In addition to a long career in law enforcement, Shannon Penn has spent more than four decades building, managing, and growing successful businesses across Mississippi. As a business owner, he has created jobs, managed employees, balanced budgets, invested in local communities, and built companies through hard work and integrity. Those experiences have strengthened the leadership, accountability, and decision-making skills he will bring as Sheriff of Rankin County.
Cups Espresso Café
1995 to Today
For nearly 20 years, I have had the privilege of owning and operating Cups Espresso Cafe in Brandon, Mississippi. Cups has given me something I value greatly—the opportunity to meet and listen to people from all walks of life. Over the years, customers have shared their families, businesses, successes, struggles, and concerns with me. Those relationships have taught me that people want leaders who will listen to them, treat them with respect, and be accountable for their actions. Owning a small business has also taught me the importance of hard work, responsibility, managing people, solving problems, and keeping my word. I believe those same principles—trust, accountability, transparency, and service—are essential to leading the Rankin County Sheriff's Department.
Penn’s Lawn & Landscaping Maintenance
1991 to Today
Founded around 1991, Penn’s Lawn & Maintenance has grown into a successful commercial construction and maintenance company that continues to operate today. As owner and manager, Shannon oversees business operations, employees, project management, budgeting, and customer relationships. Depending on project demand, the company employs approximately 40 people and continues to grow while providing quality services throughout the region.
Real Estate Investment and Property Leasing
1991 to Today
Throughout his business career, Shannon reinvested the proceeds from his successful businesses into real estate. He built a portfolio of residential and commercial properties, including land, commercial buildings, and condominiums throughout Mississippi and Alabama. Managing these investments has provided decades of experience in financial planning, long-term investment, property management, and responsible stewardship.
Penn’s Sports & Family Entertainment
1990 to 2000
In the early 1990s, Shannon founded Penn’s Sports & Family Entertainment, a company that partnered with churches, chambers of commerce, municipalities, festivals, and community organizations to help raise money through family entertainment events. The business featured attractions including electric bull rides, climbing walls, trackless trains, and bungee jumping activities. Organizations received a share of the proceeds, helping support local programs and community events. After years of successful operation, the business was sold in the 1990s.
Affordable Rent-to-Own
1992 to 2005
After the success of his first rent-to-own business, Shannon opened Affordable Rent-to-Own in Pearl, Mississippi. As owner and manager, he again directed all aspects of the business, applying the same commitment to customer service, sound management, and responsible financial practices that made his earlier venture successful.
King of Wings Restaurant
1993 to 2000
In 1993, Shannon became the sole owner of King of Wings Restaurant. Managing a staff of approximately six employees, he was responsible for every aspect of the business, including operations, hiring, budgeting, customer service, and financial management. The experience further strengthened his ability to lead people and successfully manage complex daily operations.
Canton Rent-to-Own
1987 to 1990
Shannon Penn began his entrepreneurial career in the early-1980s by opening and operating Canton Rent-to-Own. As the owner and manager, he oversaw every aspect of the business, including customer service, inventory management, collections, and daily operations. After successfully growing the business, he sold it in the late 1980s.
A Record of Leadership
Whether serving in law enforcement or operating successful businesses, Shannon Penn has built a career centered on hard work, accountability, and service. His experience leading employees, managing multimillion-dollar assets, creating jobs, and making difficult decisions has prepared him to lead the Rankin County Sheriff’s Office with professionalism, transparency, and integrity.