GLOBAL CONVERSATIONS WITH THE FLY PROF.-Earl N. Caldwell II

By Earl Caldwell

Welcome to the first edition of Global Conversations With The Fly Prof.

Each month, I’ll introduce you to a range of individuals, businesses, places, and ideas that I hope will spark curiosity, conversation, and creativity. This series is not just a platform to share what I’ve seen and experienced, but a space to learn together through global perspectives.

Although I hail from suburban Chicago, my journey has taken me far beyond the Midwest. In 2004, I relocated to Accra, Ghana, and that move set the tone for a lifelong engagement with the African continent and its diasporic connections. Before and after the pandemic, I have continued teaching as an Adjunct Professor at Loyola University Chicago School of Law, where I focus on Sports and Entertainment Law and related intersections with NIL, branding, and technology.

Lately, I’ve expanded my scope to explore business and partnership opportunities in several African countries including Uganda, Kenya, Morocco, Nigeria, and Zimbabwe. The convergence of my academic work, entrepreneurial pursuits, and ongoing relationship-building across Africa has inspired this series. It’s a reflection of the growing intersection of law, business, technology, culture, and creativity—not only across the U.S. and Africa but within the broader global community.

And while I know a little bit about a lot of things, I’m fully aware of how much more there is to learn. These conversations—our conversations—are my way of sharing what I do know, and more importantly, discovering what I don’t.

So, I invite you to join me as we explore people and projects across business, education, technology, culture, and community—and examine how they intersect in this rapidly shifting world.

I’m often asked, “Why did you move to Africa?” The answer traces back to my very first trip to the continent—a visit to Egypt after graduating from Morehouse College. That journey left a lasting impression on me and planted a seed that has grown ever since. One thought has guided me from that moment forward:

“To contribute to the growth, development, and progress of Africa.”

It is in that spirit that I launched Global Conversations With The Fly Prof.—a platform grounded in connection, contribution, and cross-continental engagement. Through these conversations, my hope is to continue honoring that original commitment by sharing stories, building bridges, and spotlighting those working toward Africa’s continued advancement in business, culture, education, and beyond.

In the U.S., we are widely familiar with STEM education, which emphasizes Science, Technology, Engineering, and Math. Recognizing the unique challenges faced by law students pursuing careers in sports and entertainment, I created The Different STEM®—a platform designed to explore the global intersection of Sports, Technology, Entertainment, and Media.

The Different STEM® serves as an experiential learning environment, featuring conferences and events that bring together subject matter experts, industry practitioners, and emerging professionals to examine the rapidly evolving dynamics of these interconnected fields.

To further engage students in real-world applications, I also launched the Name, Image, and Likeness (NIL) Competition. This interdisciplinary contest challenges participants to navigate the complex ecosystem of sports, entertainment, branding, marketing, business, and law. Designed to reflect the fluid and competitive nature of NIL, endorsement, and promotional deals, the competition develops skills in:

• Contract analysis
• Business development
• Branding and identity management
• Legal and regulatory frameworks
• Strategic communications

Together, The Different STEM® and the NIL Competition aim to equip students with cross-disciplinary skills and networks that align with the future of sports and entertainment law.

Global Conversations With The Fly Prof. is a platform which will also spotlight the dynamic voices and ventures shaping the global landscape of sports, technology, entertainment, and media (STEM). Some articles in this series will introduce you to innovators, entrepreneurs, and thought leaders, including past winners of the NIL Competition, and highlight the impactful work they are doing across industries and continents.

In my first article, I’ll be sharing stories from a compelling cross-section of professionals from both America and Africa—individuals who are purposefully and strategically engaging in business within Africa and with African partners, leveraging innovation, collaboration, and cultural fluency.

As part of this global engagement, I was honored to contribute to the Future of Finance and Trade in Africa 2.0, hosted in April by the George Washington University School of Business. My role involved curating and leading a series of “Sideline Activities”—a set of interactive sessions designed to complement the main conference. These included:

• Workshops focused on actionable strategies for cross-border engagement
• A “Deal Room”, where participants could explore real-time business opportunities, partnerships, and collaborations

This work continues to highlight how curated conversations and strategic convenings can drive meaningful connections across disciplines and geographies.

The first company I partnered with as a co-host was TMI & Partners, a Business Solutions Services firm with a global footprint spanning the United States, Europe, and Africa. Known for its strategic expertise and wide-ranging capabilities, TMI provides a robust suite of domestic and international business services aimed at supporting growth, financing, and long-term strategic expansion for businesses at every stage of development.

On the domestic front, TMI assists U.S.-based businesses in securing:

• SBA Loans
• Business Term Loans and Credit Lines
• Equipment Financing
• Factoring and Purchase Order Financing
• Real Estate Financing (commercial and investment properties)

On the international side, TMI supports foreign businesses by:

• Facilitating access to U.S. capital markets
• Assisting with establishing offices in the United States
• Helping identify and engage with strategic U.S. business partners

Alvin Hartley is the Chairman and Managing Partner of TMI & Partners, bringing over 40 years of expertise in strategic planning, customer service and sales training, marketing, budget strategy, and leadership development. Throughout his distinguished career, Mr. Hartley has collaborated with high-profile organizations such as Time Warner Cable, Calvin Klein (CK) Jeans, and Black Entertainment Television (BET)—notably supporting the New York City Inner City Games, a national youth initiative co-chaired by Arnold Schwarzenegger.

ALVIN HARTLEY

He has been instrumental in securing corporate partnerships and sponsorships from leading brands including Coca-Cola, AT&T, Pepsi, Verizon, Burger King, Gatorade, KFC, Reebok, and Coors, helping to elevate major community and business initiatives.

Through TMI & Partners, Mr. Hartley oversees a full suite of business solutions across three key areas:

• Financing: Processing, real estate loans, commercial and small business financing
• Operations: Credit solution services, administrative support, and digital integration via Jotform
• Branding: Marketing and promotions, public relations, and sales management strategies

Among the international participants was Barrister Clara Ndive, a practicing attorney based in Nigeria with a client portfolio that spans Canada, China, and various countries across Africa. Reflecting on the importance of global collaboration and networking, she shared:

“This is going to be the place for us to interact and meet with our counterparts who are also investors and funders.”

Her participation highlighted the event’s role as a cross-continental platform for legal, financial, and entrepreneurial exchange.

BARRISTER CLARA NDIVE

A distinguished dignitary in attendance was Archbishop Professor Chidiebere Anelechi Ogbu, President of the Africa Diaspora Union–South Africa. His organization is dedicated, in part, to promoting investment and business engagement among African descendants across the continent.

In his remarks, Archbishop Ogbu emphasized the importance of access and connection in fostering successful investment:

“What is more important to us is to ensure that these investors have access to the country where they are going to invest. I have met my brothers and sisters—who are funders—who are here.”

His presence and message reinforced the spirit of unity, opportunity, and purposeful collaboration that defined the event.

ARCHBISHOP PROF. CHIDIEBERE ANELECHI OGBU

The “Sideline Activities” included workshops, such as the Business Wellness Toolkit presentation by Kelvin Taylor, which generated excitement from domestic and international participants. He is the founder of Taylored Analytics, launched in 2007, where he brings deep expertise in marketing strategy, data analytics, and customer intelligence to Fortune 500 companies across the retail, restaurant, financial services, utility, and telecommunications industries.

KELVIN TAYLOR

Over the course of his career, Mr. Taylor has been a frequent speaker and thought leader at major industry events hosted by organizations such as the Direct Marketing Association, the National Center for Database Marketing, and the Institute for International Research, among others.

He has built and led high-performing business intelligence teams that focus on enhancing customer lifetime value through:

• Strategic database design
• Lifestyle and behavioral segmentation
• Predictive statistical modeling

His core expertise lies in the application of statistical analysis to optimize business decision-making, helping organizations turn data into actionable insights that drive growth, efficiency, and long-term customer engagement.

The Business Wellness Toolkit provided technological solutions for new, emerging and growing businesses to assist with creating financial statements, pitch decks and Private Placement Memorandum content. Participants representing city and state government, business groups and the Co-Host TMI representatives met with Taylored Analytics during the “Deal Room” of the event.  

THE VIP MEET & GREET

The final event of the “Sideline Activities” series was a VIP Meet and Greet, held at a stunning venue on Capitol Hill owned by entrepreneur and businessman Dr. Emmanuel Irono. The evening was co-sponsored by Dennis Bunch of Bunch Cigars, who used the occasion to showcase his distinctive product—premium cigars uniquely infused with Johnnie Walker spirits, a combination not yet seen in the marketplace.

Guests gathered on the rooftop, where the atmosphere was filled with vibrant conversation, curated cocktails, a refreshing evening breeze, and the aromatic signature of Bunch’s infused cigars. It was a perfect close to the Sideline Activities—blending business, networking, and culture in a memorable and elevated setting.

As an educator, I aim to design my business events and engagements in ways that intentionally benefit and empower students. That mission was clearly reflected in the words of Natasha Torrence, a law student at Atlanta’s John Marshall Law School, who participated in the “Sideline Activities.” She summed up the experience with this powerful reflection:

“When you want to work in business, especially on an international level, you don’t realize how many resources are available. I’ve learned so much about acquiring funding and how to structure your business properly. The diversity of people from all over the world was amazing and incredible.”

These are the types of insights and opportunities that I hope Global Conversations With The Fly Prof. will continue to create—spaces where students, professionals, and global changemakers connect, share, and grow.

If you have comments, suggestions, or ideas for future topics or individuals to feature in upcoming editions of Global Conversations, I’d love to hear from you.

Prof. Earl N. Caldwell II
The Fly Prof.
 theflyprof5@gmail.com

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