Learning From Failure: 3 $100M+ Operators & Their Darkest Moments
OPERATORS · with Matt Bertulli, Mike Beckham, Curtis Matsko · September 16, 2026 · 63 min
Summary
This episode features three $100M+ ecommerce CEOs who candidly share their "darkest moments," including near payroll failure and sudden loss of critical funding. It offers invaluable lessons on navigating severe business crises, transforming potential failures into profound learning experiences. Operators will gain insights into resilience, adaptive leadership, and developing a growth mindset essential for long-term success in ecommerce.
Key takeaways
Prepare for black swan events by building robust financial models and maintaining diverse funding relationships, as demonstrated by the impact of the SVB collapse on credit lines.
Cultivate a growth mindset to view setbacks not as endpoints but as opportunities for significant personal and professional evolution, leading to more resilient leadership.
Proactively manage cash flow and financial health to avoid critical situations like being unable to make payroll, emphasizing realistic projections and contingency planning.
Develop self-awareness regarding personal hubris and decision-making biases that can contribute to business vulnerabilities, learning to lead with greater humility and foresight.
Focus on crisis management strategies, including maintaining team morale and making sound decisions under extreme pressure, to navigate unforeseen challenges effectively.
“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. Powered By Saras Analytics https://bit.ly/4a3gzVv Postscript https://9ops.co/postscript Aftersell https://9ops.co/4i3bb5 Richpanel https://9ops.co/richpanel Fulfil https://9ops.co/fulfil Northbeam https://www.northbeam.io/ Black Friday Resources https://www.9operators.com/black-friday Operators Portal https://portal.9operators.com/dashboard Operators Newsletter https://9operators.com/
What does this episode say about founder & leadership?
Prepare for black swan events by building robust financial models and maintaining diverse funding relationships, as demonstrated by the impact of the SVB collapse on credit lines.
What does this episode say about finance & fundraising?
Cultivate a growth mindset to view setbacks not as endpoints but as opportunities for significant personal and professional evolution, leading to more resilient leadership.
What does this episode say about dtc strategy?
Proactively manage cash flow and financial health to avoid critical situations like being unable to make payroll, emphasizing realistic projections and contingency planning.
What does this episode say about founder & leadership?
Develop self-awareness regarding personal hubris and decision-making biases that can contribute to business vulnerabilities, learning to lead with greater humility and foresight.
What does this episode say about founder & leadership?
Focus on crisis management strategies, including maintaining team morale and making sound decisions under extreme pressure, to navigate unforeseen challenges effectively.
