On this episode of Learning to Fly, host Bruce Mittman sits down with David Bieber—a legendary figure in Boston’s media and music scene for over 50 years.

David shares how his journey began as a college reporter for Billboard magazine, leading to a dynamic career in media after graduation. He reflects on his time at the helm of iconic Boston radio stations WBCN and WFNX during their peak in the 1980s, and discusses his collaboration with Boston Phoenix owner Stephen Mindich—offering a firsthand look at the evolution of Boston’s alternative culture and journalism.

David and Bruce also dive into David’s extraordinary pop culture archive, amassed over five decades and spanning more than one million pieces of memorabilia. He shares how the collection came together and explains that, while it isn’t open to the general public, he offers private tours by special arrangement—an opportunity for a rare glimpse into an unparalleled collection of music and media history.

On this episode of Learning to Fly, host Bruce Mittman sits down with acclaimed Massachusetts painter Thomas R. Dunlay, one of the few artists keeping the New England traditional painting style alive. Tom shares his journey from early inspiration under his father to pursuing art at MassArt—and why he left after 18 months in search of a more disciplined, classical approach.

Bruce and Tom explore his rigorous training under R.H. Ives Gammell and Roger Douglas Hunter, exploring the “boot camp” methods that honed his craft, including the precise sight-size technique. They discuss how Tom established a career capturing the light and beauty of New England landscapes with iconic works like Winter Snowfall, while mastering both art and business. Tom emphasizes the importance of teaching the next generation, a mission he fulfills through the Thomas R. Dunlay Teaching Studio.

The conversation dives into the beauty of nature, the discipline behind traditional craft, and the dedication required to preserve a nearly lost art form—offering insights for artists, creatives, and anyone striving for mastery in their field.

In this episode of Learning to Fly, host Bruce Mittman sits down with Casey Soward, President & CEO of the Boch Center—home to the historic Wang and Shubert Theatres. Casey shares his journey from a music-obsessed kid on Cape Cod to leading one of Boston’s most influential performing arts institutions, detailing the unconventional path that led him from performing on stage to running it.

They discuss Casey’s early career as a musician and audio engineer, his pivotal role revitalizing the century-old Cabot Theatre, and how those experiences prepared him to balance the preservation of historic venues with their operational demands. The conversation explores the challenges of maintaining cultural landmarks while keeping them financially viable in an ever-changing arts landscape.

Beyond performances, Casey highlights the Boch Center’s deeper mission in arts education and youth development, emphasizing the power of the arts to create opportunity and lasting impact. He also speaks about the organization's investment in the Folk Americana Roots Hall of Fame and its goal of elevating Boston’s status as a music capital. Together, they discuss the importance of leadership, resilience, and authenticity in Casey’s current role—and what it takes to succeed under the weight of both history and expectation.

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.

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.