#MichaelSaylorBTC
The Wolf of All Streets: “Michael Saylor might be one of the worst traders in modern history.” Is he serious?
Why does Melker say Saylor is a bad trader?
Scott Melker, host of The Wolf of All Streets podcast, criticized Michael Saylor in his newsletter, calling him “one of the worst traders in modern history.” He analyzed Saylor’s Bitcoin buying strategy, noting that Strategy bought over 528,000 BTC with an average price of $67,400—only slightly lower than the current price. About 20% of those purchases were above $90,000. In 2025 alone, only three out of nine buys were at low points, and even then, one was just 130 BTC. Melker suggests this reflects poor market timing.
Plot twist
However, Melker acknowledges that Saylor doesn’t care about short-term market timing. His focus is on accumulating as much Bitcoin as possible, valuing it in BTC terms rather than USD. He believes any BTC price today is still low and compares buying Bitcoin to buying U.S. land for pennies. Saylor predicts BTC could hit $13 million by 2045 and urges the U.S. to secure 25% of the total BTC supply.
Melker ultimately admits timing the market is nearly impossible and praises Saylor’s long-term vision. He argues that current prices still offer companies a rare chance to invest near Saylor’s cost basis.
While Saylor’s timing might seem flawed, his strategy isn’t likely to lead to bankruptcy unless Bitcoin crashes to $16,000—a scenario experts find highly unlikely. Melker’s bold claim is more tongue-in-cheek, highlighting the difference between trading and long-term investing.