Arianna Huffington: The Prolific Media Mogul

How She Built The Huffington Post Into a Juggernaut

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Arianna Huffington

After researching Arianna Huffington for hours upon hours this week, there’s one word I’d use to describe her and the companies she’s created: prolific.

Arianna has authored 15 books, built multiple companies worth hundreds of millions of dollars each, and has been able to reinvent herself again and again.

Oh, and did you know she didn’t start The Huffington Post until she was 54 years old?

Her story is fascinating and there’s a lot to learn.

Let’s get to it.

Early Days

Born Arianna Stassinopoulos in Athens, Greece in 1950, Arianna loved to read at an early age.

She loves to tell the story of her 5th birthday party when her mother had invited her best friends, but Arianna eventually told them to go home because they were interrupting her reading.

Her father was a newspaper publisher who experienced varying levels of success in the industry, ultimately having each of his papers fail, just like his marriage to Arianna’s mother when Arianna was eleven years old.

By age 14, Arianna decided she wanted to attend Cambridge, a dream that her mother encouraged her to pursue:

They all said, “You don’t speak English. We have no money. It’s hard even for English girls to get into Cambridge, so forget about that.”

My mother said, “Okay, let’s find out how you can get to Cambridge. I’m sure we can make that happen.”

So she found out that I could take what they call GC, general certificates of education which you needed to get, and you still do, to get into English universities from the British Consul.

But then I would have to take a special Cambridge exam, then I could apply for a scholarship. Of course, I needed to start learning English.

Arianna Huffington

It’s difficult to overstate just how important her mother was in her life.

In a Vanity Fair interview, Arianna, while tearing up, would expand on her mother’s impact on her:

There was always that combination of making me believe I could do anything and that if I failed she wouldn’t love me any less. It was absolute, unconditional love. You could try anything, because failure was not a problem.

Arianna Huffington

It’s remarkable what having even one true believer can do for someone’s psyche.

Arianna, as you’ll soon find out, never seemed to lack that belief that she could indeed do anything and she’d work hard to make something of herself.

When she was 16, Arianna took the leap and moved with her mother to England to complete the entrance exams for Cambridge, eventually getting into the university.

At Cambridge, she became president of The Cambridge Union, a prestigious debating society within the university, which was a huge deal at the time:

What happened is that when I was elected, it was front-page news. It’s hard to believe, but The Times, The Guardian, they had front-page pictures of me on this throne that the president sits on. I was invited to do every show you can imagine.

Arianna Huffington

Arianna immersed herself in the organization:

I just threw myself into it. I went to every debate. I must literally have sat there with my mouth open. I was so spellbound by the spectacle of great speakers and people being moved or angered by their words.

Arianna Huffington

That learning experience helped Arianna develop skills she would use in the ensuing decades, providing the perfect complement to her growing ambitions.

Books & Politics

A serendipitous moment during one of Arianna’s debates led to her writing the first of 15 books:

That’s when, in the course of one of the debates at which I was speaking as president, which was televised – because all of the debates were televised – a publisher saw the debate and asked me to write a book based on the views I expressed in the debate.

So it truly was defining because I had no intention of being a writer. It sounds like everything that happened to me was not intended. I got this letter from Reg Davis-Poynter, who had just actually published Germaine Greer’s book, The Female Eunuch. He asked me if I would write a book expressing the views that I had expressed in the debate. I wrote back and said, “I can’t write.” He said, “Can you have lunch?” He took me to lunch and offered me a modest advance.

He said, “If it turns out you can’t write, I’ll have lost, [I think it was] £6,000 for a year.” Otherwise, he said, “I will publish the book.”

That was my first book. It changed the trajectory of my career because I had just gotten into the Kennedy School of Government to do a post-graduate degree there, which I dropped in order to write the book.

Arianna Huffington

Arianna was only 22 when her first book, The Female Woman, was published and 23 when it became a best-seller in 1973 after she went on an international book tour.

Her second book, After Reason, published in 1978, was rejected by 37 publishers, something she’d later reflect on:

One of the low points in my life was when my second book was rejected by 37 publishers.

By rejection 25, you would have thought I might have said, “Hey, you know, there’s something wrong here. Maybe I should be looking at a different career.”

Instead, I remember running out of money and walking, depressed, down St. James Street in London and seeing a Barclays Bank. I walked in and, armed with nothing but a lot of chutzpah, I asked to speak to the manager and asked him for a loan.

Even though I didn’t have any assets, the banker – whose name was Ian Bell – gave me a loan. It changed my life, because it meant I could keep things together for another, yes 13 rejections! And then I got an acceptance. It makes the point that failure isn’t the opposite of success, but, as my mother often said, a stepping stone to success.

Arianna Huffington

In 1980, she left London and moved to New York City, a place she seemed to make an impact on almost immediately.

Arianna made more than a million dollars from the Maria Callas biography she wrote in 1981, a book that came with allegations that Arianna had plagiarized passages of it, and by 1983 she had a profile written about her in New York Magazine, a testament to her growing influence.

After moving to Los Angeles in 1984 with her mother to finish writing her fifth book, a biography of Pablo Picasso which she received a substantial six-figure advance for, Arianna was introduced to Michael Huffington, a Houston oil millionaire whom she’d eventually marry in 1986, taking his surname.

Through Michael, Arianna would get more involved in politics.

In 1992, she made her political stage entrance when her husband, a Republican, was elected to Congress. His father’s oil company, Huffco, which sold for $600 million in 1990, funded his political ambitions when he made $70 million from his share of the company.

Arianna made her presence felt in politics as well.

A 1996 memoir by political consultant Ed Rollins described Arianna as, “The most ruthless, unscrupulous, and ambitious person I’d met in thirty years of national politics.”

A few years later, after a very public divorce where she reportedly made $25 million, and with growing political ambitions of her own, Arianna ran for governor in the 2003 California gubernatorial recall election, which turned out disastrous for her, but she later put a positive spin on it:

If you don’t internalize failure in a way that paralyzes you, it is very empowering. You say: “Hey, I failed. But I’m here, and I’m healthy, and my children love me and I have great friends. Life is ahead of me.” Suddenly, you’re willing to take even bigger risks.

Two years later, she’d get her redemption in a different arena - digital media.

Starting The Huffington Post

It’s important to understand the state of blogging in the early 2000s.

As Arianna would later describe in 2017, blogging was looked down upon initially:

By 2000, I started seeing that a lot of very rich conversation was moving online. A lot of people that I loved and admired were not going to be part of it because they were never going to start a blog. At the time, bloggers were seen as people who couldn’t get a job and were blogging – remember the cliché – from their parents’ basement, right?

Arianna Huffington

By 2005, Arianna decided to flip blogging on its head, elevating the medium by deciding to launch The Huffington Post:

I decided, together with my co-founder, Kenny Lerer, to launch The Huffington Post in 2005 as two things.

One was a collection of bloggers commenting on anything from the events of the day to food to movies, anything at all.

One of our sayings was, “If you have something to say, say it on The Huffington Post.” It was also a journalistic enterprise, where we practiced conventional journalism, investigative journalism. At the beginning, the blogging part was the dominant part until we started raising and making money to be able to hire journalists.

The first day we launched was kind of a new day for blogging. Because suddenly, we had on our front page people like Nora Ephron and Walter Cronkite and Joan Cusack and Larry David, people who had never blogged before.

It began the process of elevating blogging to something that, of course, we all do. There’s no journalist who isn’t blogging at the same time. Gradually, we started adding journalists. We ended up winning a Pulitzer for investigative journalism. From the beginning, I saw HuffPost as a combination of the best of the old and the best of the new.

Arianna Huffington

Along with Kenny Lerer, who was a former AOL executive, Andrew Breitbart and Jonah Peretti would join Arianna as co-founders of The Huffington Post.

Andrew Breitbart, who had worked with Arianna previously, was the first assistant for Matt Drudge, working at the Drudge Report, a conservative news aggregation website. Andrew surprised many people at the time with his decision to help launch The Huffington Post, a website that was thought to be the progressive version of the Drudge Report after Arianna had changed from Republican to Democrat around 2004.

Jonah Peretti, who would later become the co-founder and CEO of BuzzFeed, would say of Andrew:

He taught us a lot of things early on. He explained about looking at the British newspapers late at night because they would sometimes break news before the U.S. papers. He cared about getting links up seconds or minutes faster than other publications and was obsessive about that.

Jonah Peretti

Andrew was very creative but also hard to contain and wouldn’t end up lasting long at The Huffington Post.

Jonah, who has his own fascinating background, had worked together with Kenny Lerer on a few projects previously and was convinced by Kenny to join forces with Arianna and the team to build The Huffington Post.

Remember what I mentioned earlier about Arianna’s neverending self-belief?

Well, this was the first time she had been an editor or publisher, but she didn’t let that stop her.

The Huffington Post would raise $2 million to get off the ground.

At launch, Arianna had several celebrities, many friends and contacts of hers, blog their opinions.

We’re not talking about five or ten either. There were around 300 of them!

These included a variety of influential people across Hollywood and in politics, many relationships Arianna had cultivated for decades.

How did she do it? She made it very easy for them to contribute:

These are the kind of people I had met and I wrote them and basically my pitch was, “You wake up in the morning and you have something to say, I know you do, about the events of the day, about a movie you saw last night, about anything. But you’re busy, you have a book to write, you have a company to run. Sure, you could write it for The New York Times, but you have to deal with editors and processes. You don’t really bother. Just send it to us.

Arianna Huffington

Even with this star power, many people didn’t initially think The Huffington Post would succeed, with the website getting scathing reviews after its May 9, 2005 launch.

But that didn’t matter, because the site just grew and grew.

Growth At All Costs

Early on, The Huffington Post grew largely through SEO and endless split testing, taking a data-driven approach to optimizing each headline.

They also used a brute-force aggregation strategy for attention:

Above all, from its founding in an era dominated by ‘‘web magazines’’ like Slate, The Huffington Post has demonstrated the value of quantity. Early in its history, the site increased its breadth on the cheap by hiring young writers to quickly summarize stories that had been reported by other publications, marking the birth of industrial aggregation.

This strategy also relied on their controversial contributors’ network, where unpaid bloggers wrote for the site. This eventually grew to more than 100,000 unpaid writers by 2018 before being shut down.

Arianna wanted the site to be interactive, allowing comments from readers, and, early on, she paid her daughters $5 each to moderate comments on the site.

Only a year after its launch, in May 2006, Arianna Huffington was named one of the world’s 100 most influential people by Time magazine.

The Huffington Post at this time had between 760,000 and 1.3 million unique monthly visitors, depending on the source, and by all accounts was succeeding:

Huffington announced the hiring of Melinda Henneberger, a former reporter for the The New York Times and Newsweek, in an effort to create original content generated by a salaried employee.

Huffington seemed to be inviting everyone she encountered to blog, including the doctor who had tended to her broken foot.

Money was coming in; in June, the JWT advertising agency bought all the site’s advertising space for a single week to promote such clients as JetBlue, Levi’s, and Ford, at a cost reportedly in the low six figures. Newsweek included Arianna on its cover for its story on women and power.

By September, they had 1.5 million unique site visits.

A year later, in September 2007, The Huffington Post raised another $5 million and the team had grown to 43 employees.

However, the business was taking a toll on Arianna.

In 2007 she collapsed from exhaustion, breaking her cheekbone after hitting her desk and falling on the floor.

At the time, she was working 18-hour days, 7 days a week, and disregarding her health.

With its ever-expanding scope, The Huffington Post started its first foray into localized versions of the site in 2008, starting with Chicago. It was part of a plan Arianna had to roll out local versions in dozens of cities.

By this time, the site had two thousand contributors and in February 2008 its traffic had surpassed the Drudge Report for the first time, with 3.7 million unique visitors, a number that would grow to 5.1 million by August.

In a profile of Arianna in The New Yorker around this time, we get a glimpse of how she operates:

Admirers of Huffington often say the same things about her drive and her level of intensity as her detractors do.

David Lack, who has known the family for years, told me, “Arianna will fight on, and she takes no prisoners. A lot of times, she has no conscience, either, about some of the damage she does behind her. She always goes on and figures it will fix itself by moving forward. And I give her credit. Only in America!”

The growth of The Huffington Post during this time also came on the heels of the 2008 presidential election, a time when they were getting 50% of their traffic from political coverage.

They’d raise $25 million and hire a new CEO, Eric Hippeau, after the election and continue expansion, passing The Washington Post’s traffic by the fall of 2009, with 10 million unique monthly visits.

Wanting to further expand but lacking the capital to do so in 2010, at a time when Arianna had moved back to New York City from Los Angeles, she would meet a man named Tim Armstrong, Chairman and CEO of AOL, at a media conference in the city, a meeting which would end up being fortuitous.

$315 Million

By 2010 The Huffington Post had almost 25 million unique monthly visitors, but grander ambitions.

The site generated $31 million in revenue that year, but less than $1 million in profit.

At the same time, AOL had an ambitious plan in place at the end of 2010 for the future of the company:

So eager was AOL to boost its content-driven traffic that in late 2010 it devised a strategy, The AOL Way.

Management set markers: Monthly story production rate was to rise from 33,000 to 55,000, video from 4 percent of the content to 70 percent. All staffers were to write between five and 10 stories a day.

To help them make those numbers, AOL produced a 60-page handbook filled with graphs, content flow charts, and such exhortations as “Each article should be profitable and generate at least 7k PVs/story.”

Editors were to “Identify High-Demand Topics”; guidelines were provided to “breaking, seasonal, and evergreen.” Editors were commanded to calculate a story’s “profitability consideration.” “Site leaders” were expected to have on hand no less than eight packages that could produce $1 million in revenue.

One employee anonymously told Business Insider, which broke the story, “AOL is the most fucked-up, bullshit company on earth.”

Arianna’s ambitions for The Huffington Post at that time aligned with AOL’s and in chatting with Tim at that time, she would say:

He asked to meet with me privately, and he said: “What do you want to do with The Huffington Post?” And I said, “I want to be a global company, I want us to be everywhere in the world.”

AOL ended up buying The Huffington Post for $315 million, with Arianna personally netting $21 million from the deal.

At the time of the sale, The Huffington Post had almost 25 million unique monthly visitors, 148 journalists on payroll, 18,000 unpaid bloggers, and was receiving 4 million blog comments per month.

The newly formed The Huffington Post Media Group would have a combined 117 million unique monthly visitors in the United States and 270 million globally.

Arianna became the group’s President and Editor-In-Chief, with content that included “Engadget, TechCrunch, Moviefone, MapQuest, Black Voices, PopEater, AOL Music, AOL Latino, AutoBlog, Patch, StyleList, and more.”

Tim Armstrong would say of Arianna at the time:

Arianna is a singularly passionate and dedicated champion of innovative journalistic engagement, and a master of the art of using new media to illuminate, entertain and enhance the national conversation. Arianna is a remarkable person and she will continue to create remarkable outcomes for the combined company.

Tim Armstrong

Though Arianna joined AOL in the deal, others left:

Notably absent from the agreement was a non-compete clause. Ken Lerer left and started his own venture capital firm, Lerer Ventures, which Eric Hippeau soon joined.

Peretti left for BuzzFeed. Berry would leave several months later and take up residence across a spacious room from Lerer Ventures—one floor below the original Huffington Post newsroom.

HuffPost resided in the sleek lower Broadway office of AOL. Of the three founders of the Huffington Post, only Arianna Huffington remained. In a sense, she was just getting started.

The Up And Down AOL Ride

While it initially seemed like The Huffington Post would be a good fit at AOL, that changed relatively quickly:

A clash of cultures, however, was soon evident. Many of AOL’s sites did little more than promote their sponsors; AOL Real Estate, for instance, was mainly a home for Bank of America ads, next to stories about the joys of mortgage refinancing.

In an attempt to restore some semblance of editorial integrity, Huffington fired the freelancers who worked for the site and replaced them with young staff members.

Many were recent graduates of Yale — her feeder of choice — whose chief qualification, aside from the obvious, was a willingness to work for a pittance. But the hiring spree was rushed and filled the sites with fledglings. Page views plunged, irking corporate sponsors.

David Segal, New York Times

By April 2012, Arianna’s responsibilities at AOL had been reduced:

At first, many on Armstrong’s team had been awed by her energy and range, but they quickly grasped that these didn’t always translate into results.

‘‘No one else could give a commencement speech at Smith one day, meet the prime minister of Japan on Tuesday and debate the Middle East on MSNBC on Wednesday,’’ one former executive said. ‘‘But that doesn’t mean she knows the ins and outs of running Moviefone.’’

It didn’t help that AOL stock, following the acquisition, had fallen to less than $12 by August from just above $20 at the time of the purchase half a year earlier.

At some point, Huffington stopped going to meetings of AOL executives, and in April 2012, an organizational reshuffling quietly moved every AOL site except The Huffington Post out of Huffington’s portfolio. Her tenure as AOL content czar was over.

David Segal, New York Times

Unfortunately, it didn’t get much better later that year when top executives at AOL wanted to move Arianna into a “Popemobile” role, where she’d mainly promote the site and not run any day-to-day operations.

It was clear things weren’t exactly working.

But why?

Mainly, it was due to a few strategic decisions that turned out poorly, like her HuffPost Live initiative which flopped and her “What’s Working” project which never took off.

Nonetheless, The Huffington Post continued to grow, making $146 million in revenue by 2014.

By June 2015 The Huffington Post had 200 million unique visitors per month.

Arianna’s company was as prolific as ever, with a team that was producing a staggering amount of content:

Today, The Huffington Post employs an armada of young editors, writers and video producers: 850 in all, many toiling at an exhausting pace.

It publishes 13 editions across the globe, including sites in India, Germany and Brazil. Its properties collectively push out about 1,900 posts per day.

In 2013, Digiday estimated that BuzzFeed, by contrast, was putting out 373 posts per day, The Times 350 per day and Slate 60 per day. (At the time, The Huffington Post was publishing 1,200 posts per day.)

David Segal, New York Times


That’s insane.

But that amount of content, in the display advertising game, works.

Native advertising, where the content matches the look and feel of the content around it on the website, was also something The Huffington Post made use of:

The Huffington Post offers to make its advertisers custom quizzes, listicles, slide shows, videos, infographics, feature articles and blog posts. Prices start at $130,000 for three pieces of content. This is where size matters; top-tier sites can fetch premium rates because advertisers know their messages could be seen by millions.

Just like The Huffington Post’s content, Arianna herself is nonstop, forcing her team to keep up with her or leave:

Even as she oversees an international news operation, Huffington spends most of her days and nights in a globe-spanning run of lectures, parties, talk shows, conferences and meetings, a never-ending tour that she chronicles in a dizzying Instagram feed.

Her stamina is a source of awe to members of what she calls her A-Team — the A is for Arianna — a group of 9 or so Huffington Post staff members who, in addition to their editorial duties, help keep her in perpetual motion.

Within the organization, A-Team jobs are known to be all-consuming — but also, for those who last, a ticket to promotion later on. While some stick around for years, many A-Teamers endure only about 12 months before calling it quits or asking to be transferred.

The work environment to churn out all that content, as you can imagine, is intense.

Of course, it would be intense at any global internet news site constantly competing for attention.

This environment often led to burnout, a problem Arianna would work to solve in yet another career reinvention, embarking on a new journey in 2016 and leaving her namesake company.

Thrive Global

In August 2016, more than a decade after founding The Huffington Post, Arianna stepped down from her role as editor-in-chief.

A Vanity Fair piece at this time outlines just how far she had risen during her time running The Huffington Post:

Despite a relative lack of experience in journalism, business, and technology—as a wealthy divorcee who had written several books and unsuccessfully run for governor of California—she had turned the Huffington Post into one of the most recognizable media brands of our time.

Within a decade, the site became part of the media firmament and Huffington became a global brand unto herself. She was a regular at the annual World Economic Forum, in Davos; a ubiquitous talking head on television; a budding lifestyle guru; and the keeper of one of the more prodigious Rolodexes in the industry. She counted among her friends everyone from Charlie Rose to Ann Getty and Henry Kissinger to Barbara Walters. She divided her time between a mansion in Brentwood, California, and an $8 million apartment in SoHo.

William D. Cohan, Vanity Fair

The piece went on to describe Arianna’s marketing savvy, understanding of the Internet’s endless possibilities, and intuition that people in her network wanted to share their thoughts online.

Building off of her book Thrive, which was a No.1 New York Times Bestseller that promoted well-being, Arianna launched Thrive Global in August 2016.

Thrive Global is a platform to help improve employees’ well-being, taking a science-backed approach.

The company most recently raised an $80 million round of funding in 2021 that valued it at more than $700 million.

While, yes, this was a different time for companies raising venture capital, when funding was much more free-flowing, it shows the scale of Arianna’s ambition for the company and how far it had already come in a few short years.

The Key to Arianna’s Success

It’s undeniable that Arianna Huffington has lived a remarkable life.

While she’s had her share of failures, she built two companies worth hundreds of millions of dollars, published 15 books, and developed relationships with some of the most influential people in the world across multiple industries.

She’s an incredible networker, has a relentless work ethic, and she’s not afraid to pursue ambitious ideas that seize the white space in a market.

Her Huffington Post co-founder, Jonah Peretti, described one of her standout abilities as being able to “make weak ties into strong ties.”

She created lasting relationships with people again and again, working hard to foster those relationships which have undoubtedly paid off for her in a big way.

Another friend of hers, the comedian Bill Maher, would say of Arianna:

If Arianna wants to be your friend, I mean, give up, you’re like a weak swimmer in a strong tide. I went with her to some big party—I was, like, “Oh, where’s Arianna?” and, next thing I know, she’s sitting on the couch with Rupert Murdoch, chatting away like the old friends of the world.

Bill Maher

Arianna stands out in her ability to build relationships compared to any founder I’ve covered so far and if there’s anything you can take away from her story it’s the value of building a great network.

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