Bringing Empathy to Entrepreneurship with Sherry Deutschmann




Sherry Deutschmann was raised in North Carolina with a strict upbringing, but chose Nashville as home to develop her career. Now she’s a serial entrepreneur, the founder of LetterLogic and BrainTrust. Learn how her drive and empathetic character led her to become one of the strongest women in entrepreneurship in Nashville.



Raised in North Carolina in a strict household and religion, Sherry found her own way in life when she arrived in Nashville as a single mom. With hard work and determination, Sherry worked her way up the ladder. It was with an internal pull to be an entrepreneur and, most notably, her approach to leading people that made her into one of the most successful female entrepreneurs in Nashville. 

Deutschmann describes her father as a “curious, hardworking and interesting man.” He was also a bit of a disciplinarian. While her dad was intimidating and difficult, Sherry found the motivation to approach him about her family’s discomfort. Her bravery was met with anger and frustration by her father, however, after some reflection, her father softened and thanked her. “You’re the smartest youngin’ I got,” he says. 

Deutschmann proclaims that growing up as a Jehovah’s Witness and being a middle child helped her later in life with her entrepreneurial success as the founder of LetterLogic and later BrainTrust. “I believe Jesus gave me that role.” Walking door to door to talk about Jesus gave her the experience needed to step into her first job in Nashville. 

“(I was) raised in a world where women are to be quiet and not to be vocal and not to complain, and so I didn’t.” Married at 18, experienced a first kiss at the altar, and unaware of the fact that her husband was an alcoholic, Deutschmann felt trapped in a marriage that later developed into physical abuse too. With courage and determination, she left her husband with her daughter and moved to Nashville. 



It was then that she decided to use her door-to-door experience to help her get her first job at a car dealership. She pinched her way through her finances to get by without credit cards, insurance or a support network. An event with her daughter scraping her foot and having an infection that almost led to losing her leg or her life was a pivotal moment in shaping Sherry into the empathetic leader that she is today. Ultimately, selling cars led to other commission jobs with waste and print companies. She started making great money when she was printing invoices for hospitals. While being the ideal employee that went above and beyond, she saw how an overworked and exhausted workforce led to the downfall of the company she worked for. While it crumbled, she saw the opportunity to do it better and gave it her all to build it herself, all while putting people first. When her ideas for improving the business by taking care of employees were shunned, she finally decided to step out on her own to build a business her way.



LetterLogic was born and not only did she thrive and have happy customers, but her focus on people first gave way to growth on the bottom line. Lunches with CEOs, generous incentives, pay raises and covering 100% of medical expenses are just a few examples of how Sherry built a great company culture at LetterLogic. 

Deutschmann shares that while she had seller’s remorse after selling her company, and it took some time to come to terms with, she’s happy now and in a great romance with her husband who is also an entrepreneur. Today, she’s the Founder and CEO of BrainTrust, a VC that supports women-led entrepreneurship.

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