How Masayoshi Son Built SoftBank on the Go Big or Go Home Bet
The CEO Diary with Fexingo: Leadership Lessons, Executive Decisions, and Corner Office Stories · 2026-05-29 · 11 min
Episode notes
In this episode of The CEO Diary, Lucas and Luna break down Masayoshi Son's leadership at SoftBank — specifically the bet on Alibaba that made him a billionaire and the Vision Fund's high-stakes strategy. They explore how Son's willingness to write massive checks and accept extreme volatility shaped SoftBank's rise and occasional stumbles. With specific numbers on the Alibaba return and the WeWork fallout, they ask: is Son a visionary or a gambler? Plus, a conversation on what founders can learn from his conviction-heavy decision-making. Tune in for a deep dive on one of tech's most polarizing CEOs. #MasayoshiSon #SoftBank #VisionFund #Alibaba #WeWork #VentureCapital #CEOLeadership #BoldBets #JackMa #TechInvesting #BusinessStrategy #TheCEODiary #FexingoBusiness #BusinessPodcast #LeadershipLessons #HighRiskHighReward #SonStyle #FounderMindset Keep every episode free: buymeacoffee.com/fexingo