Genius, Delusion, and Billion-Dollar Bets: A Softbank Insider's Tech Finance Odyssey

Alok Sama shares 5 key insights from The Money Trap: Lost Illusions Inside the Tech Bubble.

What’s it like to be at the intersection of big money and big tech? Well, it certainly can be a wild ride, at least according to Alok Sama. Alok was a veteran Morgan Stanley banker when he joined the leadership team at Softbank and started making eye-popping deals alongside that company’s legendary founder, Masayoshi Son — one of the most influential technology investors in the world. Alok shares these adventures — and their toll on his mental health — in the new memoir The Money Trap: Lost Illusions Inside the Tech Bubble. Here’s Alok to share 5 of his key insights.

The 5 Key Insights 

1. Be crazy, my friend.

2. …but don’t get too crazy.

3. The money trap.  

4. Beware artificial stupidity.

5. If you need a friend, get a dog.

1. Be crazy, my friend.

To succeed as a technologist, sometimes you need to be a little bit crazy. Like Masayoshi Son, who hits targets nobody can see and wants to be remembered as “the crazy guy who bet on the future.”

In the mid-nineties, Masa foresaw the internet revolution. At the height of the 2000 tech bubble, he owned 8 percent of all internet stocks, briefly making him the richest person in the world. He also had an agreement to buy a third of a small online bookseller called Amazon, but he ran short of cash. Later, he bought a struggling phone company five times the size of his SoftBank, based on a vision of connected smartphones—before the iPhone existed. He also made a $20 million bet on a Chinese schoolteacher with “strong and shining eyes” and turned it into the greatest venture investment of all time: a $100 billion stake in Alibaba. His audacious $32 billion acquisition of chip designer Arm Holdings was a bet on a tomorrow of “connected and intelligent things” and is now worth almost $200 billion.