Why Your AI Gets Worse The Longer You Use It (with Jack Taubl from Ocean.io) | Ep. 1

Your AI was working great, and then it started handing back the same twenty companies it gave you last month. On this episode of Pipeline, Joseph Lewin talks with Jack Taubl, Director of Sales at Ocean.io, about why AI output decays the longer you work inside one chat, and what to do about it. Jack's explanation is structural. Providers earn their margin on the efficiency of their models, so a long thread gets compacted to control cost, and quality erodes by design rather than by accident. His fix takes three steps a seller can run Monday morning: work inside a project instead of one endless thread, load that project with real grounding documents like a prospect's most recent 10-K, and set a scheduled action that rebuilds your daily briefing on a fixed refresh. He runs his at 4:00 a.m. to keep credits down. What you can use by Monday: Move broad, open-ended work into a project instead of one long chat, so every new chat inherits the context from the others. Upload real grounding documents into the project knowledge before you ask for anything, like a prospect's most recent 10-K. When an answer feels off, open a fresh chat inside the same project and switch the reasoning model instead of arguing with the drift. Set a scheduled action that rebuilds your daily briefing on a fixed refresh, so the list you work from is current. Ask specific questions with an end in mind. Ambiguous questions return ambiguous results every time. Pipeline is short conversations with GTM peers who are actually filling pipeline right now, so you leave with something you can use by Monday. New episodes weekly on Apple Podcasts, Spotify, and wherever you listen. Produced by Podcast 2 Pipeline.