Masayoshi Son may be about to pull off his signature move – doubling down. Having already invested over $1.5 billion into OpenAI, the SoftBank boss could throw another $25 billion into the artificial intelligence company, according to a Financial Times report on Thursday. Previous double dips like WeWork and Uber have yielded distinctly mixed results, but the timing of the Japanese investor’s latest gambit deserves its own level of weird. As recently as last week, OpenAI might have seemed a sensible bet. The group run by Sam Altman, which launched ChatGPT in late 2022 and touted 100 million weekly active users within a year, was in

It’s not only British royals Prince Harry and his wife Meghan seeking “financial independence” from erstwhile supporters. After office-space innovator WeWork’s nightmarish failure to go public last fall, scooter-sharing outfit Lime is the latest startup whose vision now includes making a profit. Lime co-founder and boss Brad Bao said on Thursday that the company would exit 12 cities, about 10% of its markets. He said micromobility, the on-message term for scooters and such, had evolved too slowly. Jobs will also be lost. It’s a marked shift from the try-everything approach that has characterized startups across the shared economy and led

A direct listing is “just an IPO without the O,” says Barry McCarthy, finance chief of music-streaming outfit Spotify Technology. McCarthy’s company, worth $26 billion in early December, used the non-standard method to go public in 2018, and $12 billion workplace-messaging service Slack Technologies followed in 2019. Investors can expect more. Direct listings could start borrowing features from initial public offerings, and the whole notion may jump across the Atlantic. McCarthy suggested in a panel discussion hosted by investment bank Goldman Sachs in October that the traditional way of going public was “chronically broken” – a sentiment shared by venture

Remember Webvan? The ill-fated online grocer was one of SoftBank Group boss Masayoshi Son’s first Silicon Valley forays in the 1990s. It didn’t work out so well as an investment. After this fall’s WeWork rescue, a third shot will encounter more investor skepticism. A lot of folks made bad bets during the internet’s early days but SoftBank’s misses were outsized, even then. As the bubble burst, the Japanese group’s shares lost almost all of their value from 2000 to 2002, reflecting a paper loss of more than $70 billion for Son. Webvan, like WeWork, had a big-name founder in Louis

Peloton Interactive’s claim of tech status depends on too much spin. It’s true that like many companies that have recently floated shares or plan to do so, such as Uber Technologies and The We Company, the stationary bike outfit burns lots of cash and gives founders supervoting rights. But Peloton’s core business needs to retain online customers in an exercise market prone to fads. That’s far from a sure bet. Sales pitches for initial public offerings contain a fair amount of hype, and Peloton doesn’t hold back in its prospectus. It calls itself a technology, media, software, product, experience, fitness,