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The Art of Betting on the Inevitable: Why Shorting Private Market Fantasies is a Fool’s Errand for the Desperate

Buck Valor
Written by
Buck ValorPersiflating Non-Journalist
Wednesday, November 26, 2025
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A hyper-realistic, dark satirical digital painting of a golden unicorn with a skeletal face melting into a pool of black oil. In the background, a group of faceless men in pinstripe suits stand on a crumbling pile of dollar bills, holding empty champagne glasses and staring at a neon sign that reads 'VALUATION' which is flickering and broken. The sky is a toxic, bruised purple, and the landscape is a desolate, grey financial district wasteland.

Ah, the 'private market.' That hallowed cathedral of obfuscation where 'valuation' is a word used by people who find 'reality' too restrictive for their creative writing exercises. We are currently witnessing the terminal stages of a financial hallucination so profound it makes the Dutch tulip mania look like a sensible long-term bond play. The latest siren song for the bored and the cynical is the proposition of 'shorting' these private-market behemoths—the so-called 'bubbly' firms that have spent the last decade burning through venture capital like a trust-fund brat in a Vegas high-roller suite. But, as the headlines begrudgingly admit, trying to bet against these paper-mâché empires presents 'fearsome challenges.'

Of course it does. You can’t easily bet against a lie when the liars own the casino, the chips, and the very air you breathe. In the public markets, if a company is a disaster, you can at least borrow the shares and pray for gravity to do its job. But in the private world, these 'unicorns'—a term that perfectly captures their fictional nature—exist in a vacuum of accountability. They are protected by a phalanx of venture capitalists who are incentivized to keep the valuation inflated until they can dump the carcass onto the public via an IPO or a desperate acquisition. Shorting a private firm is like trying to bet that a ghost will trip over a shadow; the mechanics simply aren't built for those who live in the world of tangible consequences.

The 'fearsome challenge' is not just a lack of liquidity; it’s a total absence of truth. These firms don’t report to the SEC; they report to a board of directors comprised of the very people whose net worth depends on ignoring the fire in the basement. The Left, in their usual performative dither, will scream about 'transparency' and 'wealth taxes' on these unrealized gains, oblivious to the fact that the 'wealth' in question is often just a collective agreement to pretend a money-losing delivery app is worth forty billion dollars. They want to tax the steam rising off a steaming pile of nonsense. Meanwhile, the Right will defend these 'job creators' with a fervor that suggests they actually believe a company that loses two dollars for every dollar it earns is a triumph of Western capitalism. They aren’t creators; they are arsonists who have convinced the neighborhood that smoke is a sign of progress.

To short these firms, one must navigate a Byzantine labyrinth of 'secondary markets' and 'derivative swaps' that are about as transparent as a bucket of tar. Even if you manage to find a way to bet against the next 'disruptive' AI startup that is actually just three guys in a basement manually answering queries, you are fighting an uphill battle against the sheer inertia of institutional stupidity. Pension funds and sovereign wealth funds have dumped trillions into these private pools, and they cannot afford for the bubble to burst. They will throw good money after bad, propping up the 'bubbly' firms with more 'bridge rounds' and 'down rounds' that are just elaborate ways of saying they’re rearranging the deck chairs on the Titanic while the iceberg is already halfway through the hull.

It is truly a pathetic spectacle. On one side, you have the tech bros—those vapid, fleece-vested parasites who think 'disruption' is a substitute for a business model. They sell a future that never arrives to investors who are too arrogant to admit they’ve been fleeced. On the other side, you have the short-sellers, the vultures who think they are smarter than the herd. They aren’t. They are just the janitors of the financial apocalypse, hoping to scavenge a few gold teeth from the rubble. They think they are the 'adults in the room' because they see the rot, but they are still trapped in the same decaying building as everyone else.

The reality is that the private market has become a sheltered workshop for the billionaire class, a place where the laws of economics are suspended by mutual consent. Shorting them is 'fearsome' because the market is no longer a mechanism for price discovery; it is a mechanism for ego preservation. When the collapse finally comes—and it will, with the boring predictability of a sunrise—don't expect a moment of clarity. The Left will blame the 'greed' of the short-sellers for 'destroying' companies that were already dead, and the Right will blame 'regulatory overreach' for dampening 'innovation.' Neither will admit that the entire edifice was built on the foundation of cheap money and the bottomless gullibility of people who believe that math is optional if your pitch deck is shiny enough.

So, by all means, look for a way to short the bubbles. Search for the clever derivative that lets you profit from the inevitable gravitational pull of zero. But don't be surprised when you find that the 'fearsome challenges' are insurmountable. In a world where the currency is delusion, the person telling the truth is always the one who goes broke first. It’s not a market; it’s a suicide pact in a tailored suit, and honestly, watching it all unravel is the only entertainment left in this stagnant, intellectually bankrupt era.

This story is an interpreted work of social commentary based on real events. Source: The Economist

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