Issue No. 22Week ending Sunday, May 31, 2026725 episodes · 3,189 write-ups
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The Most Intense Workplace Culture in America | The Journey from $0 to $2.6BN Valuation

With Harry Stebbings, Nico · Sunday, May 31, 2026

Harry Stebbings interviews Nico, the co-founder and CEO of Corgi, a $2.5 billion valued insurance company, about his extreme workplace culture. Nico discusses his philosophy on winning, 7-day work weeks, living in the office, and a unique hiring approach focused on commitment. The conversation also delves into Corgi's unconventional strategies like the 24/7 Corgi Cafe, fundraising tactics, and Nico's perspectives on the future of AI, sales, and the venture capital landscape.

Key takeaways

  • No Weekends for 'Winning': Nico explicitly states, "If your days off happen to be Saturday and Sunday every week, then you will not have a place at Corgi." This isn't a suggestion; it's a foundational hiring principle at a multi-billion dollar company. Read more →
  • Corgi CEO Nico champions losses as "beautiful" because they represent the fixed cost for achieving "asymmetric upside" in business. Read more →
  • Nico, the co-founder and CEO of Corgi, a $2.5 billion insurance company, follows a counter-intuitive fundraising rule from Brian Chesky: "never take the highest price." Corgi consistently opts for the second or third highest offer. Read more →

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