Saylor: Named one of the least successful traders in modern history by WoAS
On April 8, 2025, Scott Melker, host of the podcast The Wolf of All Streets, made a striking claim in his daily newsletter, The Wolf Den. He declared Michael Saylor, co-founder of Strategy and renowned for his extensive Bitcoin investments, one of the worst traders in modern history. Melker elaborated on his reasoning, but… is he for real?
Why is Melker so critical of Saylor’s trading skills?
In fact, Melker assigned Saylor a low rating as a trader primarily to highlight a broader issue regarding the fundamental challenge of market timing. However, let’s start with some context.
As of April 8, Strategy possesses over 528k bitcoins. Melker examined the prices at which Strategy made its large-scale BTC purchases and found that approximately 20% of these acquisitions were executed above $90,000, while the average price over the last 4.5 years of purchases stands at $67,400, just $10,000 shy of the current price.
Melker points out that Saylor only capitalized on the dips during three of nine Bitcoin purchase instances in 2025, with the remaining purchases occurring at higher prices. Additionally, Melker notes that in these three instances of buying the dip, one example involved the purchase of “only” 130 bitcoins, a far cry from Saylor’s usual purchases of thousands at a time. This minimal purchase did not significantly benefit Strategy in terms of cost savings.
These observations portray Saylor as making rookie mistakes in determining the right moments to acquire additional Bitcoin. Furthermore, it appears that in over 4.5 years, Strategy’s investment growth has not been as substantial as the surrounding hype suggests. Given that bitcoins are acquired by increasing Strategy’s debt, it may come off as though Saylor lacks a solid strategy.
A twist in the story
However, anyone familiar with Saylor’s speeches and interviews understands that his approach to Bitcoin does not hinge on the USD price at the time of purchase. Saylor is far more focused on accumulating as much Bitcoin as possible, meaning that one of his key metrics is not the USD price but the percentage of total supply acquired. Regarding price, Saylor simply states that one bitcoin equals one bitcoin.
During his talk titled ‘Bitcoin for America,’ he reminded his audience that 78% of the United States was purchased for just $40 million. He likens investing in Bitcoin to buying American real estate for pennies. For Saylor, any Bitcoin price today feels low. He believes that we are essentially early adopters. He also advocates for the U.S. government to acquire up to 25% of the total Bitcoin supply in order to maintain its leadership in the global Bitcoin landscape. To provide context, in February 2025, Saylor predicted that by 2045, Bitcoin could be valued around $13 million per unit.
Melker comprehends Saylor’s rationale quite well, continuing his article by arguing that Saylor’s market timing should not be a basis for judgment. Melker confidently asserts that market timing is generally unattainable (unless you’re Warren Buffett). He writes that we might understand market timing to the extent that the current Bitcoin price remains low. Saylor’s focus is on long-term value rather than short-term gains. Melker states:
There’s never been a more opportune moment for companies to enter the Bitcoin market at a cost basis close to that of Strategy. While replicating their scale might take time, the chance to accumulate Bitcoin near Saylor’s average is a rare gift from the market.
While it’s clear that Saylor is not focused on short-term impacts, Strategy is making real investments in Bitcoin at specific prices. However, as Melker noted, many of these were executed at “wrong” moments. Experts suggest that even if Strategy is experiencing some capital erosion, bankruptcy is unlikely. For example, Crypto Quant CEO Ki Young Ju stated that the Strategy would only face bankruptcy if an asteroid struck the Earth.
He noted that only if the Bitcoin price falls to $16,000 and Strategy remains inactive might it face bankruptcy. Despite the current global economic challenges, it seems highly improbable that Bitcoin could drop to that level. The last occurrence of Bitcoin priced at $16,000 was in early January 2023. Melker suggests that if Saylor wanted to enhance his market timing skills, “he could contact Ray Dalio or Ken Griffin and have a team of analysts and researchers providing him fresh models in no time.” Thus, The Wolf of All Streets playfully critiques the notion that Saylor is one of our era’s worst traders.