Issue No. 43Week ending Sunday, October 25, 2026645 episodes · 2842 articles
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Advice Line with Seth Berkowitz of Insomnia Cookies

With Guy Raz, Seth Berkowitz, Kahindo Mateene, Tara Gillman, Carol Deshon · Sunday, October 25, 2026

Guy Raz and Insomnia Cookies founder Seth Berkowitz advise three business owners facing critical growth inflection points, covering inventory rationalization, overcoming product education barriers, and marketing when purchasers differ from end users. Berkowitz also details Insomnia Cookies' strategy to reach 1,800 company-owned locations without turning to franchising, emphasizing the principle of earning growth through local customer love.

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Key takeaways

  • Seth Berkowitz built Insomnia Cookies toward a target of 1,800 company-owned locations by rejecting franchising and waiting for proven demand before signing leases. Read more →
  • Tara Gillman founded Sauna Société to sell wool sauna hats rooted in Finnish and Russian banya traditions, but struggled with an online customer education barrier. Read more →
  • Kahindo Mateene watched annual revenue crash from $268,000 in 2023 to $50,000 after wholesale cancellations from accounts like Anthropologie, Nuuly, and Shopbop. Read more →

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