8 Lessons from the Career of Softbank’s Masayoshi Son

Few characters are more enigmatic or misunderstood than Masayoshi Son, the billionaire founder and CEO of SoftBank, the Japanese media technology conglomerate. In Japan and in western media, he is cast as a dreamer, financial engineer, and speculator — an object of suspicion who has risked financial ruin more than once in a five-decade career.

His life story is a Forrest Gump-like journey through all the key moments in recent business history: from the launch of the personal computer to the birth of the internet, the dotcom boom and bust, the rise of China, the global financial crisis, and the advent of artificial intelligence. As the British writer Simon Nixon observed in a review of Gambling Man, my biography of Son, “He seems to have known everyone and owned everything, or at least tried to buy it.”

According to the author he was interested in researching and writing about Son to better understand how his formative years shaped his career and what leaders in both the East and West can learn from both his successes and missteps as a corporate manager and investor. Here are eight key lessons:

1. Turn adversity into advantage.  Masayoshi Son was born in 1957 on the edge of a shanty town on the island of Kyushu, the second son in a Korean-Japanese family (zainichi) that lived under a Japanese alias in an attempt to avoid discrimination. His father was a bootlegger, pig breeder, loan shark, and owner of pachinko gambling parlors.  From his earliest years, Son faced prejudice, but, watching his father, he learned how to hustle. Then, instead of joining the gambling underworld, he left Japan at age 16 to study in California. It was a liberating experience. On his return home, Son set up a software distribution business called SoftBank, the foundation of a future global empire.  When he was 24, married with one young daughter and expecting a second child, he was diagnosed with Hepatitis B and given three to five years to live. Thanks to pioneering treatment, however, he survived. Overcoming all these early obstacles gave him an extraordinary self-belief and allowed him to survive the brushes with corporate death he would later face.
2. Persist.  Son’s career is a study in perpetual reinvention. He started as a software distributor but, after losing 97% of his paper wealth in the dot-com crash, he pivoted to broadband and the mobile internet in Japan. Then he acquired Sprint in the United States and, six years later, despite prolonged resistance from the U.S. Federal Communications Commission, pulled off a merger with T-Mobile, creating a “third force” in the country’s telecoms industry.  Son has made a practice of never taking “no” for an answer.
3. Bridge east and west.  Son did not invent, control, or own a breakthrough technology. He was not supported by U.S. venture capital, private equity, or the capital markets. Unlike China’s tycoons, he has never been a card-carrying member of the communist party. Instead, as someone fluent in both Japanese and English, he has acted for many years as a bridge between the United States and Asia, and a gateway to the mass markets of Japan and China.
4. Seek mentors and mentees.  In Japan, Son is known as “the old man killer.” His charm and confidence endeared him at a young age to a succession of veteran businessmen and engineers.  Later, Son became a tech mentor himself to Saudi Crown Prince Mohammed bin Salman.
5. Go big or go home.  Son is a master of outrageous gestures. He talks in seven- to ten-figure numbers, sometimes scribbling down zeroes on a “napkin contract” covering a deal or a potential hire.  Son is the master of leverage. SoftBank has regularly featured among the world’s top ten most indebted companies. His preferred approach is to borrow money so he can pay cash at prices most would consider to be over the odds but which he would consider a bargain in the longer term.
6. Don’t let love outweigh logic.  While we can learn much from Son’s triumphs (Yahoo!, Alibaba, ARM), we can also draw lessons from his biggest mistakes (WeWork, Wag, and WebVan).  When he focuses, as in the early days of the Sprint takeover, he can be a formidable operator, but more usually he is a creature of enthusiasms and sometimes guilty of credulity. He is particularly prone to “founder syndrome,” falling so in love with a charismatic entrepreneur like WeWork’s Adam Neumann that he fails to adequately stress test their strategy and leadership. 
7. Beware mercenaries.  Son has long relied on fixers to help him navigate outside Japan. As SoftBank grew bigger, he pulled off a succession of high-profile hires, many executives drawn from the Indian diaspora who were ambitious, highly educated, and money-driven. Many were trained mathematicians who applied their engineering skills to finance rather than academia. Over time, their presence, alongside other Indians, particularly those drawn from the Deutsche Bank network, began to change SoftBank’s culture, not always for the better. The business became more cut-throat, infighting broke out at the top between Rajeev Misra, head of the Vision Fund, and Marcelo Claure, a Bolivian-American COO and Sprint boss.  Masa played helpless — hardly an advert for managerial leadership.
8. Focus on the future.  Son was focused of the future, specifically artificial intelligence, a long-standing passion. In 2024, he made two investments amounting to a $2 billion stake in Sam Altman’s Open AI. He is now selling down other positions in his portfolio so he can shift the money to “deep AI” targets. This week, he joined President Trump at the White House, along with Altman and Oracle’s Larry Ellison, to announce up to $500 billion in investment in AI infrastructure, such as data centers. He is back at the top table of investors, staging his fifth and most serious business comeback.