Insomnia Cookies CEO Sells to Krispy Kreme, Warns Entrepreneurs It’s a Lonely Path

Seth Berkowitz, founder and CEO of Insomnia Cookies, recently made headlines after selling his cookie empire to Krispy Kreme—and he hasn’t shied away from sharing what he’s learned along the way. His message to new entrepreneurs is blunt: success can be isolating, and the ride is more solitary than glamourous. 

The Deal & The Growth

• Insomnia Cookies was co‑founded by Berkowitz while he was a student at the University of Pennsylvania. Over time, the late‑night cookie delivery brand gained traction across college towns.  
• In 2018, Krispy Kreme acquired a majority stake in Insomnia, helping the brand scale infrastructure, marketing, and reach.  
• More recently, Berkowitz and Insomnia bought out Krispy Kreme’s remaining stake for around $75 million, enabling full control by Insomnia’s ownership group.  

The Warning: “It Can Be Lonely, It’s a Solitary Life”

Despite the success and millions made, Berkowitz warns aspiring business owners that entrepreneurship is emotionally and mentally demanding:

• He says that leadership often comes with isolation—at critical moments, entrepreneurs can feel alone with decisions, pressures, and burdens.  
• Success doesn’t always bring relief from stress; with growth comes accountability, gravity, and constant scrutiny. The brighter the spotlight, the heavier the load.  
• Berkowitz emphasizes that many people see the outward glamour—big deals, brand growth, wealth—but trouble doesn’t wait at the door. You must be prepared for conflict, fatigue, and the cost of ambition.  

Lessons for Entrepreneurs

1. Don’t mistake attention for understanding
   Fame or visibility doesn’t mean others grasp your challenges. Guard your mental space and build trusted support.
2. Plan for burnout and isolation
   Build a team, take breaks, get mentors, and establish boundaries. Loneliness should not be a surprise.
3. Maintain control where possible
   As Berkowitz did, reacquiring ownership or maintaining equity gives you more freedom to steer the brand long term.
4. Value integrity and culture
   Success without substance or ethics often backfires. Treat your team, customers, and legacy with care.
5. Be honest in public storytelling
   When you’re credited only with wins, people forget the losses. Speak truthfully about failures and friction—that builds trust.