Masayoshi Son invested in the digital currency in late 2017, around the time it surged to its record high of US$20,000. He sold his shares in early 2018 as the currency was collapsing. Bitcoin is currently valued at around $7,500. (Wall Street Journal)

Talking point: The Japanese businessman is no stranger to risky investments—like his US$20 million early investment in Alibaba that turned into US$100 billion. While those bets typically pay off, Son’s track-record isn’t flawless. In the mid-1990s, Softbank invested US$2.1 billion in Ziff Davis, a computer magazine publisher, and US$1.5 billion in semiconductor-maker Kingston Technology, both of which the fund sold at significant losses three years later. Son’s bad investments are exceptions in his portfolios—both personally and as CEO of Softbank. Under Son, the world’s biggest venture capital firm holds substantial stakes in blockbuster tech companies Uber, Flipkart and WeWork. Still, that a sophisticated investor like Son can lose a fortune in Bitcoin underscores the powerful allure and risk surrounding the speculative cryptocurrency.