What Insomnia Cookies’ Founder Learned After Selling to Krispy Kreme

Seth Berkowitz’s late-night cookie empire proves growth and loneliness often rise together.

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When Seth Berkowitz began baking cookies in his dorm at the University of Pennsylvania, few imagined his midnight snack idea would become a multi-million-dollar enterprise. Two decades later, his company—Insomnia Cookies—has become synonymous with warm, late-night desserts delivered to college campuses across America.

Yet success brought an unexpected side effect. In a recent Fortune interview with Seth Berkowitz, the founder reflected, “It can be lonely. It’s a solitary life.” His comments highlight an under-examined truth about entrepreneurship: growth magnifies both opportunity and isolation.

From dorm ovens to corporate boardrooms

The original business model was simple: warm cookies delivered until 3 a.m. to hungry students. In interviews like How I Built This with Guy Raz, Berkowitz recalls bootstrapping operations and taking orders by phone before apps existed. By 2003, he’d opened the first physical store, leveraging the idea of “warmth on demand.”

Over the next decade, Insomnia Cookies expanded rapidly across major college towns. As of 2025, the chain has over 350 stores, with plans to reach 1,800 locations worldwide, according to Baking Business.

The company’s valuation surged when Krispy Kreme acquired a controlling stake, estimating Insomnia’s worth at $350 million. In 2025, the doughnut giant sold its remaining 34 percent share for $75 million, confirming that the niche late-night dessert concept had become a global brand.

The invisible cost of success

The entrepreneurial story we like to tell—innovation, acquisition, celebration—often skips the inner cost. Berkowitz, still leading the company he founded, describes the “weight of being responsible for everyone’s dream.”

He’s not alone. Research from the Harvard Business Review shows that half of CEOs report feelings of loneliness, and 61% of those say it negatively affects their performance.

Entrepreneurial loneliness isn’t simply about working late—it’s about bearing disproportionate emotional load. When Berkowitz notes that success can feel solitary, he echoes the late Tony Hsieh’s observation that “entrepreneurship is about being comfortable being misunderstood for long periods.”

The tension intensifies post-acquisition. As reported by The Philadelphia Inquirer, once Krispy Kreme took over, Berkowitz had to reconcile the founder mindset—fast, experimental, intuitive—with corporate structure and investor expectations.

Balancing ambition with burnout

To his credit, Berkowitz tried structural fixes. He introduced a four-day corporate workweek, an experiment in sustaining productivity while reducing exhaustion—profiled in Wharton Business Daily.

The program wasn’t just a perk; it was a philosophical stance: burnout can erode creativity faster than competition can.

A Stanford study found that output per hour declines sharply after 50 hours of weekly work—evidence that even the most passionate founders can hit diminishing returns. Berkowitz’s acknowledgment that “you can’t sprint forever” reflects a maturing awareness in entrepreneurial culture.

Loneliness by the numbers

• 72% of entrepreneurs report mental health concerns, according to a UC Berkeley study.

• 49% of founders experience at least one form of burnout during high-growth phases.

• Entrepreneurs are 2.8× more likely to experience depression than the general population.

These data frame Berkowitz’s words not as confession, but as community service. By normalizing vulnerability, he invites founders to reframe “solitude” as a condition to manage—not a weakness to hide.

Lessons for emerging founders

1. Redefine success beyond valuation — Money validates execution, not fulfillment.

2. Prioritize mentorship and community — Join peer networks like Entrepreneur’s Organization or alumni founder circles.

3. Embrace downtime as strategy — Creative insight often arrives when the system resets.

4. Structure emotional check-ins — Treat mental health like quarterly audits.

When Insomnia Cookies expanded internationally, Berkowitz learned that “scale changes everything”—including how founders perceive themselves. His latest interviews reflect not fatigue but perspective: a realization that success without connection can feel strangely hollow.

Closing reflection

Entrepreneurship is both a creative act and a psychological endurance test. Seth Berkowitz’s story shows that even multimillion-dollar exits cannot insulate founders from the quiet battles of identity, fatigue, and isolation.

His message is clear: building a company is easier than building the inner stability to sustain it. True leadership demands both.

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