Vivek Ramaswamy's crypto resolve faces early test with Strive now $400 million-plus under water on Bitcoin holdings, while bearish analysts predict a 'death spiral' for crypto industry
The Trump acolyte jettisoned his RIA as he embraced a Bitcoin treasury company, imbuing crypto with free market values -- stemming from bypassing banks and governments
6 min read
Brooke's Note: Vivek Ramaswamy is wicked smart. Diversification is for dummies. Buying lots of different stocks is an admission that, on some level, it's anyone's guess what goes up and what goes down. It's also an admission you can't stomach the ups and downs of a single asset, a sign that you are not a True Believer. With Strive, Vivek is all in, combining intellectual conviction, ideological conviction and faith in his own faith in free markets by buying a pure portfolio of Bitcoin. He's free to bail out, or double down. It's an unenviable test.
Vivek Ramaswamy's crypto treasury company is now sitting on unrealized Bitcoin (BTC) losses of around $422 million amid a “crypto winter” that has shaved $2 trillion off the crypto industry.
Strive Asset Management, the New York City ‘anti-ESG’ asset manager, is one of dozens of so-called crypto treasury firms (CTFs) to suffer a blood bath. Unrealized CTF losses surged to $19 billion between Oct. 2025 and Feb. 5.
Bitcoin fell to a low of $63,295.74 this week, its weakest level since Oct 2024, a month before Republican Donald Trump, the self-proclaimed crypto president, won the U.S. presidential election.
Prices peaked at an Oct. 6 high of $123,857. See: Vivek Ramaswamy sells anti-ESG to RIAs to nab quick $1 billion of AUM, but it's all 'Kabuki theater,' analyst says.
Bitcoin's surge started in 2024, propelled by the launch of U.S. spot Bitcoin ETFs, favorable regulatory sentiment, and increased corporate treasury adoption, according to media reports.
Ramaswamy jumped into the game on a wave of Trumpian hype, attributing American values of sovereignty, self-reliance, and individual liberty to Bitcoin.
Critics liken it to a “Ponzi scheme” because Bitcoin lacks intrinsic value like currency or hard assets. Now its facing its first big test.
Burried value
Famous investor Michael Burry, who arguably predicted the 2008 financial crisis, has come out swinging against Bitcoin in recent weeks.
Burry predicts a "death-spiral" that will hammer markets and potentially smash Bitcoin Treasury firms, pioneered by Michael Saylor's Bitcoin treasury MicroStrategy. See: Vivek Ramaswamy's 'pure insanity' plan achieves liftoff
"Sickening scenarios have now come within reach, if Bitcoin falls another 10%," he said in a Feb. 2 Substack post. Saylor's Strategy would find itself billions in the red and capital markets "essentially closed" to it, he noted.
He isn't even the most bearish analyst. Richard Farr, chief market strategist and partner at Pivotus Partners, just lowered his price target on cryptocurrency to zero.
"No serious central bank will ever own something where Michael Saylor controls the float," he writes, in a note.
When Burry issued his warning, Bitcoin stood at $75,874.71.
By Feb. 5, its value had fallen 15%, to $64,856.11.
It has since recovered, but continues to trade down 8% – close to the threshold of Burry's tipping point.
For his part, Saylor told CNBC today (Feb. 10) the firm will buy Bitcoin “forever,” – even if he is now sitting on $5 billion in paper losses on his BTC holdings.
Acid test
Strive's pivot to become a Bitcoin treasury shop – after a hum-drum but successful liftoff as ETF shop and classic RIA – could also prove truly defining.
Last May, Strive raised $750 million – it has since raised more – to kick off its Bitcoin treasury. Strive also added its own dose of unusual financial engineering to the Saylor model.
It rolled up ‘distressed’ companies to raise funds from an arbitrage between a company's share price and its net cash holdings. See: Vivek Ramaswamy jumps on the next new thing, a Bitcoin treasury.
“Funding secured & ahead of schedule … nothing stops this train,” Strive Chief Financial Officer Ben Pham stated in a pair of late May and early June “X” posts.
Nothing, perhaps, except a major slump in Bitcoin's price.
The firm's Bitcoin bet has, for the time being, saddled it with enormous unrealized losses.
On Jan. 29 alone, Strive bought 334 Bitcoin, then priced at $88,228 each, or $29.5 million, taking its Bitcoin holdings to 13,132 BTC, then valued at $1.17 billion.
Today, 334 Bitcoin would cost $23.2 million, or $6.3 million less.
Nose bleed
Strive shares (ASST) nosedived 9.5% today to $9.18, cutting its market cap to $572 million. The stock is down 96% from the 52-week high of $268.
The off-the-cliff price drop in crypto also wiped 44% off Bitcoin's $2.46 trillion market capitalization, which now stands at $1.38 trillion, according to Coinmarketcap data.
Launched in 2022, Strive began life as an “anti-ESG” asset manager. Then, “MAGA” investment from backers like Paypal co-founder and billionaire Peter Thiel, and vice president J.D. Vance injected $30 million. See: JD Vance joins MAGA backers at Ramaswamy start-up.
It announced a reverse merger with Asset Entities Inc. in May 7, 2025, to become a publicly traded Bitcoin-focused asset manager. The move marked a sea change in strategy.
It then went all-in on crypto, when it ditched one of its key means to potentially diversify its revenues away from a dependence on any one market – the RIA it spent $4 million developing
Strive also spun off its RIA as “Thryve,” a completely independent firm last October. See: Strive's RIA spins out as 'Thryve' – minus Vivek.
Ramaswamy handed Strive day-to-day duties to CEO Matt Cole soon after launching his campaign for president in Feb. 2023. He dropped out in January 2024, and has since announced a run for Ohio governor with Trump's blessing.
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