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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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Ethereum exits: Investors depart its ETFs and the Ethereum Foundation shrinks (again)

On Monday, two researchers announced they were leaving the nonprofit organization tasked with supporting the second-largest blockchain network, adding to a growing exodus from the Ethereum Foundation.

Carl Beek, who helped architect the early design of ethereum’s beacon chain, will end his seven-year tenure with the foundation at the end of the month, while research scientist Julian Ma, who focused on product and growth work, has also decided to leave after four years.

Beek and Ma deepen a recent bout of turnover. Last week, the foundation said in a blog post that lead developers Barnabé Monnot and Tim Beiko are moving on from the organization. In April, Josh Stark, who was on the Ethereum Foundation leadership team for five years, left, as did Trent Van Epps, who organized Protocol Guild, which provides funding to core developers. The string of departures has raised concerns among those in the ecosystem.

“There have been a lot of disagreements about where ETH should move, whether from an issuance or architectural standpoint,” Laurens Fraussen, a research analyst at data provider Kaiko, told Sherwood News. “I’d assume the people leaving are either looking for greener pastures or don’t agree with the way the EF is being run.”

The foundation exodus comes as investors exit from ethereum ETFs. The investment vehicles saw more than $86 million in outflows on Monday, making six straight days of outflows, the longest streak since March, according to SoSoValue.

Meanwhile, an address identified as Galaxy Digital has a $2.3 million short position on ethereum using 20x leverage on Hyperliquid, data from blockchain analytics firm Nansen shows. The price of ethereum stands just under $2,110 as of 12:10 p.m. ET. With an entry point of $2,203, the firm has an unrealized gain of $102,000.

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Ethereum falls faster than bitcoin as crypto tape turns red

The second-largest cryptocurrency is nearing the $2,100 mark, declining more than 9% in the last seven days, a steeper decrease than its older sibling bitcoin, which is also suffering.

Ethereum ETFs have had five consecutive days of outflows combining for $255 million, data from SoSoValue shows.

Meanwhile, Goldman Sachs and Harvard University both filed 13Fs showing each pulled back their exposure to ethereum.

Goldman now holds nearly $178 million in BlackRocks iShares Ethereum Trust ETF, down from $679 million, according to its latest 13F filing. It also exited its $394 million position in the Fidelity Ethereum Fund as well as a smaller position in ETHZilla, while adding $67 million of the iShares Staked Ethereum Trust ETF.

Harvard completely trimmed its ethereum exposure. The endowment did not report any ethereum ETF holdings in its latest 13F filing, submitted Friday, but showed an $86.8 million position in BlackRocks iShares Ethereum Trust ETF in its previous 13F filing in February.

But ethereum bulls remain: treasury behemoth BitMine Immersion Technologies continued its accumlation of ethereum, albeit at a slower pace. Over the past week, we acquired 71,672 ETH, Chairman Tom Lee said in a Monday press release. We view the recent pullback of ETH to below $2,200 as an attractive opportunity. The firms unrealized loss now exceeds more than $7.3 billion.

Traders aren’t so bullish: prediction market-implied odds of ethereum breaking $2,500 in May stand at just 7%, a sharp drop-off from a week ago, when the probability was at 57%.

(Event contracts are offered through Robinhood Derivatives, LLC — probabilities referenced or sourced from KalshiEx LLC or ForecastEx LLC.)

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