Failure Is An Option: Reflections of a Silicon Valley CEO

A raw, clear-eyed portrait of what it’s really like to run a startup in Silicon Valley, told by someone who has lived it again and again.

For nearly three decades, Mike Grossman has been at the center of the world’s most mythologized innovation hub, leading early-stage, venture-funded tech companies through the highs, heartbreaks, and near misses that define life in the Valley. He has raised millions, managed boardroom crises, built great teams, and navigated moments when everything seemed one bad quarter away from collapse.

Failure Is An Option gathers forty-four sharp, candid essays shaped by years in the trenches. Together, they form a mosaic of what leadership really looks like when the cameras aren’t rolling: the moments of absurdity, fear, luck, and endurance that make or break a company and the person leading it.

Unflinchingly honest and darkly funny, Grossman dismantles the myths of startup success and offers an insider’s view of what it means to build under pressure. This is not a playbook or a victory lap. It is a collection of truths about ambition, uncertainty, and the art of holding it together long enough for the story to make sense.

For founders, investors, and anyone who has ever wondered what Silicon Valley is really like, Failure Is An Option offers an antidote to the glossy founder myth and a reminder that authenticity, humility, and a sense of humor are what keep you in the game.

MIKE GROSSMAN is a six-time Silicon Valley CEO who has spent nearly thirty years leading early-stage, venture-funded technology companies. Over his career, he has raised capital from twelve venture firms, three public corporations, and dozens of angel investors, navigating everything from $400 million acquisitions to fire-sale endings. Before becoming a serial entrepreneur, Mike worked at McKinsey & Company, Johnson & Johnson, and Intuit. His writing blends sharp humor, humility, and hard-earned perspective on what it truly takes to survive in the startup world. Silicon Valley CEO is his first—and, he insists, likely his last—book.