Work is too important to leave to bad advice.

Winning at Work is the career podcast for ambitious 20 to 40 year olds who want real guidance — not recycled LinkedIn wisdom or motivational fluff from people who've never actually had to make hard calls.

Host John Caldwell has lived one of the most unlikely careers in business. He spent his twenties and thirties managing artists and running a record label, selling 40 million records along the way. He then pivoted into the online gambling and poker industry, rising to the top of one of its most competitive eras. Two completely different worlds. The same hard lessons about people, power, politics, ambition, and what it really takes to build something.

Every episode of Winning at Work tells a story. The stories are about people John worked with — the brilliant ones, the manipulative ones, the ones who burned out, the ones who quietly outlasted everyone. They're about situations he navigated, mistakes he made, and moments that changed how he thought about work and life.

Topics include career strategy, corporate survival, managing up, managing down, hustle culture, entrepreneurship, leadership, workplace politics, building loyalty, and knowing when to stay — and when to go.

This is not a guest interview show. This is not a theory show. This is one person, 35 years of real experience, and the kind of straight talk your most successful mentor would give you if they had nothing left to prove.

For people climbing the corporate ladder. For entrepreneurs building from scratch. For anyone trying to figure out what winning at work actually looks like — on their own terms.

New episodes weekly.