In this episode, we’re joined by serial entrepreneur and investor Terry Hsiao to explore the defining shifts that have shaped Silicon Valley from 2000 to 2025—from the dot-com boom and bust, through the rise of mobile and cloud, to today’s AI-driven transformation and the restructuring of venture models. Terry’s journey spans from engineer to serial founder, investor, and educator, bridging startup communities across the U.S. and Taiwan. He reflects on how each wave—from the internet era’s obsession with “eyeballs,” to the mobile revolution powered by the iPhone and AWS, to the post-COVID reinvention of venture—has redefined what it means to build and invest. Beyond taking a company public, Terry now mentors founders and investors on both sides of the Pacific, offering insights on what it takes to thrive in the decade ahead. Powered by Firstory Hosting

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