The Hard Thing About Hard Things is one of the best books I’ve read recently and one of those books whose subject matter is unlikely to interest most of you, but the execution is so good that you ought to read it anyway. The best books transcend their subject; this is probably the best passage in an already great book:

Most business relationships either become too tense to tolerate or not tense enough to be productive after a while. Either people challenge each other to the point where they don’t like each other or they become complacent about each other’s feedback and no longer benefit from the relationship.

Implicitly, you could strike the adjective “business” and replace it with a lot of others… or perhaps strike it altogether and still achieve a similar effect. I’ve often felt exactly what Horowitz is describing but never conceptualized it that way. Over and over again, I found myself marking passages and putting checkmarks next to them. In most books, that practice falls off a third of the way through; in this one, I kept going to the very end.

Many sections just demonstrate that Horowitz gets things. Like:

“What would you do if capital were free?” is a dangerous question to ask an entrepreneur. It’s kind of like asking a fat person, “What would you do if ice cream had the exact same nutritional value as broccoli?” The thinking this question leads to can be extremely dangerous.

Wishful thinking can block useful thinking. Which most of us don’t think, or don’t think consciously.

He’s thinking about antifragility before Nassim Taleb wrote the eponymous book:

The close call was a sign to me that the entire operation was far too fragile. I got another sign when our largest competitor, Exodus, filed for bankruptcy on September 26. It was a truly incredible bankruptcy in that the company had been valued at $50 billion a little more than a year earlier. It was also remarkable because Exodus had raised $800 million on a “fully funded plan” just nine months earlier. An Exodus executive later joked to me: “When we drove off a cliff, we left no skid marks.” It Exodus could lose $50 billion in market capitalization and $800 million in cash that fast, I needed a backup plan.

I’m surprised there aren’t more novels set among venture capitalists or startups. The drama is all there. Maybe most writers don’t realize it, but Horowitz is good at stakes and drama. His stories are too often to quote in full, but they’re full of narrative drama and tension in a way most books aren’t. And some character descriptions are as good as anything in fiction:

Wow. I had no idea who I was dealing with until that point. Understanding how differently Frank viewed the world than the people at Opsware helped clarify my thoughts. Frank expected to get screwed by us. It’s what always happened to him in his job and presumably in his personal life. We needed something dramatic to break his psychology. We needed to be associated with the airport bar, not with his job or his family.

Horowitz had an epiphany and he acted on it. Hard Things could be seen as a series of epiphanies, and we get to follow him through.

We’re often told to attend to data, likely because most people don’t, but once you attend to data, “Sometimes only the founder has the courage to ignore the data.” Like Peter Thiel, Horowitz argues that your life is not a lottery ticket and that markets are often wrong (or at least that insiders can see things that the outsiders who create market values cannot):

If I’d learned anything it was that conventional wisdom had nothing to do with the truth and the efficient markets hypothesis was deceptive. How else could one explain Opsware trading at half of the cash we had in the bank when we had a $20 million a year contract and fifty of the smartest engineers in the world? No, markets weren’t “efficient” at finding the truth; they were just very efficient at converging on a conclusion—often the wrong conclusion.

Almost anyone trying to do anything useful should be thinking about what good ideas are not being pursued: “Wall Street does not believe Opsware is a good idea, but I do.”

“The wrong conclusion:” if markets can converge on “the wrong conclusion,” so can individuals and societies. Some of Hard Things can be read as a critique of American society: “My single biggest personal improvement as CEO occurred on the day when I stopped being too positive.” American society is regularly considered to be positive, but in a way that isn’t necessarily founded on skill or improvement. The “self-esteem” movement is part of this trend, even though moving towards self-efficacy would be an improvement. In class, when I started teaching I was often too positive. Now I’m less positive and more likely to emphasize that growth often comes from pain and struggle. The deadlift doesn’t get higher without some pain, and the best lifters learn to love the pain. Same with intellectual, psychological, or emotional growth. Yet we have a society that shies away from those truths.

I’ve heard about Hard Things many times but this recommendation tipped me into reading it, and I hope my recommendation tips you. The best books can be read many ways and applied to many situations, and this is one of the best. I didn’t expect it to be, which makes it all the more delightful.