The Real Reason Leaders Struggle To Build Billion Dollar Brands | Curtis Matsko

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In this deep-dive conversation, Jordan West welcomes Curtis Matsko, founder and CEO of Portland Leather Goods, to unpack exactly what it takes to build—and lead—a billion-dollar brand in 2025. 

From humble beginnings in a single-stall garage to scaling a global operation with hundreds of thousands of square feet of manufacturing, Curtis shares the raw decisions, leadership principles, and mindset shifts that have fueled exponential growth.

Timestamps:

• 00:07 – Intro: “How do you build a billion-dollar brand in 2025?”
• 01:44 – The march from $1 M to $100 M, and why most entrepreneurs stumble before this line in the sand.
• 03:30 – Curtis’s top five hair-trigger decisions—what happened when playing it safe would have killed the business.
• 10:30 – The moment Jordan realized he needed to “level up” personally and professionally.
• 17:11 – Why today’s market turmoil is a gift in disguise for anti-fragile leaders.
• 19:23 – Firing as an act of service: how letting people go can be the best thing you do for them—and your company.
• 25:44 – Crafting authentic LinkedIn posts: a peek inside Curtis’s morning ritual.
• 41:04 – Curtis’s path to sobriety and why it shaped every business choice he’s made since.

What You’ll Learn

• The Exponential Playbook
  How Curtis and his team consistently doubled revenue year-over-year—from $1 M to $2 M, then to $4 M, $8 M, and beyond—and why hitting that first $100 M profitable milestone is the real launchpad for a true empire.
• Thinking Two Stages Ahead
  Why surrounding yourself with leaders two levels above you is non-negotiable, and how “the law of the lid” caps your team’s potential to your own.
• Decision-Making Under Pressure
  Five pivotal “50/50” calls Curtis made that could have broken the company—yet, with the right game-plan, became its greatest catalysts.
• Anti-Fragility & Opportunity in Adversity
  Turning a brutal $3 M liability hit and industry-wide headwinds into your greatest competitive advantage.
• Building & Pruning A-Player Teams
  The ruthless kindness of firing someone “for their own good,” and why investing years to find the right leaders pays exponential dividends.
• Sobriety as a Leadership Superpower
  How mastering addiction taught Curtis the art of clear, decisive action—and why life’s toughest battles prepare you for business’s biggest wins.
• Personal Branding for Scale
  Real-world LinkedIn tactics that don’t just generate followers, but open doors to boardrooms, partnerships, and talent pipelines you never dreamed possible.

Guest info:
Linkedin: linkedin.com/in/curtis-matsko

Twitter: twitter.com/CurtisMatsko 

Website: https://www.portlandleathergoods.com/

If you’re ready to break through your own ceiling—whether you’re at $1M, $100M, or beyond—this episode will give you the blueprint to think bigger, move faster, and lead harder than ever before.