Seth Berkowitz, the founder of Insomnia Cookies, started his cookie delivery business in college out of frustration with late-night food options. He shares his journey from dorm room cravings to building a $350 million brand. The conversation dives into the challenges of securing investment, navigating academic life while running a business, and expanding into a national chain. Berkowitz discusses the trials of resilience during the 2009 financial crisis and the creative strategies that led to the business's growth and success in a competitive market.
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Quick takeaways
Seth Berkowitz identified a market gap in late-night food delivery during college, inspiring him to create Insomnia Cookies from a simple dorm experiment.
Despite facing numerous challenges, including financial struggles and operational downsizing, Berkowitz's resilience led to a strategic pivot that revitalized the business.
The partnership with Krispy Kreme in 2018 provided Insomnia Cookies with essential resources for growth and increased brand visibility in a competitive market.
Deep dives
Inception of Insomnia Cookies
Seth Berkowitz's journey began in 2001 at the University of Pennsylvania, where he identified a gap in late-night food delivery beyond pizza and Chinese takeout. Inspired by his experiences and his penchant for sweets, Seth experimented with baking cookies in his dorm and distributing flyers to promote his new venture. The initial response was modest, but after an appearance in the school newspaper dramatically increased demand, the orders surged overnight. This marked the beginning of Insomnia Cookies, a brand that would grow from a college experiment into a multi-million dollar enterprise.
Challenges and Resilience
Despite early enthusiasm, Seth faced significant challenges as the business evolved, including financial losses and the departure of his initial business partner. He encountered the harsh realities of entrepreneurship, having to cut his team, stop paying himself, and face the possibility of bankruptcy. Overcoming these hurdles required continuous adaptation and a pivot back to the core concept of delivering high-quality warm cookies. This resilience and willingness to return to basics ultimately led to a turning point, allowing the business to gain traction.
Expansion and Growth
As Insomnia Cookies began to find its footing, Seth recognized the need for growth beyond the University of Pennsylvania. He secured funding primarily from friends and family, which facilitated expanding to other campuses like Syracuse University and the University of Maryland. This expansion was accompanied by establishing operational systems to maintain consistent cookie quality and delivery efficiency. By focusing on this combination of strategic growth and operational excellence, Insomnia Cookies gradually grew its presence in the competitive food market.
Navigating Economic Crisis
The 2008 financial crisis posed another significant challenge, leading to reduced investor confidence and tightening capital availability. During this period, Seth dramatically downsized operations and worked tirelessly on the ground to maintain business continuity. Despite overwhelming odds, he adapted strategies to leverage the recessionary environment, discovering that cookies provided a small indulgence during hard times. This resilience during the downturn allowed Insomnia Cookies to survive and eventually thrive as demand began to grow once again.
Technological Transformation
The introduction of the iPhone and the subsequent rise of app-based ordering transformed Insomnia Cookies' customer engagement and service efficiency. By integrating technology into the ordering process, the company could reach customers more effectively and streamline operations. This transition helped the brand quickly regain lost momentum and reposition itself for future growth. As Insomnia evolved with consumer needs, Seth embraced the digital landscape that ultimately propelled the company into a fast-expanding phase.
Partnership with Krispy Kreme
In 2018, Insomnia Cookies established a significant partnership with Krispy Kreme, which acquired a majority stake in the company. This partnership was vital as it provided the necessary resources and expertise to refine operations and expand brand visibility. Under Krispy Kreme's umbrella, Insomnia Cookies benefited from strategic insights that facilitated steady growth, despite the uncertainties introduced by the COVID-19 pandemic. The collaboration helped solidify Insomnia's position in the market as a go-to late-night dessert provider.
When Seth Berkowitz was in college, he was the cookie guy on campus. He’d grown frustrated that the only food he could get delivered late at night were standards like pizza or Chinese food. He had a sweet tooth, and he craved warm, homemade chocolate chip cookies. So he took matters into his own hands and started making and delivering cookies to students at his school. The operation soon went from a silly side hustle to a real business - and then an all-consuming struggle. But today, after decades of detours, long-shot decisions, and near-bankruptcies, Insomnia Cookies is now a $350 million dollar business.
This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by Andrea Bruce with research help from Katherine Sypher. Our audio engineers were Robert Rodriguez and Maggie Luthar.