Step 1: Get the StarMaker page high enough to trigger the "#1 Fan" email from Ken
Step 2: Go to his house in Sunbridge (I don't think that you have to agree to his offer to meet his mom, since she's in the bedroom of the same house)
Step 3: Go to the bedroom in Ken's house and choose the first option (the one above "What are your greatest gaming achievements?").
Step 4: Advance through that dialogue and talk to her again: the first option has now changed to "Can you teach me hacking?", and will take you to "a word game where you guess game titles that have had vowels removed. ("Age of Empires" was the hardest one for me to remember, but your mileage may vary)
Step 5: Repeat for ~3-5 days until you get the "Hacker" title.