Tampa Bay Business and Wealth hosted its November CEO Connect at Aqua at Westshore Yacht Club, where business leaders gathered to hear from Ashley Butler, a Tampa entrepreneur who owns Ice Cold Air and is the November cover star of TBBW.
Guests watched the sunset over the marina while Ashley shared how early struggle shaped her work ethic, how mentorship changed the path of her life and how she built a business that now supports about 100 people.
Speaking with Bridgette Bello, CEO and publisher of Tampa Bay Business and Wealth, Ashley talks about the power of relationships, the truth behind leadership loneliness and the need for community investment.
She also shares direct advice for business owners growing fast who want to stay focused on their mission.
About Ashley Butler
Ashley Butler was born at MacDill and raised in Port Tampa. She grew up helping her family keep the lights on and took her first steps into entrepreneurship before high school.
Today, she owns Ice Cold Air, which generates more than $12 million a year and is on track to reach $35 million.
She and her wife Adrien lead with a focus on service, training and economic mobility. They also created the first $25,000 Black Leadership Network endowment in their names at the University of South Florida.
Fireside chat
Bello: How have your first days as a TBBW cover star been?
Butler: This community is rich and generous. It has given me every single thing. People have been calling me Cover Girl, which is pretty funny. The love has not changed because this community has always shown up for me. It is mind-blowing.
Bello: Can you share an opportunity that came from a relationship, not a business plan?
Butler: When I was at USF, I replied to an ad in the Oracle that talked about making full-time money part-time. I met Wendy Poling and then her father, Mark Poling. He took me to the Village Inn on Dale Mabry and ordered a special pancake. He said he wanted me to have it because I was special.
Mark became the dad I did not know I needed. He taught me grit and hard work. He told me to always have a passport and made sure I got one. That opened the chance to live in Frankfurt and build a sales team. Every step of my journey came from people in this community who gave me opportunities they did not have to give.
Bello: How would Tampa change if more leaders invested in the next generation?
Butler: My mom needed a chance. Many people do. Some are single parents. Some made mistakes. Some are trying to return to society. They need people who believe in them.
Small acts matter. You can clear lunch tabs at a school or pay for overdue books. You can mentor students. You can help a family fill out FAFSA. You are blessed to be in a room like this. Someone opened a door for you. Now shine your light for someone else.
Bello: Leadership can be lonely. When did you feel that the most?
Butler: I once cried in the shower because things were piling up. I read about entrepreneurial suicide. I did not feel that way but I understood how someone can get there.
I grew up poor, so I always knew how blessed I am now. If I had to start from today, I would be fine. But I needed someone to talk to. A friend told me it was not healthy for me to carry everything alone.
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Then Laura Webb invited me to EO (Entrepreneur Organization). That room changed everything. These were people with more money than me but the same fears. I also did therapy for seven years. Six hours a week. Individual and group. It helped me stay grounded.
Bello: How do you stay authentic in a social media world?
Butler: My marketing department does not like me. I check social media maybe once every 30 days. I leave my phone at the door when I get home. I like privacy. If you need me call Ice Cold Air. That is the best way to reach me.
Bello: Talk about a moment when asking for help changed an outcome.
Butler: The Tampa Bay Business Accelerator helped me a lot. JP Morgan brought in Joe Parker from Aberdeen Associates. I learned so much that I started meeting him for coffee every three months. I did the same with Michael Flores.
Genuine connection is my secret sauce. When it came time for a major business decision, I already had the right people to call. They helped me plan. Then I closed the deal.
Bello: What advice do you have for business owners who are scaling fast and worried about losing their why?
Butler: EOS (Entrepreneur Operating System). If you have not read Traction, you should. You need a vision traction organizer. You need rocks. You need a meeting pulse. You need a clean plan.
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Entrepreneurs get distracted. You need mentors. You need to stay focused. When the plan stops working, you change the plan, not the goal.
Your core values must anchor everything. I keep my core value chip with me. It helps me stay grounded.
Takeaway
Ashley Butler’s story shows the strength of grit, community and clear values.
Her path from Port Tampa to leading a growing $12 million business is a reminder that leadership is not about perfection. It is about service, discipline and the people who help you rise.
She stayed after the event to speak with guests, answer questions and encourage anyone who wanted to take a step forward in their own leadership journey.
November’s CEO Connect was presented by PNC Private Bank, Little Saint Nick Foundation, CareerSource Tampa Bay, The Entrepreneur’s Source and NOW CFO, with event support from Eventing Tampa Bay, Empowering Creative and Video Light and Sound.
Scene’s from TBBW’s CEO Connect
