Having been a copywriter for 38 years, I always start with this ad: “Have You Ever Wondered How The Man Who Drives The Snowplow Gets To The Snowplow?” Here you have a feature and a benefit. It isn’t necessarily one or the other. Your job is to ask: Is it something the reader hasn’t seen or thought about before? More importantly, is it logical? If you live in a state where there’s lots of snow, yes, you’ll wonder how the guy gets to his snowplow. This intrigues the reader. You must intrigue to sell. It also affects you, the reader, especially if you’ve been snowed in (and who hasn’t?) With your example of “1,000 songs,” Jobs didn’t create the ad, although he might have said to Chiat/Day (maybe Lee Clow), “Look, this little device lets you load 1,000 songs.” Nobody had said that before. Again, clearly a benefit but also a feature. Think of it like reporting. I remember Hunter S. Thompson covering the Pulitzer murder trial in Miami. He arrived late so all the salient facts had been reported in the newspapers. Thompson rumaged around and found out Roxanne Pulitzer used a tuba or some crazy thing for sex(this goes back a long way). The point is, Thompson realized all the usual information was out there, so he took an unknown fact (something the other reporters didn’t care about), and turned it into a brilliant piece of reportage. Always say to yourself, “What is it that nobody else sees here?” And please stay away from “People don’t buy products, they buy a better version of themselves.” I’m sure it sounds great in a presentation but it means absolutely nothing. ALWAYS LOOK FOR THE WONDER. THAT’S IT.

I did a poor imitation of Don Draper for 40 years before writing my first novel. I'm currently in the final stages of a children's book. Lucky me.