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Michael Saylor, MicroStrategy founder and former CEO and current executive chairman.
MicroStrategy’s Michael Saylor (Joe Raedle/Getty Images)
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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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XRP treasury firm trend grows as Evernorth, backed by Ripple Labs, enters the arena

The fifth-largest cryptocurrency by market cap, XRP, is getting a new treasury firm: Evernorth.

The firm will list on the Nasdaq and expects to raise over $1 billion in gross proceeds from SBI, Ripple Labs, Pantera Capital, Kraken, and GSR, according to a press release. Chris Larsen, cofounder and executive chairman of Ripple, also announced investing 50 million XRP tokens worth $124.5 million. Net proceeds are dedicated for open-market acquisitions of XRP.

Evernorth joins a number of firms stockpiling XRP, such as VivoPower International, Trident Digital Tech Holdings, and Webus

The announcement comes during a fragile period for crypto markets, but the latest news has boosted XRP’s price and the asset is back to flat over the last seven days.

$1.2B

Crypto liquidations reached $1.2 billion in the past 24 hours, according to CoinGlass data, as bitcoin continued its downward trajectory. Bitcoin suffered $458.24 million in liquidations, with the bulk of them — over $334 million — in long positions. Meanwhile, the second-biggest crypto, ethereum, saw the second-biggest figure for liquidations yesterday, with $278 million.

Bitcoin slipped as far as $103,856 early Friday morning, its lowest level since July, and is down 13% in the past seven days. The sell-off dragged the total crypto market cap down to $3.67 trillion, down 5.5%. Underscoring the market anxiety, CoinMarketCap’s fear and greed index is now at 28.

Bitcoin ETFs also suffered, registering $536 million in outflows on Thursday. The Ark 21 Shares Bitcoin ETF took the biggest hit, with $275.15 million in outflows. Since Monday, bitcoin ETFs have seen $864.5 million in outflows. 

Maja Vujinovic, CEO and cofounder of digital assets at FG Nexus, told Sherwood News that bitcoin’s slump looks like a classic risk-off chain reaction.

“Credit jitters and trade tensions pushed money into gold at record highs while leveraged crypto longs were forced to unwind. Once the liquidations exhaust and policy fog clears, the same macro buyers chasing safety today are likely to hunt value in BTC again,” Vujinovic said. 

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