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In The Blink Of AI with Georgie Healy

How to Stop Your AI Agents From Breaking with Josh Clemm, VP of Engineering at Dropbox

Josh Clemm, VP of Engineering at Dropbox, joins Georgie Healy to cut through the noise and get to what is actually happening with AI agents right now. Josh has scaled engineering teams at LinkedIn and Uber Eats, founded his own AI venture, and is now building Dash, Dropbox's context layer designed to make agents dramatically more reliable. This is someone who has been on the coalface of this technology longer than most.

In this episode Josh introduces two ideas that will change how you think about AI at work. Context rot, the reason your large language models quietly get dumber the more information you give them. And work slop, the plausible sounding but completely hollow output that gets generated when AI tools are used without intention. He also delivers the most reassuring reality check of the year for anyone feeling overwhelmed by the idea that everyone already has a fully functioning team of AI agents working for them.

They also get into how the index approach behind Dash solves what real time fetching cannot, why the next AI breakthrough might actually come from old fashioned software engineering principles, and the two engineers Josh considers the greatest builders of their generation and why neither of them was asked to build what they built.

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Day One® exists to help founders and startup operators make better business decisions more often

Subscribe for helpful content from other successful founders, operators and investors

Join 755 other founders & investors receiving our emails. They're cool, are you? :)

* Regrettably, mel@canva.com is not on our list… yet.

Day One® is a registered trademark of W2D1 Media Pty Ltd. All rights reserved. © 2026 W2D1 Media Pty Ltd.