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.

On this episode of Learning to Fly, Bruce is joined by Larry Calderone, President of the Boston Police Patrolmen’s Association, who recently negotiated one of the best contracts for the union since 1965. The episode explores Larry’s career path, challenges along the way, and the evolution of modern policing. Larry emphasizes his deep-rooted commitment to advocating for his peers and touches on the importance of compassion, discretion, and continuous improvement in law enforcement practices. He describes the delicate balance between upholding the law and maintaining public trust and how he has successfully been able to navigate both.

Massachusetts state auditor Diana DiZoglio joins Bruce on the mic as they discuss and debate governmental accountability and Diana’s unconventional journey into politics-highlighted by how she’s overcome resistance and adversity both personally and professionally.