Following the initial coverage that Penny received, he was soon added to the Deathbox Skateboards team by owner Jeremy Fox (Deathbox was later merged with Bash Skateboards and was re-branded as “Flip”). In 1993 Penny appeared in the inaugural Flip video The Long Overdue, alongside Geoff Rowley, Alex Moul, Andy Scott and Rune Glifberg—the video was made by Goff.

In 1993 Penny made his first international video appearance in 411VM’s “Issue 2” and was featured in a “Wheels of Fortune” segment—Penny was 16 years of age and the segment features footage from the Radlands Skatepark in Northampton, UK. At the age of 16 years, Penny was sponsored by Flip, Independent, Droors, Union and SS20.

In late 1994, Flip left UK shores and relocated to Huntington Beach, California, US, the “heart” of world skateboarding. Along with other team members, Rowley, Scott and Glifberg, Penny exerted a significant impact on the skateboarding sub-culture with his small part in the Flip industry section in 411VM’s “Issue 11”; his switch frontside flip at the Carlsbad Gap; and a five-trick downhill run that ended in a backside tailslide on a nine-stair handrail. By the end of 1995, Penny had received acclaim from notable professional skateboarders, such as Tony Hawk.

Penny returned to Radlands in 1994 for the UK Championships and finished in 6th place; US contestant, Mike Santarossa, won the contest.

In December 2011, Penny was identified as the twenty-first most influential skateboarder of all time by Transworld Skateboarding magazine; however, Phillips had first revealed his perspective on Penny in 2009:

In a 2012 interview, Penny identified the five skateboarders that have been the most influential throughout his career: Daewon Song, Rodney Mullen, Danny Way, Chad Muska and Steve Caballero. He also acknowledged contemporary influences, such as Quim Cardona, Paulo Diaz and Sean Sheffey—”People that are slightly interesting; make it more fun; make it more enjoyable; more original skateboarders; stylish skateboarders”.

In July 2013, professional skateboarder Paul Rodriguez identified Penny in his “top ten” list of professional skateboarders, explaining that “Tom to me was like a mythical figure … To me his style was my favorite in skateboarding just the way moves, the way he did his tricks, it looked so lazy and so buttery.”