Book release June 9

Sometimes we can create our own luck. But often things just happen.

The buzz

  • "'Failure Is an Option' strips away the mythology of Silicon Valley and replaces it with something far more valuable: truth."

    —Brad Smith
    President, Marshall University; former Chairman and CEO, Intuit

  • "An entertaining and authentic collection of highly engaging anecdotes, hard-won life lessons and unbelievable stories …"

    —Kelly Bayer Rosmarin
    CEO and Group Managing Director, Australian Unity; former CEO, Optus

  • "The format is great and the storytelling is terrific. "

    —Carlos Rodriguez
    Former CEO and Executive Chair, ADP

  • "If you’re looking for a realistic portrayal of the entrepreneurial journey, this is it."

    —Kewsong Lee
    Founder and CEO, BellTower Partners; former CEO, The Carlyle Group

  • "It’s candid, insightful, and quietly reassuring for anyone who’s in the arena and looking around to see if they're doing it correctly."

    —Greg Sands
    Founder and Managing Partner, Costanoa Ventures

  • "Grossman constructively challenges the fantasy of an endless success spiral."

    —Jeffrey Sonnenfeld
    Lester Crown Professor of Management Practice at Yale; founder of the Yale Chief Executive Leadership Institute; author of FIRING BACK (Harvard) a study of leadership resilience.

  • "'Failure Is an Option' is a refreshing and deeply human look at the courage it takes to lead with heart."

    —Amy Errett
    Founder and CEO, Madison Reed; former General Partner, Maveron Ventures

  • "It’s a candid account of missed calls, hard trade-offs, and good and bad luck that come with building something new."

    —Christiana Smith Shi
    Founder, Lovejoy Advisors; former President of Direct-to-Consumer, Nike; former Senior Partner, McKinsey & Company

Book & author details

  • Short stories
    Failure Is An Option combines 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.

    Insider’s view
    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.

  • Mike Grossman is a six-time Silicon Valley CEO with nearly thirty years leading early-stage, venture-funded technology companies. Earlier in his career he worked at McKinsey & Company, Johnson & Johnson, and Intuit. His writing blends sharp humor, humility, and hard-earned perspective on startup life. This is his first—and, he insists, likely his last—book.

  • Publisher: Ideapress Publishing
    Publication date: June 9, 2026
    Language: English
    Length: 201 pages
    ISBN-13: 978-1646872466

44
Stories

44 Stories

It’s About the Money.

It’s About the People.

A Fool and Their Money Are Soon Parted.

Hail a Taxi.

Less Is More.

It’s About the Money. It’s About the People. A Fool and Their Money Are Soon Parted. Hail a Taxi. Less Is More.

A Little Knowledge Is a Dangerous Thing.

Hero Ball.

Beggars Must Be Choosers.

Mirror, Mirror on the Wall.

Hey Kool-Aid!

A Little Knowledge Is a Dangerous Thing. Hero Ball. Beggars Must Be Choosers. Mirror, Mirror on the Wall. Hey Kool-Aid!

The Real Silicon Valley.

Timing Is Everything.

Feeling Lucky?

What, Me Worry?

Keeping It Together.

The Real Silicon Valley. Timing Is Everything. Feeling Lucky? What, Me Worry? Keeping It Together.

Wait, who wrote this?

Mike Grossman has spent more than 30 years in Silicon Valley as an executive and entrepreneur. He has been CEO of a diverse array of innovative, VC-funded software companies (Inflection, LiveCapital, Tempo, Attributor, SugarSync, and Zetta), all of which were ultimately acquired.

His experience also includes leadership positions at Intuit and Johnson & Johnson and board roles at a variety of companies, including Quicken and Borders. Mike started his career as a management consultant for McKinsey & Company in San Francisco and Sydney.

In addition, Mike holds an AB in Economics and a JD from Harvard University. He is passionate about his family, his cats (four at present), international travel, science fiction films, tennis, basketball, and creative writing (when time permits). This is his first book.

 “Refreshingly honest. Also mildly traumatizing.”

— A VC, probably : )

 “Finally, someone admits that failure happens”

— Every founder who's ever pivoted

 “I laughed. I cried. Mostly I felt seen.”

— You, after reading this

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