My review of Gambling Man by Lionel Barber

I finished reading Gambling Man by former FT Editor Lionel Barber last night. The book tells the story of Masayoshi Son, founder of Japan’s Softbank, which might on the face of it sound like old news what with a new occupant of the Oval Office this week. But make no mistake: Gambling Man is a brilliant book, almost certainly unrivalled in its telling of the Softbank story, but also very hard to beat in my opinion in terms of framing this story within the big political, economic, technological and geographical trends of the past thirty five years, virtually all of which were deftly navigated by Masa and all of which are expertly re-told along the way by Lionel Barber.

A big part of Masa’s success derives from the fact that he is no one-trick pony, albeit that the vast majority of his various endeavours over the years have benefited significantly from historically low short-term interest rates (first in Japan in the 1990s, and most other rich countries since 2003). Having profited handsomely by bring the best of the rest of the world to Japan in the 1990s (e.g. re-selling Microsoft software), Masa launched himself on the global stage starting in the early 2000s, his public profile probably culminating with the launch of Softbank’s Global Vision fund in 2017 before business soured somewhat thereafter (difficulties from which Masa has always bounced back from historically, to be fair).

Reading this book now, I was reminded that while it is easy to think of the development of the Internet, Globalisation and the rise of China as being one big story from the period 1995-2005, it is in fact three separate stories, each of which occurred more in series than in parallel (though there were undoubted feedback loops), and any one of which would probably still have occurred even in the absence of the other two.

Masa’s most profitable business bet over the years was to back Jack Ma and his once fledging Chinese company, Alibaba. Backing him repeatedly over years, Masa overruled the judgement of virtually everyone he knew. But having been right when all others were wrong then came to cloud his thinking when – years later – virtually everyone also told him to be wary of WeWork, which Masa continued to bankroll long beyond the point where he probably should have cut his losses (now with the benefit of added hindsight, of course).

With short-term interest rates having finally moved up from the rock-bottom lows they were pegged at for most of the period 2005-2020, and with none of the investee companies in his Global Vision Fund having done anything like as well as Alibaba or ARM Technology, the going is probably now tougher for Masa, and it’s perhaps easy to think that his influence in shaping the biggest business stories is finally waning. He’s proved his doubters wrong before, of course. But even if it is true, the life and times of Masayoshi Son are hard to beat in terms of business excitement across a variety of business undertakings across multiple continents, especially for someone still in business as opposed to having been brought crashing back to earth.

Whoever Masa son reminds you of as you read Lionel Barber’s story – I variously thought of Richard Branson, Matt Moulding, Prince Alwaleed Bin Talal and P T Barnum along the way – it will still probably pale into insignificance as compared to the people Masa himself compared himself to: Genghis Khan, Napoleon and Emperor Qin. If nothing else, this goes to show the scale of Masa’s ambition, of which the late Steve Jobs once famously said “the people who are crazy enough to think they can change the world are the ones who do”.

Gambling Man by Lionel Barber is a great book which easily deserves to make the shortlist (never mind the longlist) for FT/Schroders Business Book of the Year 2025, when the list is published later this year. If you don’t know anything about Softbank, you’ll learn both about it AND the big changes that shaped the world in the last thirty-five years. But even if you are a Softbank insider, there is still lots of insight in this great book about why what Softbank did along the way really mattered and, in at least some ways, how it all made the world at least a slightly better place.