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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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Hyperliquid reclaims all-time high

HYPE, the native token powering perpetuals exchange Hyperliquid and its underlying blockchain, rebounded to reclaim its all-time high previously set at the start of the month.

Treasury firms Hyperliquid Strategies and Hyperion DeFi have also rallied as the token increased double digits in the last 24 hours to trade as high as $76.70, rising past its record price set nearly two weeks ago, according to CoinGecko. In the interim between all-time highs, HYPE pulled back to around $53.

The token has several tailwinds, the first coming from ETF flows. Since their inception in May, HYPE ETFs have yet to record negative weekly outflows, posting a cumulative total net inflow of $171.8 million, per SoSoValue.

The second comes from Hyperliquid spending basically everything it earns in fees to buy HYPE, a mechanism embedded into the protocol’s codebase.

The venue’s buyback funding mechanism is set to add a new source of yield. Validators of the network activated “AQAv2,” which means stablecoin deployers will share about 90% of reserve yield revenue on their supply within the protocol.

Around $6.1 billion of Circle’s USDC resides in Hyperliquid, per DefiLlama. Accrual begins on August 26 and the first payment is made on October 3, the network announced in its Discord channel last week.

A substantial amount of capital is riding on different positions of HYPE. In total, a move down to under $53 would result in the liquidation nearly 1.8 million HYPE worth of leveraged long positions on the on-chain perps venue, or $131.7 million, data from CoinGlass shows. For the upside, a climb above $100 results in the liquidation of more than 3 million worth of leveraged HYPE short positions, or $221.5 million.

HYPE’s rebound to all-time high comes after Michael Selig, chair of the Commodity Futures Trading Commission, defended his agency’s decision to approve regulated perpetuals, or futures contracts without expiration dates, CNBC reported on Monday.

Last month, the CFTC approved bitcoin perpetual futures trading in the US through regulated prediction markets firm Kalshi and an affiliate of centralized exchange Coinbase.

“Perps are highly likely to become lightly regulated and thus approved in the US,” said David Pakman, head of venture investments at CoinFund.

“We expect to see perps for many different types of assets, from commodities to equities,” Pakman told Sherwood News.

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Crypto market snaps back as sentiment lifts, with altcoins from ethereum to XRP soaring

The market capitalization of the crypto industry has jumped around $83.2 billion in the last 24 hours, with privacy-focused token Zcash and worldcoin, the native cryptocurrency of the network backed by OpenAI CEO Sam Altman, leading market gains, jumping over 22%.

But the last 24 hours have been good across the board:

Investors have been eager to see some positive signs around the Iranian conflict ending, coupled with hopeful outlooks around the CLARITY act, both breathing some life into assets, Kairos Research cofounder Ian Unsworth told Sherwood News.

Simon Shockey, a crypto strategist at crypto wallet infrastructure firm Privy, said the upswing stems from several things converging. He pointed to how alt markets broadly were very oversold following the bug found in Zcash that shook confidence.

Friday, Zcash founder Zooko Wilcox said Anthropic didn’t find any more serious bugs with the Zcash protocol after Shielded Labs requested the AI firm run a security audit of the network with Mythos.

Shockey added that the pool of willing sellers has dwindled. Even if structurally, AI is a much more compelling and asymmetric bet in the eyes of allocators, many of these crypto assets have simply run out of marginal sellers despite some shorter-term narrative-driven pumps. The only people left to sell at this point are the teams themselves and VCs.

Net-net: oversold conditions plus exhausted seller bases plus a macro backdrop thats stabilized equals a snapback, especially in names that have real usage or community conviction behind them,” Shockey told Sherwood.

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