1999, the first Toorcon event started, 5 years after the world-wide web went live and if we were lucky enough, we got to show off our brand new Pentium III laptops at this San Diego-based conference. IOT was a non-existent nomenclature, but it did exist in embedded systems, PBX’s, gas station credit card terminals and Quotrons stock quote machines attached to 56k baud modems. Digital was a word, Cyber wasn’t. A hacker in it’s purest form was found at these conferences, many of them still hoping that the industry would accept their culture-for-hire (as demonstrated in the conference topics of the time) all the while Cult of the Dead Cow introduces the first world-wide remote-access-tool (RAT), scaring the masses rather quickly. Privacy was a questionable problem to solve both technically and socially, and electronic voting security was merely theory. An echo chamber of information sharing and discovery. 2017, The microphone is on, hackers are the cool kids and in some case celebrities, and election hacking is considered commonplace and unsurprising. Teenagers with your TV’s can take down half the Internet for free by going into a place known as the deep and dark web while today we can’t even fill the security roles in our businesses and governments worldwide with enough hackers to help us. This talk will explore the evolution of the hacker both technically and socially, with highlights of today’s problems in IoT, malware, and the merger of traditional intelligence as information security defensive and offensive disciplines.