Before Earn Your Leisure became one of the top business podcasts in the world, its roots were planted in classrooms and community programs. Troy Millings, an educator, and Rashad Bilal, a financial advisor, teamed up to bring financial literacy to teens in Greenburgh, New York.
Operation Crossroads: Where Earn Your Leisure Began
Their program, Operation Crossroads, was more than just an internship; it was a crash course in real-world finance. The duo noticed that for many participants, it would be their first paycheck, and they didn’t want that moment to be wasted. Millings and Bilal taught them how to save, invest, and share their earnings, building a foundation for smarter financial habits long before adulthood.
Operation Crossroads was designed to provide teens not only valuable work experience but also critical financial education that is often lacking in traditional schooling.
Troy Millings explains, “We were gonna pay kids for being part of an internship program, and it was gonna be their first time coming in contact with their own money. If they didn’t learn the discipline of what to do with it, we knew what their futures would look like.”
The program also aimed to help young people explore potential career paths early, allowing them to decide what they were passionate about or what they wanted to avoid before investing years and resources in college or training.
While they no longer run the program themselves, it continues to this day, carrying forward the same forward-thinking approach that helped lay the foundation for what would eventually evolve into Earn Your Leisure.
Building a Financial Education Empire
Today, Earn Your Leisure is more than just a podcast; it’s a comprehensive financial literacy platform. Their offerings include:
- EYL University: An online community with over 12,000 members and 200+ webinars covering investing, entrepreneurship, real estate, and more.
- You Deserve to Be Rich: A New York Times bestselling book that breaks down wealth-building strategies into actionable steps.
- EYL Network – A collection of shows and content focused on business, finance, and culture.
- Invest Fest – An annual festival that blends business education with entertainment.
Invest Fest: The Festival That Changed Financial Education
In 2021, Earn Your Leisure expanded their vision by launching Invest Fest, an event that blends the energy of music festivals with financial literacy and business empowerment. Unlike traditional conferences, Invest Fest features large stages, food trucks, celebrity guests, and a marketplace that supports hundreds of small businesses.
The festival draws thousands of attendees from across the country, and this year will feature powerhouse speakers including Steve Harvey, Issa Rae, Magic Johnson, and Tyler Perry. The upcoming 5th annual Invest Fest, scheduled for August 22–24, 2025, in Atlanta, promises to be its biggest yet. The event will spotlight emerging trends, including artificial intelligence, technology, and global entrepreneurship.
Words of Wisdom from Rashad Bilal and Troy Millings
When asked what advice they would give their younger selves, the founders kept it simple and powerful:
- Rashad Bilal: “Just start whatever idea you have. Don’t wait for the perfect moment.”
- Troy Millings: “Invest early and often. You don’t need a lot of money to start.”
From a community internship program to a global financial literacy movement, Earn Your Leisure continues to empower people of all ages to build wealth, pursue their passions, and live life on their terms.
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