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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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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 mid-afternoon, 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, according to 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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Meme coins have lost all their 2026 gains and continue to dive

Despite having an early lead in year-to-date gains, meme coins have round-tripped and bled even more. 

For example, frog-based token pepe was up 75% in the first four days of January, but is now about 8% lower than where it started the year. Dogecoin, shiba inu, bonk, pengu, dogwifhat, and trump tell a similar story: posting a positive gain and then slumping into the red. 

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The year-to-date price performances of the top meme coins by market capitalization (TradingView)

Meme coins, cryptocurrencies based on internet jokes that are often critiqued for lacking utility, are reflexive: they can lead gains during bullish market conditions, but see sharper declines in bearish ones. The entire category of meme coins has shed 25.8% of its valuation in the year so far, data from blockchain analytics firm Artemis shows.

The price action of meme coins comes amid a broader market decline that saw bitcoin drop to $63,000 last week as its peers revisited cycle lows

“The market has, in large, been bleeding, whether major, altcoin, or meme,” according to Nicolai Søndergaard, research analyst at on-chain data firm Nansen. “It is not surprising to me to see that larger memes as well have been trending down.”

He told Sherwood News, “If we also consider the fact that there are less active wallets now compared to a few months ago, it also makes sense that larger ‘household’ memes would decline as money shifts around to the next shiny thing.”

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