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ABOUT OSE

Olive Street Entertainment (OSE) is a Cape Breton company founded in 2010 by Stephen Muise and Jenn Sheppard, driven by a passion for live performance and production. With more than 30 years each in various facets of the entertainment industry, performing, writing, producing, directing, designing, and supporting artists, we have put that experience to work through OSE. Since its inception, our homegrown company has produced, managed and and/or contributed to large-scale tours (Men of the Deeps), high-end galas (The Lamplight Gala, Miners Museum), community fundraisers (United Way Cape Breton), music productions (Rock Around the Decades), tribute shows (The Legends Series at Savoy Theatre, Vinyl 33 Tributes), and music & comedy pairings (The Island Girls, Yours Truly Cape Breton). Our work also encompasses radio, voice-overs, narration, audio branding and commercials, alongside the management of two busy, seven-piece dance bands (High Society & The Privateers). We tend to fly under the radar (IYKYK), but our reputation has grown through positive outcomes and word of mouth. We’re not afraid to roll up our sleeves, and after years in this business, there’s not much we haven’t seen... from community meetings to packed beer bashes. Our perspective is unique, shaped by years of being part of the work, on stage and behind the scenes.

OSE Partners

Stephen Muise

Stephen Muise, Co-Owner of OSE, is a respected educator, conductor, and business manager of the world-famous Men of the Deeps. He has served as musical director for countless musicals and as a director and producer across a wide range of productions. Stephen’s many contributions to the arts have been recognized with an Honorary Doctorate from Cape Breton University, the ECMA Stompin’ Tom Award, and a Canadian Band Excellence Award for his work connecting youth with professional artists in the industry. Always excited to design and shape a new vision, or help to bring someone else's to life, Stephen brings knowledge, professionalism,

and passion to every project.

Jenn Sheppard

Jenn Sheppard, Co-Owner of OSE, is a multi-faceted artist and entrepreneur with a broad background in the entertainment industry. A singer, songwriter, and comedic performer, she has built a career that spans music performance and production, original comedy, and marketing support for organizations across Cape Breton. Her professional path has included stage performance, radio, television, event management, voice work, audio branding, graphic design, video production, and both script and speech writing in entertainment and political circles. This range of experience gives her a clear, practical view of the business and a knack for turning ideas into results with creativity and professionalism.

OSE recruits additional team members based on project requirements. We happily hire excellent and experienced stage managers, hosts, wranglers, runners, etc, when needed. 

Gallery

© 2025 by Olive Street Entertainment Company

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