In an effort to enhance marketing efforts, he collaborated with James Vincent and Duncan Milner at an ad agency currently known as TBWA/Media Arts Lab, receiving guidance from Lee Clow, who was in semi-retirement. Together, they aimed to create compelling advertisements that would resonate with audiences.

The result of their initial collaboration was a subtle and evocative commercial showcasing a man in casual attire, comfortably reclining while engaging with various media like emails, a photo album, and articles from the New York Times on his iPad. Notably, the ad featured no dialogue, instead focusing on the imagery of a book titled "Steve Jobs," authored by Walter Isaacson, which served as a significant touchpoint.