By Gretchen Webster

WESTPORT — Four young entrepreneurs, all graduates of Staples High School, held the attention of nearly 400 people at the Westport Library on Monday as they recounted how they started their own technology businesses, now generating millions of dollars.

Hosted by Startup Westport,“an ecosystem of entrepreneurs, investors and innovators,” the event paid tribute to Staples High School’s computer science program and celebrated its alumni who worked hard to build their own businesses — all by the age of 26 years old or younger.

“Collectively, they have raised $100 million,” panel moderator Molly O’Shea said, introducing the four panel members:

• Dylan Diamond, co-founder and CEO of Saturn Technologies, a company that developed a calendar system used by millions of high school students across the country, now moving into colleges.
• Max Hammer and Josh Karol, co-founders of CrowdVolt, a live event ticket marketplace.
• Jack Sharkey, co-founder and chief technology officer of Whop, an online resource of digital tools to start a business and build a network.

O’Shea, the moderator, is the founder of Sourcery, an online news source for tech companies and venture capital funding.

The panelists engaged in a wide-ranging discussion of entrepreneurship, including how they established their tech businesses, the challenges and problems they encountered and advice for others contemplating a startup.

Some, including O’Shea, started their careers in business by selling lemonade at Compo Beach, and others said they resold second-hand sneakers online while in middle and high schools.

Several speakers credited the “Introduction to Programming” class at Staples for sparking their interest in tech, which eventually led to building their own technology companies.

“I fell in love with that class,” Sharkey said, while Hammer mentioned how impressed he was that one of his tech teachers at Staples “left a corporate job to go into teaching.”

The digital field has increased the opportunities to create new businesses, the young entrepreneurs agreed.

“It’s so easy to build things now,” Sharkey said. “Now is the time to take a risk because it’s never been easier.”

The panelists also agreed that AI is a boon to startup businesses, not a threat as some people believe.

“Don’t use it to get ahead, just use it to not get behind” and, for instance, use AI to do the administrative work of the business, Diamond advised. 

Several said that deciding to drop out of college to build their businesses, coupled with a lot of hard work, especially in the beginning, posed the most challenges in creating their startups.

“Focus on building it and making it better” in order to succeed, Karol said.

The four panelists were asked during a question-and-answer period what their best advice was for others interested in starting their own enterprises. 

“Behave ethically,” Hammer said.

“Optimize learning,” was Karol’s answer.

“Hire people smarter than you,” Diamond responded.

And Sharkey’s advice was, “Don’t pretend you know. You’ll figure it out as you go.” He also elicited laughter from the audience with another piece of advice: “Shoot for the moon. If you miss, you can always get a job.”

The panelists were introduced by Cliff Sirlin, the president of Startup Westport. “We hope to inspire the next generation of entrepreneurs,” he said. Westport’s “extraordinary school district,” he said, gives its students a solid foundation to build a business.

At the end of the evening, First Selectwoman Jennifer Tooker read a proclamation celebrating the accomplishments of the Staples High School computer science program.

Freelance writer Gretchen Webster, a Fairfield County journalist for many years, was editor of the Fairfield Minuteman and has taught journalism at New York and Southern Connecticut State universities.