Kindergarten may have prepared us all for life, but the casino floor can prepare you for your career in infosec. Hackers and gamblers are cut from the same cloth, and security professionals can learn a lot from the interplay between advantage players and casino countermeasures. By examining some famous examples of players who beat the house, using both legal and illegal tactics, this talk will help newbies learn how to think about security problems and give veterans a few new ideas as well.Securtle is a portable threat detection tool that alerts its user to their real time digital risk environment. The tool utilizes a color shifting strategized shell (Green, Yellow, Red) to give users of all ages and knowledge level a simple real time risk exposure reading of their digital environment. An appealing and portable turtle, the Securtle uses both passive and active BL/BLE and Wifi tools to rate and then convey Internet of Things (IoT) risks, active attacks, and tracking tools - all of which are currently used to steal data, modify user devices, track users, and even target physical safety of individuals; especially children, older adults, any other vulnerable population. Attachable to either a backpack or keychain ( as a future direction), the Securtle rides along with its user as an ambient risk indicator shifting from green to yellow as its digital environment increases in risk level. Additionally, when the intrusion detection tools receive an attempted unsolicited scan, connection, or attempts at modification - the turtle shifts red, alerting the user that malicious activity is in process. This mixed threat alert gives users the information they need to make simple defensive choices and basic mitigation actions to disable threats in their digital ecosystem.