Aspiring Entrepreneurs Day: What Happens When a Community Invests in Its Future
Our Aspiring Entrepreneurs Day, hosted through the Calandrino Foundation, Inc., was one of those days that reminds you why you do what you do. The initiative came to life in a way that exceeded every expectation. What started as a vision to give young students real-world exposure to entrepreneurship turned into something much bigger with a full day of learning, connection, and community.
And before the day even began, we experienced a moment that set the tone for everything that followed.
A Meaningful Start: City of Winter Park Proclamation
On April 22, we attended the City Commission meeting where the Mayor Sheila DeCiccio and Commissioners Elizabeth Ingram, Craig Russell, Kris Cruzada, and Warren Lindsey officially declared April 23 as Aspiring Entrepreneurs Day.
To stand there and hear the City of Winter Park recognize the value of investing in the next generation of business owners was incredibly meaningful. It wasn’t just a proclamation. It was a signal that this community believes in entrepreneurship, in education, and in creating opportunities for young people to see what’s possible.
We are so grateful to the Mayor and all of the Commissioners for their support and recognition. Moments like that remind us that when local leadership and local businesses align, real impact can happen.
The Vision Behind the Day
Through the Calandrino Foundation, Inc., Phil and I have always believed that exposure is everything.
Many of these students may not grow up in entrepreneurial households. They may not see firsthand what it looks like to start, grow, and sustain a business. And yet, with just one day of real-world interaction, that perspective can shift.
The goal was simple:
Give students access
Show them what’s possible
Let them see themselves in these roles
And most importantly, surround them with people who are doing it every day.
Kicking Off at the Winter Park Chamber
We began the morning at the Winter Park Chamber of Commerce, thanks to the support of Stacey Cox, who helped coordinate the space and connections to make the day possible.
The students arrived ready with some excited, some nervous, all curious.
We started with opening remarks, sharing gratitude for the many people who helped bring the program back after a six-year hiatus, and setting the tone for the day ahead.
Phil followed by sharing his own story growing up in an entrepreneurial household, becoming a business attorney, and now having the privilege of working with hundreds of businesses and families. He also tied in business into our nation’s 250th birthday.
We then heard from Hung Nguyen of Seacoast Bank, who spoke to the students about his own path and what it takes to build something meaningful. His message reinforced an important truth: there is no single path to success, but there is always value in showing up, learning, and taking the first step.
Students Stepping Into the Spotlight
From there, the students took the stage.
Each one presented their business idea with some rooted in technology, others in service, others in pure creativity. There were ideas focused on health, community, pets, education, and innovation. What stood out wasn’t just the ideas themselves, but the confidence it took to stand up and share them.
For many, this was their first time presenting in a setting like this.
And they did it.
Taking Learning Into the Real World
After the Chamber, we took the experience beyond the classroom and into the real world.
Track Shack
Our first stop was Track Shack, where the students were able to see a business that has become a cornerstone of the Orlando community.
We are incredibly grateful to Natalie Casey and the Track Shack team for welcoming us and sharing their insights. There is something powerful about seeing a business that has not only succeeded but has also built a lasting connection with the community it serves.
AJ’s Chocolate House
Next, we visited AJ’s Chocolate House, where Edwin Jablonskas opened his doors and gave the students a look into the world of specialty retail and craftsmanship.
This stop was a favorite for many combining creativity, product, and experience in a way that made entrepreneurship feel tangible and fun.
Winter Park Nines
We wrapped the day at Winter Park Nines, where Greg Pasquale hosted us and gave students a behind-the-scenes look at operations in a completely different type of business environment.
From retail to hospitality to experiential businesses, the students were able to see the diversity of what entrepreneurship can look like.
The People Who Made It Possible
This day would not have happened without an incredible group of people and organizations who gave their time, resources, and support.
We are deeply grateful to:
Amanda Benson and Shannon Herring (Miller Construction), who worked alongside me over the past several months to bring this program back to life
Tara Harry and Global Elite Transportation, who generously donated the bus and made the logistics of the day possible
Stacey Cox and the Winter Park Chamber of Commerce, for hosting us and helping connect the pieces
Hung Nguyen and Seacoast Bank, for speaking to the students and supporting the program
Natalie Casey and Track Shack, for welcoming us and sharing their experience
Edwin Jablonskas and AJ’s Chocolate House, for opening their doors and creating a memorable stop
Greg Pasquale and Winter Park Nines, for hosting and giving students a behind-the-scenes perspective
Andrew McIntosh of McIntosh Media Group, for capturing the day so thoughtfully
And of course, the City of Winter Park, for recognizing the importance of this initiative and supporting it in such a meaningful way.
Recognizing Participation and Engagement
We also want to recognize Orangewood Christian School, which earned the Most Entrepreneurial School Award for their level of participation and engagement in the program.
Their students showed up prepared, engaged, and ready to learn and it made a difference in the overall energy of the day.
What This Day Really Represents
At its core, this wasn’t just a field trip.
It was a reminder that:
Exposure creates opportunity
Confidence is built through experience
Community support matters more than we sometimes realize
In my work, I see every day how business owners shape not just their own futures, but the futures of their employees, their families, and their communities.
Through Phil’s work at Forward Law Firm and my work advising businesses on growth and real estate decisions, we are constantly reminded that entrepreneurship is one of the most powerful tools for creating generational impact.
Yesterday was a small but meaningful step in showing that to the next generation.
Looking Ahead
This is just the beginning.
We are excited to continue growing the Calandrino Foundation, Inc. and expanding opportunities like this for students in our community.
We’ll be sharing more photos and video from the day soon, and I hope those who were involved take a moment to reflect on the impact they made.
Because they did.
And for the students who participated, I hope this day planted a seed—one that grows into curiosity, confidence, and maybe even a future business of their own.
Closing
I’m incredibly grateful.
Grateful for the students.
Grateful for the community.
And grateful to be part of something that brings people together in a way that truly matters.
If you’re someone who believes in investing in the next generation of entrepreneurs, I’d love to connect. This is something we’re building with intention, and the impact is only as strong as the community behind it.