In 1996 I came across Cisco’s annual report, which included a CD-ROM presentation by CEO John Chambers titled The internetworking takes off. At that point, there was absolutely no sign of a dot-com hype, though Alan Greenspan thought otherwise in his irrational exuberance speech of December 1996.
At almost the same moment, Yahoo! went public. A colleague of mine—a passionate investor in (bio)technology—subscribed to that IPO. While the initial stock performance was disappointing, the shares surged in the second half of 1998.
After Christmas 1998, thanks to Yahoo!’s explosive rally, I realized that we did not have enough internet names in our equity universe. We were focused more on the “old economy” than the pricey “new economy.” Still, one special name entered our universe: SoftBank. It was fascinating that SoftBank’s stake in Yahoo! was worth more than the entire SoftBank share price. In 1999, SoftBank’s stock multiplied twentyfold; CEO Masayoshi Son had recognized early on that the internet would be a success. Later he repeated this feat with Alibaba.
From internet pioneer to AI giant
Since the 1990s, Masayoshi Son has emerged as one of the most influential players in the global technology industry. This Japanese billionaire of Korean descent positioned himself as a bridge between Silicon Valley and Japan, enabling him to strike groundbreaking deals such as the 2008 iPhone launch in Japan. That deal gave SoftBank a decisive edge in the Japanese mobile market and showcased Son’s ability to forge strategic partnerships.
Son’s investment philosophy is defined by bold bets on future technologies. His biggest successes—early stakes in Yahoo!, Alibaba, chip designer Arm, and ByteDance (TikTok)—demonstrate his ability to spot trends early and go all in. His investment in Alibaba generated tens of billions for SoftBank and cemented his status as one of the world’s most successful tech investors.
But his track record also includes spectacular failures, with WeWork being the most painful. That investment cost SoftBank billions of dollars and highlighted the risks of Son’s aggressive strategy. The collapse of the co-working firm raised questions about his judgment and appetite for risk.
The Trump connection
What now sets Son apart from other tech investors is his unique relationship with President Donald Trump. This bond dates back to Trump’s first term, when in December 2016 Son pledged a 50 billion dollar investment at Trump Tower. Upon Trump’s reelection, he doubled that pledge to 100 billion dollars, underscoring his strategic thinking about the US market.
The recently announced Stargate deal illustrates the true scale of Son’s American ambitions. Together with OpenAI’s Sam Altman and Oracle’s Larry Ellison, he pledged a staggering 500 billion dollars to build AI data centers. These large-scale projects position SoftBank as a crucial foreign investor in strategic sectors such as artificial intelligence and semiconductors.
Son’s approach to the US market reflects his insight into local political dynamics. While other foreign investors often face resistance or suspicion, Son is welcomed in Washington. His concrete job-creation promises and willingness to invest in physical, strategically important infrastructure make him an attractive partner for the Trump administration.
Geopolitical shift
Notable is Son’s strategic pivot from China to the United States. While SoftBank still holds significant stakes in Chinese firms such as ByteDance, the trend in recent years has clearly shifted toward America. This move reflects not only broader geopolitical tensions between the superpowers but also Son’s pragmatic approach to global investing.
His close ties with Trump, however, carry risks. Japanese diplomats have expressed concern about Son’s role as an unofficial gatekeeper between the two nations. When critical discussions at the highest level bypass traditional diplomatic channels, a potentially fragile situation arises for both countries.
Future and risks
For investors, Son remains a visionary with both spectacular successes and painful failures to his name. His close ties with Trump may open doors, but they also create new vulnerabilities. At a time when technology and geopolitics are increasingly intertwined, Son embodies the complexity of modern international investing.
Looking back at the 1990s, when SoftBank was still a relatively unknown player with an undervalued stake in Yahoo!, Son’s expansion into a global technology empire is remarkable. The question remains whether his current US strategy will be as successful as his earlier bets on internet giants, or whether new challenges await him. What is certain is that the Japanese billionaire will continue to play a central role in shaping the global tech industry, thanks in part to his unique position between East and West.
Han Dieperink is chief investment officer at Auréus Vermogensbeheer. Earlier in his career, he served as chief investment officer at Rabobank and Schretlen & Co.