What happens when financial education becomes more than a podcast — and turns into a media platform, educational ecosystem, live event business, and global community?
In this conversation, Earn Your Leisure co-founders Rashad Bilal and Troy Millings sit down with Ian Schwarzman on Built Different to discuss the journey behind one of the most recognizable financial education brands in their community. They talk about friendship, entrepreneurship, financial literacy, content creation, business growth, Investfest, education, and the long-term vision behind Earn Your Leisure.
Rashad and Troy explain how their relationship began years before Earn Your Leisure, when they met as kids on the set of the movie Eddie. Their friendship continued through school, different career paths, and eventually business ventures. While Rashad pursued a career as a financial adviser, Troy worked in education, giving both of them very different professional experiences that eventually became important parts of Earn Your Leisure.
Watch More: US Tech Jobs in Crisis? AI Layoffs, H-1B Visa Changes & Indians Returning Home
The conversation explores how their different personalities and skill sets helped shape the business. Rashad describes his experience working as a commission-based financial adviser for 12 years, while Troy explains his background as a teacher and his desire to bring practical financial education to young people. Their third partner, Mike, contributed technology, videography, and behind-the-scenes media expertise.
The origins of Earn Your Leisure were not initially about building a massive company. Rashad originally viewed content and social media as a way to connect with potential financial-advisory clients. But after producing financial-literacy content, appearing on local programs, and discussing business and money topics, their audience began to grow.
One particularly successful piece of content involved breaking down the 50 Cent Vitamin Water deal. The clip attracted significant attention and helped grow Rashad’s social media audience. Eventually, viewers began asking where they could find the full conversations. The demand for longer-form content eventually became one of the catalysts for launching Earn Your Leisure as a show and podcast.
The discussion also looks at the gap between traditional education and practical financial literacy. Troy explains why his experience in education made him increasingly interested in teaching subjects such as money, entrepreneurship, investing, and financial decision-making. He describes seeing a need for financial education that could reach students beyond the traditional classroom.
Another major turning point came when people from around the world began interacting with their content. Troy recalls seeing messages from people in places such as Tokyo and Kuwait while he was still working in education. That international audience helped him realize that the platform could potentially reach far more people than a traditional classroom could.
The conversation then moves into the growth of Investfest, the annual event that became one of the major components of the Earn Your Leisure ecosystem. According to the discussion, Investfest grew from approximately 4,400 attendees to around 30,000 people per day. The event combines financial education, entrepreneurship, business, entertainment, networking, and live experiences.
Rashad and Troy also discuss the challenges of getting mainstream recognition for an event centered around financial literacy and entrepreneurship. They talk about the difference between having a large, highly engaged audience online and being recognized by traditional media and financial institutions.
Another important part of the conversation is their approach to financial information. They emphasize that their content is intended to provide information and perspectives rather than guarantee investment returns. They encourage viewers and listeners to conduct their own research and take responsibility for their financial decisions.
The discussion also explores the future of Earn Your Leisure beyond podcast rankings. The founders describe a broader vision involving Investfest, books, educational programs, a paid community, international expansion, and projects in Africa. They discuss their interest in reaching audiences outside the United States and expanding their financial-education mission globally.
The conversation eventually turns toward legacy. Rashad and Troy describe empowerment and impact as important parts of how they hope their work will be remembered. They discuss helping people learn about investing, homeownership, entrepreneurship, business ownership, and financial decision-making.
This episode provides a behind-the-scenes look at how two longtime friends turned conversations about money into a much larger business and educational platform — and how financial education, media, community, and live events can intersect.
Watch the full conversation to learn more about:
• How Rashad Bilal and Troy Millings first met
• The story behind their longtime friendship and business partnership
• Rashad’s 12-year career as a financial adviser
• Troy’s experience as an educator and teacher
• How their third partner Mike contributed to the media side of the business
• The origins of Earn Your Leisure
• How social media helped grow their audience
• The 50 Cent Vitamin Water story that attracted major attention
• Why viewers started demanding a full podcast
• The role of financial literacy in education
• How international audiences changed their perspective
• The evolution of Investfest
• How Investfest grew from thousands of attendees to around 30,000 people per day
• The relationship between financial education and entrepreneurship
• Their approach to sharing financial information
• Why they emphasize doing your own research
• The challenges of gaining mainstream recognition
• Their expansion into international markets
• Their plans and projects connected to Africa
• Their broader vision beyond podcast rankings
• The importance of community and live events
• Their thoughts on empowerment, impact, and legacy
Whether you’re interested in entrepreneurship, investing, financial literacy, business media, content creation, personal finance, or building a community around education, this conversation offers an inside look at the strategy, experiences, and ideas behind Earn Your Leisure.
Watch until the end for the conversation about legacy, the future of Earn Your Leisure, and the special collectible cards presented to Rashad and Troy.
Disclaimer: This video is for informational and educational purposes. The discussion includes personal opinions, experiences, and perspectives about business and finance. Nothing in this video should be considered personalized financial, investment, tax, or legal advice. Always conduct your own research and consult qualified professionals before making financial decisions.