Having designed over 700 typefaces, Tobias Frere-Jones is as close to a living legend as the modern typeworld has. As a former partner at Hoefler & Frere-Jones (now Hoefler & Co) and the principal designer of Frere-Jones Type, Frere-Jones has designed fonts for the Obama 2008 campaign, the New York Times, the Whitney Museum, and even Martha Stewart.
In this video, Frere-Jones explains what got him into type design in the first place. ("It was an intersection between being a writer and working with language and being a painter and concentrating on form that I never thought I'd find.") He also shares the best compliment he ever got as a typeface designer: When the Wall Street Journal switched to his Retina typeface, an elderly reader wrote in to say that since the switch, he no longer had to put on his glasses to follow his stocks.
But it's not all reminiscing. Frere-Jones also goes over some of the design lessons he's learned in type, such as the fact that sometimes it's just as much a design decision to leave something alone as it is to change it, and that being able to recognize trends is perhaps the most important skill for a type designer to have: "There are few if any rules in typeface design, but trends provide reliable directions on the way things will move."