‘What I always admired about him is his ability to see what the world could look like in 10 years time, and buy into a business that may not actually exist yet’ – Alok Sama talks to Professor Florin Vasvari about working with the iconic founder of Softbank, Masayoshi ‘Masa’ Son and his new career.

Google ‘Alok Sama’ and a veritable deluge of headlines from the world’s most respected business and financial titles pops up.

Alok has written a book – a widely-applauded biographical memoir of his time as President and CFO of SoftBank Group International, where he worked hand-in-glove with the technology firm’s visionary founder Masayoshi Son – or Masa, as Alok affectionately refers to him during a recent London Business School Summit Series event, where Alok was the guest speaker.

Of course ‘Masa’ needs little introduction.

Introducing Masa

A Japanese businessman and early investor in the internet stocks of the mid-1990s, including Yahoo,
Masayoshi Son briefly became the world’s richest person in 2000 before losing most of his wealth in the dot com crash. Tokyo-based Masa was already doing iconic deals before launching the audacious $100 billion Vision Fund in 2017.

A real-life fever dream, with a valuation of at least 30% greater than the entire venture capital market at the time, the Vision Fund swiftly became known for committing eye-popping, head-turning sums to high-potential technology firms on a mission to transform sectors and industries through digital capability, robotics and AI.

Launched with seed money from the Kingdom of Saudia Arabia and the United Arab Emirates (UAE), Masa’s Vision Fund is famous for its bold bets, making billions of dollars on backing Alibaba in its earliest days, while losing billions of dollars on its investment in WeWork, a startup offering co-working and on-demand workspace that once promised to reinvent the concept of the office.

There was also the incredibly successful $34 billion acquisition of UK semiconductor ARM Holdings Plc, a company whose chips are the backbone of almost every single smartphone processor today, a not-as-successful $9 billion investment in US ride-hailing app Uber and many, many other smaller investments across technology verticals, including fintech, ecommerce and ultra-fast grocery delivery. Alok believes the fund can be credited with catalysing the amount of capital available for technology start-ups and scale-ups – “Before the Vision Fund, you didn’t have multibillion VC funds – now you do”.

In the room where it happens

For many of these iconic deals and historic handshakes, Alok Sama, who had been a Managing Director at Morgan Stanley, working in capital markets in London, New York, Hong Kong and India, was right there at the table with Masa, his hand firmly on the rudder. This includes orchestrating Softbank’s $59 billion super-complex mega-merger of SoftBank-owned Sprint and T-Mobile.

So, it’s little wonder Alok’s debut “The Money Trap: Grand Fortunes and Lost Illusions Inside the Tech Bubble” is listed one of Bloomberg’s Wall Street books of 2024 and the global financial media can’t get enough of Alok Sama right now. After all, which self-respecting student of finance, investing and business wouldn’t be insatiably keen to get a behind-the-scenes reveal on what happened inside those boardrooms and build a fuller picture of the type of person who can get name checked in the Guinness Book of World Records for losing the most of money ever – $75 billion in financial assets between 2000-2003 – only to carry on and become even more successful?

Apart from the delicious sense that you have secured a pass to one of the world’s most exclusive clubs, the book has the pace, style and tone of a sassy thriller, with an opening Raymond Chandler would be proud of – no doubt literary influences inspired from his year at New York University where he completed a Master of Fine Arts between 2021 and 2023 in anticipation of embarking on his next chapter as an author.

it is clear Alok is proud of the book, much more animated when discussing some of its more philosophical themes, such as money’s role in the pursuit of happiness (read the title again to see what Alok thinks about that) then the nitty gritty of dealmaking, or explaining how as a banker, he made the transition to investing. Yet Alok fans, mostly LBS students, alumni and bankers wanting a piece of VC action, still wanted to know and the Delhi-born mathematician obliged with a humility that is not frequently apparent in the super rich and successful.

‘A series of fortunate accidents’

“Mostly my career has been a series of fortunate accidents,” Alok says. “I didn’t set out to be a banker. In my book, I tell the story of how I actually wanted to be an academic. My father introduced me to somebody whom he thought was a mathematician but taught statistics at Wharton, and that’s how I ended up there.” After completing his MBA, Alok joined Morgan Stanley – another happy accident. “If you are going to work, I thought I may as well get the biggest bang for my buck. It was just luck that I happened to get offered a job at Morgan Stanley, which from a cultural perspective was awesome.”

Alok says Morgan Stanley was good to him, moving him around to keep him on his toes. He led the firm’s communications practice in Europe and the telecoms, media and technology (TMT) practice in the Asia-Pacific region, as well as establishing operations in India. All this over a period of more than two decades. But nobody ever dreamed of becoming an investment banker, least of all Alok, and he left the bank in 2003.

Meeting Masa and joining SoftBank was another ‘fortunate accident’. Alok was already over the age of 50, and not really looking to getting sucked into something so intense. But the curse of having friends in high places… Nikesh Arora, Google’s one-time Senior Vice President was heading to SoftBank in 2014 to steer the company’s investment strategy. He persuaded Alok to take a meeting with Masa – an invitation he couldn’t really turn down.

“We had lunch and it jumped out at me that Masa was unlike anyone I’d ever met. I’d heard of him as a result of his rise and fall in the dot com boom and bust. In the year 2000, he owned about 8% of all internet stocks, which is mindboggling. He didn’t get out in time and lost most of his money.

So, did Alok’s sharp banking skills prepare him for life on the other side of the fence? The answer might surprise you. In terms of deal pricing, yes, but mostly no. Alok laughs. “Masa used to chide me, saying that I needed to be less of a cook and more of a hunter. If it was up to me, I wouldn’t have touched Alibaba (which turned out to be one of Masa’s most successful investments). Jack Ma was a school teacher with no business experience. My trained methods of assessing value in companies were the opposite of helpful.”

Alok adds: “The truth is technology valuations do not matter. When you are investing in technology transformation, you must be able to visualise a world 10 years out. If the business succeeds, it won’t matter if your valuation was $100 million or $200 million or $600 million. Because the business will be worth $10 billion and maybe $20 billion or $30 billion. Of course, it may not work out but that’s the price you pay. This is what I admired about Masa – his uncanny knack of seeing the future and betting big on it.”

Other standout takeaways

The one thing that was completely unique about the Vision Fund was its leverage in the form of mezzanine capital. This allowed it to pay a cash dividend without pulling money from its LPs.

Some see China and the US locked in a geopolitical arms race to dominate the AI future, but framing it like that is unhelpful. “AI is simply a productivity tool, just as the internet before it. It matters less which LLM you are using, then that you are using one to deploy AI in your business. If you are not, your firm is toast.

One thing Alok would tell his eight-year old self?
Don’t worry be happy – and study the classics to learn concepts like hubris – very important for working in the capital markets

Hear more about what Alok Sama had to say about developments in AI and being the wingman for Masayoshi Son in the video recording.

Alok Sama was in conversation with Florin Vasvari, Professor of Accounting and Academic Director of the Institute of Entrepreneurship and Private Capital at London Business School.