Young Boss with Isabelle Guarino
YOUNG BOSS is a place for young bosses and entrepreneurs of all industries to collaborate and chat about the expected (and unexpected) challenges of being a successful, young professional in today's business environment. Tune in weekly for discussions about leadership, personal growth, networking & building relationships, raising capital, business strategy and SO much more.
Young Boss with Isabelle Guarino
How I Become a Music Technology Mogul
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
Josh Simons has been building businesses since most kids were just building sandcastles. Lemonade stands. Go-karts he leased out. Hustles that taught him early how money moves and how people work.
At 17, Josh dropped out of school and made a feature film, not just for fun, but as a real business. Budgets. Hiring. Deadlines. Pressure. It was his first crash course in entrepreneurship, and it burned him out just as fast as it lit him up. In his early twenties, he hit reset mowing lawns, cleaning toilets, and actually living life for a minute.
Then music pulled him back in. Josh started a band and naturally ran the business behind it too. That’s when he saw a massive gap in the industry: musicians had platforms to stream, monetize, and build audiences… but nowhere to actually connect. LinkedIn wasn’t built for creatives.
So he built what didn’t exist.
VAMPR - the “Tinder for musicians.” A hyper-granular networking platform that grew to over 1.7 million users and changed how artists collaborate globally. That success eventually led to a strategic exit into Australia’s public music tech ecosystem with Vinyl Group, turning VAMPR into part of a broader music technology portfolio.
But Josh’s real superpower isn’t just ideation, it’s evolution. He knows teams change as companies scale. Skillsets shift. Ego gets shelved. Transparency wins.
From bootstrap hustle to tech exits, Josh Simons proves one thing: the path isn’t clean but resilience compounds. And the entrepreneurs who survive the dark chapters are the ones who end up rewriting industries.
Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.
And remember, youth is your power.