Stroll invested in bringing Pierre Cardin fashionwear, and then Ralph Lauren clothing, to Canada. Along with Hong Kong investor Silas Chou, Stroll invested in clothing designer Tommy Hilfiger. In the 2000s, Chou and Stroll invested in Asprey & Garrard.
Stroll is married to Belgian-born Claire-Anne Stroll (née Callens), who runs a fashion Business called Callens. They have two children, and have residences in Geneva, Switzerland as well as on the island of Mustique, Saint Vincent and the Grenadines. Their son Lance Stroll is a racing driver who competed in the 2017 Formula One season with Williams Martini Racing. Their daughter is Chloe Stroll.