Back in 2023, Katie Gailes was flirting with retirement. While on a Zoom meeting with Entrepreneur Support Organizations in the Triangle — and despite wearing red glasses and lipstick and being, as Gailes describes herself, “my usual feisty self” — she labeled herself an “official little ol’ lady.”
It didn’t take long for people to declare that she’d misidentified herself and needed to find a more accurate description. As soon as “The Entrepreneur Whisperer” left her lips, the collective response was: “That’s it!”
Since that meeting, Gailes, a Holly Springs resident, has realized “I am The Entrepreneur Whisperer. I can see opportunities and solutions that my clients cannot see. I can listen to what they say and then tell them what they mean. I can take complex business concepts and make them make sense to new entrepreneurs. And I can develop workshops and programs that address the real challenges entrepreneurs face.”
Along a career path that has taken a lot of “twists and turns,” and after abandoning her FBI agent dream, Gailes became focused on affording herself a life. During her 18 years with IBM, she performed multiple roles and worked in many business areas, but it was earning her MBA — and interacting with people from 39 different countries in a class of 40 students — that cemented Gailes’ understanding that despite all of her business training and perspective being based on IBM, “there are many ways to do business.”
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She would leave IBM twice to work with smaller companies, the first time as a PR consultant and the second to help a European company set up a US subsidiary. In 2006, however, Gailes decided to focus on marketing and business strategy consulting for small businesses.
She was a Growing America Through Entrepreneurship counselor with the NC Rural Economic Development Center and consulted with small businesses when the NC General Assembly eliminated most of the funding for the nonprofit. Around the same time, she was also holding small-business marketing workshops for community colleges.
Gailes then started counseling with the Wake Tech Small Business Center part time and was asked by the college to take on other projects. One was to redefine the entrepreneurship center, which she was later asked to join as Wake Tech’s first director of entrepreneurship initiatives.
While in this role — one that Gailes says couldn’t have succeeded as it did with its programs anywhere but in Wake County — she created the LaunchWakeCounty umbrella program, which, as of 2020, was active in nine Wake County municipalities and had trained over 600 small-business owners and entrepreneurs, approximately 70% of whom were minorities and/or women. Gailes also created the LaunchWakeTech umbrella program for Wake Tech students, which was active in the barber school, natural hair practitioner course, cosmetology course, and graphic design two-year degree program.
After leaving the college to serve as senior director of membership and DEI&B for the National Association for Community College Entrepreneurship, a role she held for 11 months, Gailes decided to retire.
But thanks to a “workaholic gene” in her family, she ended up being even busier than before. Gailes admits, “I can still do too much and still don’t have a magic formula for setting priorities, but I do try to stay focused on my personal vision statement and prioritize those things that are consistent with how I want to live.”
And how she wants to live is echoed in who she knows herself to be: an assertive introvert and creative problem solver.
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After receiving numerous awards and statewide recognition for her leadership, Gailes admits that, surprisingly, she never set out to be a leader, per se. “I wanted to do important things and to be recognized for my impact,” she says. “Many leaders are not at the top of the org charts. If you want to know if you are a leader, look around. If you see people who believe in a shared vision and want to be on this journey with you, then you are a leader.”
But starting her career in 1977 unfortunately meant that other people’s preconceived notions and biases were frequent journey mates. The best response, according to Gailes? “Always success and exceeding expectations. When I could, I did.”
Yet, despite the “rugged individual” being widely celebrated in the US, Gailes notes that successful people and strong leaders “work with and through others. They leverage collaborations and relationships to bring others with them on the journey.”
Collaboration and partnerships continued to play a role for Gailes when she realized that traditional retirement, or semiretirement, something she describes herself as “failing at miserably,” wasn’t going to work for her and that she needed to name her business — which focuses on entrepreneurship coaching and training, entrepreneurial mindset development, and strategic planning. “Cute names are great,” Gailes says. “But I decided that my name was just fine, thank you very much.” Thus, Katie Gailes & Company.
When it comes to women entrepreneurs, Gailes asserts that women “have always had excellent leadership capacity.” Growing up between two very large brothers meant that she had to hold her own with them and their friends, so she learned to fight; early in her life, she was called volatile and strident. “I am still intense,” she admits.
When it comes to women as leaders, Gailes believes the greatest negative impact has been society’s view of a leader as a man. “If I owned 53% of IBM stock,” she says, “I could call all the shots because I would be a majority owner.” Women constitute the majority of this country’s citizenry; women are majority owners. When women “do not support other women professionals,” Gailes contends, “it says a lot about what we believe about ourselves.”
And what does Gailes believe about herself?
For someone who got their first job at 12 stacking wood for a carpenter for $2 per day, was the first woman marketing manager in the Roanoke Virginia IBM branch office, and has worn multiple business hats and been appointed to numerous positions — to include advisory board for the Wake Tech Business Administration curriculum program and board of directors for the Carolina Community Impact CDFI, NC Women Business Owners Hall of Fame, Greater Raleigh Chapter of the National Association of Women Business Owners, and the United Strings of Color — she describes herself as “a poor barefoot country girl who likes digging the dirt and playing with plants.”
The intensity that marked her youth has given way to “a calm intensity that comes with maturity” and a thoughtful approach to her business and personal life.
Not long ago, Gailes was in a women’s discussion group deliberating with others over which rooms they felt they belonged in. “Finally,” Gailes announces, “I am able to say that I belong in whatever and whichever the hell room I choose to be in.”
