This week on The American Cycling Report, we sit down with Mike Weiss, the driving force behind St. Louis–based Big Shark Bicycle Company and the longtime organizer of the iconic Gateway Cup. For more than three decades, Mike has been a central architect of American bike racing—building events that span the full spectrum of the sport, from grassroots criteriums to nationally recognized series. In this conversation, we explore how the Gateway Cup has not only survived but evolved, the behind-the-scenes realities of race promotion in today’s cycling economy, and what it takes to sustain community-first events in a changing landscape. We also dig into the relationship between retail, advocacy, and racing; the lessons learned from organizing dozens of events; and Mike’s candid perspective on where U.S. criterium and grit racing are headed next. If you care about the past, present, and future of American bike racing—and the people who keep it alive—this is an episode you won’t want to miss.