Founder of Skylight Shares Lessons on Passion and Persistence at CEL Speaker Series

What do Harvard Business School and SCH Academy have in common? They both recently welcomed Michael Segal, founder of Skylight, as a speaker.

The Center for Entrepreneurial Leadership (CEL) relaunched its Founders and Leaders Speaker Series, hosting Segal, a Philadelphia native, as its first presenter of the academic year.

“My hope is that students leave each session seeing a bit of themselves in the stories they hear—that they recognize their own potential to shape change and lead with purpose,” says Ed Glassman, executive director of CEL.

Segal's company, Skylight, produces the popular digital frame, launched on Kickstarter in 2015, and a calendar to “keep families connected.” He shared important insights with CEL students in separate Middle and Upper School sessions, framing entrepreneurship as an art of harnessing internal "magic" to drive purpose and persistence.

Segal shared his entrepreneurial journey, which began with several failed businesses after college. “The foundational lessons I learned from failing eventually guided me to success," he said, emphasizing the value of early breakdowns. 

Ten years later, Skylight is now a 75-million-dollar business with more than 150 employees. Segal advised budding entrepreneurs to build a supportive team, identify a strong purpose, and dedicate the necessary time to grow their venture, noting that success often requires many years of passionate perseverance. He said that the product or venture should make "eyes light up,” because that feeling will get founders through the difficult times.

“If I have to distill one thing to take home,” he said, “it’s not about intelligence; it’s sort of about grit, and it is definitely about energy. You’ll have to have energy to summon the will, the magic, to convince others. You have to be thoughtful about how you harness that magic inside of yourself.”

The event featured student participation, with two students practicing their pitches with Segal. One of these students, Harmonee Summers '27, founder of WeBloom—an all-in-one activism app that empowers young people to learn, connect, and take real action on global issues—later interviewed him for WeBloom’s YouTube channel, where he detailed his core business philosophy: the "job to be done." This approach prioritizes solving a customer’s emotional need (such as reducing family stress) over simply building new technology. Segal also emphasized the importance of lean development and rapid iteration, advising Summers and her listeners to focus on a clear benefit, use free tools to test ideas, and target the small group of passionate early adopters who will ultimately champion the product.

“One of the most important things I learned from the pitch feedback and our interview was how to maintain interest in my app and clarity about its purpose,” said Summers. “Mr. Segal emphasized the importance of pitching my idea in a way that resonates with short consumer attention spans, while not downplaying my idea, and it has given me much to think about!”

Upcoming speakers include the co-founder and COO of Hotel Tonight, Jared Simon, and the CTO of URBN, Dave Hayne.