At this time last year, the phrase "Left Shark" was unknown—despite all the data that goes into planning the Super Bowl halftime show. With Lady Gaga singing the national anthem Sunday, who knows what Las Vegas is fielding bets on? (The color of her shoes is one.) But you can be sure they're examining all the data from previous years to fully monetize the occasion.

Between Boomers, Gen X and Gen Y (Millennials), there are more intergenerational workers in the workforce and customers for business content at one time than ever before. But the content consumption habits of Millennials are turning the industry upside down. How do you reach a generation with endless choices and ingrained belief that content should be free?