In front of a panel of sharp, business-minded “sharks” — aka alumni and parents serving as judges — six groups of Upper School students made their pitches on January 16, 2026. This Demo Day followed the two-day Startup Experience, led by Startup Experience founder Henrik Scheel, with helpful visits from alumni and parent mentors.

DriveGuard’s goal is to help older people stay safe while driving. Their slidedeck featured a fictional user “Grandma” who, perhaps, keeps her blinker on by mistake or drives 15 miles below the speed limit. The innovative app would alert her: “Speed up a little, Grandma,” said by a member of the team with deadpan delivery, which got a laugh from the crowd. The product would also help younger users who may be driving at reckless speeds by limiting distractions while on the road. The target customers who would pay for the service: those in the sandwich generation whose parents and teenagers may benefit from the reminders.

RookieNIL offers a platform for student-athletes to practice their self-marketing skills, while giving local businesses an opportunity to secure young talent at affordable prices for advertising purposes. The team already reached out to one family-owned, local restaurant that was interested in learning more and potentially negotiating a deal with a student for an Instagram collaboration.

Speak Up speaks to the real need that students and young professionals have to up their public speaking game. The group’s test subjects indicated a number of challenges faced by young speakers, including stutter, pronunciation, lack of eye contact, and use of filler words. The solution offers a virtual assistant that gives feedback along with audience simulation. The group presented a promo video that included an example of such feedback.

AeroGlide envisions a fleet of fully autonomous, AI-enabled robot tow trucks that will help airlines more efficiently deliver planes to gates once on the ground. Their service would dramatically reduce fuel needs — and by extension, costs — by addressing the issue of fuel burned inefficiently while taxiing on the runway. This group spoke to a Southwest Airlines pilot who said this idea could work in both the private and commercial sectors.

Old-Style Footwear, another venture to help the elderly, focused on preventing falls through motion-sensor-enabled footwear. These stylish and self-charging shoes will help keep folks vertical and looking sharp. The shoe also incorporates a supportive arch that helps propel users forward, making the exercise of walking both more efficient and enjoyable.

Pocketwise is a coaching app to teach young teens about financial literacy. Through their research, the team found that some parents don’t have the time and/or interest in helping their children in this realm, with the devastating results of teens who don’t understand the consequences of their poor financial decisions. The product rises above the competition because it includes a debt system simulator and forces a user to think about a purchase before completing the transaction, a feature that their test parent said she’d appreciate.

Throughout the presentations, sharks offered tips: Don’t read from notes or the screen; be familiar enough with the material that you can speak to it naturally. Simplify the problem you are trying to solve. Reach out to schools or businesses where you already have connections. Go for out-of-the-box markets you haven’t thought about yet.

As the judges convened outside the Reading Room, Scheel spoke to students. “This was the beginning of your entrepreneurial journey.” He provided potential next steps boys could take, like finding a mentor and launching the business or signing up for the spring Entrepreneurship elective. 

Scheel first brought Startup to Gilman in 2015, but this is the first time he’s integrated AI coding to such a great extent, using the platform loveable.dev. The newly available tools gave students the ability to quickly develop their market research, conduct feasibility and competitive analysis, and create a landing page for their company websites. “Because we’ve allowed these tools, we’re setting the bar higher in terms of the quality of the pitches,” Scheel said. Some teams realized, after doing an AI feasibility study, that their businesses weren’t terribly realistic. Because these early steps in the process didn’t take as long as in past years, they were able to pivot and work on with new, better ideas.

“I’m always impressed with the Gilman students,” said Scheel. “There is an amazing sense of curiosity. They really want to learn these things.” At the beginning of day one, Scheel asked the participants who wanted to be an entrepreneur. They all raised their hands.

When the judges returned, they announced the winner, SpeakUp, noting that the problem the group solved is very relatable and that the business is marketable. One shark added with a smile that “the presenter looked like a CEO.” The judges reiterated that there is “no perfect venture” and to expect challenges along the way. The students were encouraged to know when to listen to feedback and when to stand firm.

The people’s choice winner — voted on by all students, faculty, and staff present — was RookieNIL.

“Starting a business takes guts,” said judge Cheo Hurley ’92, P’30, PP. “Don’t be afraid. Keep doing it.”

View photos on SmugMug

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Thank you to all our judges and mentors!

Judges:

• Cheo Hurley ’92, P’30, PP - President and CEO at THG Companies
• Kelvin Liu, P’27 - Chief Product Officer at Infinity Bio, Inc.
• Christopher Sachse, P’34 - Chief Executive Officer at Network Coverage

Mentors:

• Ryan Kamauff ’03 - Cloud Architect at VMware
• Zach Landers-Portnoy ’06 - Chief Revenue Officer at Tricerat
• Robb Lawrence P’28, ’33 - Entrepreneur in Residence at University of Maryland, Baltimore
• Kevin Robbins ’94 - General Partner at Blue Delta Capital Partners
• Jason Pappas ’86 - Founder & Managing Partner at Antson Advisors