Inside Seth Berkowitz's Entrepreneurial Journey with His Cookie Company, Now Worth $200 Million

In the tumultuous journey of entrepreneurship, there are inevitable moments when obstacles seem insurmountable and dreams appear to slip away. It is during these critical junctures that the true test of resilience emerges, separating those who are truly passionate about their dreams from those who are not. A similar narrative unfolded for Seth Berkowitz, the CEO, and co-founder of Insomnia Cookies, who drew inspiration from his wife to keep pushing forward.

Founded in 2003 by Jared Barnett and Berkowitz during their time at the University of Pennsylvania in Philadelphia, Insomnia Cookies emerged in response to the demand for late-night bakery delights.

Specializing in warm cookies, baked goods, and ice cream, the United States-based chain ensures that no one misses out on the indulgence of their sought-after treats. With over 260 locations worldwide, the company has garnered widespread acclaim.

In 2023, Insomnia Cookies boasted a remarkable revenue of $200 million, according to CNBC. Its trajectory reached new heights following Krispy Kreme's stake acquisition in 2018, which propelled its valuation to hundreds of millions of dollars. However, like many businesses, Insomnia Cookies also encountered financial challenges along the way.

Amid numerous unsuccessful attempts to generate revenue, Berkowitz faced the difficult decision of downsizing his team. Reflecting on the challenges, he recalls, "2009 and 2010 were some of the hardest years ever at Insomnia Cookies." He emphasizes the necessity of downsizing to reduce costs, resulting in the corporate team being reduced to only himself and a finance associate.

During these trying times, Berkowitz recounts his arduous experiences, stating, "I’m literally peddling cookies throughout the country at like 2 o’clock in the morning. I'm lugging dough to Syracuse, New York, every week and down to Philly and fixing generators."

Feeling overwhelmed by the relentless demands of his solitary endeavors, he contemplated giving up during one of his solo trips. It was then that he reached out to his wife, Rebecca, seeking guidance. Rebecca's words of encouragement and unwavering belief in Berkowitz and his venture served as a turning point.

She reminded him, "You believe in this. You’ve always believed in this. People love what you sell, and I believe in you. Just go make it happen." Berkowitz acknowledges the impact of her support, stating, "I’ll tell you, for that one moment, I wasn’t sure [about Insomnia]. She kind of flipped me over back to a believer."

Driven by determination, Berkowitz devoted countless sleepless nights to refining a revenue model that would propel his business forward. Despite experimenting with various setups, nothing proved as effective as storefronts with fast delivery options.

He reflects, "By 2012, Insomnia was able to fund the opening of a new location with its internal cash flow for the first time, finally making the company self-sufficient." This marked the beginning of an extraordinary journey.

The company's success continued to soar when Krispy Kreme increased its stake to 74.5%, acquiring approximately $139.5 million. Berkowitz, reflecting on this monumental achievement, recalls, "None of it would’ve happened if he’d given up during Insomnia’s toughest days. When I talk about the brand and our journey, [I often say] that Insomnia Cookies is a perseverance story."