Conversation Strengthens Community: Takeaways from a Diversity Dialogue

In this Diversity Dialogue, we heard from three local Black business owners about what inspired them to start their businesses and the challenges they still face.

Jaymes McCloud founded J.H.W. Enterprises Property Management, Inc. in March of 2018. Currently, as CEO, he leads a dynamic team of dedicated professionals in expertly managing & caring for close to 300 multifamily, commercial and residential properties valued at more than $20 million, across South Carolina, Georgia and Maryland. Motivated by a desire “to do property management the right way,” Jaymes guides his team in applying an integrity-led approach in effectively capturing market rent, identifying qualified tenants, stabilizing facilities expenses and offering transparent reporting to property investors.

Dr. Shawn Mitchell was born and raised in Charleston, SC. After graduating dental school and completing his residency program, he practiced in Memphis, TN until deciding to move back home to pursue his dream of creating a technologically savvy dental start-up. In January of 2020, Dr. Mitchell opened SweetGrass Dental Associates in Charleston, where he is committed to introducing the most innovative technology and techniques. When Dr. Mitchell is not working on patients, he is an avid photographer/videographer and has also launched SweetGrass Clothing Co. with his brothers.

Regina Robinson worked most of her career in nonprofit accounting and brought her nonprofit mindset with her as she ventured to start her own company. After working in the transportation industry for five years as business consultants, Regina and her husband founded Prime Time Logistics in 2018. Their passion for the trucking industry and the people in it inspired them. Regina brought her nonprofit background and her passion for the industry to build a company that works every day to give back to the industry.

In addition to being successful business owners, these three individuals are working to positively impact their communities. J.H.W. Enterprises’ principle is “providing quality living to people throughout out region.” Rejecting the gentrification mindset, the organization aims to take a “C Class” neighborhood and provide “A Class” living at affordable rates. At SweetGrass Dental Associates, Dr. Shawn Mitchell specializes in full mouth rehabilitation and focuses on bringing innovative technology to underserved populations. He also embraces his Gullah/Geechee heritage and works to keep it alive. Prime Time Logistics operates under the principle that every truck driver, dispatcher and operator is a leader in the making. Regina was proud to share that Prime Time Logistics is bringing employment opportunities to those who may not otherwise be given them, like individuals who were formerly incarcerated.

After hearing about these three companies and their impact on their community, we were excited to learn more about their journeys to entrepreneurship.

What inspired you to go into your business field?

Dr. Mitchell shared that the first time he went to the dentist was when he was in middle school and his older brother was in dental school. Later on, when Mitchell was in college, he knew he wanted to be in healthcare but wasn’t sure what field. His first experience with dentistry in middle school opened his eyes to the field, but he felt like it was his brother’s thing – he didn’t want to take that from him.  Eventually, his brother convinced him to come see what dentistry was all about. Dr. Mitchell saw the opportunity for him there – owning a business, caring for people and still maintaining a good quality of life.

Regina Robinson has always been fascinated with trucks. When she and her husband would drive from Charleston to Corpus Christi and she had the night driving job, she was always interested in the trucks and their drivers they were sharing the road with. Regina and her husband started Prime Time Logistics while they both had full-time jobs because it was their passion. She shared that she worked the dream from 6-9 a.m. and funded the dream from 9-5.

Jaymes McCloud’s entrepreneurship journey started after he moved back to Charleston and could not find a job. He started his company in a classroom, working at a school desk. For his first year, he managed a single property for $60 per month. By the next year, he had grown his portfolio to over 80 properties.

What is your advice for others trying to start a business?

While these business owners’ stories of how they got to where they are now are vastly different, there is one think in particular that rang true for them all: perseverance.

Dr. Mitchell’s advice was to rely on your faith, saying that new Black entrepreneurs will probably not be encouraged or have people backing them. Rather, their faith in their own skills and capabilities will drive them forward, making success even more satisfying. Jaymes reminded that while having a W-2 and being an employee is comfortable and provides a safety net, that can be taken away at any moment. Running your own business means you have the control – but don’t misunderstand that to mean it’s easy.

Regina echoed Jaymes’s sentiment by emphasizing the importance of being prepared if you are going to take the leap and start a business. It won’t be easy – even some of the people closest to you will doubt what you are doing – you have to be mentally prepared to push through those challenges and keep going. You have to be willing to put in some long hours and serve in multiple (or all) of your company’s roles, from CEO to operations to accounting to marketing. It is crucial to know the challenges of running a business and to also understand all the aspects of your business. For example, Regina decided to get her CDL – she didn’t need it to run the company, but it helps her have a deeper understanding of what her company does and what her employees experience.

Challenges for Black-owned businesses

Maybe the most important part of the discussion was when the panelists started discussing the challenges they face as business owners, particularly as Black business owners. All three agreed that the top challenges for them are resources and opportunities.

Specifically when it comes to funding, our panelists expressed frustration about their own and other Black-owned businesses’ experiences with difficulty securing funding. Jaymes shared that despite having a great relationship with his bank, he has not been able to access funding. His call to action for organizations like the Chamber is to provide businesses direct access, through resources and connections, to existing local and regional loans, grants and work options. Echoing Jaymes’s sentiment, Dr. Mitchell felt that oftentimes, the minority-owned business community finds out about opportunities or resources after it’s too late. From his own experience, he struggled from just not knowing what was out there. If business owners don’t know what resources exist or how to access them, they will never be able to take advantage of them. Creating transparency in opportunities and ensuring that businesses are aware of those opportunities is critical.

Regina emphasized that access to resources was her biggest challenge as a business owner, whether that’s financial resources, opportunity or just having a seat at the table and being in the room when discussions are had or decisions are made. Regina shared the struggle she faces when she is being told no from every direction, creating a difficult situation where her business is stuck and cannot grow.

“We’re playing catch up. There are people that have been in our industries that have decades and generations or experience. Now we’re playing catch up and our downfall is that we don’t have access to these resources.”

Regina Robinson, Prime Time Logistics, LLC

The importance of access to resources that these three business owners felt cannot be overstated. Knowing about and being able to take advantage of funding and resources is so critical for the success of minority-owned businesses. This is where the Chamber can come in. First, we must listen to the needs of the business community, especially the minority-owned business community. Hearing and understanding the challenges is paramount. Armed with this knowledge, we can use our position and partnerships to connect businesses with the resources that they need.

Getting to know the three businesses in this session, the individuals who lead them and the challenges they face is just one step in the Chamber’s DE&I Initiative. One step along the way to ensuring that we are the voice of the entire business community and that we are leading our region’s businesses in creating a climate where everyone has the opportunity to live, learn and earn.


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