Failure Is an Option

Mike Grossman, 2026

Learn what running a startup actually demands, from firing people you hired too fast to knowing when effort cannot beat bad timing, and how leaders stay steady anyway.

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8 parts, about 14 minutes to read.

Why read it

Shows startup leadership as it feels from the inside, where hard work and good teams still fail because of timing and luck
Offers practical habits for steadying yourself, focusing on inputs you control, and handling layoffs, bad news and boards honestly
Mike Grossman tells short true stories from the six companies he led, admitting costly mistakes instead of polishing a success story

Who it is for

First time founders and startup chief executives
Managers facing layoffs, pivots or cash crunches
Early startup employees wondering what the boss is weighing

What the summary covers

Failure Is an Option1 min
Effort Meets What You Cannot Control2 min
The Emotional Discipline of the Job1 min
Money, People, and Principles2 min
Adaptation Without Drift2 min
Leading Through Other People2 min
Truth, Power, and Sustainable Speed2 min
Regret, Responsibility, and Endurance2 min

Recommended by

Jeffrey SonnenfeldLester Crown Professor of Management Practice at Yale
Grossman constructively challenges the fantasy of an endless success spiral.
Kewsong LeeFounder and CEO, BellTower Partners; former CEO, The Carlyle Group
If you’re looking for a realistic portrayal of the entrepreneurial journey, this is it.

About the author

Mike GrossmanSilicon Valley technology CEO who led six venture funded software companies
- Has spent more than 30 years in Silicon Valley as an executive and entrepreneur; CEO of six VC funded software companies, all ultimately acquired
- Held leadership positions at Intuit and Johnson & Johnson and board roles including Quicken and Borders
- Began as a management consultant at McKinsey in San Francisco and Sydney
- AB in Economics and a JD from Harvard University
- Failure Is an Option is his first book, and he says likely his last

Read it alongside

Goes deeperYour Turn
Mike Grossman says no other priority mattered once a company ran out of cash, and he found only six weeks left at SugarSync. Bas Bergmans explains why profit alone does not protect it: profit is not cash and cash lags, so leaders must change the operating decisions behind it, treating first what can kill the company first.