Harvey CEO Winston Weinberg: Why You Should Reinvent Yourself Every 4 Months

This might be my favorite episode yet. Harvey’s Winston Weinberg is the canonical 2026 hypergrowth CEO. He takes us inside what it's really like to scale from zero to $190M run rate in just a few years. What stands out? His obsessive intensity and willingness to do uncomfortable things on a weekly basis. Winston shares how he cold-messaged thousands of lawyers to land his first customers, why he deliberately chose the hardest enterprise law firms as his first target customers, and how he thinks about hiring and org structure when everything breaks every four months. We also explore his unconventional background - he wasn't a developer, was new to the legal industry, and figured out sales from scratch. It's raw, honest, and incredibly practical for any founder navigating (or hoping to navigate) the chaos of hypergrowth.