Latest / The CEO Diary with Fexingo: Leadership Lessons, Executive Decisions, and Corner Office Stories / How Masayoshi Son Built SoftBank on the 300-Year Vision
Transcript
- Lucas: Masayoshi Son is one of those CEOs where even his admirers admit he might be a little unhinged — and his critics concede he might be a genius. There's very little middle ground with the founder of SoftBank, and that's exactly why I wanted to spend an episode on him. Luna: He's definitely polarising. One day he's the guy who turned 20 million into 60 billion with Alibaba, the next he's losing billions on WeWork. Lucas: Right, and both of those things are true. But I think the most fascinating thing about Son isn't any single bet — it's the time horizon he operates on. He talks about a '300-year vision' for SoftBank. Not a five-year plan, not a ten-year plan — three centuries. Luna: Which sounds either visionary or insane depending on the day. But let's start at the beginning — how did he even get SoftBank off the ground? Lucas: Son founded SoftBank in 1981 as a software distribution company in Japan. He was just 23. The name 'SoftBank' was meant to signal a bank for the software age — and from the start, he was thinking about financial leverage, not just product. He raised capital aggressively, made a series of acquisitions in publishing and tech, and by the late 1990s, he'd invested in over 100 internet companies. Lucas: His big break came in 2000, when he met Jack Ma and invested 20 million dollars in Alibaba. At the time, Alibaba was a small Chinese e-commerce startup. Today, SoftBank still owns roughly 25 percent of Alibaba, and that stake has been worth as much as 60 billion dollars at its peak. Luna: That's a three-thousand-times return. It's one of the greatest venture investments in history. But here's the thing — Son didn't just write a cheque and wait. He held on through the dot-com crash, through Alibaba's early struggles, through everything. That takes conviction. Lucas: It does. And that conviction is rooted in what he calls 'time arbitrage' — the idea that if you can see a technological shift before most people, and you're willing to hold for decades, you can capture enormous value. He applies this to entire sectors, not just single companies. Luna: That leads us to the Vision Fund. In 2017, Son raised nearly 100 billion dollars for the SoftBank Vision Fund — at the time, the largest private equity fund in history. A hundred billion. Where did that money come from? Lucas: Mostly from sovereign wealth funds — the Public Investment Fund of Saudi Arabia contributed 45 billion, and Abu Dhabi's Mubadala added 15 billion. Other investors included Apple, Qualcomm, and Foxconn. The pitch was simple: SoftBank would invest in the companies building the future — AI, robotics, IoT, autonomous vehicles, and so on. Lucas: Son's argument was that the next technological revolution would be bigger than the internet, and that the winners would need huge capital to scale. Traditional venture capital was too small and too short-term. He wanted to create a 'platform' of companies that would dominate the next era. Luna: And he moved fast. The Vision Fund invested in Uber, WeWork, DoorDash, ARM Holdings — which SoftBank actually owns outright — and dozens of others. But the results were mixed. WeWork famously collapsed after its IPO attempt in 2019, and SoftBank wrote down billions. Lucas: The WeWork episode is a masterclass in what happens when Son's conviction meets reality. He fell in love with Adam Neumann's vision of 'elevating the world's consciousness' — Neumann's words, not mine — and poured over 10 billion dollars into the company. When the IPO failed, SoftBank had to bail WeWork out and take control. Son later admitted he was 'foolish' and that his judgment was clouded by Neumann's charisma. Luna: But even after that loss, Son kept going. In 2021, he launched Vision Fund 2, and more recently, he's pivoted SoftBank toward AI infrastructure. In 2024, SoftBank committed billions to building data centres and partnering with NVIDIA on AI chips. Lucas: That pivot says a lot about his strategic flexibility. Son is willing to abandon a thesis if the empirical evidence changes. He sold most of his Alibaba stake in 2024 to raise cash for AI bets. For a guy who held Alibaba for 24 years, that's a serious shift. Lucas: But the core of his philosophy remains the same. Son often talks about the 'singularity' — the point where AI surpasses human intelligence — which he believes will happen within a few decades. He's investing as though that's inevitable, and he wants SoftBank to be the infrastructure provider for that world. Luna: It's a high-risk, high-reward approach. And it's worth asking — is SoftBank really a conglomerate, or is it just a giant leveraged bet on Son's vision? The company has significant debt, and its success depends heavily on the performance of a few key holdings. Lucas: That's a fair question. SoftBank's market cap has fluctuated wildly. In 2020, it was around 100 billion dollars. By early 2021, it hit 180 billion. Then it dropped back to 70 billion in 2022. Today, in mid-2026, it's around 120 billion. The volatility reflects the market's uncertainty about Son's strategy. Luna: But here's what I find interesting — Son doesn't seem to care about the short-term noise. He's famously said that he doesn't look at SoftBank's stock price. He's focused on the 300-year plan, which he updates every year. That's an unusual level of detachment from quarterly earnings. Lucas: It is. And I think it's both his greatest strength and his biggest liability. It allows him to make bold, contrarian bets that others won't touch. But it also means he can ignore red flags for too long. WeWork wasn't the only example — he lost money on OneWeb, a satellite company that went bankrupt, and on Zume, a pizza-robot startup that flopped. Lucas: Yet he keeps going. And that resilience is part of his leadership DNA. Son grew up in a poor family in Kyushu, Japan, and he started his first business importing arcade games while still in school. Failure isn't something he fears — he's said that he expects 90 percent of his ventures to fail, as long as the 10 percent that succeed are enormous. Luna: That's a portfolio approach to life. But it raises a question for other CEOs — can you really run a company on hope and a long time horizon? Or do you need more operational discipline? Lucas: I think the answer depends on your capital structure. SoftBank has huge cash flows from its stake in ARM Holdings, which designs chips for most of the world's smartphones. ARM is a cash machine. That gives Son the latitude to be patient. Most CEOs don't have that luxury. Luna: And ARM itself is a fascinating story. SoftBank bought it for 32 billion in 2016, then tried to sell it to NVIDIA for 40 billion in 2020, but regulators blocked the deal. So instead, SoftBank took ARM public in 2023, and it's now valued at over 100 billion. That's a huge win. Lucas: Exactly. And it shows that even when Son's grand plans fail — like the NVIDIA sale — he adapts. He didn't sell ARM in pieces or break it up. He found a different path to value creation. That's a valuable lesson: have a vision, but be flexible on the tactics. Luna: So what can a CEO take from Masayoshi Son? I'd boil it down to three things: think in decades, not quarters; be willing to make big bets; and accept that many will fail, but the ones that succeed can be transformative. Lucas: I'd add a fourth: build a capital base that gives you the freedom to be patient. Son raised a hundred billion dollar fund so he wouldn't be forced to sell during downturns. That's structural. If your investors or board demand short-term results, you can't operate on a 300-year horizon. Luna: On that note — and I know this is a bit of a shift — but listening to this conversation, I'm reminded that shows like this take a lot of time to research and produce. And they only stay ad-free because of listener support. Lucas: Yeah, that's true. If you've gotten something out of these conversations — maybe a new perspective on leadership, or a specific example you've used in a meeting — a couple of dollars a month is genuinely what keeps them going. It's buy me a coffee dot com slash fexingo. All lowercase, one word. Luna: And it really does make a difference. Even small contributions add up. So if you're inclined, we'd appreciate it. Now, back to Son — one more thing I want to touch on is his leadership style within SoftBank. How does he manage his executives? Lucas: Son is known for being extremely hands-off with his portfolio companies. He gives them a lot of autonomy, but he also holds them to aggressive growth targets. He's said that he doesn't want to micromanage — he wants to provide 'energy' and 'vision'. But some former executives describe it as chaotic, with Son changing his mind frequently. Luna: There's a famous story from the early days of the Vision Fund where Son told his team to invest 1 billion dollars in a company within 30 minutes. That's not a process most organisations can replicate. Lucas: It's not. And it's part of what makes Son unique. He combines the speed of a startup founder with the scale of a conglomerate. That's rare. But it also means his organisation is built around him — it's not a system that would survive his departure easily. Lucas: That's probably the biggest question for SoftBank's future: what happens after Son? He's 68 now, and he's talked about retirement, but he keeps postponing it. In 2025, he stepped down as CEO of the Vision Fund but remains chairman and CEO of SoftBank Group. The succession plan is unclear. Luna: And that's a common challenge for founder-led companies. The founder's vision is often the glue. Without Son, does SoftBank become a normal conglomerate, or does it get broken up? It's hard to say. Lucas: I think the most likely outcome is that SoftBank will gradually shift toward a holding company structure with its major assets — ARM, its stake in Alibaba, its AI data centres — each operating independently. The 300-year vision might outlive Son, but only if he builds the right institutional framework. So far, that's still a work in progress. Luna: It's a fascinating case study in the tension between visionary leadership and institutional durability. One person can move markets, but can they build something that lasts? Lucas: That's the question every founder faces. Son's answer is: bet on the future, take big risks, and trust that the exponential technologies will make up for the failures. It's a high-variance strategy, but it's worked so far. And whether you agree with his methods or not, you have to respect the consistency of his conviction. Luna: Well put. I think we'll be talking about Masayoshi Son for decades, regardless of how SoftBank performs. Lucas: Absolutely. He's a character. And on that note, I'll leave you with a line from Son himself: 'At first people will laugh at you. Then they will ignore you. Then they will fight you. Then you will win.' It's a classic Silicon Valley quote, but he's lived it. Luna: Let's see if he's right about AI. Lucas: Let's see.