What happens when you trade a cushy Target supply chain job for a risky startup role with no salary for five months? For Brandon Winter, former CRO of Stukent and founder of Fundraise Genius, it led to helping build Stukent from zero to serving over a million students across 80 countries. Going behind the scenes of Stukent's meteoric rise, Brandon reveals how Stukent grew from a makeshift warehouse office (complete with a porta-potty!) into an ed-tech powerhouse that revolutionized digital marketing education. Through stories of shared hotel rooms in Singapore and intense strategy meetings, Brandon breaks down the delicate balance of building a sales culture that drives astronomical growth while maintaining team cohesion. Get an insider's look at how early-stage compensation negotiations work, why having a mission bigger than money attracts top talent, and what it takes to transition from "player-coach" to true sales leadership. For founders looking to build high-performing sales teams and professionals considering the leap into startups, this episode offers an unfiltered look at both the grind and glory of startup life.