinely supportive but you have to be willing to voice your challenges and needs. This openness to seeking help while maintaining your vision is a delicate balance that can significantly accelerate your progress when mastered.
What advice would you give to aspiring entrepreneurs who are looking to make their mark in the industry?
Always be open to listening to experts. While you might think you know your company best, the wealth of experience from advisors and industry specialists is invaluable. Their feedback has consistently helped us see our product from fresh perspectives. When you're immersed in something daily, you develop blind spots; you know it so well that you start missing problems or opportunities that are obvious to others. Having these fresh eyes on our product has uncovered numerous possibilities we hadn't considered. At the same time, balance external input with your own vision and deep understanding of your mission. The most successful entrepreneurs I've observed maintain this balance, welcoming expertise while staying true to their core purpose. This approach leads to innovations that are both visionary and practical.
What advice would you give to other HBCU entrepreneurs around fundraising?
Fundraising is important, but don't dedicate so much time to it that you forget about building your product. It's a delicate balance between building, hiring, and fundraising; all three require consistent attention. If you're just starting out and seeking your first check, take as many meetings and attend as many events as possible. Pitching is a muscle that needs constant training so you're always ready when opportunity strikes. Become comfortable with consistently taking meetings and refining your pitch each time. A practical tip that's served us well: at the end of every meeting, always ask for introductions or inquire if they can feature you in their newsletter. These small requests can create unexpected pathways to your next investor. The fundraising journey is a marathon, not a sprint; maintaining momentum on product development while securing capital is the key to sustainable growth.
What is one word to describe your journey so far?
Faith.
Where can readers/listeners/viewers learn more about your business?
Instagram @ourfreedom.ai
TikTok @ourfreedom.ai