Opening Bid Unfiltered Why Insomnia Cookies keeps winning late night
Apr 2, 2026
Seth Berkowitz, founder and CEO who turned a college cookie startup into a multi-hundred location delivery bakery. He discusses late-night delivery as the brand's core. He explains site selection near campuses and pizza clusters. He recounts scaling from beeper days to warm delivery, product development shaped by fans, ownership chapters, and an ambitious plan to reach 1,800 bakeries.
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Focus Relentlessly On The Core Experience
- Stay disciplined and focus on what works: prioritize retail bakeries in late-night locations and fast, warm delivery.
- Seth cut experiments like fro-yo and food trucks to concentrate energy on consistent warm delivery from stores.
Classic Comfort Drives Category Resilience
- The cookie's enduring appeal comes from nostalgia and hominess combined with late-night energy, creating a unique emotional product fit.
- The chocolate chunk cookie is the dominant SKU, proving classics outperform novelty in this category.
Krispy Kreme Sale Sharpened Strategic Focus
- Seth sold Insomnia to Krispy Kreme and found the partnership emotionally gratifying and strategically enabling.
- Krispy Kreme helped sharpen Insomnia's focus on warm delivery and positioning during the relationship.