On this episode of Learning to Fly, host Bruce Mittman sits down with Charlie Moore—the high-energy, Emmy Award-winning host of Charlie Moore No Offense. Known to millions as "The Mad Fisherman," Charlie has been a dominant force in outdoor television and sports media for over three decades.

Charlie shares how his journey began as a young entertainer working the crowds at the Winthrop Marina on his father’s boat, eventually transforming a failed outdoor retail business in Beverly into a media empire. He reflects on his early days at NESN, where he relentlessly harassed executives for six months until they gave him a segment on the show Front Row—a move that eventually led to his own half-hour special and a decade-long run on ESPN with Beat Charlie Moore.

Charlie and Bruce dive into the grit required to build a syndicated brand, Charlie’s refusal to sell his "IP" to Hollywood giants, and his transition into the spirits industry with successful lines like Mr. Pickles Gin and Puncher’s Chance Bourbon. He offers a firsthand look at the evolution of outdoor lifestyle programming and his mindset as an entrepreneur who refused to take "no" for an answer.

Preserving his legacy through his own app and global syndication, Charlie discusses the importance of staying true to one's roots while constantly reinventing the brand. It is a rare glimpse into the life of a man who turned a passion for fishing and comedy into a household name.

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.