Prominent American angel investor and entrepreneur Jason Calacanis has predicted that $180 would be a "generous" price target for business intelligence firm Strategy (MSTR) based on the level of risk of debt load. The 54-year-old entrepreneur has added that the stock is in "uncharted territory." "No one has ever bought imaginary money with massive debt, nor has anyone cornered the market on Bitcoin at this level," Calacanis said. As reported by U.Today, Calacanis recently predicted that Strategy's Bitcoin bet would fail this year, arguing that the company should be trading at a discount to net asset value (NAV). The shares of MicroStrategy were down nearly 6% on Monday. The company's market cap has now shrunk to just $71 billion. MSTR is now down by another 4% in pre-market trading. Meanwhile, the price of Bitcoin has now plunged below the $90,000 level, reaching an intraday low of $88,614. Meanwhile, the company is on the cusp of surpassing 500,000 BTC in total holdings. Following its most recent $2 billion purchase, its average purchasing price now stands at $66,357.