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

9/24/24 9:32AM

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.

Sage D. Young16h

Solana drops to price not seen since February as Drift exploit rattles sentiment

Solana has historically seen its largest price declines on Thursdays, and today is no exemption as the crypto industry reels from the over $270 million exploit that occurred yesterday on Drift, a trading venue native to the solana blockchain.

The price of solana has decreased 5.5% to around $78, a level not seen since February, data from CoinGecko shows.

Drift was one of the largest protocols on the solana network by total value locked, which now sits at nearly $245 million. The total value locked on solana has shrunk by nearly $1 billion since the incident, per DefiLlama.

Exploit likely involved from social engineering

The attack, which has turned into a wider contagion event, is unsettling for those in the industry. It did not come from a bug in the protocol’s smart contracts or programs. “Humans remain the bottleneck,” Mert Mumtaz, cofounder and CEO of solana development firm Helius, said in response to the incident.

The exploit involved unauthorized transaction approvals likely facilitated through social engineering. The sophisticated operation “appears to have involved multi-week preparation and staged execution,” the team said on Thursday.

Omer Goldberg, founder of risk management firm Chaos Labs, added, “The DeFi [decentralized finance] ecosystem continues to grow in scale, but not in operational security.”

“Protocols now have custody of hundreds of millions in user funds while depending on admin key setups that would be considered unacceptable in TradFi for a fraction of that AUM [assets under management],” Goldberg wrote on X.

“Most hacks come down to the simple act of one clicking a link they shouldn’t have clicked. These are picking up in pace, be extra cautious clicking any link or file,” continued Helius’ Mumtaz.

Yaël Bizouati-Kennedy

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Optimism around bitcoin’s trajectory is fading following Trump’s address, as whales continue to offload

Bitcoin has been stuck in a narrow range for the past few weeks, seemingly incapable of breaking in either direction.

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$270M

Sage D. Young4/1/26

April 1 is known as a day for funny pranks. However, a popular trading venue on the solana blockchain, Drift, is suffering from an ongoing exploit today, on-chain data shows.

“Drift Protocol is experiencing an active attack. Deposits and withdrawals have been suspended. We are coordinating with multiple security firms, bridges, and exchanges to contain the incident. This is not an April Fools joke,” the team said on social media at 2:58 p.m. ET.

TheBlock reported the exploit is at least $200 million, while blockchain sleuth Lookonchain estimates the figure is $270 million. It could be even more. At this range, the Wednesday hack is among the largest ever, according to the exploits ranking dashboard from Rekt.

Drift’s exploit is concerning for those within the crypto industry. Solana treasury firm DeFi Development Corp. allocates a portion of its balance to on-chain strategies to generate yield, including Drift, though the firm announced it had no exposure to the protocol and “was not impacted by an alleged exploit affecting the platform,” per its press release.

Drift also provides to qualified users sACRED, a derivative token of a tokenized feeder fund that is linked to Apollo Global Management Inc.’s traditional Diversified Credit Fund.

Sage D. Young

4/1/26

Google Research: Quantum computers a “serious threat” to 6.7 million bitcoin, including Satoshi’s coins

“Their fast-clock architecture could crack a private key in 9 minutes, while bitcoin blocks take 10 minutes on average. That changes the threat model entirely.”

Yaël Bizouati-Kennedy

Oof

3/31/26

Bitcoin treasury firm Nakamoto bought high and sold much, much lower as bitcoin suffers another bad quarter

Bitcoin is on track to close the first quarter of 2026 down more than 24%.

MicroStrategy is bad at timing the market

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Solana drops to price not seen since February as Drift exploit rattles sentiment

Exploit likely involved from social engineering

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