Aaron co-founded the website CheeseheadTV.com in 2007 with Live X founder Corey Behnke. What started as a simple Wordpress blog grew to become one of the most popular Packers sites on the Internet. Together, Nagler and Behnke created and co-produce Packer Transplants, a show that began as a 20 minute podcast that grew into a one-hour live weekly Internet broadcast. Aaron's work with Cheesehead TV caught the eye of Bleacher Report, who approached him about helping them improve their NFL coverage. Aaron helped launch and grow B/R's NFL video group. After B/R, Aaron went on to work with Sports Illustrated's video group. In the spring of 2016, he helped launch SI's first live stream covering the NFL draft as a second screen experience for fans following along in real time.
In August of 2016, Aaron joined Gannett covering the Green Bay Packers for PackersNews.com. Aaron helped grow the paper's social audience, including cultivating new audiences for PackersNews content on Instagram and Snapchat. Aaron also began his popular daily Facebook Live chats with readers during this time. In August of 2018, Aaron joined Behnke at LiveX as Director of Content & Social. He is involved with all content efforts at Live X while spearheading video and content efforts for Cheesehead TV.