Sep 14, 2016 ยท 6 minutes

We’ve now seen what several elections look like in an era of YouTube, Twitter, and Facebook.

But this election cycle, the story isn’t just the impact of social media, but social media cash. I don’t mean grassroots organizations leveraging the Web like Howard Dean, Barack Obama and Bernie Sanders achieved. I don’t mean anything like that.

I mean the battle of the billionaires enriched by social media.

On one side there is [disclosure: Pando investor] Peter Thiel, enriched by an early investment in Facebook, whose support of Donald Trump was so mystifying that half of the Valley engaged in hopeful fantasy fiction that maybe he was some sort of Trojan Horse determined to sabotage the campaign from within. Others close to Thiel, simply shrugged, shook their heads or like his former PayPal co-founder Max Levchin said he had to check the calendar to make sure it wasn’t April 1.

Answering back in conviction was CRV, a venture firm enriched by an early investment in Odeo which would pivot into Twitter. CRV’s partners aren’t billionaire-rich, but they made a strong “F- Trump” statement as a firm, something no other Valley firm has been willing to do.

But largely those were just statements, lines in the sand, an investment of “brand” and influence.

More recently as Trump, yet again, narrows the polls, we’ve seen the social media billionaires start throwing around actual, fucking cash. Large amounts of cash.

Facebook’s co-founder Dustin Moskovitz and his wife Cari Tuna have committed a huge $20 million to defeating Trump, writing:

If Donald Trump wins, the country will fall backward, and become more isolated from the global community. This distinction is starkly caricatured by his #1 “policy” position: the literal building of a wall between us and our neighbor.

Moskovitz was an actual Facebook co-founder, not a guy who had the same idea for a college social network as a dozen other people and sued his way into that title. He was at one time the country’s youngest billionaire. And since he no longer has a role at Facebook, he has the ability (or, some might argue, courage) to have strong convictions and put his cash behind them.

This week, Reid Hoffman, LinkedIn’s co-founder and an early Facebook angel, has opened his checkbook. He has thrown back Trump’s gross birther words in his face writing the following:

In 2012, Donald Trump called President Obama “the least transparent president in the history of this country.”

Then he offered to donate $5 million to charity if President Obama would release “his college records and applications” and his “passport applications and records.”

Now, in 2016, Trump is facing a similar challenge from a 26-year-old Marine Corps veteran named Pete Kiernan.

On Crowdpac.com, Kiernan hopes to raise at least $25,000. Then, if Trump releases his tax returns by October 19 (the final debate), Kiernan will donate the money he has raised to non-profit organizations that assist veterans, including Team Rubicon, the Special Ops Warrior Foundation, and theYellow Ribbon Fund. For a complete list, visit the campaign’s main page...

...But taking Trump’s own 2012 offer to President Obama into account, I’d like to assist Kiernan in his campaign. If Kiernan’s campaign hits or exceeds its target, I will match the total amount he reaches with a 5x contribution, up to $5 million.

As of the time I’m writing this, the campaign is at about $130,407. Hoffman added from TechCrunch Disrupt today on the prospect of a Trump presidency: “When I get out of denial, I think waking up in terror would actually be an accurate statement. Since their Stanford days, Thiel and Hoffman have fiercely debated politics, but much of that was theoretical.

While it’s tempting to see moves like Hoffman’s and Moskovitz’s as countering Thiel’s, it was Moskovitz who pointed out to me that Thiel hasn’t actually given any money to Trump.

He’s donated to Carly Fiorina and others, but not Trump.

Just think about that for a moment.

Thiel has invested millions into destroying Gawker-- a campaign waged in secret-- while not spending a single dime to do what he exhorted the country should do from the stage of the Republican National Convention: That is, elect Donald Trump.

And you thought Thiel’s endorsement of Trump couldn’t get any weirder.

For months the arguments I’ve been having with people in the Valley go like this:

“Isn’t it horrible that a man who was an immigrant and has profited so greatly from immigrants co-founding his companies or buying them would endorse someone like Trump?”

“Yeah, but we don’t really know why he is doing this...You don’t have to agree with everything to support a candidate…”

“Right, but there’s a difference in giving someone’s campaign a few thousand dollars just in case you need a favor if they win and serving as a delegate…”

Apparently, the ever contrarian Thiel sees that backwards: Standing on stage at the RNC and serving as a delegate for Trump is somehow less of a commitment to his cause than actually giving him a single red cent. Which is strange because presumably Thiel could afford to lose a few thousand bucks, a lot easier than any challenges he’s thrust onto Founders Fund-- or yunno, companies that depend on President Obama’s policies like Joshua Kusher-founded Oscar Health-- with his Trump endorsement.

Sure, some have tried to argue his fight against Gawker was equally damaging to his reputation. I’m not sure the broader tech world sees it that way. And in that case, he seemed to fear as much, hence the secrecy of the campaign.

There are all sorts of explanations about what is “going on” with Thiel’s endorsement of Trump, mostly by people who have never met the man. I have refrained from that game, because I know him well enough to know his logic almost always surprises me. I have heard from a few close to him what he’s told them about the move. Others (Like Levchin at the time of that interview) just haven’t asked.

There is one difference between the two moves that have captivated the press this year: While the news came out the same summer, the two decisions were embarked upon ten years apart from one another. Thiel was much more obsessed with privacy ten years ago. He was far less cemented as a modern icon of Silicon Valley. Indeed, he wasn’t even a liquid billionaire then.

I remember some advice Thiel gave me earlier in my career -- closer to the ten years ago time-- when I suffered from a lot of manufactured “scandals” by trolls, internet mobs, and all the usual gender baiting underbellies of the Web. “Embrace and extend,” he said. People want to think you are a crazy, self-promoting, egotistical, mouthy woman who refuses to know her place, let em. Run with it even. He compared it to the Ann Coulter strategy of media, and while she’s abhorrent, that’s not actually terrible advice when the world wants to twist you into something you are not.

The last time I interviewed Thiel on stage, around the time of his book’s publication, he tried to distance himself from the radical seasteading libertarian caricature that the media had of him…. The one that even inspired Mike Judge.

Is it possible, he’s just taking his own advice years later?

Who knows, other than Thiel. What we do know is that whether it’s his endorsement of Trump or his fight against Gawker, lately Thiel’s money and words move in opposite directions from one another, like so many of his seemingly contradictory views on tech, religion, science, and politics.

And Gawker would probably tell you the money was a lot more devastating.