When Nathaniel Badder '94 was a student at Gilman in the early 1990s, “entrepreneurship was a funny five-syllable word I could barely pronounce,” he said. The irony would be that not only would he try his own hand in entrepreneurship but he would go on to teach an Upper School class on the subject.

Throughout the spring course, alumni advisors (listed below) visited the students to deliver real-world advice on topics such as business development, marketing, and sales. With some basic knowledge, the class divided into teams and formed “businesses.” At the end of the semester, Badder organized Demo Day, a “Shark Tank”-style competition where each team of students presents their idea to a panel of judges. Badder referred to the panel — made up of Cheo Hurley '92, founder, president, and CEO at THG Companies; David Zinreich '94, lead advisor at Black Diamond Financial; and Head of School Henry P. A. Smyth — as dolphins instead of sharks, because of their friendlier nature.

In front of their peers and teachers at assembly on Friday, May 5, three teams stood on the stage to pitch their ideas. The audience was told to keep three criteria in mind, as they would have a chance to weigh in as well: What problem was the business idea addressing? How viable was the solution? Was their pitch convincing?

First up was BlipNews, an app where, in a world of misinformation spread via TikTok and Instagram, teens and college students could get reliable news. The subscription would cost users $20/year, which the presenter reminded the audience was less than two steak bowls with guac and chips from Chipotle, “which I know many of you buy seven days a week.”

The dolphins asked the group how they would eliminate bias in their news, how they would drum up sales, and whether they had thought about how the emergence of AI would affect their business.

Next up: Ski-Fold, touted as “the future of skiing.” The would-be product is a pair of skis that folds into thirds and can fit into a case sized for a TSA-approved carry-on bag. The team said they would target advanced skiers who would want to travel with their own skis, which they would price at $1,400 a pair.

Hurley complimented their presentation and coached them on expanding their target demographic. “Get an engineer to design it, and get it patented,” he said. “There is a niche of people who will purchase this product.”

Finally: Slumberland, where “Our dream is for you to dream better.” The lively presentation began with a relatable question for the audience: “Have you ever had a bad night's sleep?” The team talked through the problem of poor-quality sleep and presented their solution — an over-the-bed dome that blocks out light and sound. Their target market was college students, especially athletes, who need sleep to do well in school.

The dolphins advised the group to expand their market to older customers as well as directly to hotels and colleges, and praised them on their professionalism before and during the presentation.

Ultimately, only one team could prevail. Voted by the audience and determined by the dolphins, Slumberland was declared the winner, based on their clear and concise business plan and excellent pitch. Zinreich congratulated all the students and gave them encouraging advice about their futures in business: “Without failure, there’s no success.”

Watch Demo Day below.

Entrepreneurship Class Alumni Mentors

• Jason Finkelstein '94, CMO at Gladly
• Gilman Entrepreneurship Network:
  • Haftan Eckholdt '83
  • Colin Hamil '00
  • Bryan Moore '12
  • Collin Wallace '02
  • Garrett Weinstein '14
  • John Wise '96
• Jason Griswold '93, Co-Founder & CRO at REIN
• Harris Jones '80, Managing Partner at Swallow Point Ventures
• Nick Owsley '93, Co-founder at TipHero
• Scott Proctor '89, CIO and VP of Finance at Twenty/Twenty Therapeutics
• Dr. Manan Shah '03, Founder of Wyndly
• Chris Watson '11, Senior Materials and Process Engineer at Virgin Orbit

Entrepreneurship Class Demo Day Alumni Judges

• Cheo Hurley ’92, Founder, President, and CEO at THG Companies
• David Zinreich ’94, Lead Advisor at Black Diamond