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Episode 15: Files episode artwork

Oct 20, 2026 25 min

Episode 15: Files

from My Claude Journey Hosted by Shachaf Aviv

What actually happens when you attach a PDF or a massive spreadsheet to a chat? In this episode, we reveal the two distinct paths file uploads take: direct context loading for PDFs and documents versus Python sandbox code execution for spreadsheets and data files. Learn why running code over data keeps context costs low, how Claude generates downloadable Excel, Word, and PDF files from scratch, and why you must always inspect generated formulas and formatting yourself.

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Episode 15: Files

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This episode is 25 minutes long.

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This episode was published on October 20, 2026.

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