INNOVATING ON THE EDGE: How Two Millbrook Alums Turned Friendship into a Force for Big Ideas

From Case Hall to startup ventures, David Levy ’99 and Morgan Conrad ’99 have always had a spark for mischief and creative collaborations. Their story isn’t just about the bonds formed at Millbrook—it’s about how out-of-the-box thinking can evolve into a bold new model for fundraising and entertainment.

“We’ve been friends since 1996,” Morgan recalls, and that camaraderie has formed the foundation of every project they’ve launched since. Whether pranking emails to announce an unplanned free day or launching a tech startup rooted in social psychology, these two alums are redefining what it means to create with purpose. Back in their Millbrook days, David and Morgan were yin and yang. David was “an actor, and not very athletic,” while Morgan “did the sports.” But what bound them together were shared moments in the dorm that on some occasions evolved into innovation disguised as pranksterism. David fondly recounts one of his legendary “email pranks,” where he impersonated Headmaster Drew Casertano and, along with close friend Marko Guzijan ’99, declared a surprise free day via email blast—then a rather young technology. “It was the most amazing night of luck in my life at Millbrook,” said David, “and I honestly believe that Mr. Casertano let the whole thing go just to help us.”

Post-Millbrook, Morgan attended Denison University and began his professional career as a financial analyst at John A. Levin & Co. and then CIBC World Markets. After a three-year run at Atlantic Street Capital, he founded Morgan Investment Company, which he continues to run today. David graduated with a bachelor’s degree from Ithaca college and jumped immediately into writing and filmmaking, producing a dozen indie movies, including the 2012 psychological thriller Would You Rather, which Morgan co-produced. While Would You Rather was picked up by IFC and still generates buzz around Halloween as a classic thriller, the film industry’s unstable revenue model prompted a pivot for David. “I was sick of not making money,” he explains.

That frustration, combined with his fascination for what people are willing to do for money—“the concept behind Would You Rather”—sparked the genesis of their latest venture: Cajole. When David pitched the idea to Morgan, based on meme-fueled celebrity fundraisers during the SAG strike, it wasn’t long before the duo was back in business together.

Cajole is both platform and spectacle—a fusion of GoFundMe, Kickstarter, and reality TV stunts. Users propose cash-backed challenges for others, sometimes celebrities, to perform odd or meaningful tasks for charity or entertainment. “We had Morena Baccarin pour a bucket of nacho cheese over her head,” David says, “and one of the Trailer Park Boys got buried alive for us.” These viral stunts aren’t just gimmicks; they test the boundaries of social capital, group dynamics, and the art of persuasion—hence the name Cajole. “What are people willing to do for money?” David asks. “That’s the concept.”

Still in its early stages, Cajole officially launched online in August 2024 and continues to grow. Their grassroots tactics are complemented by strategic budgeting, influencer outreach, and an ambassador program designed to build a self-sustaining user base. “I’ve never felt such pressure about being fiduciarily responsible for other people’s money,” David admits. “But I just want to make sure I’m constantly doing what I need to do for this company to grow.” Morgan’s business acumen balances David’s creative drive, and their shared vision keeps things steady as they navigate the startup landscape.

Reflecting on their journey, Morgan and David agree that their 30-year friendship and diverse skill sets have uniquely positioned them for this ride. “We each spent the last 30 years figuring out different skills,” David says. “And hopefully these skills will come together and form the ultimate Decepticon that will make our lives much better.” With roots in camaraderie, nurtured by the freedom and encouragement of their Millbrook years, their story is proof that sometimes, the best ideas start with a prank—and end with a platform that just might change how the world gives.