Sep 21, 2017 · 7 minutes

Back in 2015, I wrote a story about a trio of tech moguls who had turned their sights (and sites) on fixing journalism. It was seemingly an altruistic move, and I believe a well intentioned one at its core.

There was Pierre Omidyar, who committed $250 million with First Look Media, after mulling a purchase of the Washington Post.

There was Evan Williams, who started Medium, chagrined at what the Internet had become in no small part due to his previous company, Twitter.

There was Chris Hughes, of the Facebook dorm room, who purchased The New Republic.

At the time, I pointed out struggles each was having and said the central quality each was missing in becoming a media mogul was the willingness to engage in confrontation, a quality that has only become more essential in a time when the President is encouraging his crowds to berate journalists and companies like Uber are threatening smear campaigns to silence them.

The only direct response was Evan Williams telling me to “fuck off” and then immediately backpeddling and insisting he was only kidding. I believe the “fuck off” was more sincere than the backpeddling, which kind of makes my point.

One of the three has certainly adapted, and it may be the most surprising: Pierre Omidyar.

Omidyar has become one of the few Silicon Valley billionaires to regularly and aggressively call out the Trump administration on issues from immigration to healthcare to Russian collusion in the election. He doesn’t just amplify or share the Intercept’s reporting-- he goes on the attack himself, directly from his Twitter account.

A recent sample:

Sure, that’s how many of us spend our days. But for a billionaire, sadly, it’s a sign of remarkable courage. As Andrew Ross Sorkin wrote in an article about Reid Hoffman -- another outspoken one (and a Pando investor). Hoffman has received continual pressure from his fellow billionaires to shut up, even during the campaign when many people assumed Hillary Clinton would win.

Mr. Hoffman said he almost didn’t make his political views — and [his “Trump Cards”] card game — so public because he worried, as did his family and friends (who originally counseled him against it), that he might become a target for Mr. Trump and his Twitter account — or worse.

“People are fearful that, especially in a circumstance where he might be in a position of extreme power as a potential presidential candidate, that that would be used in a retaliatory way, that would be used in vengeful way,” Mr. Hoffman told me in an interview. “Everyone gets worried about being attacked, and part of the logic and mechanics of bullies is that they cause people to be fearful that they’ll be singled out and attacked.”

Mr. Hoffman continued: “It’s the same thing like on school grounds, when people won’t go help the kid who is being bullied because they’re worried that the bully will focus on them.”

This is bizarre isn’t it? Shouldn’t part of the fun of being a billionaire be that you can do and say whatever you want?

Back in the early 2000s with the pain of the dot com crash still fresh, I heard so many of the early builders of the social media wave talking about wanting to make their “Fuck you” money.

When I asked what that amount was, the total ranged from a few million to $50 million. The person who told me $50 million (who is now a billionaire btw) had done the math on what point he could have financial independence, a house and could buy a plane…. I guess his “fuck you”s would extend to the airline industry. (My total, for what it’s worth, is lower than all of those: Paying off my mortgage, and setting aside college tuition for my kids. Not that I know what a more outspoken “fuck you money” version of me would look like…)

Somewhere along the line in building and investing in some of the largest companies on the planet-- including Facebook and Twitter which are being investigated and criticized for potentially putting our planet in danger by helping elect Donald Trump--  many of these same people have become so insanely rich that they rapidly passed through the “fuck you” Garden of Eden and back into the “Fiduciary Duty” land of fear and cowardice.

Their “Fuck you” multiplied in ways they never dreamed. And it became “Oh I couldn’t possibly...” money. Money changes you, I guess, and insane amounts of money change you even more.

That’s what makes Omidyar’s transformation so singular and worth adding a postscript to my 2015 piece. He was outspoken against Trump before Elon Musk, despite Trump denying climate change-- an issue Musk cares about so greatly, he has committed hundreds of millions of dollars of his own personal fortune to.

No one who knows those two men would have ever anticipated that: A version of the world where Omidyar speaks his mind, while Musk sits muzzled hoping to inspire change by having a seat at the table.

Least of all, Omidyar himself!

Omidyar declined to buy the Washington Post in part because of this aversion to conflict. From Vanity Fair:

Omidyar is admittedly conflict-averse, and when considering the Post,“I just remembered instances in my history where when people aren’t fully aligned, when they haven’t bought into the vision, it’s really difficult and it’s actually a little bit draining. It’s not something I look forward to dealing with in the morning. I thought about myself actually in the role of leading a cultural transformation—that would mean dealing with talented people who fundamentally disagreed with me in some cases.” When he imagined that scenario, he realized that he wanted to avoid it. “I said, O.K., fine, that’s maybe not a great idea.” He indulged a small laugh. “Ultimately I think sanity returned.” 

Of course, you can argue that Omidyar has a reason he can be so outspoken when someone like Musk cannot: He is not currently running a large company that could be retaliated against. He has no shackles of fiduciary duty. Still, you could say the same for lots of Web 1.0 moguls who remain silent.

Here’s the kicker: In recent weeks, Omidyar hasn’t just become a critic of the GOP and Trump… safe targets, after all, in most of his social circle. He has gone full-barrel after Facebook.

Even Hoffman has remained mum publicly on Facebook’s potential role in the election, from what I’ve seen.

It’s particularly remarkable given the cozy social ties so many of these billionaires have. Let’s remember: It was Omidyar who played a large role in initially giving (Facebook board member and Trump supporter and rumored candidate for an Intelligence Post in the Trump Administration and a Pando investor) Peter Thiel, Elon Musk, and Reid Hoffman their fuck you money, when eBay bought PayPal. It was eBay that also bought (Facebook board member and Pando investor) Marc Andreessen’s second company for $1.5 billion, leading to Andreessen and Omidyar serving together on eBay’s board for several years.

Attacking Trump is easy. Or… it should be. Attacking other members of this cozy billionaire class puts the admittedly conflict adverse Omidyar in the stunning and sudden role of most combative tech billionaire.

Longtime Pando readers know we were one of the rare publication not throwing roses at Omidyar’s feet when he founded the Intercept. Early on, we’ve criticized his mixed messages on whether or not he was meddling in editorial at First Look’s properties, and raised questions about whether his $250 million investment in journalism was a loose commitment or a firm one.

And we weren’t wrong. A lot of our early reporting was later on cited by publications like New York Magazine and Vanity Fair when the company ran into challenges, let go of some of its louder voices, and seemed to change its strategy.

Perhaps he does have what it takes to be a media mogul after all.