Book Review: The Hard Thing About Hard Things

This is a pretty popular book amongst tech CEOs, and based on my conversations with ‘not that’ person, the book seems to be flying under the radar. It shouldn’t. It’s relevant across all verticals despite its briefer history of time approach through the last 20 years of technology.

**History buffs will like the story-telling, and 20-30 somethings will learn a lot about the olden days of the Internet.

Simply put – this book is a no-brainer (actually takes a fair amount of brains to read and ponder) and a must read for all aspiring CEOs, wannabe CEOs, executives (present or future), and anyone who wants to know how their boss thinks and/or should be thinking.

This pretty much sums up anyone with any kind of ambition to lead people…thus, I could have just said that.

As the title suggests, this is not a ‘rah rah’ 10 steps to building a ‘unicorn company’ (a billion dollar company) type of book…it’s actually antithetical to that. As the quote below suggests, this is the book to equip leaders for when the stuff hits the fan. As you and I both know, stuff hits the fan far more often than we would like to admit with our business model, staff, our market, the product…the list could go on.

“Every time I read a management or self-help book, I find myself saying, “That’s fine, but that wasn’t really the hard thing about the situation.” The hard thing isn’t setting a big, hairy, audacious goal. The hard thing is laying people off when you miss the big goal. The hard thing isn’t hiring great people. The hard thing is when those “great people” develop a sense of entitlement and start demanding unreasonable things. The hard thing isn’t setting up an organizational chart. The hard thing is getting people to communicate within the organization that you just designed. The hard thing isn’t dreaming big. The hard thing is waking up in the middle of the night in a cold sweat when the dream turns into a nightmare.”  Ben Horowitz

This book is not hard to read in the sense of being slow, boring or using abstract concepts. It’s hard in the sense that it will hit you between the eyes, possibly causing you to lose hope while simultaneously finding it, and create a few freak out moments and possibly make you cry.

Ben’s style is bloggy, direct, coffeeshop convo-esque and drops rap lyrics at each chapter’s outset, clearly confusing the stereotypical 50+ white male CEO…but he makes it work and still makes it appeal to that audience.

It’s a top 5 for me. Buy it here on Amazon.

A few bullet points that do not do this book justice:

  • If you want an easy-going professional career, avoid being a CEO like the plague
  • Discusses ‘The Struggle’ – the process every entrepreneur goes through and some advice on how not to punk out and quit…and identifies who does quit and who stays the course
  • Great practical stuff is covered like: firing an executive, demoting a close friend, handling promotions, when to/when not to hire ‘been there done that’/old people
  • ‘Success’ doesn’t equal a big exit or overflowing with cash – it equals building a good place to work
  • The difference between a Peacetime CEO and a Wartime CEO and how very few people can be both
    • Steve Jobs (Apple) was a wartime CEO, not Peacetime CEO
    • Eric Schmidt (Google) is a peacetime CEO, not a wartime CEO
  • Learning to be a good CEO takes years, identifying a CEO priori experience is hard…but sometimes a board/management should take a shot based on the person vs. their resume
  • Creating management debt, i.e. laying off people in a matter that robs them of their dignity, will create a debt that you can never repay for the staff who stay…and other examples that create that debt
  • There are no rules