Gruber authors the Apple enthusiast blog Daring Fireball and produces its accompanying podcast, The Talk Show.

[3][4] In 2004, Aaron Swartz and Gruber worked together to create the Markdown language,[5][1][2] with the goal of enabling people "to write using an easy-to-read and easy-to-write plain text format, optionally convert it to structurally valid XHTML (or HTML)".

[12] The site is written in the form of a tumblelog called The Linked List, a linklog with brief commentary, in between occasional longform articles that discuss Apple products and issues in related consumer technology.

In June 2007, Gruber and Dan Benjamin began co-hosting an independent podcast featuring conversations and commentary on trends, mainly focusing on technology at thetalkshow.net.

Apple Inc. senior vice president (SVP) of worldwide marketing Phil Schiller appeared as a guest on the live episode of The Talk Show during WWDC 2015 in San Francisco.