Professional Business Consulting

Harold Diggs is a visionary entrepreneur, transformational leader, and dedicated community strategist whose work has impacted youth, young adults, families, and entire neighborhoods across Baltimore City and Baltimore County for more than two decades. As the Executive Leader of Young Successful Leaders Inc. (YSLI) and President of Cottda One Cooperative, Harold has built a reputation for designing innovative programs that blend youth development, financial empowerment, community engagement, and restorative practices to create sustainable and measurable change.

Harold’s passion for mentorship and community transformation began in 2005 after a personal tragedy that shifted the direction of his life. Since then, he has mentored hundreds of youth, young adults, and adults, providing guidance, leadership, and life-changing support through programming that strengthens emotional wellness, financial stability, and personal success. His dedication has led to thousands of hours in direct mentoring and community uplift, with programs featured in local media for their impact on violence prevention, youth leadership, and economic mobility.

A multifaceted leader, Harold has served as President of the Southwest Neighborhood CDC, President of the Edgewood Neighborhood Community Association, and a vital contributor to community revitalization efforts throughout Southwest Baltimore. His leadership includes developing community gardens, organizing neighborhood cleanups, supporting housing initiatives, and teaching families the tools needed to build financial literacy and generational wealth. Harold is also the founder of Harold Diggs Coaching, where he trains emerging entrepreneurs, community leaders, and youth-service professionals in leadership, business development, and strategic systems-building.

Harold’s extensive training reflects his commitment to excellence and community capacity-building. He is a graduate of Innovation Works’ BOOST Program, the United Way Community United Training Program, and the Cllctivly Community Cohort, where he deepened his skills in nonprofit development, social entrepreneurship, and community-centered leadership. Harold also serves as a Board Member of the Mutual Housing Association of Baltimore (MHAB) and a Board Member of C.O.T.T.D.A One Development Cooperative Inc., contributing to strategic planning, housing equity, and community-building initiatives across the city.

In addition to nonprofit leadership, Harold is well-trained in Crisis Prevention Intervention (CPI), Trauma-Informed Care, Social-Emotional Learning (SEL), and Restorative Practices, all of which inform his approach to supporting youth and families. He also leads entrepreneurial

ventures in landscaping, janitorial services, event design, property revitalization, and behavioral health—expanding economic opportunity and workforce pathways for community members.

Harold’s mission is simple yet powerful: to build youth, families, and communities through leadership, mentorship, and economic empowerment—one person, one street, one block, one neighborhood at a time.

Harold Diggs is a transformational entrepreneur and community architect whose leadership has shaped youth empowerment and neighborhood revitalization efforts throughout Baltimore. His mission is simple but powerful: build people, build communities, and build systems that last.

Harold is best known for his work with Young Successful Leaders Inc. (YSLI) — a youth entrepreneurship, leadership, and financial literacy organization created after he reimagined and expanded the Cottda Foundation through a pivotal collaboration with Mr. Clayton. Under his leadership, YSLI has grown into a citywide force for youth development, empowering young people to become leaders, innovators, and builders in their own communities.

With more than 20 years of experience in youth and family development, Harold has mentored hundreds of young people and guided families through some of the most challenging moments in their lives. His work has been featured in newspapers and television programs for its effectiveness in building safer, stronger, and more resilient communities.

Harold’s expertise spans across:

● Business development

● Community engagement

● Entrepreneurship

● Program design and innovation

● Organizational and leadership development

As an entrepreneur and executive, he leads a diverse portfolio of ventures, including:

● Apple O Designs & Event Planning — Partner

● Cottda One Cooperative — President

● Young Successful Leaders Inc. — Executive Leader

● Edgewood Neighborhood Community Association — President

● Cottda One Landscaping, Janitorial & Property Services — Executive Director

● Shubiedoo Demo LLC —

● Cottda One Behavioral Health Services — President

● HaroldDiggs Business Coaching — Founder

● YSLI Enterprise

He is also certified in Trauma-Informed Care, Social-Emotional Learning trained (SEL), Restorative Practice trained, and Crisis Prevention Intervention (CPI).