In this episode of the OODAcast, host Matt Devost is joined by Alok Sama, author of The Money Trap, for a compelling conversation about Sama’s journey from modest beginnings in India to leading some of the most ambitious investment efforts in tech history. Sama recounts his early days in Delhi, the unlikely path to Wharton, and his time at Morgan Stanley before stepping into the eye of the storm as President and CFO of SoftBank. Alongside Masayoshi Son, he helped deploy the groundbreaking Vision Fund, a $100B initiative that forever changed the scale of tech investing. Sama offers behind-the-scenes insights into the wild ride of investing in giants like Uber, WeWork, and ARM, reflecting on how bold vision and massive capital shaped, and sometimes distorted, the future of technology.

The discussion explores SoftBank’s unique investment philosophy, Masayoshi Son’s prescient bets on AI, and the tension between visionary investing and the practical constraints of managing enormous capital pools. Sama shares candid lessons from massive wins and public missteps, including the now-infamous WeWork saga. He also delves into how a high-stakes smear campaign impacted his health and priorities, offering an unflinching look at the personal costs of operating at the top of global finance. Throughout the episode, Sama’s honesty, humor, and humility shine, echoing the voice that made his book so impactful.

Beyond business, the conversation turns deeply personal. Sama reflects on what really matters after decades of chasing financial success. He opens up about regrets around time lost with loved ones, the role of humility in leadership, and how ancient Indian philosophy helped him reframe his priorities. Now entering a new chapter focused on writing, mentoring, and giving back, Sama offers timeless advice for entrepreneurs, investors, and anyone navigating high-pressure careers. This episode is a must-watch for those curious about the intersection of power, capital, and purpose.

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Additional Links: Alok on X

Book Recommendation: The Rings of Saturn by W.G. Sebald