Alok Sama, former president and CFO of SoftBank Group International, and Charles Assisi, co-founder, Founding Fuel, discuss Sama’s memoir The Money Trap: Grand Fortunes and Lost Illusions Inside the Tech Bubble.
Building on the ideas in the book, Sama talks about his experiences in banking and tech, and his transition to writing. He reflects on his interactions with some unique personalities—political leaders like Bill Clinton and Narendra Modi, and tech giants like Elon Musk and Mark Zuckerberg. He also dwells on the complexities of SoftBank’s founder Masayoshi Son, the thinking behind his biggest tech investment bets—and how that reshaped the venture capital world.
He talks about the challenges and opportunities in the tech industry, including the importance of energy efficiency in AI and the potential of Indian semiconductor manufacturing, especially the context of China’s dominance.
Highlights from the conversation
(Editor’s Note: You can jump directly to the highlight by scrolling the video above to the mentioned timestamp. Or, you can watch it on YouTube and jump to any of the chapters.)
03:35 The money trap, smear campaign, and committing to writing
“Even if you're bored, even if you're stressed out, it's just really, really difficult for people to walk away with lots of money… I was completely in that money trap… My departure from banking came about in a rip roaring bull market. My client was the highest fee paying client in Europe. And then it went from being a $100 billion market cap company to nothing. In that business, you're worth only the revenues you’ve clocked in from your last deal, or your clients. That's how it goes. And I became a target—I was forced out.”
11:22 Impressions of politicians—Dick Cheney, Narendra Modi, Bill Clinton
“This gets to an issue that I tease out in the book, which is one of identity for immigrants….
I'm in Delhi, and I'm meeting Narendra Modi… this is my Prime Minister. So I go up to him, and very respectfully, lower my head, and I do a Namaste. But he just ignores the Namaste, and he shoots out his hand and gives me a very firm handshake… I have this impression of myself as a local boy in my hometown… but he's thinking of me as this American, English banker.”
15:26 Integrating into the Silicon Valley, setting up Morgan Stanley’s investment banking business in India, and working in Japan and SoftBank
Morgan Stanley in India: “It helped that I surrounded myself with people who were integrated… [among] the first people I hired was Jyotiraditya Scindia. He was the junior-most person in my team. He was my analyst… When I met him, I was thinking, this is one of those Indian style politician’s son, give him a job kind of meetings. He was incredibly respectful, serious, really bright, earnest, and turned out to be a terrific hire.
“I have this wonderful story about [his father Madhavrao Scindia]... He would never get his secretary to call. He would always call himself… He would always start the conversation by saying, are you available? As opposed to, I want to… Jyotiraditya was exactly like that….”
Silicon Valley: “Being Indian in the valley is not a challenge. It's dominated by Indians.”
SoftBank: “I don’t miss the pay chequeI miss hanging out with Masayoshi Son. He was fun, and I miss all the people he surrounded himself with.”
24:17: Elon Musk and Mark Zuckerberg
“If you accept that climate change is a challenge, Elon Musk has done more to address that problem than anyone on the planet… Creating Tesla, the electric car company, is a very big deal. From an engineering perspective, from a technology perspective, it's not as simple as you take a car and you plonk an electric battery in it… Now, what don't I like about Elon Musk? For a man who's accomplished so much… some of the things you're saying and some of the things you're doing now, and you kind of just locked yourself into this buffoonery around politics.”
“With Zuckerberg, I have a fairly cynical view of social networks.”
27:48 On leaning to the left or the right, and Ayn Rand
“Economically, and this comes from growing up in India in the 1970s and ’80s—kind of in the License Raj, Indira Gandhi is part that—that would turn anyone right wing, because there's a giant experiment going on in terms of how not to run an economy, and it failed miserably.”
30:39 Silicon Valley’s ‘The India Story’ thesis
“We're at probably close to peak hype when it comes to India. The only point I would make in defense of the ‘this time, it's different’ argument is that I think, relative to say, the last bull market, the Indian market this time is driven much more by domestic capital—which is healthy…
“India is incredibly seductive, and people sometimes lose track of the fact that in terms of spending power, the numbers are incredibly small.”
34:15 China, SoftBank and Masayoshi Son
The risk in China: “A team of us at Morgan Stanley were charged with taking China Unicom public. At the time [mid 1990s]... you just had China Mobile. The Ministry of Communications decided they needed a second carrier, and they gave us the mandate to create this carrier and take it public. So basically,... they agreed to give them spectrum, licences, management team… And my key learning from that is, if it's just so easy to create this company, it is equally easy to unravel it…
“The whimsical nature of capitalism in China. You know, one minute, it's glorious to be rich, and now all of a sudden you really don't want to be on the list of the top 10 richest people in China, because that just makes you a target… there's that overlay of risk, and I was always aware of that from my dealings in China….
“From a SoftBank perspective… after what happened with Alipay with Alibaba… that was terrible because so much of the value was tied up in Alibaba.”
Masayoshi Son’s bets:
Alibaba: “I [asked if he was] thinking about selling Alibaba when the company went public… [he’d been invested for] well over 15 years, you probably think of taking some chips off the table, right? You invested 40 million… it’s now worth 50 billion…. Masa pushed back, and he was right, because the company's value went up over 200 billion, as I recall… but there is the overlay of diversification [for risk management in investing]. The argument that prevailed on Masa, that Nikesh [Arora] and I prevailed on him that, look, let's lighten up, particularly if you're thinking in terms of big acquisitions like ARM… Softbank had already acquired Sprint, was unable to merge Sprint with T Mobile, so you had this struggling phone company which was… over $30 billion in debt for SoftBank…. If you want to stay on the acquisition trail, you really do need some liquidity. So that's the argument that prevailed… we sold close to 10 billion stake.”
Son’s legacy: “There's a lot of runway left… His big legacy so far has been getting big bets in a kind of this ‘crazy guy who lives in the future of ideas’—he's proven that out, and he's gotten these big bets spectacularly right. Mark to market gains of well over $100 billion, Vodafone Japan, $40 billion—these are phenomenal numbers by any standards. Alibaba, fully realised. That's his legacy—seeing around corners, living in the future, identifying technology trends early and getting them spectacularly right.
“He upped the ante for most people… Now people routinely talk about billion dollar funds—not just funds. People talk about billion dollar individual investments in companies, in artificial super intelligence, without a penny in revenue, $5 billion valuation, $1 billion invested, right?... A lot of it is the impact of SoftBank. It just raised the stakes in terms of people raising more money and more money being thrown at technology.
45:36 The ARM deal, semiconductors, AI and a potential NVIDIA challenger
“The Masa Son and the SoftBank aspect is really important to understand. If there is such a thing as a first love for Masa, it is semiconductors… ARM was a company he'd followed and coveted…. Part of ARM's secret sauce has been energy efficiency. Bookmark that comment, because energy efficiency is absolutely crucial to what's happening with AI…. AI is increasingly going to move to the edge of the network. By the edge of the network, I mean smartphones and autonomous cars…. ARM has the potential to, over time, compete with NVIDIA in data centres.”
53:58 Make in India
“It is the right thing, not only for India, it's the right thing for the world, because you don't want to be so completely reliant on TSMC, which is the case today…. One of the spot points when it comes to geopolitical volatility is the China - Taiwan axis.
56:50: Big tech’s discomfort with taking on debt
“At the root of it is this fundamental insecurity… And you should be paranoid. Because even Google—arguably the ultimate cash cow, quite possibly in the history of mankind, in terms of how phenomenal their search business is as a cash generator. How dominant it's become. They need to be fairly paranoid because something like Perplexity comes along, and people who use Perplexity say, I ain’t going back to Google. So you know, AI is a real technology challenge to Google.”
59:14 Inflated tech valuations
“In the public markets, no; in the private markets, yes.”
1:01:50: Masayoshi Son, the futurist
“The art of writing is to bring out the richness and the complexity of people without categorising them as good or bad… Masa Son’s ability as a technologist, to peek into the future is unmatched. He did it with smartphones. He did it with e-commerce in China. He did it with AI… The hype about AI, ChatGPT—this stuff is only a year old. Masa Son was talking about this in 2014.”
