On November 20, 2014, Stronach co-chaired Covenant House Toronto's Executive Sleep Out 2014 Edition with Tim Lieweke (MLSE President& CEO). Stronach, along with more than 80 other community and business leaders, spent the night sleeping outside (in −18 °C!) to raise awareness and critical funds to support the programs and services that help youth transition from a life on the streets to a life of opportunity. The 2014 Sleep Out was the most successful in the three-year history, raising more than $939,000.