Jason Calacanis, one of the best-known angel investors, recently questioned Saylor's strategy. 

Calacanis, who is known for placing early bets on such companies as Uber and Robinhood, said that the company was "tipping into memestock madness." "Why would anyone pay $1 for 80 or 90 cents worth of Bitcoin?" he asked. 

In response, Saylor argued that Bitcoin "represents the digital transformation of capital." By issuing fixed income and equity backed by the largest cryptocurrency, MicroStrategy is accelerating this transformation.

However, Calacanis does not seem to be swayed by the explanation, noting that the company's strategy appears to be too complicated to explain in simpler terms. 

As reported by U.Today, MicroStrategy announced a record-shattering $5.4 billion Bitcoin purchase on Monday. 

On Monday, the Bitcoin price plunged to as low as $92,775. Bitcoin's plunge coincided with a corrective pullback recorded by gold. 

Calacanis, like many other analysts, is curious to know what's going to happen to the company if the Bitcoin price suffers a major crash. `'Hey, if Bitcoin goes to $1m he’s a genius and if it goes back down to 30-40k, what happens?" he asked. 

Lionel Laurent, a Bloomberg Opinion columnist, mentioned a severe Bitcoin drop as a major risk faced by the company. 

In 2018, Calacanis predicted that the flagship cryptocurrency had a 70% chance of crashing to zero. Now, such a dramatic scenario has less than a 5% probability, according to the prominent angel investor.