This piece is excerpted and adapted from Gambling Man, my new biography of SoftBank founder Masayoshi Son. Known to friends and rivals alike simply as “Masa”, the Japanese business titan is arguably the 21st century’s most powerful industry leader who remains far from a household name globally.
Born in 1957, Masa grew up on Japan’s western island of Kyushu. Standing just over 5’5”, almost always dressed in polished smart casual attire, he spent years living in California. While his natural charm is legendary, he bores easily. Visitors to his cavernous Tokyo office—home to a conference table long enough to match the one favored by Russian heads of state—can be out the door in five minutes or end up staying for two full hours.
Across his career, Masa has built businesses as a software distributor, early dotcom investor, broadband provider, and mobile network operator. Today, through the SoftBank Vision Fund, he holds the title of the world’s largest venture capital investor. Over the past two decades, the assets he has invested in or controlled add up to a staggering $1 trillion. In December 2016, he met then-U.S. President-elect Donald Trump and pledged to invest $100 billion across the American economy.
My book is full of never-before-shared stories about Masa: how he bankrolled Chinese internet giant Alibaba after a six-minute speed meeting with Jack Ma; how he personally scaled hundreds of Silicon Valley startups; how he lured former Google executive Nikesh Arora with a $320 million compensation deal scrawled on a napkin. But my favorite by far is the untold tale of how Masa plotted with Steve Jobs to bring the iPhone to a global audience.
At the turn of the millennium, Masa held the title of the world’s richest person—if only for three days. After the dotcom bubble burst, he lost 97% of his fortune. But he never abandoned his unshakable tech optimism, launching a new broadband service in Japan under the Yahoo brand. His core dream was to pair a mobile carrier with Yahoo Broadband, giving Japanese consumers access to data, images, and messaging all on one handheld device. The only missing piece was a breakthrough consumer product that could let him compete with his archrival NTT Docomo, then Japan’s unchallenged market leader and the most valuable company on Earth by market capitalization. The man who delivered that missing piece was his old friend Steve Jobs.
The bond between Masa and Jobs was one of a kind. Both were autocratic mavericks brimming with unshakable self-belief and an uncanny ability to anticipate future technological shifts. Both had a deep grasp of design, engineering, and consumer behavior. Masa once lined 50 different telephone handsets on a wall in his Tokyo office, so he could test every feature before locking in SoftBank’s own product design. He has long loved quoting Jobs’ iconic line from Apple’s 1997 Think Different ad campaign: “The people who are crazy enough to think they can change the world are the ones who do.”
Masa first crossed paths with Steve Jobs in the mid-1980s at the annual Comdex tech trade show in Las Vegas. It was not until summer 1998 that the two held their first in-depth conversation, sitting under a cherry tree at the Woodside, California estate of Oracle CEO Larry Ellison, a fellow Japanophile and mutual acquaintance.
Ellison’s home was less a private residence and more a self-contained village, a sprawling compound of intricately crafted wooden buildings modeled after a Japanese imperial palace. The 23-acre estate took nearly a decade to design and build, complete with a man-made lake and a waterfall that could be toggled on and off with a switch. All buildings were constructed without nails, with mud-plastered walls engineered to withstand a 7.3 magnitude earthquake. In total, Ellison’s tribute to Japanese culture and history was valued at roughly $70 million.
While small talk around the table that day centered on the absurdly high internet stock valuations of the era, Masa and Jobs were already focused on what would come after the dotcom bubble popped. “I told him I was putting all my focus on the internet—and he agreed the internet was the future,” Masa recalls. Both men saw a paradigm shift on the horizon. Nasdaq fluctuations were one thing; the arrival of a fully connected world, with Apple leading as an innovator and SoftBank serving as investor and operator, was an entirely different, transformative future.
By that point, Apple was already one of the world’s most valuable companies, with a lineup of blockbuster products ranging from Mac laptops to the iPod. Just like Masa, Jobs was paranoid about rivals stealing his ideas. No Apple project was more top-secret than the iPhone: the touchscreen smartphone that would go on to sell billions of units and revolutionize personal communication forever.
Per Masa’s account, during a 2005 trip to California, he showed Jobs his own hand-drawn sketch of a mobile-enabled iPod with a large display that ran Apple’s operating system. The new device, he predicted, would be able to process data and full-color images. Jobs brushed off the sketch but could not resist dropping hints about his own secret project:
Jobs: “Masa, don’t give me your shitty drawing. I have my own.”
Masa: “Well, I don’t need to give you my dirty piece of paper, but once you have your product, give it to me for Japan.”
Jobs refused to share any more details, but Masa spotted a faint smile cross the Apple CEO’s face. After more pushing, Masa secured a follow-up meeting at Jobs’ Tudor-style country home in Palo Alto. At that meeting, Masa claims Jobs agreed in principle to give SoftBank exclusive distribution rights for the iPhone in Japan. “Well, Masa, you are crazy,” Jobs told him. “We have not talked to anybody, but you came to see me first. I’ll give it to you.”
Nothing was put in writing. There was no discussion of price or shipment volume. It was nothing more than a gentleman’s agreement, built on the assumption that Masa would secure the capital to build or acquire a Japanese mobile business. “It was super confidential. I never saw the product before it arrived in Japan [in 2008],” Masa claims. “Steve never even told me the name.”
The story carries a mythic quality, given that Jobs gave his word a full three years before the iPhone launched in Japan. Yet that promise likely gave Masa the confidence to buy Vodafone Japan, the British-owned market also-ran that famously used soccer icon David Beckham in its marketing. The acquisition was a highly leveraged deal—the largest in Asia at the time—but Masa gambled that he had an industry-changing product waiting in the pipeline. Whatever the exact timeline, Masa pulled off the distribution deal of the century, allowing him to build a profitable consumer mobile business in Japan and massively elevate the SoftBank brand.
On March 17, 2006, Masa closed his $17 billion deal to buy Vodafone Japan. Two weeks later, Jobs flew to Tokyo, where Masa held the Apple CEO to his word. “You didn’t give me anything in writing, but I made a $17 billion bet based on your promise,” he said. “You had better feel a tiny bit of responsibility.” Jobs laughed and replied, “Masa, you are a crazy guy. We will do what we discussed.”
By spring 2006, Masa was in a tremendous hurry. New rules were about to let Japanese mobile users transfer their existing phone numbers to competing carriers. Unless SoftBank launched a compelling new product or pricing offer, it risked losing hundreds of thousands of customers to NTT Docomo and second-place carrier KDDI.
Steve Jobs was also racing against the clock. Three years earlier, he had been diagnosed with a rare form of pancreatic cancer, but he delayed surgery, allowing the cancer to spread to his liver. From the day of his operation in October 2004, he knew he was living on borrowed time. Publicly, he insisted to colleagues and investors he was cured. Privately, he was more focused than ever, devoting every waking hour to two top-secret projects: the iPhone and a new tablet computer called the iPad.
Apple launched its first 2G iPhone in the U.S. in summer 2007. The device was incompatible with the more advanced networks already in use in Japan. For that reason, Japan’s telecom giants only saw Apple as a designer and manufacturer of personal computers and music players, and could not imagine the American company launching a game-changing product in their market. Masa, by contrast, understood immediately that Steve Jobs was about to upend the industry as faster mobile technology became dominant across the globe, including Japan.
In November 2007, AT&T CEO Randall Stephenson—whose company distributed Apple’s 2G iPhone in the U.S.—accidentally let the cat out of the bag. Speaking at a Churchill Club business event in Silicon Valley, Stephenson let slip that Apple’s next iPhone would be 3G compatible. From then on, even as more than 2 million American consumers enjoyed the groundbreaking experience of the iPhone’s responsive touchscreen, the tech industry was abuzz with rumors of Apple’s next-generation product.
Within weeks, NTT Docomo CEO Masao Nakamura held talks with Jobs at Apple’s Cupertino headquarters, followed by Masa himself. This suggests the exclusive iPhone distribution deal may not have been as watertight as Masa believed, though he later claimed he stayed in regular contact with Jobs, sharing input on features for the Japanese iPhone. “I created all the characters, the emoticons that went in the iPhone,” he says. “I gave him many ideas.”
(The claim is bold, but Masa has always had an artistic streak: he is a skilled amateur painter working in the early Impressionist style, and he has a sharp grasp of consumer preferences. How closely Jobs listened to his Japanese friend is another matter.)
Both Masa and Docomo were desperate to secure rights to the new 3G-enabled iPhone, a tri-band device that worked across multiple networks and could be rolled out globally. Docomo’s phones operated on a 2-GHz network in Japanese cities, switching to a more reliable “platinum band” 800-MHz service in rural areas with fewer cell towers. The catch: NTT’s dual-band network required extensive testing to ensure seamless handoffs between bands, putting the iPhone launch at serious risk of delay.
Because risk-averse Japanese regulators favored incumbent players, SoftBank was forced to settle for the less powerful 2.1-GHz spectrum. But that spectrum had one key advantage: it was single-band and covered the entire country, so no handoff between networks was required.
Technology mattered, but personal chemistry mattered far more. “There was a deep connection between Masa and Steve Jobs,” says Ron Fisher, SoftBank’s U.S. lead who attended several meetings between the two men. “Jobs understood that when you are trying to change consumer behavior in a place like Japan, you need a maverick.”
On June 4, 2008, Masa announced SoftBank would sell the iPhone, confirming he had beaten Docomo to the punch. Distribution in Japan launched the following month. By September 2011, when SoftBank lost its iPhone exclusivity, its Japanese mobile market share had grown to 23%, up from 17% when it acquired the Vodafone Japan business. Steve Jobs’ bet on SoftBank was vindicated, and the success also highlighted Masa’s ability to scale rapidly, overcoming a tangled web of logistical, regulatory, and marketing obstacles.
Thanks to the iPhone, Masa built SoftBank Mobile into a top-tier Japanese operator. This became the springboard for his 2013 acquisition of a controlling stake in U.S. carrier Sprint, which later merged with T-Mobile to create a third major competitor in the U.S. telecom market. Along the way, he shifted back from mobile operator to global tech investor. He acquired UK-based advanced chip designer Arm Holdings, and later tried to merge it with Nvidia, now the world’s most valuable company. Nvidia founder Jensen Huang remains a good friend and still teases Masa that he sold his 5% stake in 2019, missing out on a windfall on par with his early Alibaba investment.
Masa’s core passion today is artificial general intelligence, a technology he believes will have a greater impact than the microchip, the internet, and the mobile phone combined. “I have to be in this revolution,” he told me in our last interview in Tokyo. “I have to participate.”
In summer 2024, SoftBank invested $500 million in OpenAI. Before that, the Financial Times reported Masa was ready to put up $1 billion to develop “the iPhone of artificial intelligence” in partnership with Sam Altman and Jony Ive. The device would be the first major consumer hardware product of the AI age. If the vision comes to fruition—and never count Masayoshi Son out—it would be a fitting legacy to his friendship and collaboration with his mentor and partner Steve Jobs.
Copyright © 2025 by Lionel Barber. From the book Gambling Man by Lionel Barber, published by One Signal Publishers, an imprint of Simon & Schuster, Inc. Printed by permission.