AI Summary
5 min readSeth Berkowitz built Insomnia Cookies from a dorm-room delivery operation into a national chain approaching 400 company-owned bakeries. On this episode of the Advice Line, he fields calls from three founders wrestling with growth, marketing, and brand positioning. But the deeper conversation turns on a philosophy he returns to again and again: you have to earn the right to grow.
The case against franchising
Insomnia Cookies owns and operates nearly all of its 300-plus bakeries, with only four licensing arrangements for airports and stadiums. That is a deliberate choice, not an accident of history. Berkowitz acknowledges that franchising could get the company to its goal of 1,800 locations much faster. But he argues that the business is uniquely hard to franchise: it operates late nights, is highly seasonal, and runs on multiple channels (delivery, walk-in, catering). More importantly, he believes that owning the stores gives Insomnia something franchising would erode: the ability to innovate fast. "Having the ability to think of something new, bring it into the store, test it and deploy it, and then roll it out without a crazy amount of complexity or pushback is pretty special," he says. That speed, he argues, is how the brand stays relevant nearly 25 years in.
Earning growth by watching the consumer
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What you'll learn
- 1 (01:57) **Seth Berkowitz Introduces Himself & Insomnia Cookies' Strategy** - Seth, founder of Insomnia Cookies, joins Guy Raz to discuss the company's current state and guiding philosophy.
- 2 (06:55) **The Lifecycle of the Insomnia Customer** - Seth describes how the brand follows its customers from college through adulthood.
- 3 (08:08) **Caller 1: Kaindo Matene – Luxury Special Occasion Fashion** - Kaindo, founder of the brand Kaindo, describes her pivot from a broad fashion line to focusing on special occasion wear rooted in her Congolese heritage.
- 4 (11:57) **Seth's Advice to Kaindo: Narrow Focus & Activate Locally** - Seth advises Kaindo to avoid broad digital ads and instead double down on her proven products and in-person community.
- 5 (16:52) **Guy Connects the Thread: Simplicity Wins** - Guy and Seth discuss the universal lesson of focusing on a simple, core product.
- 6 (20:12) **Caller 2: Tara Gilman – Sauna Societe** - Tara, founder of Sauna Societe, introduces her premium sauna hat company and the challenge of building a brand around a new ritual.
- 7 (25:54) **Seth's Advice to Tara: In-Person Education is Key** - Seth advises Tara to lean into the power of live demonstrations and B2B partnerships rather than broad digital ads.
+ Full timestamped outline available in the app
Show Notes
Today’s callers: Kohindo from New York is looking to reboot her African-rooted fashion brand after losing a few key retailers. Then Tara from San Diego considers avenues to educate consumers about the benefits of her wool sauna hats. And Carol from Houston wonders whether to market her collegiate purses and accessories l to students or their gift-giving family members.
Plus, Seth lays out his ambitions to quadruple Insomnia’s locations and become a global chain — without turning to franchising.
Thank you to the founders of Kohindo, Sauna Societé, and Desden for being a part of our show.
Be sure to listen to Insomnia Cookies’ founding story as told by Seth on the show in 2024.
This episode was produced by Casey Herman with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Annlie Huang.
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