Beware the Bitcoin Circus: Saylor’s Strategy is a Joke (Literally)

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Prominent angel investor Jason Calacanis has recommended that investors run from Michael Saylor’s Strategy (formerly MicroStrategy) as if it were a cursed relic from a 19th-century financial séance. 🪄

Calacanis, a man who once compared Bitcoin to a “digital gold,” now insists investors simply “get exposure to Bitcoin instead.” As if Bitcoin were a self-serve buffet and Strategy was just the waitstaff tripping over the soup tureens. 🍲

Vocal Strategy bear

In a recent Twitter tirade that could’ve been titled *“The Tragicomedy of Errors,”* Calacanis reiterated his earlier claim that Strategy should trade at a discount to its net asset value (NAV)-a suggestion so bold it makes a discount on a used toaster look like a royal decree. 🏰

He also argued that Saylor’s Bitcoin hoarding is “damaging the Bitcoin brand,” a statement so meta it could’ve been written by a Bitcoin itself in a fit of existential dread. 😅

In his latest post, Calacanis warned investors to avoid Strategy stock because it’s “complicated, layered, and you lose control.” A description that could also apply to his morning coffee order. ☕

Strategy’s Bitcoin holdings? A modest 638,460 coins, valued at roughly $74 billion. A treasure hoard that would make Scrooge McDuck blush-though he’d probably just invest it in a better PR team. 💰

Strategy stumbles

Earlier this month, Strategy was snubbed from the S&P 500, a rejection so public it could’ve been a TikTok trend. Saylor claimed the company “didn’t expect to make the cut,” a line as convincing as a magician explaining how the rabbit escaped. 🎩🐇

JPMorgan analysts, however, called the snub a “major setback,” a judgment that feels less like financial analysis and more like a schoolyard punchline. After all, missing the S&P 500 is like being excluded from the school play-everyone notices, and no one quite knows why. 🎭

The benefits of S&P 500 inclusion? Index fund buying pressure, liquidity, and institutional acceptance. In short: the holy grail of finance. But if Strategy had a LinkedIn profile, it’d probably say, “Seeking relevance.” 🤷♂️

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2025-09-12 09:11