#36 From scaling Carta to $300M ARR to showing you how the rich stay tax-free and build generational wealth. | Alessandro Chesser

Episode notes

Episode 36: From scaling Carta to $300M ARR to showing you how the rich stay tax-free and build generational wealth. Alessandro Chesser helped build Carta from zero to $300M+ ARR as their first sales hire—before walking away to start Dynasty, they make billionaire-level wealth tools accessible to everyone. In this episode, we dig into the playbook behind Carta’s early sales engine, the contrarian pivot to B2C, the growth loops powering Dynasty, and why Alessandro believes most Americans are getting screwed by the current wealth system. If you’re a founder or GTM operator, this one’s packed with battle-tested lessons, failures, and play-by-play stories. Key Discussion Points: What's the secret to selling a product that doesn't exist yet?