The first music festival in Saskatchewan live-streamed to the internet, a funeral of a former Saskatchewan premier live streamed to the internet for the first time, and a WHL game live-tweeted to the world for the first time: these are some of the distinctions in Terry Massey’s evolutionary career. Terms are often invented to describe his career after he has moved into new fields. As media, new media, and social media evolve, he has stayed ahead of the times while working with small business, non-profits, and large corporations.