Year 3 / Book 44: The Hard Thing About Hard Things


44) The Hard Thing About Hard Things by Ben Horowitz

This book came to me recommended by the facilitator of the Action Learning Set I’m in for new CEOs (if I can still be counted as new 9 months in). It’s written by Ben Horowitz who I hadn’t heard of, but is clearly pretty well known for his Silicon Valley history. His story of being a founder-CEO at a tech company in the depths of the dot com boom and bust form the framework for this book, which draws on that experience to share lessons for leaders more generally.

It’s fair to say that at times Horowitz is everything you might expect from a tech leader in the venture capital, alpha male alpha brain heartland that is Silicon Valley. For much of the book, there is little room for nuance: the fact that every chapter starts with a hip-hop quite might be about referencing his background but also gives it a certain tone which some will find off-putting. To them, I imagine Horowitz might quote something from the book: “this isn’t fuckin’ chequers, this is motherfuckin’ chess”

[NB – for British readers, this is not a reference to Theresa May’s ill-fated Brexit deal, but draughts; although ‘motherfuckin’ chess’ isn’t a bad description of the complexity of the Brexit negotiations]

However, I warmed to Horowitz as the book went on – particularly the more vulnerable and honest about his own failings he became. And also the learning got stronger and the lessons more useful as the book went on. There are some great sections, particularly on HR, which are amongst the most honest and real I’ve read. I particularly liked the sections on why invest in training, the importance of 1:1s, and how to think more about creating the culture you and colleagues want in your organisation. There’s some good stuff on hiring too: how he recruits a Sales Director who doesn’t fit the Silicon Valley norm is a great example of this.

Most of all, it’s Horowitz’s honesty about how it feels that I liked most. Occasionally he talks in a way about business or investment that seems only applicable to the Silicon Valley bubble, but the way it affects him personally will resonate with many I think. Some sample highlights:

Seeing people fritter away money, waste each other’s time, and do sloppy work can make you feel bad. If you are the CEO, it may well make you sick. And to rub salt into the wound and make matters worse, it’s your fault.

To become elite at giving feedback, you need to elevate yourself beyond a basic technique like the shit sandwich

And so on. So in short, it’s well worth overcoming the occasional brash bit of arrogance or Silicon Valley-specific stuff to get to the nuggets which are particularly about people – which, as Horowitz makes clear, come before product and profit in terms of importance (and in terms of what leads to the other).

Score: 7/10

BUY IT NOW: The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

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