Execution Monsters: True Classic’s Ryan Bartlett & Ben Diamond

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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.