“Better to have it and not need it, than to need it and not have It.”
How It All Began
On December 1, 1893, Henry B. Cowan founded H.B. Cowan & Company. Today, it has established itself as a leading independent insurance agency in Tennessee, providing services to businesses and individuals for all if their insurance needs.
Cowan began the slogan, “Better to have it and not need it, than to need it and not have It.” His principles of service, loyalty and dedication still guide H.B. Cowan & Company today.
We believe insurance should be about more than just checking a box — it’s about protecting what matters most to you. As an independent insurance agency, we work for you, not the insurance companies. That means you have the power of choice when selecting a policy that meets your unique needs.
Here for You Every Step of the Way
Insurance needs change over time, and we’re here to guide you through every stage of life and business. Whether you’re buying a home, starting a business, adding a teen driver to your policy, or expanding your coverage, we continuously review and adjust your policies to ensure you have the best protection.
Meet Our Personal Lines Team
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Beverly Derryberry
Beverly is our Personal Lines Agent. She has over 30 years of experience in the insurance industry and has been with H.B. Cowan for 24 years. She is an active member of the Shelbyville/Bedford County community and has served on several boards and committees throughout her tenure at H.B. Cowan. She is a 2004 graduate of Leadership Bedford and is currently a member of the Shelbyville Women’s Club and Epsilon Sigma Alpha Sorority. She is married, has 3 children and one grandson. In her free time, she enjoys gardening, traveling, camping, and spending time with her family and two miniature schnauzers.
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Madisyn Smith
Madisyn is an insurance professional specializing in personal lines. After graduating high school in 2021, she began her career in the insurance industry and joined HB Cowan in 2024. In addition to her role in personal lines, Madisyn also manages the agency’s social media, particularly tik tok, where she creates engaging content to connect with clients in a fun, relatable way. Madisyn is a Bell Buckle native and a member of the Shelbyville Women’s Club. When she’s not working, she loves spending time outdoors with her dog, diving into a good book, and staying involved in church.
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Cindy Winchester
Cindy has been in personal lines with H.B. Cowan for 23 years. Outside of work, she enjoys antiquing, flea markets, auctions & estate sales. Her favorite thing is time spent with family & friends.
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Richard Bobo
Meet Our Commercial Lines Team
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Brett Fisher
Brett is a Commercial Lines agent and Owner of H.B. Cowan & Company. He has been at H.B. Cowan & Company for 20 years and purchased the agency along with his brother, Brad McGee, in 2014. Brett attended Cascade High School and graduated from Middle Tennessee State University in 2005 with a degree in Finance. He is very active in the community and serves on multiple boards. He is married to his wife Whitney, and they have two children, Jackson & Brynn. In his spare time Brett enjoys going to different sporting events, traveling, and spending time with his family.
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Brad McGee
Brad is a dedicated commercial insurance producer with nearly two decades of experience in the industry. He graduated from Middle Tennessee State University in 2005 with a degree in finance, emphasizing insurance. In 2006, he began his career at HB Cowan as a commercial producer, building strong relationships and helping businesses secure the right coverage for their needs. Beyond his professional life, Brad is a devoted family man. He married in 2010 and enjoys spending time with his children. An active member of his community, he participates in Rotary and is involved with Thompson Creek Baptist Church. Brad’s passion for helping others, both in his career and personal life, reflects his commitment to integrity, service, and building lasting connections.
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Cassidy James
Cassidy joined the HB Cowan team in 2021 as a dedicated Commercial Lines Account Manager. A graduate of Cascade High School, she brings a strong work ethic and a passion for helping clients navigate the complexities of insurance. Cassidy finds fulfillment in creating tailored policy solutions that offer peace of mind and protection. Outside the office, Cassidy cherishes time with her husband and their beloved animals. She enjoys the simple joys of life—attending church, cooking up delicious meals, and embracing the great outdoors. Whether she’s crafting the perfect insurance plan or spending a weekend under the open sky, Cassidy is committed to both her clients and her personal passions.
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Kari Bell
Kari is a Commercial Lines Account Manager. She joined the H.B. Cowan and Company team in 2022 with over 10 years’ experience in the insurance industry. Kari graduated from Middle Tennessee State University in 2008 with a degree in Finance and Insurance. During her time at MTSU, she served as Vice-President of University Relations for Gamma Iota Sigma. She is active in her local community by serving on various community committees and supporting her children’s sports teams. She is a member of the Rotary Club of Shelbyville, Bell Buckle Fire Department Auxiliary, and a ’23-’24 Leadership Bedford graduate. She is married to Trey. They have three children. In her free time, Kari enjoys going on camping adventures with friends and family.
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Bethany Bannister
Bethany is a dedicated Commercial Lines Account Manager with extensive experience in the insurance industry. She has been a valued member of the HB Cowan team since 2020, where she has built a reputation for her professionalism, energy, and commitment to providing exceptional service. Outside of her professional role, Bethany is a proud wife and mother of two teenage daughters. She values family time and enjoys the company of her two dogs, Hula and Goose. As an active supporter of her daughters’ interests, Bethany spends much of her time at ball fields and gymnasiums, cheering them on in their athletic endeavors. Her passion for both her family and community is a reflection of her strong work ethic and dedication to everything she does.