In this compelling conversation, Tidemark Capital founder Dave Yuan shares his journey from Bain consultant to building one of the most thoughtful voices in vertical SaaS investing. Yuan reveals his "control point" philosophy—identifying the mission-critical systems that small businesses would turn off last before going bankrupt—and explains how this approach has guided Tidemark's investments in category leaders like ServiceTitan, Toast, and OneStream. His insights into workflow gravity, data gravity, and account gravity provide a masterclass in understanding what creates defensible market positions in software. The discussion takes a provocative turn as Yuan explores AI's dual nature as both opportunity and existential threat for established software companies. He introduces the concept of "integrate surround"—how AI point solutions can gradually subsume control points by becoming the system of action rather than just record—and shares his framework for "fast waters" versus "slow waters" in AI adoption. With characteristic humility and intellectual curiosity, Yuan offers practical advice for navigating today's volatile market while building the Vertical SaaS Knowledge Project community that has become an industry touchstone for founders and investors alike.