I recently finished reading Insanely Simple by Ken Segall, the former creative head of Chiat/Day, which did Apple ads (print and television) for almost 20 years. Overall takeaway: it’s a very gushy, “Apple (and Steve) can do no wrong” tone, somewhat gossipy read that tries to shoehorn the notion of “simplicity” in various ways. The author personifies a visceral, existential dual between Complexity and Simplicity, relaying anecdotes from Apple, but also comparisons with Dell, Intel, HP and other clients for whom he’s done creative work. 

Some fun anecdotes worth mentioning:
– Did ya know Steve Jobs almost introduced a version of OS 9 that was ad-supported? The idea was to have a freebie upgrade that would show commercials upon boot up, from luxury goods like BMW, and small ads while using the OS. Thankfully it was killed. But they spent several months mocking up while conducting some business analysis. 
– Steve wanted iMac to be called MacMan for the longest time…he finally gave in when he saw packaging and models with iMac emblazoned, and of course loved it ever since. (Just goes to show you gotta do hi-fidelity prototypes or mockups to yield the most useful level of insight and understanding of design impact)
– Steve originally hated the now iconic iPod Silhouette ads of folks dancing. Wanted to do classic Apple-style large product-focused ads, but again gave in when he saw the initial prints and videos. 
Some key principles (which are names of each chapter): Think brutal, think small, think minimal, think motion, think iconic, think phrasal, think casual, think human, think skeptic, think war, think different. 
These all struck me as variations of how Steve Jobs (and Apple) did business in an unexpected, unconventional manner (compared to standard large corps like IBM or HP with committees etc.) but not really demonstrating how simplicity enables everyday practices at the office IMHO. I wish there could be more about how “simplicity” translated into everyday business functions and employee operations. But all around a fun, light read to add to the Apple mystique canon…