iMentor matches high school-aged youth (mentees) one-to-one with volunteer adult mentors based on shared career and personal interests. Matched in relationships ranging from one to four years in length, mentor-mentee pairs cultivate their relationship using a potent combination of weekly email correspondence and regular in-person meetings. The iMentor program is changing the face of youth mentoring. iMentor proves that (1) even the busiest, most successful New Yorkers have time to be quality mentors and that (2) formal mentoring programs can flourish in NYC's most isolated, low-income, and underserved communities. Since 1999, iMentor has served over 2,000 high-school students from four of the five NYC boroughs.