Darren Morgenstern is a Canadian entrepreneur with Toronto-area roots, demonstrating early entrepreneurial talent by starting at age 14 delivering newspapers for the Toronto Star and boosting subscription numbers in his route. He built a portfolio in online matchmaking services targeted at specific demographics, founding several niche dating sites including Ashley Madison in 2002. Ashley Madison became infamous for its tagline 'Life is short. Have an affair' and targeted married individuals seeking extramarital relationships, based on research Morgenstern cited suggesting 80% of men and 50% of women would cheat at some point. The site faced massive scrutiny after a 2015 data breach exposing user data, after which Morgenstern resigned as CEO. Post-Ashley Madison, he shifted focus to investing, mentoring startups, and venture capital activities, as reported in 2016. Little is publicly documented about his personal life, education, or current residences.