From $150 College Dorm to $350M Cookie Empire

Seth Berkowitz’s Insomnia Cookies journey began with frustration. As a Penn junior tired of late-night pizza deliveries, he grabbed a flour sack and started baking fresh cookies instead. What started in a college dorm with just $150 has evolved into a globally recognized brand operating over 350 locations across the U.S., Canada, and the U.K.—generating $350 million in annual sales.

Strategic Growth Through Experimentation

Berkowitz’s growth philosophy prioritizes controlled testing over reckless expansion. “I believe in trial and real experimentation with clear measurement of the testing and learnings,” he explained. Early ventures like vending trucks proved unsuccessful, prompting quick pivots rather than sunk-cost persistence. The founder demonstrates a disciplined approach: experiment quickly, measure results, and scale only proven concepts aggressively.

Customer-Centric Innovation

The brand’s success hinges on staying intimately connected to customers—affectionately called “Insomniacs.” Rather than assuming what people want, Berkowitz lets market feedback guide business decisions. He hosts regular Tasting Tuesdays at flagship bakeries and maintains constant dialogue with customers, ensuring expectations align with delivery. This customer-first mentality has proven invaluable through obstacles including the 2008 financial crisis, intense competition, and COVID-19 shutdowns.

Insomnia Cookies transcends transactional dessert sales by building emotional connections. The warm cookie experience at 2 a.m. resonates deeply with customers, transforming a simple snack into a memorable moment. With recent expansions into sports arenas for the Philadelphia Flyers, New York Knicks, and Cleveland Cavaliers, Berkowitz continues demonstrating that sustainable growth comes from understanding customers first and scaling second.