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Best Story Wins

Why AI Can’t Replace Intuition with Hiten Shah of Dropbox

17 Apr 2025

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Today, thinking about AI completely replacing humans is impossible. Why? Because it means replacing creativity, context, and more importantly, intuition. Hiten Shah, serial entrepreneur, investor, and now working on AI at Dropbox, joins Josh and Jason to discuss how smart marketers and builders are using AI as a thought partner rather than a content machine. Hiten also drops hard-earned wisdom on what marketing still gets wrong, why engineers still (and will likely always) lead the startup ecosystem , and the explanation of why “the best story wins” is more than just a nice phrase.We discuss:Why getting the best from AI starts with better prompting and pre-prompting conversations. Why the road to content quality often starts with content quantity. Augmenting vs replacing human task management with AI.The biggest myths about AI-generated content, and why it’s dangerous for your brand.

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