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Michael Saylor, MicroStrategy founder and former CEO and current executive chairman.
MicroStrategy’s Michael Saylor (Joe Raedle/Getty Images)
Weird Money

MicroStrategy is bad at timing the market

Less than 30% of MicroStrategy's bitcoin investments, in terms of dollars spent, have happened at below $40,000 per coin.

Jack Raines

In case you missed it: MicroStrategy just bought another 7,420 bitcoin for $458 million, bringing the company's total holdings to 252,200 bitcoin worth approximately $9.9 billion, with an average cost of $39,266 per coin.

While bitcoin has smoked the stock market since MicroStrategy made its first bitcoin investment in August 2020, gaining 430% vs. an 82% gain for the Nasdaq 100 index (a 5.25x outperformance), the performance of MicroStrategy's holdings has been less impressive, only gaining a cumulative ~62%.

The reason for MicroStrategy's relative underperformance: inopportune investment timing. Real-time bitcoin dashboard Bitbo has tracked all of MicroStrategy's bitcoin purchases, showing the cash spent and number of coins purchased in each investment, and we can use those values to calculate the company's average price paid per coin each time.

Since MicroStrategy made its first bitcoin investment, there have been three multi-month periods in which bitcoin traded below $40,000: August 2020 through early February 2021, May 2021 through July 2021, and May 2022 through November 2023.

MicroStrategy only bought $2.7 billion of its $9.9 billion in bitcoin during these windows, which are highlighted below in red:

The other ~$7 billion, or more than 70%, of its bitcoin purchases occurred near market highs. This is despite bitcoin trading below $40,000 in 59% of days since MSTR made its first bitcoin investment.

MicroStrategy didn't respond to a request for comment.

While MicroStrategy founder Michael Saylor has long been one of bitcoin's biggest proponents, saying it was "absolutely" a buying opportunity when the cryptocurrency's price fell below $20,000 in 2022, even he was gun-shy when prices were hovering at multi-year lows.

Even for the biggest bulls, investing during bear markets is easier said than done.

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Strategy was responsible for as much as 97.5% of all bitcoin buys from public companies in January

Bitcoin treasury company Strategy accounted for as much as 97.5% of all bitcoin purchases in January made by public companies, “single‑handedly bringing sector‑wide buying back to levels last seen in late summer,” according to a Thursday research report from data analytics firm Bitcoin Treasuries.

Strategy ended last month with 712,647 BTC on its balance sheet, or $47.9 billion, buying 40,150 BTC in January.

MSTR, Strategy’s class A common stock, is trading under the $122 level, while the price of bitcoin sits at the $67,800 mark, both down around 20% since the start of the year.

Meanwhile, asset manager Geode Capital Management boosted its exposure to Strategy and also bought into Trump-backed American Bitcoin, a 13F SEC filing on Monday shows. 

The investment firm, which has over $1 trillion in assets under management, added 175,343 shares of Strategy’s class A common stock since the previous quarter, bringing its total MSTR share count to 3.9 million, worth $477.4 million.

Geode also acquired 1.6 million shares of American Bitcoin, worth $1.8 million, a change from last quarter when the firm didn’t have a stake in the Trump-backed bitcoin treasury firm.

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Crypto platform BlockFills halts withdrawals

Crypto lending and trading platform BlockFills has halted customer withdrawals amid the current market downturn, according to The Wall Street Journal, a development that recalls the broader meltdown of the 2022 crypto bear market, albeit on a much smaller scale.

This morning, bitcoin dipped below $67,000, and it was hovering around that level midafternoon, struggling to recover from last week’s bloodbath.

“BlockFills is working tirelessly to bring this matter to a conclusion and will continue to regularly update our clients as developments warrant,” a spokesperson told the WSJ.

The Chicago-based, Susquehanna-backed company’s “suspension was put in place last week but remains in effect,” the Financial Times reported Wednesday.

The company, which serves institutional clients, handled $60 billion in trading volume in 2025, per the FT. 

Ethan Buchman, CEO of Cycles, told Sherwood News that BlockFills halting withdrawals is a harsh reminder that, despite changes since the panic of 2022, the crypto industry still has a long way to go in developing off-chain risk infrastructure with stronger standards for underwriting, clearing, and settlement.

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Ethereum ETF holders still “diamond-handing” despite hurting more than their bitcoin counterparts

Holders of spot ethereum ETFs are in more pain than bitcoin investors. 

The price of ethereum stands around $1,940 as of Wednesday morning, representing about a 45% drop from $3,500, the average cost basis of spot ethereum ETF holders, according to Bloomberg ETF analyst James Seyffart. 

The losses of ethereum ETF holders are larger than bitcoin fund investors based on available data. Bitcoin is trading at $68,822, representing an 18% slide from the the cost basis for all its ETFs of $83,983, data from Glassnode shows

While facing larger losses than their bitcoin ETF peers, the vast majority of ethereum ETF buyers have stayed put. “The net inflows into the ETH ETFs have gone from about $15 billion down below $12 billion. This is a much worse selloff than the Bitcoin ETFs on a relative basis, but still fairly decent diamond hands in grand scheme (for now),” Seyffart said on Tuesday on X.

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