Paul Barclay: Laugh Your Way to the Top

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.