You can say that business has been pretty sweet for Seth Berkowitz, founder and CEO of Insomnia Cookies. The late-night bakery phenomenon grew from a college experiment to having over 350 locations across the U.S., Canada, and the U.K. , including new spots in the arenas of the Philadelphia Flyers, New York Knicks, and Cleveland Cavaliers.

Twenty-three years into building this warm cookie empire, Seth has mastered the art of scaling while keeping original Insomniacs happy. The company hasn’t changed its philosophy and mission of delivering fresh-baked cookies — it’s just bringing them to a lot more hungry, and ultimately happy, people. He joined us on How Success Happens to share what it really takes to turn a simple craving into a globally recognized brand.

You can listen to the episode here or watch it above and read on for Seth’s insights to help you take a bite of success in three, two, one…

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Three Key Insights

1. Start Fast, But Test Everything First

Seth’s approach to growth is deceptively simple: experiment quickly, measure clearly, and only scale what works. “I’ve always been a believer in growing fast when you understand the opportunity in front of you, not just to grow for growth’s sake,” he explained. Early on, Insomnia tried vending trucks—opened one, then two, then ten. “Actually, those didn’t work, so we had to stop and pivot.” His philosophy? “I believe in trial and real experimentation, but like clear measurement of the testing and learnings. And when you feel like you have the correct data and you’re confident in the approach, then go really, really fast.”

Takeaway: Run small, controlled experiments before you commit big resources.

2. Let Your Customer Guide You, Not Your Assumptions

The origin of Insomnia Cookies came from Seth’s own frustration as a junior at Penn answering the door for the third pizza delivery of the night. “I think I slammed the pizza box on the table and yelled, ‘I want something different!'” he recalls. But here’s the key: Seth didn’t just build what he wanted and hope it worked. “From there, I just rolled up my sleeves and started baking cookies and the customer guided me from that point forward.” He constantly talks to “Insomniacs” (his customers), holds Tasting Tuesdays at flagship bakeries, and stays obsessed with their view of the business. “Make sure that our understanding of expectations are their understanding of expectations and that we’re exceeding them.”

Takeaway: Your customers will tell you what they want—if you actually listen and stay close to them.

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3. Build Connection Through Emotional Moments

Insomnia Cookies isn’t just about dessert—it’s about creating an emotional connection. Seth talks about the “emotional texture” of eating a warm cookie at 2 a.m. as an adult, something that felt both comforting and exciting. Those emotions power everything they do, from their National Cookie Day treasure hunt (100 people lined up at every store to bite into cookies, hunting for a purple buttercream) to their Valentine’s Day focus. “A warm cookie connects people,” Seth said. And like the products, they want to keep their marketing fresh. “We’re always looking to create something that’s new and unexpected and a reason to believe and enjoy the brand.”

Takeaway: Products create transactions, but emotions — and fun — create brand loyalty.

Two Great Ways to Learn More

1. Follow Seth and Insomnia Cookies at InsomniacCookies.com and on Instagram and TikTok.
2. Read this great guide to finding out what customers really want rather than guessing.

One Question to Ponder

Seth kept Insomnia Cookies alive through the 2008 financial crisis, massive competition, and COVID shutdowns by staying close to his customers and testing relentlessly.

Here’s our question for you: What’s one experiment you’ve been putting off in your business because you’re afraid of failure—and what would happen if you tested it on a small scale this week?

Send your answer to howsuccesshappens@entrepreneur.com. We’ll read the best responses on a future episode!

About How Success Happens

Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.

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