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Learning From Failure: 3 $100M+ Operators & Their Darkest Moments

September 16, 2026 · 1 h 4 min

Show notes

“We were not going to make payroll next week.”

How did three ecommerce CEOs turn rock bottom into their biggest lesson?

Matt Bertulli (CEO, Pela Case & Lomi), Mike Beckham (CEO, Simple Modern), and Curtis Matsko (CEO, Portland Leather Goods) each share the darkest moment of their ecommerce careers. What came after built the self-awareness that changed how they lead.

Curtis walks through the week Wells Fargo pulled a $20M line of credit after Silicon Valley Bank collapsed. Matt breaks down the hubris that nearly cost him payroll one Christmas. Mike shares the night a two-year venture fell apart. Their comebacks outweighed the crises, driven by a growth mindset none of them had before.

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