Ben Diamond (True Classic) - Scaling to $1B, Surviving Tariffs, and the Costco Playbook
On this episode, True Classic CEO Ben Diamond joins us to unpack:
- Why landing a plane on Catalina Island can feel like flying off a cliff, thanks to a runway optical illusion most pilots never see coming
- Ben's 3-part hiring filter (wisdom, intelligence, attitude) and the interview questions he uses to find out if someone actually has grit
- Why 2025 was the hardest year of Ben's career...and the most rewarding one
- What a Foreign Trade Zone is and how it nearly fixed True Classic's cash flow problem overnight
- Why True Classic built its customer relationship online first, years before it ever touched retail or wholesale
- How Ben splits inventory across the website, Amazon, Costco, and True Classic's own stores without one channel cannibalizing another
- The customer story Ben tells at every single All Hands, and what a father-son trip to Costco taught him about the limits of digital ads
- Why Ben calls "work-life balance" a myth and time-boxes his day instead, from 5am starts to protected hours with his daughters
- Why Ben says AI already makes him a 1,000x CEO, COO, and CMO, and why he thinks even that's underhyped
- Why Ben doesn't care about the CEO title, and the Elon Musk comparison behind what he's actually chasing
