This is obtained by completing missions for Kaitlin who can be found in the main safehouse in the City of Westminster. Kaitlin will only be in your hideout if you have either completed or have the ability to start the very first 404 mission. Once you are at the safehouse simply walk downstairs and take a right and she will be the lady standing just out front of the clothing machine (The Asian looking girl with a pony tail if that helps) walk up to her and press
to talk with her. She will give you a few side missions here and there all you have to do is finish a few of her requested side missions (a total of five) and eventually she will give you a side mission titled "A Change of Heart" Complete this mission and the achievement is yours. Hope this helps.