Execution Monsters: True Classic’s Ryan Bartlett & Ben Diamond
OPERATORS
· with Ryan Bartlett & Ben Diamond
· January 29, 2026
· 106 min
Summary
True Classic's founders reveal how they built a $300M apparel brand by obsessing over product-market fit, speed, and customer value. This episode is a masterclass in challenging conventional wisdom, making bold strategic moves, and fostering a culture of relentless execution for ecommerce operators aiming for rapid, profitable growth.
Key takeaways
Ruthlessly cut underperforming products: True Classic cut 80% of their product catalog to focus on their core, most profitable offerings, demonstrating the power of product rationalization.
Embrace speed over perfection: Prioritize rapid iteration and execution over lengthy development cycles to gain a competitive advantage and quickly respond to market changes.
Turn crises into opportunities: Tariffs, initially a threat, forced True Classic to optimize their supply chain and operations, leading to their most profitable quarter. Ecommerce brands should view external pressures as catalysts for innovation.
Challenge marketing conventions: Recognize that expensive brand activations can be overrated; focus instead on direct response marketing and understanding true customer acquisition costs.
Foundational partnerships matter: The complementary skills of a former poker player (risk assessment, strategic thinking) and a Meta executive (digital marketing expertise) created a formidable partnership, highlighting the importance of diverse skill sets in founding teams.
Brought to you by Applovin. Get access to the Operators channel expansion playbook, online masterclass, and up to $5k in ad credits. https://www.9operators.com/applovin What does it take to build a ~$300M apparel brand from scratch? Matt Bertulli and Mike Beckham sit down with Ryan Bartlett, Co-Founder, and Ben Diamond, CEO of True Classic, for their first-ever joint interview. Together, they unpack how a professional poker player and a Meta executive became one of the most formidable partnerships in DTC + built a men’s and women’s wear empire on the back of white t-shirts. From the early days of consulting on Facebook ads to their obsessive focus on fit, speed, and customer value, Ryan and Ben reveal why they cut 80% of their product catalog, how tariffs forced their most profitable quarter ever, and what it really means to “seek the truth” instead of being right. Plus, they get into AI-generated creative, why big brand activations are overrated, and the surprising power of giving away $100 poker chips to Uber drivers.
Ruthlessly cut underperforming products: True Classic cut 80% of their product catalog to focus on their core, most profitable offerings, demonstrating the power of product rationalization.
What does this episode say about d2c growth strategies?
Embrace speed over perfection: Prioritize rapid iteration and execution over lengthy development cycles to gain a competitive advantage and quickly respond to market changes.
What does this episode say about product-market fit?
Turn crises into opportunities: Tariffs, initially a threat, forced True Classic to optimize their supply chain and operations, leading to their most profitable quarter. Ecommerce brands should view external pressures as catalysts for innovation.
What does this episode say about supply chain optimization?
Challenge marketing conventions: Recognize that expensive brand activations can be overrated; focus instead on direct response marketing and understanding true customer acquisition costs.
What does this episode say about brand building?
Foundational partnerships matter: The complementary skills of a former poker player (risk assessment, strategic thinking) and a Meta executive (digital marketing expertise) created a formidable partnership, highlighting the importance of diverse skill sets in founding teams.
