Masayoshi Son isn’t recognized for half measures. The SoftBank founder’s profession has been studded with eyebrow-raising bets, every one seemingly extra outrageous than the final.

His newest transfer is to money out his complete $5.8 billion Nvidia stake to go all-in on AI. And whereas it stunned the enterprise world on Tuesday, it possibly mustn’t. At this level, it’s nearly extra stunning when the 68-year-old Son doesn’t push his chips to the middle of the desk.

Contemplate that in the course of the late Nineties dot-com bubble, Son’s web price soared to about $78 billion by February 2000, briefly making him the richest individual on the earth. Then got here the ugly dot-com implosion months later. He misplaced $70 billion personally – which, on the time, was the most important monetary loss by any particular person in historical past — as SoftBank’s market cap plummeted 98% from $180 billion to simply $2.5 billion. 

Amid that terribleness, Son made what would turn out to be his most legendary guess: a $20 million funding in Alibaba in 2000, one determined (the story goes) after only a six-minute assembly with Jack Ma. That stake would ultimately develop to be price $150 billion by 2020, remodeling him into one of many enterprise trade’s most celebrated figures and funding his comeback.

That Alibaba success has typically made it tougher to see when Son has stayed too lengthy on the desk. When Son wanted capital to launch his first Imaginative and prescient Fund in 2017, he didn’t hesitate to hunt $45 billion from Saudi Arabia’s Public Funding Fund – lengthy earlier than taking Saudi cash turned acceptable in Silicon Valley.

After journalist Jamal Khashoggi was murdered in October 2018, Son condemned the killing as “horrific and deeply regrettable” however insisted SoftBank couldn’t “flip our backs on the Saudi folks,” sustaining the agency’s dedication to managing the dominion’s capital. In truth, the Imaginative and prescient Fund truly ramped up dealmaking quickly after.

That didn’t prove so properly.

A giant guess on Uber generated paper losses for years. Then got here WeWork. Son overrode his lieutenants’ objections, fell “in love” with founder Adam Neumann, and assigned the co-working firm a dizzying valuation of $47 billion in early 2019 after making a number of earlier investments within the firm. However WeWork’s IPO plans collapsed after it printed a famously troubling S-1 submitting. The corporate by no means fairly recovered – even after pushing out Neumann and instituting a sequence of belt-tightening measures – finally costing SoftBank $11.5 billion in fairness losses and one other $2.2 billion in debt. (Son reportedly later known as it “a stain on my life.”)

Son has been mounting one other comeback for years, and Tuesday will undoubtedly be remembered as an essential second in his turnaround story. Certainly, it’s going to seemingly be recalled because the day SoftBank revealed it had offered all 32.1 million of its Nvidia shares – to not diversify its bets however as an alternative to double down elsewhere, together with on a deliberate $30 billion dedication to OpenAI and to take part (it reportedly hopes) in a $1 trillion AI manufacturing hub in Arizona. 

If promoting that place nonetheless offers Son some heartburn, that’s comprehensible. At about $181.58 per share, SoftBank exited simply 14% under Nvidia’s all-time excessive of $212.19, which is a powerful look. That’s remarkably near peak valuation for such an enormous place. Nonetheless, the transfer marks SoftBank’s second full exit from Nvidia, and the primary one was exceedingly expensive. (In 2019, SoftBank offered a $4 billion stake within the firm for $3.6 billion, shares that might now be price greater than $150 billion.)

The transfer additionally rattled the market. As of this writing, Nvidia shares are down practically 3% following the disclosure, at the same time as analysts emphasize that the sale “shouldn’t be seen as a cautious or adverse stance on Nvidia,” however somewhat displays SoftBank needing capital for its AI ambitions.

Wall Avenue can’t assist however surprise: does Son see one thing proper now that others don’t? Judging by his monitor report, possibly — and that ambiguity is all buyers need to go on.