In this high-energy episode of Friendors, host Shawn Miller sits down with Rob Hamilton, the mastermind behind Side One Entertainment, to explore what it really takes to turn a passion for music into a multi-city wedding and events entertainment company.

From starting as a working musician and jazz guitarist to leading a 150+ performer roster and managing 250+ gigs per year, Rob shares hard-won insights into scaling a creative business, building elite teams, navigating the events industry, and delivering unforgettable live experiences for weddings, corporate events, and private celebrations.

This episode is a must-watch for musicians, DJs, wedding vendors, event pros, and creative entrepreneurs looking to turn talent into a thriving, sustainable business.

• How Rob built Side One Entertainment into a multi-city brand
• The business side of weddings, live bands, and event entertainment
• How to manage talent, systems, and growth at scale
• The challenges of scaling a creative company
• Why flexibility is key in the modern event industry
• Lessons for musicians who want to become entrepreneurs

Side One Entertainment is one of Canada's premier wedding and event entertainment companies, supplying top-tier bands, DJs, and musicians for luxury weddings and large-scale events across multiple cities.

Instagram: @sideoneband
Website: http://sideone.ca/

Follow Friendors for in-depth conversations with the creators, vendors, and entrepreneurs powering the wedding & events industry.
📍 Available on YouTube, Apple Podcasts & Spotify