Podcast Summary: The Stacking Benjamins Show - "How One Entrepreneur Constructed a Better Tomorrow (with Cheryl McKissick Daniel)" SB1721

Release Date: August 13, 2025

Introduction

In this enlightening episode of The Stacking Benjamins Show, hosts Joe Saul-Sehy and OG sit down with Cheryl McKissick Daniels, the award-winning President and CEO of McKissick & McKissick. Cheryl shares her remarkable journey, detailing how her family built a multi-generational construction empire despite facing systemic challenges. This conversation delves deep into themes of entrepreneurship, resilience, and the pivotal role of family legacy in shaping successful businesses.

Family Legacy and Historical Foundations

Cheryl begins by tracing her family's roots back to 1790, highlighting the resilience and ingenuity that allowed the McKissick family to thrive through five generations in America.

“Slaves were more protected. The reason I bring that up is because in the book, we make the case of how on earth did the McKissicks stay in business five generations.” [07:40]

She explains that Moses McKissick, the family's patriarch, was taught the craft of brick-making in North Carolina—a region characterized by smaller plantations and a more familial relationship between slave owners and their slaves. This environment fostered a strong sense of community and loyalty, laying a solid foundation for future business endeavors.

Transition to Tennessee and Business Expansion

The family's move to Tennessee marked a significant turning point. Moses McKissick II, Cheryl's ancestor, was gifted as a wedding present to the Cheers family in Spring Hill, Tennessee, thereby relocating the family and expanding their business horizons.

Cheryl discusses the challenges of sustaining a family business across generations, noting the high failure rates of multi-generational enterprises. She emphasizes the strategic decisions and adaptability that kept McKissick & McKissick thriving.

Personal Journey in a Male-Dominated Industry

Cheryl candidly shares her initial reluctance to join the family business. Despite pursuing engineering—her passion—she encountered the stark reality of a predominantly male industry.

“I quickly saw that there was no future there for me. You know, you go to the executive floor, nobody looked like me. And they were all men.” [13:04]

This realization propelled her back to the family business, where she could leverage her unique perspective and expertise to drive innovation and growth.

Influence of Her Mother: Fearlessness and Integrity

A pivotal influence in Cheryl's life was her mother, who took over the business during a critical period when Cheryl's father was incapacitated. Cheryl highlights her mother's fearless approach to business and unwavering integrity.

“She was fearless. She would go tell people about her firm whether they wanted to hear it or not.” [15:50]

Cheryl recounts a specific incident at Tuskegee University where her mother insisted on upgrading the building's operable windows despite budget constraints, demonstrating a commitment to quality and client satisfaction. This act not only secured additional projects but also established McKissick & McKissick's reputation for excellence.

Major Projects and Contributions to Historically Black Institutions

Cheryl details the company's extensive contributions to historically black colleges and universities (HBCUs), including Fisk University and Meharry Medical College. She proudly states:

“We documented the black experience through our buildings.” [19:21]

Under her leadership, McKissick & McKissick has designed and built numerous significant structures, many of which are now on historical registers, underscoring the company's lasting impact on educational and community infrastructures.

Overcoming Adversity and Networking for Success

Cheryl shares a transformative moment from her childhood—a cross burning she witnessed at a neighborhood birthday party—that profoundly impacted her understanding of vulnerability and resilience.

“I understood how vulnerable we really were.” [24:12]

This experience, coupled with her later professional endeavors, underscores the importance of building strong networks. Cheryl recounts how strategic relationships, particularly with influential figures like Bertha Lewis, were instrumental in securing major contracts, such as the Brooklyn basketball arena project.

Securing the Brooklyn Basketball Arena Contract

Cheryl narrates the journey of securing a $300 million contract for the new basketball arena in Brooklyn. Initially, the company was not involved, but through diligent networking and leveraging community relationships, Cheryl was able to introduce McKissick & McKissick into the project.

“I brought on the right staff who could handle the actual work. I hired people that were actually working at the MTA at the time.” [29:57]

Her ability to transform a modest $230,000 contract into a $300 million project exemplifies her strategic mindset and operational excellence.

Lessons in Decision-Making and Personal Integrity

Throughout the conversation, Cheryl emphasizes the importance of making definitive, well-considered decisions and backing them with unwavering commitment.

“You have to make a decision and move forward with it and then make it the best you can.” [32:32]

She advocates for staying true to oneself and consistently delivering quality, highlighting that this approach not only builds trust but also fosters long-term success.

Conclusion: Building a Better Tomorrow

Cheryl McKissick Daniels' story is a testament to the power of family legacy, strategic networking, and personal integrity in building a successful, multi-generational business. Her insights offer invaluable lessons for aspiring entrepreneurs and professionals aiming to navigate complex, male-dominated industries.

“Defining yourself and being true to yourself and living that out.” [32:32]

Through resilience and a commitment to excellence, Cheryl and her family have indeed constructed a better tomorrow, leaving an indelible mark on America's architectural and educational landscape.

Notable Quotes

• “Slaves were more protected. The reason I bring that up is because in the book, we make the case of how on earth did the McKissicks stay in business five generations.” – Cheryl McKissick Daniels [07:40]

• “I quickly saw that there was no future there for me. You know, you go to the executive floor, nobody looked like me. And they were all men.” – Cheryl McKissick Daniels [13:04]

• “She was fearless. She would go tell people about her firm whether they wanted to hear it or not.” – Cheryl McKissick Daniels [15:50]

• “We documented the black experience through our buildings.” – Cheryl McKissick Daniels [19:21]

• “You have to make a decision and move forward with it and then make it the best you can.” – Cheryl McKissick Daniels [32:32]

Key Takeaways

1. Multi-Generational Resilience: The McKissick family's ability to sustain and grow their business across five generations is rooted in strategic decision-making and adapting to changing environments.

2. Impact of Leadership: Cheryl's leadership is heavily influenced by her mother's fearless and integrity-driven approach, emphasizing the importance of ethical business practices.

3. Strategic Networking: Building and leveraging strong community relationships can open doors to significant business opportunities, as demonstrated by securing the Brooklyn basketball arena contract.

4. Personal Integrity and Decision-Making: Making clear, committed decisions and staying true to one's values are crucial for long-term success and trust-building in business.

5. Legacy and Contribution: Contributing to historically significant institutions reinforces a company's legacy and underscores its role in shaping community infrastructure.

Final Thoughts

Cheryl McKissick Daniels embodies the spirit of perseverance and innovation. Her story serves as an inspiring roadmap for those looking to build enduring businesses that not only thrive financially but also contribute meaningfully to society. The Stacking Benjamins Show successfully captures her journey, offering listeners both motivation and practical insights into the world of entrepreneurship and personal finance.