Saylor himself said multiple times over the last few years MSTR was a dead company. It wasn’t innovating and he was trying to figure out how not to have to wind it down or just let it die a slow death or sell.

His earliest mentions were when framing around what he noticed with FANG and he saw it again with Bitcoin so he bought it as a means to save the company… I.e. “dead in the water”. 

 yes his company was going to have a hard time competing with Microsoft.  But he had decades of runway left.  Saying it was a dead company is a massive exaggeration he uses to justify his bitcoin purchases.  It was highly profitable when he started buying Bitcoin and still is today based on it's business-intel software