There is one universal truth that holds true in both baseball and in digital marketing; you're going to fail, repeatedly and often.

And that's O.K.

In fact, our third expert for the Digital Crash Course, Chris Pierantozzi, creative director at Saatchi & Saatchi L.A., says half of what you create will do badly.

But Mr. Pierantozzi insists that no matter how low the batting average, you have to keep testing, on multiple fronts, to make gains in this new era.

"We used to think of content as you build one thing and you just put it on everything," he says. "That is not the reality of where we are today."

Mr. Pierantozzi says it's imperative to consider the platform while producing content. It's not enough just to crop a horizontal video to fit into a vertical space on Snapchat, for example; you have to physically shoot vertical video.

"If you don't, it's not going to work. It won't look right," he says. "So you really have to think about, 'How do I create those things separately for each of those platforms that is going to work best and most native for what the behavior is?'"

But content creation is just one part of a larger effort; the ability to scrutinize each piece of content through measurement creates even more complexity.

"As an advertising industry as a whole, we've ever been that beholden to metrics or measurements in the past," he said. "It's something that is completely new to a lot of marketers, creative folks and brands."

With more accurate measurement comes more targeted content and as the battle of ad blocking looms, the less unwanted content, the better, for all parties.