Earn Your Leisure: Rashad and Troy Talk Watches, Wealth, and Legacy

This week on The Wrist Check Podcast, hosts Perri and Rashawn sit down with two cultural icons who’ve redefined the conversation around money, ownership, and access—Rashad Bilal and Troy Millings of Earn Your Leisure. Known for blending financial education with real-world storytelling, the duo joins the show to talk luxury watches, legacy, and how their journey continues to inspire a new generation of investors and creators.

The episode kicks off with a heavy wrist check featuring a gold Rolex Sky-Dweller, an Audemars Piguet Royal Oak, and a Parmigiani Fleurier, setting the tone for a conversation that bridges wealth and style. Rashad and Troy share how they first connected, what led to the creation of Earn Your Leisure, and how they began collecting luxury timepieces. They also discuss why they think the authorized dealer game is “wack” and highlight their discovery of a Black-owned watch brand from Ghana that’s breaking barriers in the industry.

From building InvestFest into one of the most influential financial empowerment events in the world to honoring Nipsey Hussle’s lasting impact, Rashad and Troy show that success isn’t just about numbers—it’s about purpose, representation, and community. This episode is a masterclass in how culture and craftsmanship intersect within the world of modern luxury.

What's On The Wrist?

with Earn Your Leisure