OPERATORS Execution Monsters: True Classic’s Ryan Bartlett & Ben Diamond
Jan 29, 2026
Ben Diamond, CEO who scaled True Classic profitably, and Ryan Bartlett, co-founder and creative lead who turned a tee into a DTC powerhouse. They trace their unlikely paths, ruthless product focus, cutting SKUs, rapid execution, AI-driven creative, and bold growth moves like international and omnichannel expansion. Expect sharp stories about risks, cash, and generosity fueling a mass-market apparel play.
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Win By Obsessing Over One Product
- True Classic won by obsessing over one narrow product truth: fit, feel, and fair price.
- Deep focus on a single hero product let them out-execute broader competitors quickly.
Focus Deeply On What Customers Care About
- Do one thing people care about and build the whole business around it.
- Stop spreading efforts wide; go deep where customers show demand.
Speed As A Strategic Edge
- Speed is a core competitive advantage at True Classic when paired with direction.
- Moving faster than peers lets you test, learn, and seize momentum before others react.