Got a chuckle out of me when I noticed the Planscope news feed ad after reading this post.
I think the important distinction here is about providing value rather than the fact Brennan used retargeting for his product. There is a lot of value in having well educated customers; particularly when their education came from you, the service provider. This is why webinars can be very effective in securing the trust of a first-time customer and elevating the lifetime value of current customers.
Teaching people how to get more out of your product helps them see the path to ROI more clearly and creates more trust.
I'm curious to see how the 5 Day Course performs as lead generation in a normal campaign vs. retargeting campaign test.