Hungry Chicago-born videographer Justin Roseman clinks a Sea Dog brew with Fred and explains why he left a safe city job, scrapped fifteen startup attempts, and moved to Florida to “do it the hard way.” He recounts the cold email that scored his first bar promo reel, the bartending and production gigs funding his dream, and the power of asking—again and again—until “yes” finally sticks. Fred counters with his three-part playbook—timing, people, persistence—and the “six-nos” sales test. Rejection, relentless networking, and blockbuster ambitions collide in this candid blueprint for creative risk-takers who refuse the easy route.