Jackie P. Taylor, entrepreneur, author, speaker, and economic development strategist
Jackie P. Taylor is an entrepreneur, author, speaker, and economic development strategist dedicated to helping businesses, communities, and individuals grow. As the Founder and CEO of Boost Strategy Group, she has built a career around connecting people to opportunities, empowering entrepreneurs, and creating pathways to economic mobility. Through her work, Jackie helps organizations activate entrepreneurial ecosystems, strengthen workforce development efforts, and ensure businesses are Seen, Supported, and Sourced®. She is also the author of several books and a passionate advocate for helping people turn their gifts, talents, and experiences into sustainable income and impact.
Who are you?
I'm Jackie P. Taylor, an entrepreneur, strategist, author, and proud community builder. At my core, I'm someone who loves helping people connect the dots between where they are and where they want to be. Whether I'm working with a small business owner, a city government, or a young person exploring their future, my goal is always the same—to create opportunities that lead to growth, impact, and lasting success.
What first made you decide to become an entrepreneur?
I've always had an entrepreneurial spirit. Even when I worked in corporate America, I found myself thinking about how to solve problems, create opportunities, and help people succeed. Eventually, I realized I wanted the freedom to build something that reflected my values and allowed me to make a bigger impact. Entrepreneurship gave me the opportunity to do both.
Was there a specific moment when you realized this was the path you wanted to pursue?
Honestly, I think I've known for as long as I can remember.
When I was a kid, I participated in one of those fundraising programs where you sold cookies and chocolates from a catalog. The person who sold the most got to choose a prize. I was determined to win, and I distinctly remember choosing a chemistry set. Now, I'm definitely not a scientist, but I loved the idea of mixing things together, experimenting, and seeing what happened. If it smoked, bubbled, or created a reaction, I was all in.
Looking back, that's entrepreneurship in a nutshell. It's about curiosity, creativity, problem-solving, and being willing to try things to see what works. I've always had that mindset.
The bigger question wasn't whether I would become an entrepreneur—it was when. For me, it was about making sure I had the right experience, the right timing, and the right circumstances to make the leap. Once those things aligned, I knew it was time to build something of my own.
What does a typical day in your life look like?
No two days are exactly the same, which is one of the things I love most. A typical day includes meetings with clients and partners, working on new business opportunities, mentoring entrepreneurs, creating content, writing, and thinking strategically about how to grow our impact.
One thing that is pretty consistent, though, is that whenever I'm working from home, my Silver Labrador Retriever is never far away. She follows me from room to room and is usually sitting right at my feet during meetings, writing sessions, or strategy calls. I absolutely love her, and she's become my unofficial executive assistant.
I also try to make time for exercise, reflection, family, and moments of stillness because I've learned that taking care of yourself is just as important as taking care of your business.
What first initiated your interest in your field or industry?
I became fascinated by the connection between business success and community success. I noticed that when entrepreneurs thrive, families thrive, neighborhoods thrive, and entire communities benefit. That realization sparked my passion for economic development, workforce development, and entrepreneurship.
What is your favorite thing about what you do?
My favorite part is seeing transformation. There is nothing more rewarding than helping someone move from an idea to a business, from unemployment to employment, or from uncertainty to confidence. Watching people unlock their potential and achieve goals they once thought were out of reach is incredibly fulfilling.
What challenges have you faced as a woman in this field?
Like many women, I've had moments where I had to work harder to establish credibility or earn a seat at the table. There have been times when my expertise was questioned before my results were seen, and times when I felt I had to prove myself over and over again.
As frustrating as some of those experiences have been, they've taught me valuable lessons about confidence, preparation, and perseverance. Over time, I learned that the best response is excellence.
What advice would you give younger women entering this field?
First, access capital like it's owed to you. Too many women are taught to bootstrap everything and carry the entire burden themselves. Learn how money works, build relationships with lenders, investors, and funding partners, and don't be afraid to ask for resources that can help you grow.
Second, trust yourself. You don't have to have every answer before you begin. Most successful entrepreneurs are figuring things out as they go.
And finally, don't wait for permission. If you see an opportunity to create value, solve a problem, or build something meaningful, take the first step.
What mindset has helped you succeed the most?
The mindset that has helped me the most is simple: "I'll figure it out."
I say it all the time. Whenever I'm faced with a challenge, obstacle, or problem, my immediate response is, "I'll figure it out." And I genuinely believe it.
That belief is powerful because it keeps me focused on solutions instead of limitations. If you're committed to finding an answer, you become more creative, more resourceful, and more resilient. Quitting or stopping has never felt like an option to me.
When I look back on my career, I've had a 100% success rate at figuring things out eventually. Maybe not always on the timeline I wanted, and maybe not in the way I originally imagined, but I've always found a path forward.
What are your hobbies outside of working?
I love traveling, especially exploring new places and experiencing different cultures. I also love being near the water—whether that's at the beach, on a waterfront, or simply enjoying the peace that comes from being around it.
And if there's karaoke involved, count me in. I love music, having fun with friends and family, and not taking myself too seriously. Some of my best memories have come from travel adventures and karaoke nights.
What is the biggest lesson your career has taught you so far?
The biggest lesson is that success is built through relationships. Opportunities often come through people who know your character, trust your work, and believe in your vision. Skills and expertise matter, but relationships, integrity, and consistency are what create long-term success and impact.
This interview and shoot were conducted by Monique Parkerin her role as a WIDD volunteer.
