E151: Be Obsessed With Results: 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 the Co-Founder and CEO of True Classic for their first-ever joint interview. Together, Ryan Bartlett and Ben Diamond unpack how a professional poker player + Meta executive became one of the most formidable partnerships in ecommerce.

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 philanthropy.

Chapters
00:00:00 The $100M Bootstrap Story
00:04:05 You Don’t Make Sense on Paper
00:10:24 Ben Saw Something Different
00:20:26 One Perfect T-Shirt Obsession
00:29:34 Why Speed Beats Everything
00:37:52 Wild Bets & Risk Tolerance
00:46:07 Fighting Fires Before the Fun
00:54:00 Building a Team That Moves
01:02:55 Ruthlessly Eliminating Products
01:12:47 The Triangle of Business Goals
01:22:00 Philanthropy & Creating Value
01:30:16 Titan 10: Rapid-Fire Questions