David Levy '99 and Morgan Conrad '99
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.
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.
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. 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.
CLICK HERE TO READ THE COMPLETE ARTICLE ABOUT DAVID AND MORGAN PUBLISHED IN THE SUMMER 2025 MILLBROOK MAGAZINE
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.
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. 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.
CLICK HERE TO READ THE COMPLETE ARTICLE ABOUT DAVID AND MORGAN PUBLISHED IN THE SUMMER 2025 MILLBROOK MAGAZINE
