He Tried Hundreds of Jobs So You Don’t Waste 10 Years in the Wrong One | Ep. 333 with Gabriel DeSanti Content Creator & Founder of Staj

He Tried Hundreds of Jobs So You Don’t Waste 10 Years in the Wrong One | Ep. 333 with Gabriel DeSanti Content Creator & Founder of Staj

March 31, 2026 · 28 min · Episode 333

About this episode

Daniel Robbins interviews Gabriel DeSanti about his unique approach to career exploration through job shadowing.

Daniel Robbins talks with creator Gabriel DeSanti, who’s building the world’s longest resume by job shadowing real workers and documenting what careers actually look like. Gabriel shares the most intense job he’s done, cleaning a hoarding apartment in a hazmat suit while roaches fell from the ceiling, and explains why the series is really about the people behind the work. They also break down how he built his voice after a decade of experimentation, why brand deal income is a roller coaster, and how his new startup Staj turns job shadowing into a marketplace so anyone can test a career before committing years to it.

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