ASOM Pod

EP69: From Monastery Life to The Steve Jobs of Leather: Curtis Matsko of Portland Leather Goods

5 snips
Oct 16, 2025
Curtis Matsko, Founder and CEO of Portland Leather Goods, shares his compelling journey from a Zen monastery to a thriving leather business. He discusses the importance of continuous reinvention, self-funding, and overcoming personal struggles with sobriety. Curtis emphasizes the value of belief over capital and the need to let go of past successes to innovate. He reveals how owning production has allowed for rapid iterations and scaling, and why staying authentic online fosters meaningful connections. His insights inspire anyone looking to transform their entrepreneurial path.
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ADVICE

Kill Your Way To The Next Scale

  • Kill 90% of what scaled you to the current milestone to reach the next level.
  • Keep only the top 10% of practices and reinvent the business to pursue bigger goals.
ANECDOTE

Zen Winter That Changed Decision-Making

  • Curtis spent a winter living with Buddhist monks practicing noble silence and long meditation sessions.
  • That experience gave him clarity that he still uses daily in decision-making.
ANECDOTE

From Dot‑Com Loss To Sobriety And Rebuild

  • Curtis built an early internet company, sold it, then lost roughly $28M in the dot-com crash and opened a bar afterward.
  • He later stopped drinking (sobriety from June 6, 2012) and used steady rebuilding to grow his company year-over-year.
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