Last week I finished reading the Fucked Companies book. It’s interesting to see a website put into book format, and I admit that I questioned how a site that thrives off of its timeliness would translate. The joy of fuckedcompany.com is that you see which companies are about to crash before it happens. The book, by contrast, is simply a recap of failures, which can at times feel like beating a dead horse: “Wasn’t that idea stupid?” Philip J. Kaplan (aka “Pud”) sneers, and while, yes, many of the ideas of the millenial internet boom were stupid, his sneering loses some of its bite when he’s talking about history instead of current events.

The book is written with Kaplan’s signature style, which is so recognizably webby that I was almost looking for the underlined hyperlinks in the text. He likes ellipses…and likes to say “ya know?” a lot. At times, I was surprised to see the text even capitalized. Regardless of his writing style, his snarkiness has no trouble translating from web to book: he’s just as sarcastic and biting as he is online, and it’s just as funny.

He’s divided the content of the book into 16 chapters with titles like “Give It Away Now,” “If It Ain’t Broke, Fix it,” and “Ahead Of Their Time? Or Just Stupid?,” each addressing common shortcomings of failed dot-coms. Each company gets a mini-essay discussing what it tried to do, and why it was such a flop. The essays are bite-sized, so you don’t have to sit and read the book front to back. Despite Kaplan’s humor, the essays are sobering in their own way: even if you know that dot-coms burned through an obscene amount of money in a remarkably short time, it’s still stunning to see just how many had $40 million dollars in 1999 and were bankrupt by early 2001.

All other things aside, it’s clear that Kaplan knows what he’s talking about. His knowledge and background in the internet industry (dude has his own “e-commerce solutions firm,” PK Interactive) gives him a strong pedestal from which to aim his snarking from: he understands how to make websites succeed, and has done so with both his business and his hobby. This gives him much more clout on the subject than, say, and economics professor would carry. The book, despite the snitty tone, actually packs a huge punch when it comes to assessing the why and when of dozens of company’s failures. Kaplan seems, almost despite himself, quite smart.

In closing, I’d like us all to muse on this photo of Philip Kaplan and John Halcyon Styn, in which the leader of the web cynics and the ambassador of online optimism meet and greet. As Geoff Kloske, Kaplan’s editor, said, “God, I bet they made beautiful music together.”