Starting as an internal sidekick for auto-renaming paperwork, Riffo was launched on Product Hunt just 60 days after its creation. As it spread to 100+ countries and brought in a flood of comments, reviews, and emails, we began to see what users truly envisioned: an AI-powered assistant to handle the tedious, time-consuming parts of digital organization. This pushed us to rethink Riffo 2.0—reprioritizing features to balance business goals with user needs while staying true to its vision. The question prompts: how do we use AI to take over the grunt work of personal file management while ensuring users can navigate, curate, and organize their digital assets at their own terms?