In 2010, Benjamin started 5by5 Studios, a podcast production outlet that currently produces nineteen shows, including several co-hosted shows such as Back to Work with Merlin Mann and The Ihnatko Almanac with Andy Ihnatko. Based on his popular podcasts, Benjamin has been called "the king of Apple talk radio" by Philip Elmer-DeWitt of Fortune Magazine and CNN.[3] In the past, he co-founded Cork'd and Playgrounder, and wrote the CMS behind A List Apart.[4] Additionally, he has made educational screencasts through PeepCode.[5][6] Benjamin has appeared on the Fox News program Strategy Room – Gadgets and Games multiple times[7] to discuss various topics.
In 2017, he released fireside.fm, a platform for podcasters.[8] Benjamin holds a B.A. in Technical Writing with a Computer Science focus from the University of Central Florida.