[3] Since rising to the top of the sport, Powers has been involved in various media, developmental, and educational projects aimed at growing the popularity of cyclo-cross in the United States through the JAM Fund, his non-profit organization, Behind THE Barriers video production company, cyclocross camps, instructional DVDs, and he has also collaborated on several cyclo-cross books including Skills Drills and Bellyaches and Mud Snow and Cyclocross.

Powers was introduced to cyclo-cross early in his cycling career as a way to stay fit at the end of the mountain bike season.

In his native New England, cyclo-cross has been a regular part of each season for decades, and Powers excelled at the short, fast, technical races.

Powers discovered that the frenetic pace and camaraderie of cyclo-cross suited his high energy and outgoing personality.

Encouraged by several friends and his coach Adam Myerson, Powers moved to Massachusetts, and changed his focus to road racing; however, Powers achieved one of his most significant victories very early in his career, when he won the 2001 Mountain Bike World Cup Cross Country event in the Junior division in Napa Valley, California.

Powers continued to race competitively in the Junior and Senior divisions of mountain biking, and was also competing in cyclo-cross in New England with the Northampton Cycling Club.

Following his move to Jelly Belly in 2004, Powers made the decision to race an entire cyclocross campaign in Europe.

[5] In the 2004 season, his last as an under-23 rider, Powers returned briefly to the United States for the national championships, where he earned a silver medal.

A pair of top five time trial results in the 2006 Vuelta de Bisbee[8] propelled him to a sixth place overall finish.

At the USA Pro Cycling Challenge, Powers got into the day's main break in stage 2,[10] eventually won by George Hincapie.

The support enabled Powers to tackle the U.S. Grand Prix of Cyclocross with renewed fervor, and he won his first major event, the Derby City Cup[11] in Louisville, Kentucky that fall.

Powers joined Chris Jones, Zach McDonald and, later, Julie Krasniak to create one of the most successful teams of the season in American cyclo-cross.

At the Deschutes Brewery Cup[26] in Bend, Oregon, Powers finally got his first victory on a course where he had had some bad luck in the past.

In 2014, Powers won his second United States National Cyclo-cross Championships title at Boulder, Colorado.

[30] The 2014/15 campaign marked one of Powers' most successful seasons of his career; he won his third United States National Cyclo-cross Championships title at Austin, Texas.

BTB-TV exclusively live streamed several productions over the two years, including the USA National cyclocross championships in Boulder, Colorado and Austin, Texas.

JAM Fund has issued up to 40 grants per year to riders who have applied to the program and have displayed commitment and enthusiasm to cycling.

Alumni include some of the most accomplished talent from the United States cyclocross scene, Ellen Noble, Stephen Hyde (cyclist), Jeremy Durrin, Anthony Clark, Rebecca Fahringer are some of the riders who rode for the JAM Fund in the past decade.