How to Solve a Problem Like Jason Calacanis


Oh, what a time to be young in the world: so much potential on the horizon: an infinite multiverse of possibilities, stemming from right this moment into that beautiful question mark of the future. Youth is wasted on the blah blah you get the point. I’m being ironic.

Never has the future seemed so apocalyptic, so inevitable, just that many ticks closer to the strike of midnight on the Doomsday Clock. I can’t imagine how terrifying life must be for those graduates who, having survived COVID and active shooter drills, are finding out the consolation prize to the millennial startup boom is recessionLite. Same crippling debt and ruinous financial forecast. No calories.

Also: no pension or pocket watch to look forward to, no career safety, no health insurance, and less reproductive freedom and economic security than their parents for the first time in history. Yes, it’s always been scary to venture into the world, but it’s got to mean something that this generation of up-and-comers will be the first to not be as well-off as the previous ones. We look on them not with envy but with pity; there is a distinct possibility that Gen Z will be the ones to witness humanity’s last pneumonic gasp before it belches itself out of existence.

Best-case scenario, maybe we get to the singularity sometime soon. But even that dystopia doesn’t seem as glamorous as “Black Mirror” promised: with their luck, Gen-Z will wake up to an eternal consciousness as a new autonomous driving feature in a next-gen combat Tesla.

Oh please, don’t waste your tears. It’s 2023: if these kids didn’t want to be used as the literal driving force in Elon Musk’s LithiuMind™ turbo tanks, they should have spent more time reading ChatGPT’s ToS.

At least so thinks Jason Calacanis, the embodiment of the schaden-Shitty Media Man-turned-venture capitalist-turned-Mr. Movies podcaster– turned “guy who texted work daddy Elon ‘You have my sword’ like a weird little LOTR LARPer.” You know, that old classic archetype.

Calacalanis goes by @Jason on X, which as everyone knows is the worst installment in a franchise that jumped the shark somewhere between Hell, Manhattan and outer space.

Much like Voorhees, Jason Calacanis loves nothing more than to terrorize young women, presumably also in retribution for having been left to drown in a shallow lake at a summer camp in New Jersey. Whether it’s taking on Taylor Lorenz on the (very-popular, still existing) Clubhouse app, Lydia Tar for being canceled in a 2022 film that wasn’t “Top Gun: Maverick” or a young woman sobbing about her first 13-hour workday, Calacanis is not afraid of rolling up his sleeves and punching down. A real-life M. Bison avatar (Musk variant) in a social media “X-Men vs. Street Fighter” throwdown.

Seriously, I am almost impressed by the mental gymnastics it must take a WFH millionaire podcaster to lecture Gen Z about how they should “teach yoga/skiing and sleep on someone’s couch” to toughen up. When Jason was younger, he caused survived three recessions! Uphill! Both ways! 

@Jason’s vibes are truly only matched by that Star Wars troll whose co-host – a literal sock puppet – agreed that a video of a woman unboxing “Ahsoka” toys was “cringey.”

But maybe you just have to get to know him? I’ll let you be the judge: when asked to anonymously sum Jason up in a sentence, here’s how the people who have met and worked with Calacanis described him:

“Used car salesman of the tech VC world.”

“What if Draco Malfoy was from Brooklyn and his dad owned a bar?”

“Reliably dogshit tweets no matter the subject at hand.”

As Jason himself might say, “Sharpen your blades boys.” Presumably, the one still attached to the sword.

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