Classroom Happenings - Entrepreneurship Studies: Stepping Up to the Pitch

Quick! Imagine you are a member of Steward’s Entrepreneurship Studies program, and you have exactly one hour to come up with a pitch that you’ll deliver to a business that wants to make its app more user-friendly. You’ve spent the semester building practical skills and chatting with local entrepreneurs who visit campus … now it’s time to team up with classmates and get to work!

In January, 15 Upper School members of the Entrepreneurship Studies program toured Startup Virginia, a business incubator that provides startup founders with strategic support and access to resources to launch, fund, and grow their business. There, they met members of the Startup team. They also chatted with Jason Herzog, CEO and co-founder of Holon Health. Holon Health is a technology first provider of primary healthcare and case management services for justice-involved individuals with substance use disorder and mental health conditions. Mr. Herzog also serves as a mentor for Startup Virginia, is a member of Steward’s Board of Trustees, and is the father of Andrew ’27 and Emma ’24. 

After learning about Holon Health’s challenge to engage clients with its app, students got to work. They had one hour to speed through the pitch process with ideas, sketches, and a very short presentation to Mr. Herzog and his two Holon Health colleagues. In teams of five, our young entrepreneurs brainstormed, jotted down notes, and settled on their final pitches. 

Dylan Olexy ’27 and his team came up with the idea to integrate a chat option into the Holon Health app, where users can communicate with others who are dealing with similar problems. 

“We pitched this idea because it could help users feel more supported and less alone,” said Dylan. “The judges really liked our idea and thought it would be a positive and useful change. What I found most exciting about the pitch process was seeing how an idea can turn into something realistic. It surprised me how much the judges focused on whether the idea actually helped people, not just if it sounded good.”

Upper School Mathematics Teacher Jennifer Maitland and Upper School Science Teacher Angela Coppola serve as coordinators of the Entrepreneurship Studies Program, which is designed to inspire innovation and foster connections between students and the local entrepreneurial community. 

Ms. Maitland noted, “Each academic year, these hardworking students can choose from two local businesses to pitch to.” During the 2025-26 academic year, one group met with CarMax employees Rusty Jordan (father of Jessica ’18 and Jack ’23) and Parker Wright ’18, who are both part of CarMax’s Financial Services and Products division. A few weeks later, these students followed up with a pitch. [Read about their presentations in our Newsroom article.] In the coming weeks, a second group of students will meet with and pitch to local furniture store LaDIFF. Ms Maitland added, “The rocket pitch at Startup Virginia was added as a result of an overwhelming response from students who wanted to participate in a pitch event.” 

Dylan noted, “The pitch experience helped me gain confidence in sharing ideas and listening to feedback, and it showed me how important innovation and teamwork are in entrepreneurship.”

Ms. Coppola added, “Pitch projects align with Steward’s core values of individuality, innovation, and inspiration, and exemplify how the Entrepreneurship Studies program offers opportunities for hands-on learning. Students who participate in pitches and complete additional program requirements also have the possibility of earning a diploma endorsement that will benefit them as they apply for college and pursue careers.”