We were lucky to catch up with Walter Mendenhall recently and have shared our conversation below.
Hi Walter, thanks for joining us today. Can you talk to us about serving the underserved.
Transforming Lives in Underserved Communities: The Stories of Keith and Jeremiah
In the heart of Chicago—where the challenges of gun violence, underemployment, and economic disparity often drown out hope—there’s a beacon of resilience and transformation: the Male Mogul Initiative (MMI). This is not just an organization; it’s a lifeline for young Black men navigating a city where opportunity too often feels out of reach.
A Second Chance: Keith Bass’ Journey from Liability to Leader
Keith Bass was just sixteen when he first walked through the doors of MMI, a high school student searching for guidance. What he found was more than mentorship; he found direction, brotherhood, and purpose. In 2020, MMI gave him his first job at their storefront—a modest beginning that became a pivotal step.
But in 2021, tragedy struck. Keith’s close friend was shot and killed right outside that same store. In a city where 80% of gunshot victims are young Black men, Keith’s response was one of fear—he began carrying a firearm, a decision that led to his arrest and the looming possibility of a three-year prison sentence.
What happened next defines the essence of MMI. Instead of turning away, the organization leaned in. They paid for Keith’s legal representation, advocated for his probation, and stood by him when others would have walked away. In a powerful conversation with MMI founder Walter Mendenhall, Keith owned his past and committed to becoming an asset rather than a liability.
By 2025, Keith’s life had transformed. He moved into his first apartment, purchased a multi-unit property, earned Google and entrepreneurship certifications, and today, serves as the Workforce Manager of Co-LLAB—training and inspiring the next generation. Keith doesn’t just share his story—he lives it, mentoring young men just like him.
From Homeless to Hopeful: Jeremiah Swint’s Rise
In 2024, Jeremiah Swint was ambitious—but homeless. With no stability and limited opportunity, he was at risk of becoming another statistic. Then he found MMI.
That summer, Jeremiah entered MMI’s leadership program, quickly distinguishing himself through his work ethic and passion. By year’s end, he became a part-time assistant facilitator and then joined the Gap Year Program. Through MMI’s Workforce Development Housing, Jeremiah secured stable housing—a critical turning point.
Then, opportunity knocked. MMI had acquired the fintech firm Help With My Loan (HWML)—a powerhouse that had already facilitated over $850 million in loan originations. Through their intensive training pipeline, Jeremiah became a licensed loan officer and is now employed full-time at HWML. From housing insecurity to financial empowerment, Jeremiah’s story reflects MMI’s mission in action.
Serving the Underserved: Why It Matters
In Chicago, nearly half of young African American men (ages 18–24) are disconnected from both school and work. Meanwhile, 80% of capital needs for Black and Brown entrepreneurs go unmet, contributing to a staggering $146 million funding gap. These are not just statistics—they are barriers that block generations from accessing prosperity.
The Male Mogul Initiative exists to break those barriers. Through its Community Wealth-Building Ecosystem, MMI tackles systemic inequities across education, employment, capital access, and public safety. Whether it’s through hands-on carpentry training, fintech workforce development, or mentorship and mental health support, MMI is committed to converting perceived “liabilities” into community “assets.”
The MMI Difference
What sets MMI apart is its multi-dimensional approach:
The Mogul Fund, a hybrid Venture/Private Equity vehicle, invests directly in community entrepreneurs.
Co-LLAB Manufacturing Hub and Logistics Training provide real-world skills and business ownership pathways.
Help With My Loan, a fintech subsidiary, opens the door to high-income careers in the financial sector.
Holistic wraparound services ensure that young men like Keith and Jeremiah are supported emotionally, mentally, and economically.
MMI doesn’t just prepare young men for jobs—it prepares them for ownership, for leadership, and for legacy.
Conclusion: More Than a Business, a Movement
Keith and Jeremiah’s journeys are proof of what’s possible when investment meets belief, when structure meets purpose. The Male Mogul Initiative serves Chicago’s most underserved by reimagining what community wealth truly means. In a city where systemic barriers run deep, MMI is building something deeper: roots, resilience, and a future for young men once written off by society.
Through MMI, they rise—not alone, but as part of a movement to reshape the narrative of entire neighborhoods. This is more than service. It’s revolution.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
About Walter Mendenhall & The Male Mogul Initiative
I’m Walter Mendenhall, a Chicago-born educator, entrepreneur, and former NFL running back. My journey into this work began not with a grand vision, but with a powerful encounter—meeting a bright, talented young man on Chicago’s West Side who, despite his potential, was dealing drugs just to survive. That moment changed my life. I realized that brilliance exists in our communities, but opportunity does not always follow. I knew then that I had to do something.
From Gridiron to Grassroots Impact
Before founding the Male Mogul Initiative (MMI), I overcame my own struggles—including a learning disability—and went on to play professional football. But the call to serve my community was stronger. In 2012, I brought together five young men in a church basement to talk about what leadership, manhood, and purpose could look like for young Black men in Chicago.
That small gathering has since grown into a powerful movement. Today, MMI has mentored and empowered thousands of young men from Chicago’s South and West Sides, helping them transition from overlooked to overachieving.
What We Do: Rebuilding Communities from the Inside Out
The Male Mogul Initiative is more than a nonprofit—it’s a Community Wealth-Building Ecosystem that develops young men into leaders, entrepreneurs, and change-makers. We solve three pressing issues that plague underserved communities:
Education and Employment Gaps: Nearly 45% of African American men (18-24) in Chicago are neither in school nor employed. Through leadership training, entrepreneurship programs, and certifications in trades and tech, MMI turns disengaged youth into workforce-ready professionals.
Lack of Access to Capital: 80% of capital needs for Black and Brown entrepreneurs go unmet. Our hybrid Venture/Private Equity fund, The Mogul Fund, and fintech company, Help With My Loan (HWML), help close that gap—originating over $850 million in loans and training young men to become licensed loan officers.
Public Safety and Community Stability: In communities plagued by violence, MMI provides safe spaces, mentorship, and mental health support while investing in real estate and job creation to revitalize neighborhoods.
Our Unique Approach
What sets us apart is our holistic, hands-on model. We combine:
Business Ownership & Incubation through Co-LLAB, Chicago’s first small business incubator for youth.
Skilled Trades Training in carpentry, logistics, and product development.
Financial Empowerment through fintech career pathways.
Wraparound Support that includes housing, therapy, and long-term mentorship.
We don’t just equip young men with tools—we surround them with a supportive ecosystem that believes in their potential.
What I’m Most Proud Of
I’m proud of the lives we’ve helped transform—like Keith Bass, who overcame personal tragedy and legal challenges to become our Co-LLAB Workforce Manager, or Jeremiah Swint, who went from homelessness to becoming a full-time loan officer at HWML. These stories are not exceptions—they are the standard of success we aim for.
I’m also honored to have received recognition such as the Chicago Innovation Award and to have been a MIT Solve semi-finalist, but my greatest achievement is seeing young men become the leaders they were destined to be.
What I Want You to Know
The Male Mogul Initiative is not just building careers—we’re building generational wealth, community resilience, and a new legacy for Chicago’s young men. Our work is personal, rooted in lived experience, and fueled by a belief that our communities have the talent—they just need access.
If you’re looking to partner, invest, or get involved with a transformative social enterprise that’s rewriting the story for young Black men in America, we’d love to connect.
We’d love to hear a story of resilience from your journey.
From the Brink: Finding Purpose in My Pain
There was a time in college when my life looked strong on the outside but was quietly unraveling within. I was playing Division I football, a dream for many and an identity I had wrapped myself in since I was a boy. Football wasn’t just a game to me—it was my idol, my refuge, my reason.
But what do you do when the very thing you love starts to break you?
At that time, everything was falling apart. I wasn’t getting any playing time. My coaches, the people I thought would build me up, tore me down with constant verbal and mental abuse. The field that once gave me purpose had become a place of humiliation. The locker room felt like a battlefield, not against opponents, but against doubt, shame, and worthlessness.
Off the field wasn’t any better. I stopped going to class. My grades slipped. My motivation disappeared. I was drowning silently in depression, wearing a brave face while feeling completely empty inside.
One night, I found myself in my dorm room, lying in bed, tears soaking my pillow. I had hit a wall emotionally, spiritually, and mentally. The thoughts that came to me weren’t just dark—they were dangerous. I began contemplating whether life was even worth continuing. I didn’t see a way out. I felt like I had nothing left.
That night, I cried out—truly cried out.
“God, if you are really real,” I whispered through the pain, “I need you now. Because I don’t know if I’ll make it to the morning.”
And in that moment, something miraculous happened.
I felt a presence wrap around me—not just emotionally, but physically. It was as if God Himself stepped into my room and held me like a newborn child. I felt comforted, not with words, but with peace—a peace that I hadn’t known in years. I fell into the deepest, most restful sleep I had ever experienced.
When I woke up, my situation hadn’t changed.
But I had.
That night didn’t fix everything. I still had challenges to face, still had to navigate a system that didn’t always see or value me. But from that point forward, I knew that my life had purpose. I knew I was not alone. And I knew I wasn’t defined by football—or failure.
That night God saved my life.
He didn’t just keep me alive—He gave me a reason to live.
Today, when I mentor young men through the Male Mogul Initiative, I don’t do it from a place of perfection. I do it from the pain I’ve survived. Because I know what it feels like to be at the edge. And I also know what it feels like to be carried back from it.
So if you’re reading this and you’re in a dark place—know this: Your pain has a purpose. And there is life, healing, and greatness waiting on the other side of it.
Let’s talk M&A – we’d love to hear your about your experience with buying businesses.
From Vision to Victory: How We Acquired a Fintech Company to Create Access and Opportunity
Yes, we bought a business. But for us, it wasn’t just about the bottom line—it was about changing lives.
We recently acquired Help With My Loan LLC, a California-based fintech company that has facilitated over $850 million in business and commercial loan originations. This wasn’t just a tech acquisition—it was a strategic move aligned with our mission at the Male Mogul Initiative (MMI): to close the capital gap for underserved entrepreneurs and create high-quality jobs for young men from historically marginalized communities.
Why We Bought the Business
Access to capital is one of the greatest barriers facing Black and Brown entrepreneurs in this country. In Chicago alone, 80% of the capital needs for minority-owned businesses go unmet, leaving a devastating $146 million gap. We saw Help With My Loan as a tool that could help change that. It gave us a platform to train our youth as licensed loan brokers, connect underserved businesses to real funding, and plug into the rapidly evolving fintech space with purpose.
We didn’t just see a business—we saw a bridge.
A bridge to opportunity.
A bridge to generational wealth.
A bridge to empowerment.
The Journey: A Deal Full of Detours
But the acquisition process? Let’s just say it was a test of faith and perseverance.
What was supposed to be a straightforward purchase turned into a year-long rollercoaster. There were moments we thought the deal was dead in the water. At one point, the original owners accepted another offer and backed out. We were crushed—but we kept believing.
Then, after months of renewed negotiation, our financing bank—who had assured us of their commitment—pulled out at the last minute. No explanation. Just gone.
Most people would’ve walked away. But we couldn’t. Not when we knew what this company could do for our mission. Not when we had young men waiting for opportunity.
So, we did what entrepreneurs do—we self-financed the deal. We bet on ourselves. We bet on our community.
What It Means Today
Today, Help With My Loan is not just an asset in our portfolio—it’s an engine driving real impact. We’ve integrated it into our Community Wealth-Building Ecosystem, training young men from Chicago’s South and West Sides to become professional loan officers. Many of these young men—some formerly incarcerated, homeless, or unemployed—are now thriving in a space they never imagined entering: financial services.
The acquisition wasn’t easy, but it was worth every twist and turn. Because now, we’re not just providing loans—we’re providing legacy.
Contact Info:
- Website: https://www.malemogulinitaitive.org
- Instagram: malemogulinitiative waltermendenhalliv
- Facebook: https://www.facebook.com/profile.php?id=100076325799425
- Linkedin: https://www.linkedin.com/in/walter-mendenhall-iv-55200787/
- Twitter: w_mendenhall
- Youtube: male mogul initiative
