Masayoshi Son rarely shows vulnerability. But speaking at a Tokyo finance forum Monday, Japan’s boldest tech investor admitted something that revealed the emotional weight of AI’s trillion-dollar arms race: he “was crying” as SoftBank sold its entire $5.8 billion Nvidia stake in November.
The confession cuts straight to the heart of today’s AI investment frenzy, so profitable that even a massive chip windfall feels like a sacrifice when deployed elsewhere.
Son insisted he didn’t want to sell “a single share,” but he needed the cash for something bigger: a $40 billion gamble on OpenAI and infrastructure like the Stargate data-center project.
The question haunting investors is whether his tears reflect wisdom or overreach.
Tears over Nvidia, billions for OpenAI: Inside Son’s high-stakes capital shuffle
SoftBank first invested in Nvidia in May 2017, years before the AI boom transformed it into the world’s most valuable chipmaker.
The company had trimmed that position in 2019 for $3.3 billion, then quietly rebuilt it, only to liquidate the entire stake in October for $5.83 billion.
The timing was brutal. Nvidia was soaring past $5 trillion in market value, a threefold increase in two years, cementing its role as the infrastructure backbone of the AI revolution.
Yet Son’s language was clear: not distress, but strategic choice. “I don’t want to sell a single share,” he told the FII Priority Asia forum on Monday.
I just had more need for money to invest in OpenAI, invest in our opportunities, so I was crying to sell Nvidia shares.
This was no doubt about Nvidia’s future: it was math about priorities. SoftBank committed $7.5 billion initially to OpenAI in early 2025, with a planned $22.5 billion follow-up by year-end.
Add the Stargate project’s multi-billion-dollar infrastructure commitment, and the liquidity demand becomes clear.
Son was choosing between owning more of the world’s best chip company or controlling stakes in what he believes will be the world’s dominant AI platforms.
Gamble or genius? What Son’s ‘painful necessity’ says about the AI Bubble debate
Here’s where Son’s tears get complicated. He explicitly rejected the idea that Nvidia is overpriced or that AI faces a bubble, a stance that puts him at odds with increasingly skeptical investors.
Instead, he doubled down: when “super intelligence” arrives in roughly 10 years, AI and robotics will generate at least 10% of global GDP, worth around $20 trillion annually.
That math, Son argued, justifies the $10 trillion cumulative investment now flowing into the sector.
The irony is sharp. In 2019, SoftBank’s Vision Fund suffered a historic $18 billion loss, with 47 portfolio companies written down as valuations collapsed.
Son himself admitted he’d “let the fish that got away” when Nvidia shares he sold in early 2019 ultimately exceeded $150 billion in value by 2024.
Now, he’s repeating the bet but inverted, selling Nvidia to own the models and platforms he believes will matter more than the chips.
Analysts see a portfolio-allocation pivot from infrastructure plays to ecosystem control.
By cashing out Nvidia, Son repositions from owning the “picks and shovels” to owning the “gold mines”.
Whether that historical parallel holds, or whether he’s simply learned from past regrets, will be tested as OpenAI’s valuations balloon and the broader AI spending cycle matures.
Son’s tears, in the end, reflect an uncomfortable truth: even tech’s biggest risk-takers sometimes sacrifice sure wins for bigger bets, and pray the gamble pays off.
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