The Man Behind The Milo: A Chat With The ‘Supervillain’ CEO Of MILO, Inc.

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Rob Shimshock Education Reporter
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Conservative provocateur Milo Yiannopoulos insists he only acts like a supervillain, and instead says that Alexander Macris, the CEO of his new company, is the one truly deserving of the title.

Macris detailed his path to spearheading the firebrand’s multifaceted media enterprise, MILO, Inc., as well as the company’s unconventional strategy, in an exclusive interview with The Daily Caller News Foundation.

From West Point Student To Gaming Executive

Macris attended West Point for three years, but eventually resigned to pursue a liberal arts degree.

“I was very near the top of my class academically and very near the bottom of my class physically,” Macris told TheDCNF. “I ultimately concluded that I wasn’t cut out to be a very effective soldier in the way that I would like to be.”

Macris majored in military history at Binghamton University and subsequently “did what other smart kids do who are humanities majors and can’t get jobs” and attended law school at Harvard. He graduated magna sum laude and had a job ready for him at Wachtell, Lipton in mergers and acquisitions law, a job he ended up turning down.

“Just before I graduated, I took a course on Internet law and was introduced to the idea of being an entrepreneur,” said Macris. “We had a guest lecturer one day come in who was a 20-year-old college drop-out who had founded and now he was just retired and rich because it had gone public.”

The Harvard Law student thought being an entrepreneur could pay off, so he put together a team, raised $400,000, and launched — which aimed to foster online gaming communities — right after graduation.

Five years later, Macris launched The Escapist, a video game publication which won various awards during his management. He sold The Escapist to what would become DEFY Media in 2012, and joined the company as its senior vice president of gaming.

Macris became known as DEFY Media’s “turn-around specialist,” boosting traffic for several of its properties. He described the audience profile for one enterprise with which DEFY Media tasked him, entertainment and humor site

“They liked NASCAR. They liked NFL,” said Macris. “They liked college sports. They liked guns. They liked hunting. They didn’t like Europe. They didn’t like environmentalism. They didn’t like golf. So just laying that out, what person am I talking about? It’s pretty clear, I’m talking about the heartland American voter. I’m not talking about a coastal elite.”

Spearheading MILO, Inc.

The media entrepreneur said that the travel requirements of his job at DEFY, which required him to fly from his home in North Carolina to Los Angeles every other week, were becoming wearisome. Yiannopoulos approached him in 2016 with the seedling idea for what would become MILO, Inc., a company which would cater to the same disregarded slice of America as did Macris’s DEFY properties.

Macris compared the media industry to the automobile industry to describe the contempt held for a huge demographic of its potential audience.

“The way I think about it is it’s as if the only thing that the car industry was making were family-friendly sedans and Toyota Priuses,” said Macris. “And they were completely ignoring the market for pickup trucks, Jeeps, and sports cars. And if you said, ‘well we should make pickup trucks, Jeeps, and sports cars,’ they would say, ‘well, why would you want to sell cars to racists?’”

Noting that advertisers held a similar progressive political persuasion to that of media elites, Macris explained that MILO, Inc. attempts to avoid relying on an advertising model by adopting a consumer-based revenue stream via a diverse assortment of assets such as Dangerous Books, the company’s book publishing arm, a live touring division, and a merchandise wing. (RELATED: Milo Sues Simon And Schuster For $10 Million, Announces Independent Book Publication)

“If you want to summarize [MILO, Inc.], what we’re doing is taking the left-wing tactics that they have developed since the 1920s [activism, direct action, radical crowd based activity] and we’re bringing that to important conservative causes like protecting our border, strengthening our industry, preserving our free speech rights,” said Macris. “And it’s working.”

As for his day-to-day life as CEO, Macris emphasized the need to prioritize, as well as the time commitment required from other employees and himself.

“We have employees doing venue booking at night in California,” he said. “Then we have employees doing Facebook posts on U.K. time in the morning. I’m on calls anywhere from 9 a.m. in the morning to 3 a.m. at night. It’s very, very intense.”

In addition to the aforementioned segments of the company, MILO, Inc. also plans to expand into TV. But instead of making Yiannopoulos into a “castrated creature that’s kowtowing to the left,” Macris and MILO, Inc. plan to shift the framework of acceptability for the television medium, moving the Overton window of permissible ideas to the right.

The CEO described how the left shifted the Overton window on gay marriage, with progressives first asserting that gay individuals should have the right to form civil unions. That opinion then became the most widely accepted opinion until progressives began advocating for gay marriage; slowly but steadily, gay marriage became the dominant view.

“Conservatives have traditionally responded to that by always racing to the middle and winning elections in the short term,” said Macris. “So conservatives will figure out wherever the 50th percentile is, the median voter, and they will embrace that person.”

Macris said he and Yiannopoulos joked about releasing a book entitled “Conservative Victories In The Culture War: 1929-2015.” Yiannopoulos would describe recent events in a foreword and then turn to “great [conservative] heroes of the past…” and the remainder of the book would be blank.

“You get this never-ending tug to the left as edgy progressives move [the Overton window] leftward and cautious conservatives move to the center,” said Macris, saying that MILO, Inc. desires to adopt the same strategy, but for the right. “Rather than trying to rush to the center, we carve out a space on the right and move the center towards us.”

The CEO asserted that the company has already succeeded in that effort. (RELATED: EXCLUSIVE: Milo Yiannopoulos Talks Leftist Tactics, Trump And His New Book ‘DANGEROUS’ [VIDEO])

“Five years ago, conservatives were still getting de-platformed on campus, but nobody was talking about it,” he said. “Half of the press on Free Speech Week was positive on us and blasted Berkeley for not allowing conservative speakers on campus. Jeff Sessions, one of the most important leaders in the country, blasted Berkeley and said we need to be looking at free speech on campuses. That’s moving the framework.”

MILO, Inc.’s upcoming projects include the publication of Pamela Geller’s Fatwa: Hunted in America through Dangerous Books and a December tour of Australia.

(Editor’s Note: This reporter worked with Milo Yiannopoulos as an intern in 2015 and contributed to Breitbart from 2015 to 2016.) 

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