How Portland Leather Built a $200M Brand with Curtis Matsko

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Today’s guest is Curtis Matsko, the founder and CEO of Portland Leather Goods—a cult-favorite brand known for vertical integration, creative risk-taking, and profitable direct-to-consumer growth.

While many startups chase trends and funding rounds, Curtis took a different route. He started with a single leather journal, focused relentlessly on craftsmanship, and scaled a business that now approaches $200 million in revenue—with no outside capital and no Amazon listings.

Portland Leather is proof that great businesses aren’t built by hacks or hype, but by clarity of purpose and operational discipline. In this conversation, we dig into the systems behind the growth, the culture Curtis has built, and why staying profitable was never up for debate.

What You’ll Learn:

• How Curtis grew Portland Leather Goods to nearly $200M without outside funding
• The mental models and mindset shifts that helped him scale
• Why vertical integration became a key part of their strategy
• How the team plans, prototypes, and iterates faster than competitors
• Ways Curtis balances operational leverage with lean headcount
• Why a company should build systems, not rely on “heroes” to save the day
• How to know if—and when—you’re ready to sell
• Why staying profitable is the most underrated growth strategy in DTC
• What real customer loyalty looks like—and how to earn it

About Curtis Matsko:

Curtis is the founder and CEO of Portland Leather Goods, a vertically integrated DTC brand based in Oregon. Under his leadership, the company has grown into one of the largest leather bag manufacturers in North America, serving millions of loyal customers while maintaining strong profitability.

A self-described contrarian, Curtis believes in building slowly, intentionally, and with joy. He’s rejected conventional wisdom on fundraising, marketing, and outsourcing—and has created a brand culture that prioritizes innovation, autonomy, and craftsmanship.

When he’s not scaling operations, Curtis is sharing lessons from the journey on LinkedIn and his YouTube channel, encouraging other entrepreneurs to think long-term and build on their own terms.

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