In 2021, the name Michael Wolff evokes one thing—tabloidy access journalism that is not afraid to burn sources to get a provocative story.

During the last presidency, it was what he specialized in, writing two books on the topic of Donald Trump that were generally based on his closeness to the former president during his early years in the White House.

As a journalist myself, I find Wolff’s ability to get attention (and draw controversy) with this work fascinating, and worth researching. He is particularly good at leveraging the buzz of the internet to drive even more conversation around his work. Which makes sense, because that’s how his career really took off in the ’90s—as one of the earliest book publishers focused on the rise of digital media.

Wolff, a one-time New York Times reporter whose career has straddled journalism and entrepreneurship for decades, started his publishing imprint at the very beginning of the ’90s, but by the end of it, he was ready to burn it all down—a move that somehow raised his profile significantly.

Here’s what happened in-between.

Starting the Internet Book Trend

As I wrote a couple of years ago, I friggin’ love old books dedicated to getting on the internet for the first time, in part because they effectively set digital culture in stone at a time when the internet culture was moving around quickly, like electrons inside of an atom.

A book I wrote about in 2017, Free Stuff from the Internet, was largely useless in the modern day, with just a handful of the many links buried inside of it still functional.

Net Guide, Wolff’s initial entry into this subgenre of digital publishing that he edited and helped write with a number of other authors, is similarly useless. Inclusive of paid online services rather than simply the open internet, most of the services it highlights don’t even exist anymore.

Nonetheless, the guide is important as a historic relic—and it had the backing of some of the internet’s early elite. The foreword was written by John Perry Barlow, the cofounder of the Electronic Frontier Foundation.

The back page was literally a full-page ad for Wired, a magazine that was only a few months old at the time of the book’s release. The front had this quote from Wired founding editor Louis Rossetto: “Net Guide is the TV Guide to Cyberspace!”

(Wolff met Rossetto and his business and life partner, Jane Metcalfe, before they had created the iconic magazine, and likely took some inspiration of his own.)

And given its pedigree—beyond being published by Random House, it was edited by Michael Wolff—it was a little bit slicker than some of the other entries. It looked like it was built for 1994, but it had a nice layer of polish. (Somewhat ironically, it looks a lot like a giant classified section, a concept the internet famously killed.)

It felt like the publishing industry’s first big effort to “get” the internet, complete with a ringer at the helm, but to Wolff’s great credit, he seemed to know what he was doing at first. In his list of acknowledgments for Net Guide, Wolff showed a surprisingly mature, if optimistic, view of what the internet (and internet analogues such as Compuserve, BIX, and America Online) had collectively provided as a resource and communications medium:

Undoubtedly, the greatest resource in creating this book was Cyberspace itself. Hundreds of sysops and system administrators have provided us with guidance and information, and thousands of email correspondents have answered our calls for help and suggestions. Truly, this book is a reflection of the vast bounty of the Net, from the far-flung indexes that we’ve relied on, to the FAQs that we’ve consulted, learned from, and quoted here, to the posts we’ve used as “cybernotes” to show the tone and concerns of the Net, to the photographs and illustrations, which we’ve used as examples of the incredible collection of images that float freely in the great digital scrapbook of Cyberspace.

A lot of people, from a lot of different walks of life, are represented in this book, and Wolff’s team of writers and editors had to talk to a lot of them, but the internet had yet to define the shape of any of the many subcultures that appeared. Memes were new to the digital scene—but the internet had given people interested in topics as diverse as jazz, amateur radio, and dating a place to hang out. (There is a section related to the internet’s quote-unquote red light district, which was pretty busy even in 1994.)

The success of the first book, released just before the World Wide Web went mainstream, quickly created an opportunity for Wolff to build an early internet empire. With the backing of Random House, Wolff turned Net Guide into a full-fledged series, with numerous books dedicated to a variety of niche topics—essentially a For Dummies for the kind of person who was already pretty savvy about pop culture, but perhaps needed a little help when it came to the internet. Alberto Vitale, Random House’s president and CEO, was excited about what he had in his hands.

“This publishing program reflects our strong commitment to this new medium,” Vitale said in a news release from the time. “We believe that the online world may well offer consumer growth rates not seen since the early days of television. What’s more, we believe that by focusing on content, this new computer book category will have tremendous appeal for a mass-market audience.”

Wolff’s company, soon called Wolff New Media, would publish a number of books under the Net Guide banner (including a dedicated book about the internet’s relationship with Star Trek), and later launch a series of internet ventures, most notably Your Personal Net, which had a lucrative three-letter domain name.

But his efforts wouldn’t always win him friends.

Michael Wolff, Junk Message King

Wolff’s efforts to sell guides specifically for the internet put him in an interesting position as a journalist: He was one of the first people to advertise online. And the way he chose to do so might have created one of his first high-profile internet controversies.

In late 1994, Wolff began promoting the book Net Chat through Usenet by sending out a variety of messages to prominent newsgroups, signed with his name, in an effort to fact-check that the listings for each group were correct and get community feedback.

Here’s an example (in screenshot form, with link over this way) of what one such message looked like, from alt.slack, the newsgroup for The Church of the Subgenius:

But as the book was already out at this point, it also had the side effect of promoting the book, which netizens of late 1994 weren’t quite so happy about. To a number of them, it looked like the big publisher guy was trying to get a bunch of attention by junking up a bunch of newsgroups with a bunch of self-promotion. (A certain canned-pork-related term was used to describe these messages.)

This came at a time not long after immigration lawyers Laurence Canter and Martha Siegel decided to annoy Usenet to high heaven with promotional materials. This led to the creation of tools that existed to essentially mass-cancel messages from Usenet users that were deemed particularly abusive.

One Usenet regular, a Finnish person nicknamed Cancelmoose who had created an article-cancelling tool called “cancelbot,” decided Wolff’s efforts to highlight entries from his book fit the bill of what cancelbot was designed to remove. So they cancelled Wolff’s messages. The result effectively prevented Wolff from posting in about 9,000 newsgroups.

In a long comment in response to the mass cancellation, Wolff wrote:

To say the very least, we have been stunned and amazed by the reaction to our posts. In one sense, of course, we accomplished what we set out to do—not first and foremost to sell what we’ve written, but to have people read what we’ve written. In another sense, we are pleased to have been the lightning rod for issues dear to our writing hearts—protecting anyone’s right to write and publish.

Internet culture was still new at the time, so this story got portrayed in interesting ways in the media, often supportive of Wolff’s viewpoint. The Baltimore Sun described the situation as such: “An Internet terrorist is systematically removing every message the New York-based author of well-known Internet books posts in cyberspace.”

In the article, Wolff claimed he was getting cyberbullied by someone spoofing his email address.

“I’m actually getting threatening e-mail from myself,” Wolff told the Sun. “Someone is making it clear they can make my life miserable.”

Whether he was or not, it’s clear that Wolff had struck a nerve with his attempt to organize Usenet culture for purposes of selling books.

A 2005 book on the phenomenon of mass-mailing on the internet noted that, on Usenet at least, Wolff’s reputation took a serious beating as a result of the incident. Commenters were not kind. One of the earliest commenters who called out Wolff was Jay Maynard, who (not kidding) later gained internet fame as the early meme “Tron Guy.”

Responding to Wolff’s claim that he was banned because he was promoting a commercial product, Maynard wrote: “Of course, it couldn’t have been because you posted 150 nearly identical messages to 150 newsgroups, now could it? Perish the thought.”

“Eventually both Wolff and his books faded away,” the book inaccurately stated.

Michael Wolff’s Burn Book

At the height of his Net Guide empire, Wolff adeptly understood that the internet was going to shift with the addition of a less-technical public.

“Online communication used to be about source code and UNIX commands; now it’s about playing games, paying taxes, and forming personal relationships,” he said in a 1994 press release, a statement that is largely still true today. It was the basis of a book empire that led to more than 30 titles, including Net Marketing, a book with the tagline “How Your Business Can Profit from the Online Revolution.”

Wolff could have used that book around the time it was published.

The problem is, he was less adept as a businessman during this era. But, in a way, Wolff needed this period as an internet entrepreneur to gain acceptance as what he is today—an expert at dishy tell-alls.

In fact, the first such tell-all that he wrote was, quite literally, about himself and the company he failed to maintain.

The book, Burn Rate, focuses on his efforts to turn a publishing empire into one focused on the web, along with the fact that this company he had created had expenses that grew significantly faster than its revenues. (Hence the book’s name.)

As Wolff wrote in the preface:

For several years the company hummed along in a contented and profitable manner. Then, in a two-year period beginning in 1994, when the company extended its activities, as well as its definition of media, to the internet, both its revenues and personnel expanded almost twentyfold. Its respectable profits turned to dramatic losses, and it attracted the sudden and persistent attention of bankers, venture capitalists, the press, competitors, and potential acquirers.

Wolff was running the company, but he wasn’t getting paid for it for much of this period, instead deferring payroll. Eventually he left in a blaze of glory—cashing in his chips (reportedly without care for others who hoped to do the same) and letting the company fall apart without him at the helm.

In the process, Wolff met a variety of key figures, including the founders of Wired, the top executives at AOL, and the leaders of companies he hoped would give his company a little more money to burn. And because he’s a journalist first, he took loose notes, then decided after leaving the industry (with no nondisclosure agreements to worry about) to turn the result into a book.

Wolff made clear in the book that the internet’s sheer fascination led more traditional entrepreneurs to do dumb things—such as the magazine publisher that bought the rights to the Net Guide name for their magazine, which Wolff characterized as getting “Something for Nothing.”

“The fact that the Internet is not ownable is an annoyance that few buyers are willing to accept. They know there must be something they can buy,” he wrote.

(I’ll let the book tell the best details.)

It became Wolff’s first bestseller that wasn’t just a list of things you could find on the internet—and it helped establish his modern style, complete with the reputation for sloppy reporting.

Part of the reason Wolff largely got a pass back then? He wasn’t afraid of taking aim at himself. The book painted him in not the most flattering light, and actually became more compelling because of it. One contemporary review from Salon, referring to Wolff as an unreliable narrator, highlights the book’s value as such:

In “Burn Rate” the narrator doesn’t just reveal his own neuroses and personality flaws—he un-self-consciously exhibits all the naiveté, foibles and amoral exhibitionism of Michael Wolff himself. Wolff’s narrative audacity is stunning. He is, by his own account, a man who seems willing to break any promise, sell out his employees and do just about anything else to further his own selfish interests.

When he found himself on the other side of the digital divide, failed company at his back, he had created a book that bolstered his reputation as an important journalist and cultural critic. The failures of the ’90s set him up for more business deals in the 21st century, along with a perch high up in the world of New York journalism, where he sits today.

If Michael Wolff was a comic book character, this would be a pretty impressive origin story—that of the villain who first used his greatest weapon on himself.

Wolff did other things with entrepreneurship, including launching the controversial aggregator Newser, before he went full-in on political books. But nothing he did was quite as novel as those first few years documenting the early shape of the internet.

Perhaps it’s for the best that most of the material is printed—because at least we can look back at it and gain something from it. But just like the political books he wrote a few years ago, the shelf life of those early internet books is naturally limited.