Jeff Steinman N5TJ is one of amateur radio’s most accomplished contesters—a four-time WRTC medalist and the current holder of the all-time CQWW SSB world record, set from EA8BH in 1999. His contesting journey began with responding to a classified ad in QST by Lou K4VX that led to mentorship, a teenage single-op debut, and more than 50 return visits as a guest operator. That foundation—combined with decades of strategic refinement—has shaped a career defined by both performance and humility. In this conversation, Jeff reflects on the evolution of contesting, the value of guest operating, and why curiosity—not just technology—should guide new operators. Join the conversation and subscribe for more operator-focused interviews from Q5 Worldwide Ham Radio. Special thanks to DX Engineering for supporting this episode—and for their continued commitment to Parks on the Air activators, DXers, contesters, and ham radio operators around the world.