Michael Wolff’s Internet Book Empire

The Trump administration tell-all scribe has a history with digital publishing that goes way back. In fact, he edited one of the first guides to the internet.

By Ernie Smith

Today in Tedium: When journalist Michael Wolff releases a new book, as he’s planning to do next week with his second Trump tell-all, it becomes an event—one driven by days of leaks as details of that new book find their way into the press. (He claimed, among other things, that Robert Mueller prepared an indictment of President Trump, then shelved it—a claim Mueller’s camp quickly denied.) As a journalist myself, I find Wolff’s ability to get attention (and draw controversy) for whatever he does fascinating, and worth researching. He is particularly good at leveraging the buzz of the internet to drive even more conversation around his work, whether that work is a column, a website, or a tabloidy tell-all book along the lines of what Kitty Kelley does. Wolff gets publishing, and he gets the internet, because he’s had ample experience with both. Today’s Tedium talks about the time he brought those two things together. For the first time. — Ernie @ Tedium

Today’s GIF features a shot of Wolff parsed through the lens of ASCII art and ANSI art. Today’s issue, by the way, is sponsored by Lemonade. More from them in a second.


The year Michael Wolff first launched his publishing imprint, Michael Wolff & Company. Wolff, a scribe who first wrote for The New York Times way back in 1974, has frequently straddled the line between entrepreneur and writer throughout his career, with his first book released in 1979.

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I bought Amazon’s last copy of Net Guide. (Ernie Smith)

How Michael Wolff helped kick off 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 a atom.

The 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.)

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An example of the style of an interior spread in Net Guide. A web directory done up like a classified section? How quaint!

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 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.”

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YPN.com, as it appeared in late 1996.

Wolff’s company, soon called Wolff New Media, would publish a number of books under the Net Guide banner (including a 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.

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The last time I talked about this topic, it led to the email not hitting reader inboxes, so I’m not going to mention it by name. (Mike Mozart/Flickr)

Why Michael Wolff couldn’t post on Usenet at the beginning of 1995

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:

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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, but as this is an email newsletter, I’m trying to write around it.)

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 “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.

“Online communication used to be about source code and UNIX commands; now it’s about playing games, paying taxes, and forming personal relationships.”

Wolff, explaining the lifestyle-driven approach behind the Net Guide series of books—which was perfectly timed, because he released the first one just as the internet was becoming about more than the internet itself. The book series, which at one point represented more than 30 titles, expanded to things far beyond the original mission of the book series, 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.

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Burn Rate, Wolff’s bestseller about failing at being a technology entrepreneur.

Michael Wolff’s first tell-all book was about his own failed digital publishing empire

It’s weird to consider that the Michael Wolff of 1994, the guy who created a series of hit internet books and ticked off most of Usenet, is the same dude who has become the face of modern-day “access” journalism, taking advantage of whatever sources he can get a hold of to write stories that not even Bob Woodward, the Watergate icon who has spent the last 30 years writing books about the innards of presidential administrations, has been able to pull off. Wolff is more willing to spill tea and look like a fool in the process.

But, in a way, Wolff needed this period as an internet entrepreneur to enter this new phase of his career where he can write insider-y tell-all books about powerful political figures, all while bending rules along the way.

In fact, the first such book that he wrote with this approach in mind was, quite literally, about himself. The success of Wolff’s internet guidebooks created an opportunity for Wolff to further himself in digital media, and he kept trying to grow his empire from there—despite business acumen not necessarily proving his strong point.

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 the style he’s using now on books about Trump, to the point where he got criticized for sloppy journalism back then, an issue he’s running into now.

Part of the reason Wolff largely got a pass back then? He wasn’t afraid at 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 naiveti, 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.

Do I consider myself a Michael Wolff fan? Not really, though I certainly appreciate what he represents as a journalistic figure.

I love the fact that he spearheaded such a great series of books with Net Guide (and probably got me on a few sites I wouldn’t have considered), but there are other things he’s done in his career that I’m less psyched about.

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Newser, as it looks like today. Its design has barely changed in the past decade.

Let me talk about one in particular. Around the same time that I launched a news aggregator, so did he—a still-active site called Newser that created controversy for itself by aggregating so loosely, barely even bothering to link to the original sources, that it helped lower the reputation of aggregation in general.

Wolff defended his firm’s practices as being in line with traditional newspaper rewrites. But not everyone was convinced. At one point, fellow journalist-turned-entrepreneur Sharon Waxman, founder of The Wrap, called out Wolff’s approach in a very public way:

In our 14 months of our operation, Newser.com, with an audience of about 3 million unique viewers per month, has sent us precisely 1,600 users. But it has plenty of Wrap content.

It’s arguable that Waxman and Wolff, if not for this controversy, could have been allies—their careers share many parallels. But instead, the controversy blew up enough (thanks in no small part to Wolff going on the defensive and suggesting Waxman was trying to drum up headlines for herself) that the two found themselves debating about it on CNN. (The headline of Wolff’s rip of Waxman? “Sound and Fury: Here’s What Sharon Waxman Really Wants.“ Perhaps he was unknowingly test-marketing the title for Fire and Fury?)

Just as he made no apologies for abandoning his botched company in the ’90s, Wolff was famously unapologetic about what Newser represented, at one point writing, “We aren’t stealing from the Times and other big news brands, we’re making their stuff better—or at least different. We’re doing what journalism is supposed to do best: Giving the customer what he wants.”

While Newser’s influence in the media world has waned (though The Wrap, now a reliable part of the Hollywood media establishment, is significantly more popular now than it was in 2010), it can be argued that Wolff’s work in journalism of late very much does that. The fact that he’s a controversy-courting figure underlines, really, why he’s so particularly good at the thing that he’s doing now.

In a way, whether you love or hate these books and the fact that Wolff is writing them, it’s arguable that the reason he’s so good at this is because he’s been straddling the line between journalist and entrepreneur for three decades now.

And he’s been working the internet circuit for nearly as long. Even though he’s writing books, he’s really building internet culture—just as he was in 1994.


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Ernie Smith

Your time was just wasted by Ernie Smith

Ernie Smith is the editor of Tedium, and an active internet snarker. Between his many internet side projects, he finds time to hang out with his wife Cat, who's funnier than he is.

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