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SoftBank’s CEO Masayoshi Son Is ‘Embarrassed’ About WeWork and Uber Investments

Reported by Observer
Oct 7, 2019· 3 min read
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Key Takeaways
  • • SoftBank CEO Masayoshi Son publicly acknowledged embarrassment and impatience over the conglomerate's major investment failures in WeWork and Uber, stating in a Nikkei Business interview that "the results still have a long way to go."
  • • Son signaled a strategic pivot away from the mega-funding rounds that characterized SoftBank's earlier venture strategy, telling founders to "know your limit" as the company tightens its investment purse strings following recent startup semi-failures.
  • • SoftBank pressured WeWork's former CEO Adam Neumann to resign amid IPO scrutiny and actively discouraged the We Company from pursuing a public listing, instead urging the business to focus on profitability turnarounds.
  • • The shift reflects Son's reassessment of his long-held Silicon Valley cash-burn advocacy model; he acknowledged that despite envy for U.S. and Chinese market scale, emerging growth companies from smaller markets like Southeast Asia have outpaced SoftBank's major bets.
  • • Vision Fund II's investment philosophy is undergoing recalibration toward profitability and exits over aggressive growth funding, addressing mounting skepticism in the market regarding SoftBank's track record.
Summary
SoftBank Group's chief executive Masayoshi Son has publicly acknowledged significant regrets regarding the conglomerate's major venture investments, particularly in WeWork and Uber. In a Monday interview with Nikkei Business, Son expressed candid frustration with investment outcomes, stating: "The results still have a long way to go and that makes me embarrassed and impatient." This marks a notable departure from Son's historical positioning as a venture capital advocate willing to sustain substantial cash burn for market-dominant scaling.

Son's comments reflect a broader strategic recalibration at SoftBank following high-profile investment disappointments. WeWork's failed initial public offering—which SoftBank had heavily backed—and challenges surrounding Uber's market positioning have prompted internal reassessment of the venture funding model. According to Son, the holding company's track record of billion-dollar funding rounds without near-term profitability success has left him "flustered." He acknowledged that while he previously envied the scale of U.S. and Chinese markets, growth companies emerging from smaller markets in Southeast Asia have demonstrated superior execution, leaving what he characterized as "no excuse for entrepreneurs in Japan, myself included."

The strategic implications are material for Vision Fund II's trajectory. Son has begun implementing more disciplined capital allocation, recently instructing portfolio company founders to "know your limitations," a marked shift from the unconstrained growth-at-all-costs posture that defined earlier SoftBank investments. This tightening of the purse strings directly addresses mounting skepticism about Vision Fund II's viability in a market increasingly skeptical of unprofitable unicorns.

SoftBank's direct involvement in WeWork's operational challenges underscores this shift. The conglomerate reportedly pressured Adam Neumann, WeWork's former CEO, to resign as public scrutiny intensified around the IPO filing. SoftBank was also instrumental in advising We Company to abandon its public listing ambitions entirely and redirect focus toward achieving sustainable unit economics—a recommendation that directly contradicts the growth-first strategy that characterized Son's earlier venture thesis.

These developments signal that SoftBank's investment discipline is tightening considerably, with Vision Fund II positioned to prioritize profitable exits and sustainable business models over rapid market capture through unrestricted capital deployment.

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Sources

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AlphaMaven summarised this story from the reporting below. Each link opens the original article.

Observer SoftBank’s CEO Masayoshi Son Is ‘Embarrassed’ About WeWork and Uber Investments