In the investment world, very few investors are willing to commit billions of dollars to companies that have yet to turn a profit. Yet this is precisely the philosophy embraced by Masayoshi Son, the founder and Chief Executive Officer of SoftBank Group of Japan.
He is well known for his belief that extraordinary returns require extraordinary risks. This strategy has made him one of the world's most successful venture capital investors, while at the same time exposing him to multi-billion-dollar losses whenever his bets fail.
Investments That Created Extraordinary Wealth
Alibaba
Masayoshi Son's most famous investment was undoubtedly Alibaba.
In 2000, he invested approximately US$20 million in Alibaba, then a small Chinese company founded by Jack Ma.
That decision eventually became one of the greatest venture capital investments in history.
When Alibaba was listed on the New York Stock Exchange (NYSE) in 2014, the value of SoftBank's stake surged to more than US$60 billion. At its peak, the investment was worth over US$150 billion, representing thousands of times the original investment.
This single investment alone was enough to offset losses from many unsuccessful ventures.
Other Major Successes
Arm Holdings
SoftBank acquired Arm Holdings in 2016 for approximately US$32 billion. Arm is a European technology company specializing in semiconductor chip architecture and design.
In 2020, Masayoshi Son planned to sell Arm to Nvidia, a leading American artificial intelligence (AI) technology company, for US$40 billion. Under the proposed deal, Arm would have been merged with Nvidia, and Son would have become one of Nvidia's shareholders through a share exchange.
However, the transaction was ultimately blocked by U.S. regulators on antitrust grounds.
Son then pursued an alternative strategy by listing Arm on the Nasdaq Stock Market in 2023 at an initial public offering (IPO) price of US$56 per share.
Driven by the rapid growth of the artificial intelligence industry, Arm's market value increased dramatically.
By mid-2026, Arm's market capitalization had soared to approximately US$300 billion, enabling Son to generate an estimated US$260 billion in unrealized gains.
Coupang
SoftBank was also an early investor in South Korean e-commerce company Coupang.
Masayoshi Son first invested US$1 billion in Coupang in 2015, believing that the company's true value was around US$5 billion at the time.
In 2018, through SoftBank Vision Fund, he invested an additional US$2 billion, estimating that Coupang's valuation had increased to approximately US$9 billion.
His total investment reached US$3 billion, while the company's estimated value rose to US$9 billion, generating an unrealized gain of roughly US$6 billion.
When Coupang was listed on the New York Stock Exchange in 2021, SoftBank and Vision Fund together owned approximately 34% of the company. At the time, Son recorded an estimated US$30 billion in paper profits.
Grab
Grab is one of the most recognized technology brands across Southeast Asia. Although founded in Malaysia, it is headquartered in Singapore.
It initially invested around US$1.5 billion, and through Vision Fund increased its total investment to more than US$4.5 billion over the following years.
Although Grab's share price has fluctuated since its public listing, the company remains one of the key holdings within the Vision Fund portfolio.
Investments That Ended in Failure
Venture capital investing involves exceptionally high risk. While returns can be enormous, losses can be equally significant.
The principle of "high risk, high reward" does not always produce success.
WeWork
The most famous investment failure was WeWork, which became one of the most expensive mistakes in SoftBank's history.
SoftBank invested more than US$10 billion in the office-sharing company. Masayoshi Son firmly believed that WeWork would transform the commercial real estate industry.
However, when WeWork attempted to go public in 2019, investors began questioning its business model, corporate governance, and massive operating losses.
The IPO collapsed, the company's valuation plummeted, and WeWork eventually filed for bankruptcy protection.
SoftBank is estimated to have lost more than US$11.5 billion on this investment.
OneWeb
SoftBank also invested billions of dollars in satellite communications company OneWeb.
When OneWeb filed for bankruptcy in 2020, SoftBank was forced to record substantial write-downs before the company was eventually rescued by new investors.
Total Investment Losses
During the 2021/2022 financial year, SoftBank's Vision Fund reported investment losses of approximately US$26.2 billion, making it one of the largest losses in the history of the venture capital industry.
The sharp decline in global technology stocks significantly reduced the value of many companies within its investment portfolio.
Despite these setbacks, Masayoshi Son did not abandon his investment philosophy.
He continues to believe that a handful of extraordinary investments can more than compensate for dozens of failed ones.
In high-risk investing, losses are inevitable. However, the enormous gains generated from investments such as Alibaba, Arm Holdings, Coupang, and many other successful companies have been sufficient to offset those losses. That, according to Son, is what truly matters.
Masayoshi Son's Investment Philosophy
Masayoshi Son's approach differs significantly from that of traditional investors.
He does not expect every investment to succeed.
Instead, he believes that if only five or ten companies out of every one hundred investments become global giants, the profits generated by those few exceptional winners will more than cover the losses from all the others.
This philosophy forms the foundation of venture capital investing.
Through SoftBank Capital, Vision Fund 1, Vision Fund 2, the Latin America Fund, and other investment vehicles, SoftBank has invested in more than 500 companies.
Some investments have been fully exited for profits, while others have been partially sold or are still held today. Profits have been realized through IPOs, acquisitions, direct sales, and corporate restructuring.
Lessons for Individual Investors
Masayoshi Son's story offers several important lessons for individual investors:
- High risk can generate exceptionally high returns, but it can also result in substantial losses.
- Diversification is essential because not every investment will succeed.
- Extraordinary successes like Alibaba are rare, but a single outstanding investment can transform an entire investment portfolio.
- Investors need conviction, patience, and the financial capacity to withstand significant market volatility before investing in high-risk companies.
Masayoshi Son has demonstrated that the courage to embrace risk can create extraordinary wealth.
At the same time, his history serves as a reminder that in the investment world, high risk does not only offer the possibility of exceptional rewards—it can also lead to devastating losses when an investment thesis proves wrong.
Ultimately, successful venture capital investing requires more than courage alone. It demands knowledge, experience, sound judgment, and disciplined decision-making to ensure that the frequency and magnitude of successful investments consistently outweigh both the frequency and magnitude of investment losses.
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