As a baby, he managed to flip upside-down in his jolly jumper. At age 12, he got his first skateboard, and at 49, he qualified for the British National Skateboard Team. In 2024, at age 51, as the media loved to point out, he became the oldest skateboard Olympian in history competing at the Games in Paris. 

In all the years between, Andy has competed in almost every X Games since its inception, has twenty-three X Games medals, two Guinness World Records, ten World Cup Skateboarding overall championships, a U.S. postage stamp modeled after his image, and appearances on The Tonight Show with Jay Leno, Good Morning America, and 60 Minutes. As a kid, he shoveled snow off his ramps in Massachusetts. As a professional, he has attracted corporate marketing partners including Amazon, Swatch, Lego, Verizon Wireless, and Sony eager to align their brands with his positive attitude and uncompromising work ethic. 

Andy’s down-to-earth demeanor and accessibility have distinguished him as one of the nicest guys in skateboarding. A Sports Illustrated feature once dubbed him the pro skater that is “mother approved.” Choosing to use his notoriety as a positive influence, Andy was featured in PSAs for The Partnership for a Drug-Free America. The campaign culminated at the White House, where he introduced then-President Bill Clinton, and became the first skater ever to ride down the smooth marble hallways of the west wing.

Andy serves on the Board of Directors for Grind for Life, a non-profit organization that helps fund medical travel and expenses for people with cancer. In 2007, Andy started the Clash At Clairemont, an annual skateboard fundraising festival that has raised more than $200K for Grind for Life and the Mission Valley YMCA Skatepark. 

Andy is a founding board member of USA Skateboarding, skateboarding's Olympic national governing body. He has been advocating for and participating in the design and construction of public skateparks for more than 35 years. He has also been teaching skateboarding to skaters of all levels at Woodward Camp every summer going on 35 years.

Skatercross, a new discipline in skating and Andy’s brainchild, is a skateboard race that levels the playing field between street, ramps, and parks in a high-speed, exhilarating show of talent and technique. Andy designed and built the first ever Skatercross track in 2016. 

Andy continues to skate the worldwide pro tour, encouraging people everywhere to participate in his favorite sport.