During his time in the US, Penny released video parts in the mid-1990s, such as Etnies' "Hi-Five", Transworld Skateboarding's "Uno", TSA's "Life in the Fast Lane", "Balance in the World of Chaos" and Dope Clothing's "Time for Tea". During this period, Penny also received his first cover photograph for "Transworld", in which he is performing a frontside bluntslide in Huntington Beach. Skin Phillips, "Transworld"'s former editor-in-chief, stated: "The other thing with Tom and really all the Flip guys when they came over was that they were absolutely unfazed by contests or demos. That’s just what they grew up skating."