“I don’t follow any guidelines,” Jay-Z says in “22 Twos,” one of the standout tracks on his 1996 debut, “Reasonable Doubt.” And there’s no reasonable doubt that Jay’s instincts to blaze trails have served him well. In particular, Jay has been one of the leaders of the revolution that has been unfolding for years between music and brands. Jay’s deals — from his hands and distinct voice telling the world about HP computers to his getting Budweiser to pay for a party in Philadelphia for 80,000 of his closest (and paying) friends — haven’t just put a lot of coin in Jay’s Roc-a-Wear jeans pockets. They’ve helped build Jay’s brand and paved a path for the business and brands to think even bigger about partnerships.

But occasionally, guidelines do come into play. “99 Problems” is a more apt reference point for my feelings some weeks when we get pitched by a label or a manager on a new, creative scheme to sell music to fans. “What if we bundled an album with a handset?” “What if every time a fan buys a T-shirt, they get a code to redeem a song?” “What if it’s a bottle of artist-branded perfume? A flashlight? A puppy?”

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