E291: Ajay G — Betting on Yourself and Trusting the Process

Ajay G is one of the most unique voices in New England comedy—a Boston-based stand-up comic, award-winning storyteller, startup mentor, and tech entrepreneur originally from Mumbai, India. Known for his clean, sharp storytelling style, Ajay has performed on PBS, ABC, NPR, and stages across the U.S., Canada, Singapore, Indonesia, and India. He’s also a multiple-time Moth performer, comedy festival favorite, and somehow balances life as both a comic and a serious business mind. Ajay talks with Rick about Indian culture, the challenges of assimilating to life in America, and how a colonoscopy may have accidentally launched his stand-up career. Ajay also shares his unconventional path from dropping out of Harvard University to launching his own social networking platform, which has amassed nearly five million users. Along the way, he tells wild stories about entrepreneurship, reinvention, and betting on yourself.