Their biggest backers include an unlikely group of insurance companies, mutual funds and other usually conservative bond investors. The software company turned itself into a bitcoin whale and now owns some $48 billion of the cryptocurrency.

MicroStrategy's bitcoin-backed bonds attract conservative investors despite high risks. With shares surging and critics skeptical, is the bet sustainable?

MicroStrategy may face federal income tax obligations on its significant unrealized gains, which currently exceed $19.3 billion.

MicroStrategy’s $47B Bitcoin holdings face tax risks as U.S. laws evolve, introducing a 15% levy on unrealized gains.