In 2009, Penna was again seen on the front page of YouTube with his video Guitar: Impossible, which has been covered by De Wereld Draait Door, the highest-rated primetime show in the Netherlands. On December 6, 2009, Penna was featured on FM4, an Austrian national radio station. Shortly after uploaded, his "Guitar: Impossible" video was featured on the MSN.com front page.
In 2009, Penna directed an ad in collaboration with Rhett and Link entitled T-Shirt War. It garnered international attention. Shortly after, Penna was selected as one of the top 10 new directors at the 20th Cannes Lions Saatchi & Saatchi New Directors' Showcase.