Alok Sama first set eyes on the sometime richest man on earth in 2014. It was at the fittingly opulent wedding of a member of the global tech royalty, Google’s then business chief, Nikesh Arora. In the marbled surrounds of Borgo Egnazia, a six-star resort in Puglia, southern Italy, the champagne flowed like ambrosia. An Asian couple — the woman elegantly dressed in Chanel, the man Yoda-like in a white suit — stood at a slight distance away from the other guests.
At first Sama, an investment banker then in his fifties, thought the pair must be shy or struggling with a language barrier. Then he noticed something. Every so often one of the most high-ranking business Brahmins present — the chief executive of Google, the head of Deutsche Bank, the founder of an Indian telecoms empire — would approach the man and bow deferentially, receiving a graceful smile in response. Even the actor-turned-tech investor Ashton Kutcher, who danced under the moonlight with his wife, Mila Kunis, that night, paid his respects. Who could he be, this king of the gilded elite? Then, Sama recalls, the penny dropped: “This must be Masayoshi Son.”
“Masa”, as he is known to friends, was the Japanese founder of the world’s biggest technology investment company, SoftBank. He had made some of the most inspired — and risky — bets on young technology projects in history. One, his early $20 million investment in Alibaba, China’s equivalent of Amazon, was valued at more than $50 billion at the time of that wedding. Another, his investment in Vodafone Japan, went from $2 billion to $42 billion when it floated on the stock market in 2019.
But since then, as well as the hits — including the controversial purchase of Britain’s flagship microchip giant, Arm — there have been spectacular misses, particularly WeWork, the co-working office space company that somehow convinced Son into thinking it was a whizzy technology play. SoftBank’s losses on that deal? $10 billion. Son has probably made and lost more money than anyone in history. Or, to be precise, made more, lost more, made more again, then lost more again.
Sama was Son’s right-hand man for much of the last part of that cycle, having been hired not long after that 2014 wedding — initially as Son’s in-house mergers and acquisitions banker, then his chief financial officer and, finally, company president.
“He was a visionary genius, he believed he could change the world,” Sama says, sitting in the marble kitchen of his six-story home in Kensington, the smell of honeysuckle wafting in through the patio doors. “But as he himself recognizes, he let himself be carried away by the successes of the past. It’s the oldest sin in the world, hubris.”
Now 61 and retired from the dizzying world of tech boom and bust, Sama has written an extraordinary account of his time in the jump seat next to Son. His book, The Money Trap, details the thrills and horrors of the risks he so frequently took.
As the son of middle-class parents in Delhi who struggled to afford decent food for their children, Sama was an outsider in the banking world. Bookish and gifted, he did well at school. After a math degree in India he attended the prestigious Wharton business school in Philadelphia. The culture shock was horrendous. US cities were scary by anybody’s standards in the mid-Eighties, let alone a 20-year-old from India, where, he recalls, “There was just one state-owned TV channel — two hours, black and white.”
Tensions in Philadelphia between the police and the Black rights organization Move were high, to the extent that the police dropped a bomb on a building the protesters were occupying, killing 11 people, in 1985. “There were choppers, bombs, machine guns, and this was happening literally a few blocks away,” Sama recalls. “It was, like, ‘Welcome to America.’ ”
Despite his background Sama was an instant success when he joined Morgan Stanley, the most genteel of Wall Street firms, as a 23-year-old newlywed in 1987.
“Everyone was Ivy League educated, it was a very Waspy culture, very staid. Nothing like The Wolf of Wall Street,” he says. He made a $190,000 bonus in his first year. “That’s more than ten generations of my family made, put together, over their entire lifetimes. It was unbelievable.”
At first he didn’t know what to do with the cash. “I bought my wife, Maya, this expensive Bulgari bracelet and she never wore it. I bought myself these two-tone shirts like Michael Douglas in the movie Wall Street. I looked and felt ridiculous.”
Maya, who had turned down Wharton to study arts administration before taking a job at the New York Philharmonic, has kept him grounded throughout, he says.
He made a $190,000 bonus in his first year. “That’s more than ten generations of my family made, put together, over their entire lifetimes.”
He rose rapidly at Morgan Stanley and in 1994, at just 31 years old, was sent to set up its investment banking business in India. At 33, he was a managing director. By the time the bank moved him to the UK in 2000, he says, “I was among the top-paid bankers in London,” earning “several million” dollars a year. But when Son hired him to be his M&A man, he was to enter another orbit.
Within days Sama was doing tech deals at a machine-gun pace, traveling the globe on SoftBank’s private Gulfstream jet. “I felt like [Mick] Jagger … I was living the dream.”
Son’s private dining room in SoftBank’s Tokyo offices was like nothing he had ever seen, with a view over the city’s Hamarikyu Gardens and the bay beyond. It included a traditional Japanese garden and a pavilion for Son’s priceless calligraphy collection. The food was exquisite; the wine Son’s favorite $5,000-a-bottle La Tâche red burgundy. The biggest names in tech dined there. Facebook’s Mark Zuckerberg, Sama recalls, arrived sporting his trademark gray Brunello Cucinelli T-shirt and blue jeans.
As the wine flowed, “Zuck” told the table how he set himself a yearly challenge. The previous year’s had been to eat meat only when he had killed the animal himself. He boasted that he had dispatched a chicken with his bare hands in a restaurant and shot a bison, pickling its meat. He had its head stuffed and put in the office of Sheryl Sandberg, the formidable Facebook chief operating officer at the time.
Everybody laughed, but Sama says such tales left him feeling uncomfortable about Silicon Valley’s frat-boy culture. “A lot of these people, like Zuckerberg, are more than a little bit strange. Worshipping them is way overdone.”
Son shot to fame in the 1990s when his $100 million investment in Yahoo! leapt to be worth more than $30 billion in little more than three years. By 2000, before the dot-com bubble burst, he was the richest man on the planet. Unlike most who made, then lost, fortunes in the crash, Son was quickly back on the up. His stake in Alibaba, which he bought in 2000, helped, surging in value on the back of the Chinese economic miracle. By the time Sama joined, Son was being feted as a genius again.
One of Son and Sama’s crowning deals — and easily the most high-profile and controversial in the UK — was SoftBank’s 2016 takeover of Arm for $32 billion. Son was convinced that the Cambridge chipmaker would be critical to the two technologies he believed would shape the future of the world: artificial intelligence (AI) and “the Internet of Things” (IoT), where everything from cars and traffic lights to fridges and washing machines are connected to the Internet.
Sama was tasked with figuring out how to get the deal done. The problem was, Arm was seen as a national treasure in the UK — the only real, homegrown technology star. Britain had just voted for Brexit. Selling off a crown jewel to the Japanese was hardly going to be popular as the country tried to redefine itself as a global business powerhouse.
Sama hired London’s most renowned investment banker, Sir Simon Robey, to help guide them through the negotiations. They met at Son’s mansion in Silicon Valley where Robey declared they needed to launch a shock and awe attack. “If you do exactly as I say, you will win,” he declared.
That evening Arm’s chief executive, Simon Segars, unaware of Son’s intentions, came to dine on the patio overlooking the impeccably landscaped gardens. Son was, Sama recalls, “irrepressible” as he talked about trillions of connected cars and robots and Arm’s central role in Tomorrowland. Five days later he requested an urgent meeting with Segars and Arm’s chairman, Stuart Chambers, to make his proposal — but Chambers was on holiday in the Mediterranean. Son refused to wait.
“If Stuart had been on a hiking trip to Tora Bora in Afghanistan, Masa would have parachuted in,” Sama says.
He recalls arriving by private jet at the Turkish coastal resort of Marmaris in July 2016. The two teams met at the Pineapple, one of the town’s plushest restaurants, at which they had booked every table for total privacy. Sama presented the deal before Son took Segars for a stroll to work some persuasive magic.
Talks resumed back in London. Robey smoothed over the deal with his connections in Whitehall and government while Roland Rudd, a financial PR guru (and brother of Amber Rudd, who was about to be appointed home secretary), dealt with the media. Sama recalls how Robey held lengthy conversations with the Cabinet secretary Jeremy Heywood, how Son met the prime minister, Theresa May, and Sama met the chancellor, Philip Hammond. “I was blown away,” he says. “I’ve met a few people in those positions but they don’t always come as well briefed and understanding as he was. The attitude was always, ‘What can we do to help?’”
In his book, he writes: “Old-boy networks are great when deployed in your favor, and the trinity of Robey, Rudd and Heywood, all students at Oxford, served us well.”
Sama says critics of the deal had it all wrong. “It became a little politicized, you know. ‘These guys, are they asset strippers?’ But that was the furthest thing from our minds. We wanted to grow the business.” Son promised to double the number of Arm employees in the UK within five years — a commitment SoftBank exceeded. However, when Son floated Arm at a valuation of $52 billion last year it was on the New York Stock Exchange, not in London. Many who had attacked the takeover pointed out that Arm would still be a London-listed champion if SoftBank had not got involved.
“A lot of these people, like Zuckerberg, are more than a little bit strange. Worshipping them is way overdone.”
“You can get emotional and say, ‘Oh, it should be owned by a British company,’ but what do you actually care about?” says Sama dismissively. “As long as people are being employed, more jobs are being created, more net addition to the economy … That’s what you should care about as a government.”
It was perhaps the success of the Arm deal that led to Son’s nadir. So sure was he that AI and the IoT were the next big thing that he came up with the idea of creating the $100 billion Vision Fund, borrowing big to snap up as many hot new tech companies as possible. Sama was deeply worried — and not just about the levels of debt. How would they be able to find enough good businesses to invest in — “Where would all this money go?” He and others tried to dissuade Son, who refused to listen.
Sama watched in awe as Son persuaded the world’s richest men to invest in the fund. Mohammed bin Salman, crown prince of Saudi Arabia, was the first to sign up, on a visit to Japan. The meeting took 45 minutes. Son emerged with $45 billion of Saudi cash — “One billion per minute,” as he put it. The crown prince of the UAE followed suit with $15 billion and others, including Apple and Larry Ellison, invested, bringing the total to the $100 billion mark.
As Sama had predicted, the pressure was then on for the fund to spend — which resulted in vast sums going to businesses and entrepreneurs who didn’t deserve it. The most infamous example was WeWork.
Headed by a charismatic, long-haired, pot-smoking Israeli called Adam Neumann, WeWork was basically a property company that targeted tenants from the tech sector. Sama heard early pitches from Neumann in New York, reporting back to Son that he was not convinced. WeWork had clever branding but, Sama says, it was no more a tech company than a Starbucks with Wi-Fi.
It took less than half an hour for Neumann to persuade Son otherwise — in the back of a black SUV that was driving Son to a meeting with president-elect Donald Trump. By the time Son arrived at Trump Tower, Neumann had sketched out a deal for Son to invest $4.4 billion.
With so much SoftBank and Vision Fund cash to spend, Neumann opened WeWork offices around the world at an insane pace. At one point it was London’s biggest office tenant. Neumann seems to have had a Rasputin-like grip on Son, and convinced him to pump in a further $20 billion so he could buy buildings outright — a capital-intensive idea far from the original business plan, and on top of his barmy sideshows including WeGrow, a school that replaced math and English with “yoga and soulfulness”. “I sat through Adam’s pitch to Masa in awe at the man’s audacity,” Sama recalls. On that occasion Son’s investors reined him in. But the collapse of WeWork was inevitable. Having failed to float on the stock market at a value north of $50 billion, the company filed for bankruptcy in 2023.
By that time the Vision Fund had pumped hundreds of millions of dollars into other doomed businesses: Wag, an app to find dog walkers; Zume, a company using robots to make pizzas; multiple firms that wanted to be the next Uber.
Rival tech investors urged Son to stop; the Vision Fund was driving up prices for everyone. But Vision — and SoftBank — pressed on with deal after deal. Son even chastised Sama for his repeated warnings, eventually telling him he was too much like a “cook” and not enough of a “hunter”. That stung. “The way Masa said it, it hurt. I’d made it on Wall Street, where you eat what you kill and you sometimes kill for sport.”
By then, though, Sama had begun to tire of his position, which had drawn the attention of malicious forces. An anonymous enemy had launched a smear campaign against him, hiring private investigators to go through his emails, snoop on him and his family and make accusations against him to the financial media, clearly trying to ruin his career. The Wall Street Journal later identified an internal SoftBank rival, but Sama declines to go into details about the baseless allegations. “The whole thing was a surreal experience,” he says. “Someone had obviously been through my emails … even an old application to my co-op board [the organization running his apartment in New York].” He laughs bitterly: “That was the ultimate body cavity search.”
Maya told him to quit, saying he didn’t need the money or the aggro, but he clung on. Meanwhile, his personal life had entered a brutal phase. Over the course of 111 days in 2017 he lost both parents and his beloved dog. Sama’s father had been a doctor and his son seems somewhat tortured about whether he should have done something as purposeful with his life.
“There will be readers who will be wowed by private planes, £1,000 [$1,320] bottles of wine, vacations in seven-star resorts … Others will wonder if an alternate version of Alok might have made more of an impact on the world, and left him a happier man besides.”
Eventually he did resign and embarked on a creative writing course at New York University. Yet he clearly enjoys the wealth. As we sit in his elegant west London home, I ask if he feels guilty about the money he and other bankers made when the booms they helped create turned to bust? After all, those tech crashes meant billions of dollars of pensioners’ money evaporating. He looks at me quizzically at first, but his answer is candid: “You know, honestly, I didn’t. We were all too swept up, and that’s just the nature of the business. I guess you could call it the money trap.”
Son, it seems, remains ensnared in that trap. Last year his Vision Fund lost $32 billion and Son announced he was stepping back from the day-to-day running of SoftBank. But within months, as the AI start-up ChatGPT suddenly boomed and the chip designer Nvidia’s shares shot up phenomenally, he could not resist starting up the engine again. At SoftBank’s AGM last summer, he declared “the time has come to shift to offense mode”.
As Sama puts it: “Masa Son, like Gatsby, is the single most hopeful person I have ever met, and I’m ever likely to meet again.”
Jim Armitage is the business editor at The Sunday Times of London
