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Money, technology, happiness – in conversation with Softbank’s former president Alok Sama, bestselling author of ‘The Money Trap’ >
by Madanmohan Rao [September 29, 2025]
The Money Trap: Lost Illusions Inside the Tech Bubble by Alok Sama has won the CK Prahalad Best Business Book Award at the 2025 edition of BizLitFest Bangalore.
Check out our interviews with six other bestselling authors here:
Ganesh Krishnan, Mastering Disruption: A Practical Guide to Understanding New-Age Business Models
Nitin Seth, Human Edge in the AI Age: Eight Timeless Mantras for Success
Arun Maira, Reimagining India's Economy: The Road to a More Equitable Society
Vandana Vasudevan, OTP Please! Online Buyers, Sellers and Gig Workers in South Asia
Subroto Bagchi, The Day the Chariot Moved: How India Grows at the Grassroots
Roopa Pai, Becoming Bangalore: Stories That Shaped a Hometown
Alok Sama is the former President and CFO of SoftBank Group International. He previously served as a Managing Director at Morgan Stanley, and has worked in finance and technology for over 30 years in New York, San Francisco, London, and Hong Kong. Alok holds a BA in mathematics from St. Stephen's College in Delhi, an MBA from The Wharton School, and an MFA in Creative Writing from New York University.
After over 15 years in corporate finance at Morgan Stanley, Alok switched tracks to SoftBank and plunged into Founder–CEO Masayoshi Son’s high-speed, high-risk decision-making in the tech sector. The 290-page book is a fascinating first-person account of life in the fast global lane with deals involving business leaders across continents – along with corporate jet travel and expensive La Tache wine.
Alok has high regard for Son’s infectious idealism, crazy blend of futuristic strategy and detailed operations, and ability to spot technology megatrends repeatedly – such as the internet, smartphone and AI. After around six years at Softbank (2014-2020) – which was also marred by an unfounded external smear campaign – Alok completed an MFA in Writing from New York University.
The 18-chapter book shows how tech business models get disrupted all the time, but it is important to ride megatrends and execute bets on the promising players (being a ‘hunter’ and a ‘cook’). “Monetary value is whatever the next bidder is prepared to pay,” Alok writes in the first chapter.
“Investment bankers are like martlets – birds without feet, condemned to a life of continuous flight,” he aptly describes. “Nobody walks out of the money trap,” he cautions.
Masayoshi (‘Masa’) Son successfully backed Alibaba and Arm, and his audacious $100 billion Vision Fund was raised in 2016, with large investments from Saudi Arabia and UAE. He is now pouring billions into the Stargate AI infrastructure project in the US.
Son also went beyond pure analytics to spot entrepreneurial brilliance (Jack Ma), though he missed the mark on occasion (WeWork). Above all, Son’s ambition is to bring “happiness to all” through technological development.
Alok contrasts “value investors” like Waren Buffet with “growth investors” in the tech sector like Masayoshi Son. Erratic behaviour is a “necessary trait” of outliers. Backing local champions like Snapdeal, Ola and Oyo gave Son “cult status” in India.
Technology investing is speculative, and not for the faint-hearted. “Even a proven business is constantly threatened by disruption,” Alok cautions, pointing to Blackberry as an example. But savvy investors find opportunity in every calamity as well.
Ultimately, the witty and reflective book is also a cautionary tale about how money doesn’t necessarily buy happiness, as the goalposts of desire continuously shift with each gain. Family, health and a sense of purpose are important as well.
Alok describes the loss he felt when he lost his father and then his mother. “No matter how old you are, your childhood dies with your parents,” he writes.
Writing books has been his closet ambition. “This is the first award I have received since my college days,” Alok joked, in his acceptance speech at BizLitFest Bangalore.
He believes we are now in an AI bubble, though it is hard to say how long it will last. There is certainly a lot of FOMO investing in the sector, but AI will have revolutionary effects just as the internet did from the 1990s onwards.
In this brisk interview, Alok talks about the reception to his book, his journey as an author, his reading habits, and India’s position in the global tech race.
Madan: How is your book being received? What kinds of feedback did you get?
Alok: Generally great. Readers appreciate the candour and the humour. Feedback on the writing is consistently good, which I appreciate. The main criticisms are that I don’t dig deep enough on finance issues, but that was never my intention.
Madan: You write that ‘nobody walks out of the money trap.’ Would you say you have walked out now? What are your plans now in addition to becoming an author – becoming more of a hunter or more of a cook?
Alok: Remember I am an old guy, I am happy to be walking, period! I am about two-thirds of the way through a novel (pure fiction this time) so that occupies my mind space. The rest is mostly about staying alive and healthy.
Madan: Your hobbies like music (especially jazz) seem to have worked well for you to connect with other leaders! What other hobbies can help here?
Alok: Golf, I guess – though that’s a bit of a cliche. But I don’t look at hobbies as a way to connect, I play golf because it is probably the least demanding physically.
Madan: If you could go back in time and start your financial career again, what do you think you might do differently this time around?
Alok: Maybe leave banking earlier, perhaps be easier on myself, because so much of life is serendipity.
Madan: The book offers phenomenal details of the high-stakes meetings you were in – was it a challenge to get clearance to publish such confidential information?
Alok: There’s nothing confidential in the book. What we ate in a meeting or what was said does not fall within the category of sensitive or confidential when the outcomes are known. I have signed an NDA which I respected fully.
Madan: Your book has largely focused on the digital sector – what are your thoughts now on other sectors like bio, materials or energy?
Alok: I don’t really have any such insights, it’s not my focus. I read two books a week, mainly fiction, so I am the worst person now for any type of investment or business advice. I don’t really own any individual stocks anymore.
Madan: For those of us who are not financial engineering wizards, what are some useful books or websites you would point us towards to learn about the craft?
Alok: As I said, I am out of touch, but in general I am cynical about any books or websites that purport to give investments advice. I have been in the business almost 40 years and I stick with index investing.
Madan: What was your writing like before you got your MFA in writing?
Alok: I read my earliest stuff and find it somewhat self-conscious, even pretentious.
Madan: When will we see India producing the next big tech giants – and mega-investors?
Alok: Not in my life time. Only China has the educational infrastructure to challenge the US.
Madan: What do you see as the ‘India moment’ to thrive in the AI age? How are we positioned to grab the opportunities and tackle the challenges?
Alok: India will be taking its cue from the US, just like everyone else. There’s no shame in that.
I love India but I find our national pride somewhat misplaced. We are a poor country, it takes more than a huge population to make a superpower.
Madan: What’s your next book going to be about?
Alok: Fiction, exploring themes of immigrant identity and what causes people to go over to the dark side.
Madan: Are you still indulging in fine La Tache wine each week?
Alok: Ha! Can’t handle alcohol in my old age and only Son-san can afford La Tache!
Madan: What are your parting words of advice or tips for the aspiring entrepreneurs in our audience?
Alok: Whatever you’re working on, you will falter. It’s all about how quickly you pivot or bounce back.
Madan: Any other comments or remarks you would like to make?
Alok: Be yourself—because everyone else is taken.
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