On this episode of Learning to Fly, Bruce is joined by Greg Hill, renowned radio personality and entrepreneur, who shares his journey from hosting a makeshift radio show in his garage to becoming a morning show icon on WAAF and WEEI Sports Network. The episode delves into Greg’s career path, his passion for radio, and the evolution of the industry over the past 35 years. Greg reflects on the challenges and triumphs of building a radio career, his philanthropic efforts through the Greg Hill Foundation, and his entrepreneurial ventures. He also discusses the impact of consolidation on radio and the enduring power of the medium to connect communities and create positive change.