[1] Pepper was born in Auckland and attended Westlake Boys High School.
[3] Pepper then moved to the Star and sailed with Carl Williams at the 2008 Olympics, finishing 9th.
He was a part of Team New Zealand's successful defence of the America's Cup in 2000.
[7][8] In 2009, Pepper was part of BMW Oracle Racing and skippered their boat during the Louis Vuitton Trophy Nice Côte d’Azur regatta.
[9] He sailed in the 2010 Louis Vuitton Trophy Dubai with Team Synergy.