Behind the Book: Sins of the Internet

This is the second nonfiction book in this series, and it has the longest history of anything I have written. It did not start as a book. It started around the year 2000, when my wife was alive, as a series of hand-coded HTML pages, a couple of dozen of them, put up one at a time. This was before WordPress, before the content systems everyone uses now. Just individual pages I wrote and posted because I had things to say about where the internet was going.

Over the years that collection grew into a series, and eventually I turned the series into a book. A blog-to-book project, except it predates blogs as most people think of them. The roots go back to raw HTML at the turn of the millennium, and the book that grew out of them is much deeper than the pages ever were.

What does twenty-five years of writing about the internet give you?

A vantage point you cannot fake. I was not reacting to social media last year. I started writing about the internet’s problems around 2000 and kept writing as the thing itself got worse, which means the book watched the whole arc happen in real time. I saw the promises made at the beginning, wrote about the problems as they emerged, and documented the descent the entire way down.

That matters because the book is not a snapshot of the current moment. It is a record kept across the entire life of the modern internet by someone who was paying attention from before the platforms that now dominate it existed. When I write about how far we have fallen, it is because I was there for the height, when this thing was going to democratize information and connect humanity, and I have been taking notes ever since.

Why the seven deadly sins?

Because I needed a way to organize two dozen separate pieces, and the sins gave me one. That is all it is. I want to be honest about that, because a frame like this can look like a grand claim, as if I am arguing the internet is literally sinful in some theological sense. I am not. The deadly sins are a filing system. They happen to carry moral weight, which suits the subject, but I was not building an argument out of medieval theology. I had a pile of material about the ways the internet damages people, and I needed a spine to hang it on, and wrath, greed, envy, pride, and the rest made a spine that everyone already understands.

The confessional framing that runs through the book, the idea of cataloging our digital sins and confessing our complicity, is a container, not a claim. The real substance is the specific harms, and the twenty-five years of watching them develop, not the scaffolding they hang on.

Is the anger in this book real, or a chosen register?

This is where it differs from my last nonfiction. In Ridiculous Things People Actually Believe, the anger was performed, a register I called humorous anger, a mode I chose for the material. The anger in this book is real.

It is real because I love the internet. I see it as a wonderful thing, something people can genuinely use to make their lives better. That is my starting position, and it is the opposite of cynicism. The anger is what happens when I watch that wonderful thing get deliberately turned into a machine for taking advantage of people, for scamming them, for using them. It is the anger of someone who loves what a tool could be and is furious at the people who chose to corrupt it. None of the damage was inevitable. Every bit of it was a decision somebody made, and knowing that is what makes it infuriating.

Do you write from above this, or inside it?

Inside it. I have been scammed, and I am not going to pretend otherwise.

Years ago I fell for Donald Lapre. If you do not remember him, he was a late-night infomercial pitchman who sold get-rich-on-the-internet schemes through the 1990s and 2000s, all high energy and rags-to-riches promises. What he was selling, in one of his pitches, was websites that advertised his vitamins. You bought a website and then hoped somebody would show up to buy from it. He was eventually indicted on dozens of counts of fraud and money laundering, accused of defrauding hundreds of thousands of people out of tens of millions of dollars, and he died in an Arizona jail cell awaiting trial. My wife and I bought into his build-a-website scheme, and it was a complete failure, because the whole thing was hollow. There was an envelope-stuffing scheme before that, which cost us about a hundred dollars, disappointing but a cheaper lesson.

So I know the experience of the target from the inside. I was one of the people these operators aim at, and that is part of what fuels the book. It is easy to write about digital exploitation as a thing that happens to other, more gullible people. I cannot do that, because it happened to me.

Why does that personal history matter to the book?

Because I was there before the internet had any defenses at all. I came up online before HTTPS, when security was virtually unknown, when there was almost nothing standing between an ordinary user and the people trying to exploit them. The web was wide open, and most of the people using it had no idea how exposed they were.

Over time I became more and more knowledgeable, not so much about hacking as about the malicious people trying to make money off everyone else, the scammers and con operators working in a space with almost no protections. I learned the mechanics of the exploitation by watching it operate, and sometimes by being on the receiving end of it. That is the perspective the book is written from: someone who was present in the defenseless early days, got burned personally, learned how the machinery works, and spent a quarter century documenting it as it scaled up from lone con artists into trillion-dollar platforms running the same plays at global scale.

What is the book asking of the reader?

To see the harm clearly and to understand that it was built, not grown. The chapters catalog the damage: the rage machine, the comparison trap, the attention economy, the manufactured outrage, the way children are treated as the intended targets. But the argument underneath all of it is that none of this was an accident. Every platform was designed by people making conscious choices about how to capture and direct human attention, and different choices would have produced different outcomes.

Which means different choices can still produce better ones. The last chapters turn toward that, individual habits, digital virtue, and the systemic fixes that individual willpower cannot deliver on its own. I am angry in this book, but I am not hopeless, because a thing that was built by choices can be rebuilt by choices. The point of cataloging the sins is not despair. It is to see the machine clearly enough to start changing it.

How does it fit with the rest of your work?

It is the companion to Ridiculous Things People Actually Believe, and the pair shows how I use emotional register in nonfiction. That book was mockery in a chosen comic key. This one is genuine anger from genuine love of the medium and a real history of being on the receiving end of its cons. Same instinct behind both, control of the emotional register as the core craft, but a different register for a different subject, chosen deliberately in one case and felt honestly in the other.

And like the internet it describes, the book grew by accumulation over a very long time, one piece at a time across twenty-five years, until the pattern in all those separate pieces became a single argument about what we have done to the most powerful tool we ever built.

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