What My Popsicle Stand Taught Me About Entrepreneurship

Phoebe Barlow, Team Alpha Marketing
August 04, 2025
When I was nine years old, I started my first business: a popsicle stand in the front yard. It had everything: a handwritten sign, a homemade logo, some unofficial merch, and a menu based entirely on whatever we had in the freezer. While most of my customers were neighbors, friends, and my parents (who quietly covered the cost of my “inventory”), I loved every minute of it. From dreaming up flavor names to convincing someone to buy a second popsicle, I was completely drawn to the idea of creating something from scratch. I have fond memories of the many hours I spent at my popsicle stand that summer, but looking back, it was a small spark that hinted at what would become a central part of my identity.
I like to say entrepreneurship is in my blood because I think a lot of my passion has to do with the environment I grew up in. My dad has started multiple businesses in Lexington, so talking about new ideas, side projects, and big plans at the dinner table was part of my everyday life. Entrepreneurship never felt distant or abstract, and my dad made a real effort to involve me in his ventures, making any idea I had feel within reach. I learned from him that starting a business in a city like this is less about selling something and more about solving a problem, paying attention to what’s missing, and doing the work to build something that fills that need.
That mindset really started to click when I attended one of Awesome Inc’s 5 Across pitch competitions in downtown Lexington. For the first time, I saw local founders stand up and present ideas they had poured themselves into. These weren’t celebrity entrepreneurs, corporate giants from Silicon Valley, or someone out of a textbook. Like my dad, they were people from my own community, taking risks and sharing real stories about what worked, what didn’t, and why they kept going. It made entrepreneurship feel more tangible and personal, and again made the world feel much more accessible.
Last year, I attended the Governor’s School for Entrepreneurs (GSE), a three-week summer program where students work in teams to build a business from the ground up. It’s fast-paced, collaborative, and packed with moments that challenge you. I was surrounded by people my age who were just as excited about ideas as I was, and together we dove into market research, customer interviews, and long nights figuring out how to solve a problem. It reminded me a lot of the popsicle stand, but bigger, more focused, and more impactful. GSE confirmed a couple things for me: I deeply cared about entrepreneurship in Lexington and I wasn’t alone.
Today, I’m back at Awesome Inc, this time not as a guest at an event, but as a member of Team Alpha as a marketing and events intern. This opportunity has shown me a different side of entrepreneurship: the daily work that makes a thriving startup community possible. I’ve helped plan events like 5 Across and Startup Weekend, sent out newsletters, set up chairs, and taken photos at pitch competitions. These may seem like small tasks, but they’ve helped me understand how much effort goes into creating a space where founders feel supported, heard, and encouraged.
More than anything, this internship has helped me see how community and entrepreneurship are deeply connected. A good pitch is about showing others your passion and trusting them to see the value in it, not just statistics. Networking is about showing how you can contribute to others, not just exchanging contact info. Entrepreneurship is a way of approaching the world with care and confidence that things can be improved, not just a professional ambition.
And that brings me back to Lexington. This city is full of creative, hardworking people with different backgrounds, skills, and ideas. There’s no one-size-fits-all solution for a place like this. What we need are businesses that come from within the community, led by people who understand its history and potential.
Through people like my dad, programs like GSE, and events like 5 Across, I’ve seen firsthand how accessible entrepreneurship can be when the right support is in place. When young people are given the tools, encouragement, and local examples to look up to, they begin to see entrepreneurship not as a distant dream, but as something real. Lexington proves that innovation doesn’t just live in big cities. It grows in classrooms, local events, dinner table conversations, and yes, even front-yard popsicle stands.
When access meets inspiration, real progress can be made, and Lexington, with its tight-knit community and growing support for entrepreneurs, is exactly the kind of place where the next generation can, and hopefully with my help will, build something that matters.