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October 4, 2024

A ringside seat into the wild world of SoftBank by an ex-executive

Alok Sama’s account of his six years as Softbank’s maverick founder Masayoshi Son's right hand man is at once thrilling and reflective

By Amy Jenkins

Alok Sama’s autobiography opens more like a thriller. The first thing the reader learns is that someone wants him out of the way. Desperately. So desperately, that he has to say it twice.  

The former Softbank president and CFO, ex-managing director of Morgan Stanley, with 30 years in finance under his belt and an MBA from the Wharton School, memoirs,  The Money Trap: Lost Illusions Inside the Tech Bubble, is a concentrated account of the six years between 2014 and 2020, charting Sama’s years at the Japanese investment management company SoftBank in the orbit of its founder Masayoshi Son

Alok Sama / Image: Pan Macmillan

In these six years, a lot happened. There is the shadowy plot to take down our protagonist, although this is not as sustained a thread as the prologue suggests it might be. Poison pen letters full of vague and unsubstantiated accusations of Sama’s ‘poor financial practice’, occur every so often across the memoir’s pages. If The Money Trap was a novel, this would be unforgivable, but real life is messier than fiction and sometimes life quite simply does not provide the material for a neat plot arc. The revelation at the end of his memoir that Sama cannot name the individual behind the blackmail because he cannot verify who they are is anticlimactic if understandable.  

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[See also: The glittering demise of art fraudster Inigo Philbrick]

The reader is given a ringside view of the inner workings of SoftBank. The view of the negotiating table, two seats down from Son in the SoftBank conference room, is unmatched. The acquisition of Uber becomes an explanation of surge pricing and negative revenue models before neatly segueing into a case study of Son’s ‘who wins in a fight between a crazy guy and a smart guy’ investment strategy. (Spoiler: the crazy guy is also the smart guy). If to know something well is to be able to explain it simply, Sama proves himself a master of his material.  

But Sama’s sense of character is where he really shines. Keenly aware that ‘everyone, myself included, was trying to be something they were not – act richer, be cooler, seem nicer’, Sama cuts through to the gap between the person and the projection. The glimpses are frequently insightful and, even more frequently, just plain funny.  

[See also: Confidant’s trick: What happens when a trusted UHNW adviser goes rogue?]

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Son is idealistic and eccentric. Inspired by Ryōma, a 19th-century samurai who rebelled against the shogunate, advocated against feudalism and clamoured for the modernisation of Japan, everything from the SoftBank logo of horizontal double bars to Son’s golf clubs is stamped with traces of his hero.  

Wearing his ‘crazy’ moniker as ‘a badge of honour’ Son, full of Ryōma-fueled idealism, aspires ‘to be remembered as ‘the crazy guy who bet on the future’ and brought happiness to everyone. Replying to an email asking him to dial down the crazy in preparation for meeting then-British prime minister Theresa May, Son’s response ‘was punctuated with two smiley emojis’: ‘But I am a little bit crazy!’  

SoftBank founder Masayoshi Son / Image: Shutterstock

Sama does not spare himself these incisive glances and his memoir is full of self-depreciation: faced with ‘a thuggish spy’ in Claridge’s by the name of James (no, not Bond), Sama’s impulse is to flee, but then checks himself realising he’s expected to pay for their coffee. 

Sama’s sketches are also reflective. Slowing his self deprecating wit to literary-driven reflection he draws extensively on Tolstoy, Wilde and Fitzgerald. Quotations and references litter the pages. Describing himself and his colleagues as ‘beholden to market momentum the way Tolstoy’s great men and kings were slaves to history’, has a certain grandiosity that feels at odds with the almost flippant mundanity of his thoughts elsewhere. Occasionally his references feel self-consciously literary but drawing from their understanding of greed and lost illusions to reflect upon his own life, gives Sama’s memoir a depth it would otherwise lack.  

[See also: Review: The Price Is Wrong is another work of whistling ambition from Brett Christophers]

And maybe that’s the point of The Money Trap. Sama left SoftBank in 2019 to enrol on an MFA in creative writing, just before WeWork crashed, and after the death of both his parents.  

Speaking to his fellow creative writing students, Sama says he wants ‘to write to help me make sense of it, maybe figure out what it all means’. His fellow students respond enthusiastically: ‘That’s cool. Yeah, kind of what everyone’s doing.’ 

Sama closes the exchange with a trademark touch of irony:  ‘In my world the only reason people examine their lives is to figure out ways to make more money’.  

The Money Trap. Alok Sama. Pan Macmillan. September 2024, £20.24 

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  • Senior Executive/SVP or Corporate VP or equivalent
  • Director or equivalent
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  • Head of Department/Function
  • Manager
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Visit our privacy policy for more information about our services, how Progressive Media Investments may use, process and share your personal data, including information on your rights in respect of your personal data and how you can unsubscribe from future marketing communications.
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