Want to know the paradox of digital communication? Fail small. Win big. When you test a variety of messages and assets in your websites, social channels and ad campaigns, your audience will rapidly help you optimize the relevance of your outreach. The old school called for a few, carefully-prepared messages to be delivered in bulk to the whole audience. It can work. But it’s empirically prone to bigger fails. Fresh thinking plus a willingness to fail small is today’s strategy for winning big.