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Gambling Man: Masayoshi Son’s Bold AI Vision For 2025 & Beyond | Lionel Barber

Monetary Matters with Jack Farley

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The Entrepreneurial Gamble: Successes and Strategies

This chapter examines the audacious risk-taking of a prominent entrepreneur, detailing both triumphant investments in companies like Alibaba and Yahoo, and notable missteps such as WeWork. It highlights the intricacies of negotiation styles, emphasizing personal charm alongside strategic intimidation, while also exploring the investor's unique approach to high-stakes deals. The narrative further delves into investment dynamics, particularly the significance of timing in selling and the challenges faced by companies in evolving technology sectors.

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