We’re excited to introduce you to the always interesting and insightful Dr. Lolita Cleveland. We hope you’ll enjoy our conversation with Dr. Lolita below.
Alright, Dr. Lolita thanks for taking the time to share your stories and insights with us today. How did you come up with the idea for your business?
Caring for someone other than myself became a big responsibility moving from one state to another to ensure my love one was provided for, supported and able to live their latter years as their best years. In the midst of this decision my life took adjustments. In navigating this adjustments I found myself assisting others with launching their business or nonprofit. They needed guidance, direction, strategies on how to start and what was required to start. After doing this for a couple of years my clientele base of referrals increased. I had to do a self reflection and realize that my skill set had room for me in the consulting industry. Once I realized that there was a need, I launched my consulting business and my goal was to help clients jumpstart their entrepreneurial and executive goals and vision with care and nurturing. After many of my clients provided feedback that I was relatable, personal and knowledgeable and made them feel comfortable I knew I had to help others. This allowed me to solve the problem of helping others understand what is required to start their journey.
Realizing I could help someone other than myself reach their goal and purpose was most exciting for me.

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?
Dr. Lolita D. Cleveland is a distinguished leader and philanthropist with over two decades of expertise in the nonprofit, small business, and humanitarian sectors. As the founder and CEO of CRUMB Enterprises in Chicago, Illinois, Dr. Cleveland has become a prominent figure in community development and public administration.
Holding a Ph.D. in Christian Education, a Master of Arts in Public Administration from Walden University, and a Bachelor of Arts in Psychology from Grambling State University, Dr. Cleveland has cultivated a rich educational background that underpins her professional and philanthropic endeavors.
In her roles as a Program Manager and Adjunct Professor, she passionately educates and inspires a new generation of leaders. Dr. Cleveland’s engaging teaching style and motivational skills enable her to guide individuals toward fulfilling their potential and crafting their own paths to success.
An acclaimed author, Dr. Cleveland has contributed to the “Next Level Evangelism Training Manual” and co-authored “Moments in HerStory: From Pain to Purpose II,” which delve into personal and communal transformation. Her commitment extends globally through longstanding humanitarian efforts in regions such as Mexico, Jamaica, India, Trinidad & Tobago, and Africa.
Dr. Cleveland serves as the Board Chairwoman for the Girls Like Me Project Initiative, and holds positions on the boards of Circle Ruth Women’s Ministry, Eden 360, and Diadem International, where she influences policy and program development.
Her leadership philosophy is driven by a profound belief in the power of investing in people, which she sees as the cornerstone for fostering hope, possibilities, and transformative change in communities around the world.
How did I get into my industry? After college I worked at a local nonprofit that was serving the community with resources, advocacy and education and 25 years later I am still serving the community and being a advocate for change
What type of services I provide? I provide consulting services for aspiring and new business owners and nonprofit education for new organizations.
What sets me apart? My ability to nurture the vision of my clients with tools that increase their efficiency and effectiveness.
I am most proud of ensuring that my clients are recognized for the great work that they provide to others
I want people to know that when they work with me that I hear with my heart and I lead in love to see them genuinely succeed

Can you share a story from your journey that illustrates your resilience?
It was a ‘”whiplashing tailspin” triggered by being out of work with “Nothing” at least I thought! I had a job doing what I love to do making excellent money, enjoying life and confident in whom “I” was. Then the whiplash hit. I lost my job! How was I going to take care of myself? How am I going to survive became my everyday question. How will I eat? How will I put gas in my car? After seven days of questions I did what “I” knew to do…….. I look for a job, went to the unemployment office and was hit again; I didn’t have enough to pay my rent, bills or car note. I was hurt, discouraged, anger and mad at myself. I felt like I had failed. I knew I had to do something; my reality was REAL I had nothing! No resources, I couldn’t borrow from anyone because I couldn’t pay it back and I used my savings as far as I was willing to use it. I came home after enlisting in job programs and looking to see what community services I qualified for. I was denied except for one. I cried for two days straight and I began to pray. Lord why, what did I do to deserve this? I have always did what I thought you wanted me to do. I was nice to others always lending a hand. After having a pity party. I a still voice said use what’s in your hands. What was in my hand was education, tools, resources to help others. I revamped my finances, got on a budget and started developing what I could offer to my clients to help them learn, grow and develop. This allowed me to do a name change for my business, refocus on who I was serving, what I was serving and how I would serve. I was able to thrust into my own purpose and destiny as I served others.

What’s a lesson you had to unlearn and what’s the backstory?
I had to unlearn that everything that looked negative was not negative it was pushing me mentally, physically, emotionally and spiritually into my purpose in life which was to help others which was what I desired to do. Bringing a smile to a clients face, seeing their vision come to fruition for them was rewarding. See when life do not go the way we think it should go we are easily frustrated, irritated and discouraged with ourselves. I have to learn that when trials come I have to stand in faith and be open about growth and development because my story to overcome, persevere, concur is someone else strength, boast and motivation to keep going, moving and soaring in their lives.
Contact Info:
- Website: https://www.crumbenterprises.com
- Instagram: https://www.instagram.com/crumbisme/
- Facebook: https://www.facebook.com/crumbenterprises
- Linkedin: https://www.linkedin.com/in/dr-lolita-cleveland-60863a10/
- Youtube: https://youtube.com/@crumbenterprises?si=-hb7it9HhhrnVgRT



Image Credits
Grey Matter Photography
Dusable Museum Chicago, IL

