Jan 17, 2017 ยท 4 minutes

There aren’t many winners in Trump World.

At least, there aren’t many winners outside of the deplorables, basket-cases, racists, sexists and Twitter Eggs who make up Trump’s inner circle. It’s a pretty good time to be a right wing blogger, I suppose. Or a cabinet nominee. Or President In Waiting Mike Pence.

One group that should sit firmly in the “win” column is satirists. Not only is Trump a parodist’s dream, and not only do the anti-Trump punchlines write themselves, but for the first time in generations we have a president who actually responds when mocked. Never in living memory has America had a chief executive who can be distracted from actual, concrete policy making by jokes about his tiny hands or rumors about golden showers.

Every satirist who has ever agonized over whether their art has any impact should be as happy as a Priest waking up at the Pearly Gates. Others should see a huge market opportunity: Combine the one-in-a-lifetime relevance and power of satire and comedy with the never-before ease of publishing online and there should be a glut of solidly-funded, high-profile sites popping up to take advantage. There should be a million Onions, an entire new generation of online Spy Magazines, a galaxy of SNL-type web shows.

And yet.

Where are they? Where, amongst the 30+ trillion web pages currently indexed by Google, is the new "CNN of satire," or the "New York Times of topical comedy?" I don't mean funny tweets, or personal blogs, I mean actual media startups getting actual traction and attention. Something like Pierre Omidyar's abortive The Racket, or Maer Roshan's ill-fated Punch?

Surely this is a "now more than ever" moment for a political satire startup. So why on earth are YouTube videos of Saturday Night Live -- a 40 year old broadcast TV show! -- the best the Internet has to offer when it comes to vicious, professional mocking of Trump? And why, for that matter, when Esquire.com briefly brought back Spy Magazine as an electronic publication, did it fall flat? Why are snarky tweets the best the Internet can do?

There are actually a few reasons. The first being that - duh - satire is harder than it looks.  Being funny or satirical once on Twitter is easy, but being satirical every week (or month), year in year out, and finding people to pay for it, is an almost impossible task. Particularly in the Internet age.   For all the Onion rip-offs spawned in college dorms, there remains only one Onion (and that hadn’t been truly funny since September 11th). For all the talking heads on YouTube, there’s only one SNL and there was only one Jon Stewart.  

The same “satire is hard to do well” problem is evident in every format, not just online. The magazine shelves support a dozen titles for Ostrich fanciers, but there hasn’t been a single successful attempt to bring Charlie Hebdo or even Private Eye style satire to these shores.

And the web has made things harder, not easier. Advertisers hate satire -- it’s just too risky -- and convincing readers to pay for satire is even harder than getting them to pay for news. Charlie Hebdo and Private Eye both long pre-dated the Internet and have survived in large part by avoiding it.  

Speaking of risk: Let’s not forget the influence of our old pal (and Pando investor, because I killed a dog in a previous life) Peter Thiel. With help from his pet lawyer, Charles Harder, Thiel has succeeded in putting the fear of god into anyone who might attempt to fill the hole left by Gawker which, depressing as this is, was the closest thing we had to an American version of Private Eye. Any comparable publication launching today would need to raise a hefty war chest to protect itself from a pre-emptive strike by The Pete and Charles Show.

But still. This isn’t really the time for excuses. Isn't funding dangerous businesses that might land the founder in court exactly what Silicon Valley is supposed to be good at?

Right now, millions -- tens of millions -- of Americans are watching Trump losing his mind as he gets closer the Oval office. All of those Americans, not to mention billions of other people around the world, are crying out for someone to make sense of it all. Are screaming for someone to hit back at Trump with the only weapon that harms him: Mockery. It’s not a stretch to believe that a big, high profile online satire magazine launch in America -- something combining the “don’t give a fuck” attitude of Charlie Hebdo with the reporting chops of Private Eye -- would attract a gigantic audience. Perhaps gigantic enough to overcome advertisers’ traditional resistance to advertising next to “humor.” 

In the meantime, there are plenty of Silicon Valley billionaires who could easily afford to bankroll such a publication while it finds an audience. It cost Peter Thiel a reported $10m bankrupting Gawker. That's a rounding error for tech investors, and it'd be much harder for Thiel to self-justify suing one of his own buddies.

As for the product itself: There’s no shortage of unemployed reporters and comedians to produce the content. And there must - absolutely must - be an angry 20-something editor with the energy to put all those pieces together (Has to be a 20-something, everyone older is too exhausted.)  

So where is it? Where's the Internet’s Private Eye? America’s digital Charlie Hebdo? Who is the billionaire and where is the angry 20-something who can write a joke?

This would be a really good time for some actual disruption.