In this episode of Learning to Fly, host Bruce Mittman sits down with Rob Collings, CEO and chief pilot of the Collings Foundation and president of the American Heritage Museum in Hudson, MA. Rob shares the remarkable story of how his family’s foundation grew from a small antique car collection into one of the nation’s premier living heritage organizations, dedicated to preserving and showcasing America’s military and aviation history. From restoring the legendary B-24 Liberator and launching the Wings of Freedom Tour to acquiring more than 200 tanks from famed collector Jacques Littlefield and building the immersive American Heritage Museum, Rob reflects on the passion, perseverance, and purpose he finds preserving these powerful stories. Together, they explore how the museum brings history to life—from World War I trenches to modern-day conflicts—while honoring veterans and reminding visitors of the human cost and technological triumphs that have shaped both our nation and the world.

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.