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In this talk, I will reflect on my journey of over two decades in exploring machine learning and intelligence, which began as the final PhD student of Prof. Steve Smale at UC Berkeley. Inspired by Smale's 18th problem posed in 1998, my research has been driven by a quest to understand the fundamental limitations of intelligence, exploring the intersections of dynamical algorithms, topology learning, and the development of trustworthy AI. This presentation also serves as a tribute to Steve Smale on his 95th birthday, a milestone that prompts me to honor our first meeting at his 69th.