EP#288 Failure Is an Option: Six-Time Silicon Valley CEO Mike Grossman

Six-time Silicon Valley CEO Mike Grossman joins host and producer Dr. Tom Dutta on The Quiet Warrior Show, ranked #2 on Feedspot's Top 30 Canada CEO Podcasts, for a conversation about what running a company in Silicon Valley actually feels like when the cameras are not rolling. Mike has led six venture-funded technology companies over thirty years, and all six were acquired: the largest for $400 million, the smallest in a $250,000 fire sale. He is the author of Failure Is an Option: Reflections of a Silicon Valley CEO (Ideapress, June 2026), forty-four candid, self-contained stories about luck, timing, loneliness, and the truth the glossy founder myth leaves out. In this episode: Why effort and talent do not guarantee success, and where luck and timing really rule The counteroffer he still calls his deepest professional regret, twenty-five years later The hardest layoff of his life, and what it taught him about carrying responsibility for people and their families Why he focuses on inputs over outcomes, and how that steadies a leader in a crisis What thirty years in the Valley taught him about loneliness, honesty, and holding it together Learn more about Mike and the book: failureisanoption.com Listen on Apple Podcasts, Spotify, iHeartRadio, Amazon Music, YouTube Music, Pandora, Audible, Pocket Casts, Castbox, Overcast, and wherever you listen to podcasts.