Gregory is no stranger to hard work. With over 41 years of experience in the lawn care industry, he has spent decades perfecting the art of landscaping. In 2012, he took his expertise to the next level by professionally establishing Gregory’s Lawn Service in Memphis, Tennessee. But as many entrepreneurs discover, being a master of your craft is only one half of the equation for a successful business.
“I only understood labor,” Gregory explains. “I knew how to do landscaping… I had the experience, but I didn’t know or understand business.”
The turning point came in April 2021, when Gregory picked up a book titled Up from Nothing by Operation HOPE Chairman and CEO John Hope Bryant. The message resonated deeply, sparking a desire to move beyond manual labor and into the world of building a sustainable business.
Determined to educate himself, Gregory began joining local organizations like the SBA’s “Boots to Business” program and the Memphis Minority Business Continuum (MMBC). It was through the MMBC that he was referred to Operation HOPE to help him achieve his ultimate goal: scaling his business to secure large-scale commercial contracts.
Gregory enrolled in Operation HOPE’s Small Business Development program, where he was paired with Small Business Coach Angelic Mister. Together, they began the work of transforming Gregory’s Lawn Service from a labor-intensive operation into a structured enterprise.
“Learning from Operation HOPE and MMBC, it taught me how to be more hands-on in business itself — the management side, the contract-seeking side, the bookkeeping side,” says Gregory.
One of the most critical hurdles Gregory faced was financing. Despite his decades of experience, he found that securing capital to purchase commercial equipment was a “difficult process that could either make us or break us.”
Under Coach Angelic’s guidance, Gregory focused on a key pillar of business health: credit. “Your credit has to be at a certain level,” he notes. “We had attempted several loans… unsuccessfully. But after teaming up with Operation HOPE and getting our credit squared away, we were able to secure a loan for $25,000.”
Gregory credits much of his success to Coach Angelic’s professional yet personal approach. “Miss Angelic was very professional. She was patient, she was caring,” he recalls. “She seemed to be the type of person that’ll dig until she finds answers.”
Beyond the classroom and coaching sessions, Operation HOPE provided something Gregory hadn’t expected: networking opportunities. During his graduation from the program in September 2025, Gregory was introduced to Angelic’s network partners, giving him a chance to communicate directly with potential clients about their landscaping needs.
Today, Gregory’s Lawn Service is unrecognizable from its purely labor-focused beginnings. Armed with new funding, the company has implemented modern computer and networking systems to manage operations efficiently. While they continue to serve a growing residential base, they are also pursuing — and securing — commercial contracts.
But for Gregory, a U.S. Marine Corps Veteran and Certified Master Gardener, success isn’t just about “astronomical profits.” It’s about adding value to humanity. This June, Gregory plans to bring on 10 new staffers through a youth program, providing young people in Memphis with vital work experience.
Reflecting on his journey from the mower to the manager’s chair, Gregory is quick to offer his gratitude. “Sometimes in our jobs or in our walks in life, we don’t know if we’re really making a difference, but you guys are making a difference, and I thank you.”
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