Designers of type and lettering make use of custom tools to draw and manufacture their product, this is as true today as it was in the time of punchcutting and steelplate engraving. After the design of the Surveyor family of typefaces came to a close, an exploration was made into finding an approach where custom tools could be used to help prototype the kinds of highly intricate designs that may have been too complex to otherwise consider putting into development. This process led to the design of Obsidian, a typeface that is elaborately shaded in a style that makes reference to the same nineteenth century tradition of engraved lettering as Surveyor is rooted in. Andy Clymer, a senior designer at Hoefler & Co. and instructor in the Type@Cooper program, will share a look at the design process, the custom tools involved, and some of the unexpected challenges and discoveries found while designing Obsidian.