On the latest episode of Learning to Fly, host Bruce Mittman chats with Paul Barclay, co-founder of Boston’s iconic Comedy Connection. The club helped launch the careers of comedy heavyweights like Steven Wright, Paula Poundstone, Bobcat Goldthwait, Joe Rogan, and Rosie O’Donnell (just to name a few).

Bruce and Paul share anecdotes from this legendary club as well as Paul’s other successes– like opening the infamous, South Beach-inspired billiards club and bar, The Rack, in Boston. Paul describes how savvy marketing, outrageous events, and creative PR turned The Rack into a celebrity hotspot, hosting big names like Tom Brady and Nomar Garciaparra. He also details other ventures, including running Seven Central Tavern in Manchester-by-the-Sea, serving as a Selectman, operating a farm with over 175 rescued animals, and eventually moving to coastal Maine to run a B&B.

When asked how he managed to accomplish it all, Barclay credits mentors, the press, and his staff for his success. For those looking to mirror his storied career, he recommends focusing on teamwork, trusting your instincts, and knowing when to step away from a venture that no longer feels right.

On this episode of Learning to Fly, host Bruce Mittman sits down with Dr. Charlotte de Brabandt– an accomplished businesswoman who’s had success in supply chains and technological procurement, philanthropist with a PHD, and author. Tackling all this and a breast cancer diagnosis at the young age of 35, the episode takes a deep dive into how she’s been able to achieve so much.

They discuss how she broke into a male-dominated field working across brands like Volkswagen, Johnson & Johnson, and Amazon. She details her rise in the ranks and the challenges she overcame to get there. Charlotte shares about her battle with a rare form of breast cancer while maintaining full-time work, writing books (14 in total), and engaging in public speaking. Now cancer-free, she talks about her role as a board member of the American Cancer Society and her transition into work centered around servant leadership and intentionality rather than milestone-driven success. She wrote her latest book focused on the themes of empathy, agility, and digital fluency in modern leadership.

They wrap up the podcast with Dr. Charlotte de Brabandt encouraging young women and comparing the path to success with the mountains she used to climb as a mountaineer guide. Offering the advice to bring your work sack– no matter how heavy it might be– and to put your head up, chin up, and eyes forward.

On this episode of Learning to Fly, host Bruce Mittman talks with Steven Tompkins, who has served as Suffolk County’s Sheriff for the past 12 years. Sheriff Tompkins shares his humble beginnings, describing how he earned a full scholarship to Boston College through a diversity outreach program. They explore his unconventional career path—from working as a TV producer to transitioning into public service.

Appointed Sheriff in 2013, Tompkins saw the role as a way to ‘pay it forward’ for the life-changing opportunities he had received. He explains his focus on rehabilitation, detailing programs designed to support inmates and prevent youth incarceration. Together, he and Bruce examine the systemic challenges inmates face and discuss potential reforms. Sheriff Tompkins reflects on how his unique journey has shaped his leadership and prepared him to tackle these pressing issues.

The episode wraps with Sheriff Tompkins emphasizing the power of role models, relationships, and second chances.

On this episode of Learning to Fly, host Bruce Mittman sits down with one of the biggest names in sports history, Joe Theismann. They discuss Joe’s small-town upbringing and how it paved the way for his football career. Theismann shares the story behind the marketing campaign at Notre Dame that led to a pronunciation change of his surname to rhyme with ‘Heisman’, college football’s most coveted trophy. He reflects on his post-college career and how he seized opportunities, and negotiated his own contracts. After leading Washington to a Super Bowl win in 1982, Joe recounts the good, the bad and the ugly during his playing days, including the challenges of strike seasons and his infamous career-ending injury in 1985. They explore his perseverance and the transition of his career from active player to successful broadcaster, where he launched a second act lasting over 20 years. The episode wraps with Joe reinforcing the importance of resilience and gratitude on the road to success.

In the latest episode of ‘Learning to Fly’ our host, Bruce Mittman, sits down with Jeff Friedman, a seasoned security professional and “legend in the music community” with over 40 years in the biz. Jeff shares the story of how he got his unplanned start in the security business, working at small clubs around Boston, and his rise to becoming the head of Wizard Security, where he manages security for epic concerts. He recounts wild experiences with beloved big-time bands and describes how he managed large, rowdy crowds, including a now-infamous Green Day concert. While stressing the importance of establishing strong relationships within the music industry, Jeff reflects on the joy that has ultimately come from pursuing a passion-driven career over one focused solely on financial success.

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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.