Mike Grossman

Mike Grossman has served as CEO of six venture-backed technology companies across three decades in Silicon Valley. His career has been defined not just by strategy and execution, but by navigating the emotional and ethical complexity of leadership in an ecosystem where outcomes are often shaped as much by timing and luck as by effort. In Failure Is an Option, Grossman shares 44 concise, candid reflections on what running a startup really feels like — the loneliness, the weight of difficult decisions, and the uneasy balance between mission, money, and meaning.