On April 8, 2025, Scott Melker, the host of the podcast The Wolf of All Streets, made a striking assertion in his daily newsletter, The Wolf Den. He labeled Michael Saylor, the co-founder of Strategy and notable for his significant Bitcoin investments, as one of the most ineffective traders in modern history. Melker offered his reasoning behind this opinion, but is he genuinely serious?
Why does Melker consider Saylor a poor trader?
Melker assigned Saylor’s trading skills a dismal rating primarily to emphasize a broader issue concerning the fundamental challenge of timing the market. But let’s break it down further.
As of April 8, Strategy possesses over 528,000 bitcoins. Melker examined the prices at which Strategy made its major BTC acquisitions and determined that approximately 20% of these purchases occurred at prices exceeding $90,000. The average purchase price over more than 4.5 years stands at $67,400, which is only $10,000 lower than the current rate.
According to Melker, Saylor only purchased during dips on three of the nine Bitcoin buying occasions in 2025, with the remaining purchases made at elevated prices. Additionally, it’s noted that in one of these three instances of lower BTC buying, Saylor bought “only” 130 bitcoins, a stark contrast to his usual acquisitions of thousands of coins at a time. Consequently, this approach didn’t yield substantial savings for Strategy.
These observations portray Saylor as someone making elementary errors when deciding to acquire more Bitcoin. Furthermore, it suggests that over 4.5 years, the growth of Strategy’s investment isn’t as impressive as anticipated, particularly since these bitcoins were purchased using the expansion of Strategy’s debt—raising questions about Saylor’s decision-making abilities.
A different perspective
However, those who have listened to Saylor’s speeches and interviews recognize that his perspective on Bitcoin doesn’t hinge on its USD price at the time of purchase. Saylor is significantly more focused on accumulating as much Bitcoin as possible. For him, the critical metric is not the dollar amount but the percentage of the total supply achieved. Regarding price, Saylor often asserts that one bitcoin is equivalent to one bitcoin.
In a speech titled ‘Bitcoin for America,’ he reminded listeners that the United States acquired 78% of its land for just $40 million. He likens buying Bitcoin to purchasing American territory at a small cost. To Saylor, any present price of Bitcoin seems low. He emphasizes that we are always ahead of the curve and even encourages the U.S. government to secure up to 25% of the total BTC supply to maintain its global leadership in Bitcoin. For context, in February 2025, Saylor projected that by 2045, the price of BTC could soar to around $13 million per unit.
Melker understands Saylor’s rationale quite well and continues his article by stating that Saylor shouldn’t be judged on his market-timing abilities. Melker boldly argues that accurately timing the market is virtually impossible (unless you’re Warren Buffett). He suggests that while we cannot perfectly time the market, we should recognize that today’s BTC price remains relatively low. Saylor, focused on long-term value, is not preoccupied with short-term gains. Melker notes:
There has never been a better time for companies to step into the Bitcoin space at a cost basis close to Strategy’s. While competing with them in scale may not happen soon, the chance to accumulate BTC near Saylor’s average is a rare opportunity from the market.
While it’s clear that Saylor doesn’t focus on short-term trends, Strategy does make Bitcoin investments at prices that are very real. As Melker pointed out, these were often made during what could be considered “wrong” market moments. Experts believe that although Strategy may be experiencing some financial setbacks, it is unlikely to face bankruptcy. For instance, the CEO of Crypto Quant, Ki Young Ju, remarked that Strategy would only be at risk of bankruptcy if an asteroid were to hit Earth.
He clarified that bankruptcy could only occur if BTC prices fall to $16,000 and Strategy remains inactive. Even amidst current global economic instability, it’s hard to envision Bitcoin dipping that low again. The last time Bitcoin dropped to $16,000 was in early January 2023. Melker points out that if Saylor were serious about market timing, he could consult with experts like Ray Dalio or Ken Griffin, acquiring a team of analysts and researchers to optimize his strategies. In essence, The Wolf of All Streets humorously suggests that Saylor might be one of the weakest traders of our times.