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October 8, 2025 52 mins

Aaron Levie is AI-pilled, but he’s one of the few CEOs who sees a future where AI agents work for us, instead of replacing us—helping us to do more than we could before.


Aaron’s been the CEO of Box for 20 years–long enough to see a few tech revolutions up close—and taking the company AI-first gave him a glimpse of what the next one means for us. We get into why jobs aren’t going away, the new shape of work, and what it takes to build an AI-first company from the inside.

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Timestamps:

00:00:00 - Start

00:01:30 – Introduction

00:02:36 – Why AI won’t take your job

00:06:42 – Jevons Paradox and the future of work

00:10:40 – How Aaron’s experience with the cloud era shapes his view of AI

00:19:44 – Why every knowledge worker is becoming a manager of AI agents

00:25:21 – What Aaron’s learned from bringing AI into every corner of Box

00:33:57 – What’s overhyped in AI today

00:43:31 – How Aaron balances everyday execution with innovation

Links to resources mentioned in the episode:

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