In this episode, I chat with Jordan Calderon, a 26‑year‑old serial founder with two company exits under his belt. He shares how a rebellious streak led him from college side hustles to hiring more than 100 people, why a daily 20‑minute shower doubles as his self‑improvement lab, and how treating AI as a creative partner keeps his marketing agency sharp. Jordan also reveals the networking power of his boutique wine label and reflects on entrepreneurship’s soaring wins and painful cash‑flow crunches, the mix that keeps him hooked on building.