I Helped Create the Milo Trolling Playbook. You Should Stop Playing Right Into It.

The old playbook stopped working...until Milo Yiannopoulos came along and a new generation picked it up again.

A Breitbart editor and conservative activist, Milo Yiannopolous drew hundreds of supporters and protestors to the UCCS campus where he spoke Thursday. He is known for rhetoric against feminists, and he was kicked off twitter for encouraging online bullying against Saturday Night Live star Leslie Jones.

Sign Up For Our Daily Newsletter

By clicking submit, you agree to our <a rel="nofollow noreferer" href="http://observermedia.com/terms">terms of service</a> and acknowledge we may use your information to send you emails, product samples, and promotions on this website and other properties. You can opt out anytime.

See all of our newsletters

In 2009, I helped sketch out a marketing campaign for an internet personality and blogger named Tucker Max. With a very limited advertising budget available for the independent movie he had written and produced, we had few options for getting the word out.

Maybe it was crazy but my thinking was that one of the best ways to get young men to go see a movie was to tell them they should not be allowed to see it. What ensued was several months of chaos and controversy that ultimately drove Tucker’s book to No. 1 on the New York Times Bestseller list, sold out a multi-college bus tour and ultimately sold millions of dollars worth of tickets, dvds and books.

It was a masterful bit of trolling that admittedly felt a lot more meaningful and exciting when I was younger than it does to me today: We encouraged protests at colleges by sending outraged emails to various activist groups and clubs on campuses where the movie was being screened. We sent fake tips to Gawker, which dutifully ate them up. We created a boycott group on Facebook that acquired thousands of members. We made deliberately offensive ads and ran them on websites where they would be written about by controversy-loving reporters. After I began vandalizing some of our own billboards in Los Angeles, the trend spread across the country, with parties of feminists roving the streets of New York to deface them (with the Village Voice in tow).

But my favorite was the campaign in Chicago—the only major city where we could afford transit advertising. After placing a series of offensive ads on buses and the metro, from my office I alternated between calling in angry complaints to the Chicago CTA and sending angry emails to city officials with reporters cc’d, until ‘under pressure,’ they announced that they would be banning our advertisements and returning our money. Then we put out a press release denouncing this cowardly decision.

I’ve never seen so much publicity. It was madness.

If any of this sounds familiar, it should. Because it’s basically the exact playbook that right wing blogger Milo Yiannopoulos is running on his own cross-country trolling tour. By almost any metric but political correctness, it’s been masterfully successful—his book has since been to #1 on Amazon twice, and the protests at UC Berkeley last week generated national headlines and were addressed directly by the President.

The déjà vu is not accidental. Numerous leaders of the alt-right movement read the book I published in 2012, which outlined exactly how this media strategy works. Several have told me Trust Me, I’m Lying is their bible.

It’s a sad irony for me, since I wrote the book as an explicit warning about how broken our media system was and why it needed to be fixed. As I would say in interviews, the strategies that I used were designed to market books and clothes for companies like American Apparel, but I was exposing how they worked because I worried how others might soon use them to sell something more nefarious.

I should be clear about a few things: I’m not advising Milo or the alt-right in any capacity. Though I have spoken (as well as interviewed several for this column) to several of them, I disagree with their message and their aims. I don’t think we should build a wall along the border, I have no problem with an all-female cast of Ghostbusters, I don’t think we should ban Muslims from this country and I think the first few weeks of Trump’s presidency are only a sign of the malevolence and incompetence to come.

This puts me in a somewhat unique position in which I am deeply disturbed by our current political situation but I am not so blinded by my outrage that I don’t see exactly what these media manipulators are doing. My conversations with these figures—including occasional friendly chats with Milo—brings me to this column: You guys are playing completely into their hands.

Most brands and personalities try to appeal to a wide swath of the population. Niche players and polarizing personalities are only ever going to be interesting to a small subgroup. While this might seem like a disadvantage, it’s actually a huge opportunity: Because it allows them to leverage the dismissals, anger, mockery, and contempt of the population at large as proof of their credibility. Someone like Milo or Mike Cernovich doesn’t care that you hate them—they like it. It’s proof to their followers that they are doing something subversive and meaningful. It gives their followers something to talk about. It imbues the whole movement with a sense of urgency and action—it creates purpose and meaning.

You’re worried about “normalizing” their behavior when in fact, that’s the one thing they don’t want to happen. The key tactic of alternative or provocative figures is to leverage the size and platform of their “not-audience” (i.e. their haters in the mainstream) to attract attention and build an actual audience. Let’s say 9 out of 10 people who hear something Milo says will find it repulsive and juvenile. Because of that response rate, it’s going to be hard for someone like Milo to market himself through traditional channels. His potential audience is too spread out, and doesn’t have that much in common. He can’t advertise, he can’t find them one by one. It’s just not going to scale.

But let’s say he can acquire massive amounts of negative publicity by pissing off people in the media? Well now all of a sudden someone is absorbing the cost of this inefficient form of marketing for him. If a CNN story reaches 100,000 people, that’s 90,000 people all patting themselves on the back for how smart and decent they are. They’re just missing the fact that the 10,000 new people that just heard about Milo for the first time. The same goes for when you angrily share on Facebook some godawful thing one of these people has said. The vast majority of your friends rush to agree, but your younger cousin has a dark switch in his brain go on for the first time.

This is what creates the incentives for trolls to be more and more provocative and to care less and less about what normal, middle of the group people think. With Tucker, we knew that feminists were never, ever going to like his stuff. So we wanted to leverage that anger and outrage as that incredible force that it can be. When we tried to pay to name a Planned Parenthood clinic after him, the point wasn’t to greenwash his name through charitable donations. That never would have worked. The point was that “HOW DARE YOU?!” coverage from sites like Jezebel would naturally reach a number of people who thought the whole thing was funny and absurd. It would reach the people who hate-read Jezebel. It’d also be fuel for Jezebel’s critics.

This approach requires a certain shamelessness but it is effective because it puts the dominant group into the horns of a dilemma: Ignore them and let them do something offensive or object and give them the attention they need to survive and thrive? It’s why for Milo, there is no such thing as bad publicity right now. He’s maneuvered his brand with ruthless, bulletproof perfection.

Milo Yiannopoulos in 2016.
Milo Yiannopoulos in 2016. Drew Angerer/Getty Images

It’s here that I think people are really giving the alt-right exactly what they want. One of the best ways to sow and exploit division is to look for moral hypocrisy. With the Planned Parenthood stunt, we were able to say: “Look, you claim to care about reproductive rights, yet you are turning down $500,000.” (Your smarter fans appreciate the brilliant trolling and your dumber fans really buy the argument). When protesters try to revoke someone’s right to speak or when someone like Richard Spencer is physically assaulted on camera, you’re not intimidating anyone—you’re emboldening them. You’re giving them a wonderful recruiting tool. They’re laughing all the way to the bank.

That’s what’s so misguided about what happened at UC Berkeley. From what I understand, most of the violence was perpetrated by infiltrators who were looking to sow chaos and destruction. Yet many of the peaceful protesters and organizers have admitted that they too were attempting to shut down Milo’s talk. The last thing you ever want to do is give an opponent the moral high ground—and attempts to suppress, intimidate and revoke constitutional rights do exactly that.

There is absolutely nothing that Milo has said (and more importantly, done) that ought to revoke his First Amendment right to give a speech on a college campus. It’s profoundly hypocritical for the same activists who demanded safe spaces against microaggressions to march en masse and aggressively shut down a nerdy, gay conservative immigrant with a funny name (a minority if there ever was one) until he flees under armed guard. As much as you might dislike what he’s saying—and I personally dislike it a lot—I promise, you are not setting a good precedent by preventing him from saying it. Worse, you’re giving him more people to say it to when the ensuing media coverage explodes.

If you actually want to fight back against these trolls, here’s a strategy to consider: Organize all you want, get as many people as you can to show up at their events, but don’t try to shut them down. In fact, the only thing you should try to shut down are the instigators who try to incite violence. Regain the moral high ground by saying that you absolutely respect their right to free speech.

And then, actually listen and talk to them. To me, the most effective retorts against the alt-right were when Trevor Noah had Tomi Lahren on his show and when Elle Reeve profiled Richard Spencer for Vice. Both came off looking mostly like jokes. Tomi Lahren showed her age. Richard Spencer revealed his movement to be mostly a collection of a few thousand sad dorks. Wale’s Twitter exchange with Tomi was effective too—there was no outrage, no opposition, just teasing.

They say sunlight is the best disinfectant. But it is also what allows you to see whether the emperor has any clothes. And it’s this sad, and often pathetic reality, that the collective hysteria has beneficently covered up in those it’s trying to fight. What should be seen as farce somehow looks like real fascism.

I realize there is legitimate fear of normalizing repulsive behavior. I’m not suggesting anyone give credence to real Nazi doctrine. However, historically, it’s usually true that banning and blocking usually has the opposite of its intended effect. Effective counterinsurgency usually involves bargaining, partnering and the reestablishment of norms—not hardlines. And this is already happening, Politico Magazine’s profile reveals that the jockeying for power and mainstream acceptance is pitting various factions of the alt-right against each other.

Remember how we used to think that Perez Hilton and TMZ were going to be the end of Western Civilization? Perez has had his moral makeover and the once fearless TMZ cuts deals with celebrities for access. It’s the timeless cycle of corruption and the dissipation of destructive energy.

It’s easy to sound smart and provocative when you’re the underdog. It’s easier to be reckless when you have nothing to lose. It’s also easier to create a united front when you really are being persecuted or attacked—when you’re an outsider. At least all of this is harder than expressing a coherent, cogent message for an extended period of time.

That’s the true hurdle for the alt-right to get over: Put up or shut up. The sooner you give them that chance—and stop ceding the high ground—the sooner they will falter. Or, alternatively, normalize themselves, play by the rules, or, get bored and move on. (Milo compared himself to Cincinnatus and says he wants to go back to his “farm.”)

Look at Tucker—and he’s still a friend, so I don’t mean to conflate him with anyone mentioned here—but when the controversy and outrage about his books dissipated, largely so did the sales. When he published a book of positive advice for guys—which was loved by the mostly female publishing industry and got all sorts of friendly press—it didn’t translate into success. He wasn’t an outlaw anymore. There wasn’t anything to get excited about. And now he’s moved on to other projects.

The old playbook stopped working…until a new generation picked it up again.

Ryan Holiday is the best-selling author of Trust Me, I’m Lying: Confessions of a Media Manipulator. Ryan is an editor-at-large for the Observer, and he lives in Austin, Texas.

He’s also put together this list of 15 books that you’ve probably never heard of that will alter your worldview, help you excel at your career and teach you how to live a better life.

Also by Ryan Holiday:

These Books Explain the Media Nightmare We Are Supposedly Living In
It’s Time for the Media to Do Something About Its Shameful HelpAReporterOut Problem
How the Online ‘Diversity Police’ Defeat Themselves, and Leave Us All Much Worse Off
We Are Living in a Post-Shame World—And That’s Not a Good Thing
We Don’t Have a Fake News Problem—We Are the Fake News Problem
Want to Really Make America Great Again? Stop Reading the News.
Exclusive Interview: How This Right-Wing ‘Troll’ Reaches 100M People a Month
The Real Reason We Need to Stop Trying to Protect Everyone’s Feelings

I Helped Create the Milo Trolling Playbook. You Should Stop Playing Right Into It.