Scott melker Criticizes Michael Saylor’s Bitcoin Strategy
on April 8, 2025, Scott Melker, host of The Wolf of All Streets podcast, criticized Michael Saylor, co-founder of Strategy, in his newsletter. melker labeled Saylor as one of the worst traders in modern history. But why?
Melker’s critique stems from Saylor’s Bitcoin purchasing strategy. Strategy holds over 528,000 bitcoins.Melker analyzed the purchase prices and found that 20% were bought above $90,000, while the average price over 4.5 years was $67,400. Saylor only bought at a dip three out of nine times in 2025, with one instance being just 130 bitcoins.
These findings suggest Saylor makes rookie mistakes. Though, Saylor’s approach is different. He focuses on acquiring as much Bitcoin as possible, not timing the market. Saylor believes any Bitcoin price is low and urges the U.S.government to acquire up to 25% of the total supply.
Melker understands Saylor’s logic. He claims timing the market is nearly unachievable. Saylor is interested in long-term value. Melker writes, “There’s never been a better moment for companies to enter the Bitcoin arena.”
While Strategy may lose some capital, experts believe bankruptcy is unlikely. Crypto Quant CEO, Ki Young Ju, said Strategy would only go bankrupt if Bitcoin drops to $16,000 and no action is taken. This scenario is highly improbable.
Melker’s critique seems to mock the idea of timing the market. Saylor’s strategy, while not perfect, focuses on long-term growth.
