Gregg was a two-time All-American triple jumper and PAC 12 scholar-athlete at the University of Oregon. After college, he moved to São Paulo, Brazil, to train with the Brazilian Olympic team for the Olympic Games. However, a knee injury sustained at the 1998 USA Track and Field Championships redirected his competitive passion to his business and creative life.

In search of a more creative journey, after seven years working in the software industry, Gregg sold his car and home in 2005 to embark upon an 18,500-mile self-supported bicycle trip down the length of the Americas. The blog posts and photographs created during this two-year journey earned him a National Geographic Scholarship and launched his career as a writer, photographer, and filmmaker.

He traveled the world as an adventure travel, sports, and environmental photojournalist in the ensuing years, and in 2013, Gregg founded WhereNext in Bogotá, Colombia. Recently, Gregg has produced and photographed global campaigns for Meta, Merrell, Canva, Dior, and Cat Footwear. Some of his film director credits include the feature-length documentary film “The Birders,” which helped to position Colombia as the world’s leading birding destination, a branded content film for the world’s premier luxury travel operator, Abercrombie & Kent, and the short documentary film “Surge On,” which won the Gold Telly Award for Online Commercials for Cat Footwear.

In 2022 Gregg led and financed, WhereNext’s sustainable tourism consulting team’s winning bid for USAID/Colombia's Destination Nature Activity as the local implementing subcontractor. Destination Nature Activity is a 5-year, 40-million-dollar, high-profile program that embraces the emerging nature tourism industry as a central pillar for the Government of Colombia to achieve its environmental ambitions while meeting its social and economic commitments in the 2016 Peace Accord.