The Wolf of All Streets: “Michael Saylor might be one of the worst traders in modern history.” Is he serious?

On Apr 8, 2025, Scott Melker, a host of the podcast The Wolf of All Streets, made a bold claim in his daily newsletter called The Wolf Den. He called the co-founder of Strategy, Michael Saylor, known for his multi-million Bitcoin purchases, one of the worst traders in modern history. Melker provided reasoning for this, but… is he serious?

Why does Melker say Saylor is a bad trader?

Actually, Melker gave Saylor’s trading talents such a low grade only to outline a bigger topic of fundamental inability to time the market. But first things first.

As of Apr 8, Strategy holds over 528k bitcoins. Melker analyzed the prices at which Strategy was doing its massive BTC purchases and concluded that around 20% of these purchases were made at a price above $90.000, while the average price during the over 4.5 years of BTC purchases is $67.400, only $10.000 below the current price. 

Melker outlines that Saylor only bought dip on three of nine instances of BTC purchases in 2025, while the rest of the purchases were made at a high price. More than that, Melker notes that out of these three instances of low BTC buying, one example is buying “only” 130 bitcoins when Saylor usually buys thousands of bitcoins at once. So, this time, it didn’t save Strategy much money.

All of these findings paint Saylor as a person making rookie mistakes when deciding when to buy another load of Bitcoin. Also, it may seem that in 4.5+ years, Strategy’s investment grew not that much, or at least it doesn’t match the hype. Given that bitcoins are bought via expanding Strategy’s debt, it may seem that Saylor is clueless about what he is doing. 

Plot twist

However, everyone who has seen Saylor’s speeches and interviews knows that his approach to Bitcoin doesn’t factor into the USD price at the moment of purchase. Saylor is much more interested in acquiring as much Bitcoin as possible, meaning that one of the most important metrics for him is not the price expressed in the USD equivalent, but the percentage of the total supply acquired. As for the price, Saylor will only state that one bitcoin costs one bitcoin.

In his speech dubbed ‘Bitcoin for America,’ he reminded his audience that 78% of the United States was purchased for $40 million. He compares buying Bitcoin to buying American lands for dimes. For Saylor, these days, any price of Bitcoin is low. We are always early. He urges the U.S. government to acquire up to 25% of the total supply of BTC to preserve global leadership in the Bitcoin race. Just to give you a reference: in February 2025, Saylor said that by 2045, the BTC price will reach around $13 million per unit.

Melker understands Saylor’s logic very well, and he continues his article by saying that we shouldn’t judge Saylor by his ability to time the market. Melker boldly claims that it is impossible to time the market at all (if you are not Warren Buffett). According to what Melker writes, we can time the market to the extent to which we should recognize that the current BTC price is still low. Saylor is interested in long-term value, not short-term. Melker writes:

There’s never been a better moment for companies to enter the Bitcoin arena at a cost basis that’s not far from Strategy’s. While matching them in scale is unlikely anytime soon, the opportunity to accumulate BTC near Saylor’s average is a rare gift from the market gods.

While it’s understood that Saylor is not interested in short-term effects, Strategy invests money in Bitcoin at certain prices that are real. And, as Melker outlined, on many occasions, it was made in the “wrong” moments. Experts believe that although Strategy is losing some fragments of its capital, the company is not likely to face bankruptcy. For instance, the Crypto Quant CEO, Ki Young Ju, said that the Strategy will go bankrupt only if an asteroid hits the Earth.

He specified that only if the BTC price drops to $16.000 and Strategy doesn’t take action, it may go bankrupt. Even amidst the current global economic turmoil, it is really hard to imagine that Bitcoin could drop that dip. The last time Bitcoin cost $16.000 was in early January 2023. Melker notes that if Saylor wanted to time the market better, “he could call up Ray Dalio or Ken Griffin and have a team of quants and researchers running fresh models for him by dinner.” So it turns out The Wolf of All Streets mocks us by saying that Saylor is one of the worst traders of our times.