Imagine throwing billions of dollars into startups that might never see the light of day. Now imagine doing that repeatedly, and still ending up one of the richest people in the world. That’s Masayoshi Son, the founder of SoftBank, in a nutshell. He’s like the financial version of a high-stakes gambler who somehow always walks away with the jackpot (well, almost always).
Son’s strategy? Go big or go broke. His investment playbook is not for the faint of heart, but if you want to learn how to make (and keep) money in the modern world, studying his moves is a masterclass in risk-taking. Some of his investments paid off massively, while others… well, let’s just say they’re cautionary tales.
Ready to dive into the high-risk, high-reward investments that made Masayoshi Son a legend? Let’s go!
1. Alibaba – The $20 Million Bet That Turned Into $100 Billion
Back in 2000, Son bet $20 million on a little-known Chinese e-commerce company called Alibaba. People thought he was crazy, China’s internet scene was still developing, and e-commerce wasn’t a big deal yet.
Fast forward two decades, and that $20 million ballooned into $100 billion. That’s a 500,000% return (let that sink in). If there’s one lesson here, it’s this: Find an underdog with a strong vision and bet on the future, not the present.
Pro Tip: Want to invest like Son? Start small with The Intelligent Investor by Benjamin Graham on Amazon. It’s the ultimate investing bible. 2. ARM Holdings – Buying The Brains Behind Every Smartphone
In 2016, SoftBank acquired ARM Holdings for $32 billion. If you don’t know ARM, just know this: it’s the tech behind nearly every smartphone chip in the world.
Did Son have a crystal ball? Nope, just a deep understanding of owning the infrastructure behind the industry. Instead of betting on one smartphone company, he bet on the company supplying all of them.
Lesson? Own the picks and shovels, not just the gold.
3. WeWork – The $10 Billion Disaster
Okay, not every bet can be a winner. Son poured billions into WeWork, a company that basically rented out fancy office spaces with free kombucha. The hype was real, until the IPO attempt revealed the financial disaster beneath.
SoftBank ended up losing billions, but Son still sees potential. The takeaway? Don’t let hype cloud your judgment. Always check the fundamentals.
4. Uber – Backing The Future of Transport
Son invested $9 billion in Uber, betting big on the ride-sharing revolution. While Uber hasn’t been the wildly profitable cash cow some expected, it’s still a major player in global transport.
Lesson? Disruptive ideas take time, but betting on convenience is usually a good call.
5. ByteDance (TikTok) – Catching the Social Media Wave Early
Before TikTok took over the world, Son saw the potential in ByteDance and invested billions. Today, TikTok is valued at over $200 billion, making it one of the biggest social platforms in history.
Moral of the story? Pay attention to emerging trends. The future of business is in attention and engagement.
6. OYO Rooms – Betting Big on Budget Hotels
Son saw potential in OYO Rooms, an Indian startup trying to dominate the budget hotel industry. While it had a rocky road, it still exists, proving that Son isn’t afraid to wait for long-term growth.
Lesson? Patience pays, but only if the business model makes sense.
7. DoorDash – The Food Delivery Boom
SoftBank invested heavily in DoorDash, and when the pandemic hit, food delivery exploded. The stock skyrocketed, proving that sometimes, external factors can turn a good bet into a great one.
Lesson? Think about how industries will change over time. Convenience always wins.
8. Didi – The Uber of China
Son invested in Didi, China’s ride-hailing giant, in an attempt to dominate transportation. While Didi faced regulatory struggles, it’s still a major force in the global market.
Lesson? Betting on regional dominance can be risky but rewarding.
9. Paytm – Digital Payments in India
Son invested in Paytm, India’s top digital payment platform. While the company struggled post-IPO, digital payments are still the future.
Lesson? Digital finance is a long-term game, patience is key.
10. Compass – Real Estate Reinvented
Son invested $500 million into Compass, a real estate tech company. While it hasn’t been a huge win, the bet shows he believes in tech-powered real estate.
Lesson? Even billionaires don’t always win, but they keep playing.
The Takeaway: Invest Smart Like Son
Masayoshi Son’s story is a wild mix of massive wins and brutal losses. The key lessons?
- Bet on future trends, not just what’s hot now.
- Look for companies that own the infrastructure, not just the product.
- Be patient, real wealth takes time to grow.
- Take calculated risks, but don’t ignore red flags.
Want To Start Your Investment Journey?
If Son’s story has inspired you, start with the basics! The Intelligent Investor is a must-read for anyone serious about building wealth. Grab your copy now on Amazon and take your first step toward smart investing!
Over to You!
What’s the riskiest investment you’ve ever made? A stock? Crypto? That $10 latte from Starbucks? Drop your answer in the comments below!