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.