From thought-provoking conversations on their show to reaching the masses in the event space, Troy Millings and Rashad Bilal have quickly become a dynamic duo, taking over the investment and financial sector.

“I think we were always thinking ahead. We never looked at it as just a podcast, we always looked at it as a business,” Bilal told AFROTECH. “And, you know, in business, you have to expand. If you’re not expanding, you’re just contracting. So, we always looked at what other verticals could be added. Whether it’s merch, live events, a network, or developing curriculum, it’s always about what’s next.”


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He continued: “We never just looked at it as if we were just having a show. That was just the first thing that we actually did, but it was always looked at as a platform, as a business… so that’s still how we carry it.”


Building An Empire

On building something from the ground up, Millings says he is most proud of the accelerated growth and large impact he and Bilal have had on the community thus far, especially when it comes to their InvestFest endeavor.

“I think the best thing is the response to what we’ve been presenting,” he shared. “To grow from 3,500 to 14,000 [attendees] lets us know that the work we’re doing is not going unnoticed. People really appreciate it, and it’s actually changing lives, which is something that we don’t take lightly. Every time we get to have an event like that, we get to meet people and they get to tell us stories about the information that they’ve heard, or the person that they met to help change something in their lives. And, I mean, that’s the most humane act, right? Inspiring somebody to help change, and we get to see that in real time. That’s the biggest thing, and I think as we grow and we scale we’re always looking to improve.”

As the duo works to help the community learn about the importance of generational wealth, they also reflect on who helped teach them various financial literacy lessons.

Early Financial Lessons

“My dad was always an entrepreneur and was in financial services so I kind of had an early introduction from him,” Bilal recalled. “And then I’ve always just been really passionate about business. I was watching movies at a young age about business and finance from ‘Wall Street’ to ‘Barbarians at the Gate,’ so I learned a lot from cinema. And then, reading books. ‘Rich Dad, Poor Dad,’ I read that when I was young, at age 18, and that was something that was life-changing for me. It made me look at business in a different way, and I just became even more passionate about it.”

What’s more, in the near future, Millings and Bilal aim to continue sharing the knowledge they’ve come across with their community.

Continuing The Original Mission

“What’s next is what started the foundation of what ‘Earn Your Leisure’ has been all of these years and that’s education,” Millings shared. “We’re currently working on some financial literacy curriculum with the New York City Department of Education to figure out what that looks like. Whether it becomes an elective or something that’s required for secondary levels of education or elementary levels of education to have, it’s something that’s missing.”

He continued, “Our roots started in the classroom, and it’s fitting to go back to that. So, that’s the first piece, trying to make something that’s a mandate, from a curriculum standpoint, not just for New York City — the largest school district — but for the state, and then maybe something that’s federally mandated. And we don’t want to stop there, because financial education is something that’s not just an American issue, it’s a global issue.”

It’s clear that Bilal and Millings are poised to continue expanding “Earn Your Leisure” to greater heights, and during their 2023 InvestFest, the two received a financial boost to do so.

According to a press release shared with AFROTECH, they were presented a $1 million investment from Hip-Hop mogul Sean “Diddy” Combs.

“I am so impressed with Earn Your Leisure’s mission. It’s one of the most disruptive platforms in the fight for economic empowerment and equality. Rashad and Troy are making financial literacy cool for our community,” said Diddy in a statement. “I’ve given them a challenge to go beyond talking about finances and put that knowledge into action for others to see the process. I’m excited to see how much people learn by watching the strategies be put to use in real-time.”

The $1 million will go toward a fund “designed to make investments based on the methodologies discussed” on their “Earn Your Leisure” platform.

Additionally, money made as a result will go directly to Diddy’s three Capital Preparatory charter schools in New York and Connecticut.

“Partnering with the legendary Sean ‘Diddy’ Combs to infuse a million dollars into the Earn Your Leisure fund is more than just a collaboration—it’s a seismic shift in generational wealth. This isn’t just about money; it’s about the convergence of vision, hustle, and a commitment to rewriting the rules. We’re not just opening doors; we’re building new doors, new rooms, new floors. So remember, it’s not just a million dollars; it’s a million dreams, a million futures, and a million reasons why you should never stop betting on yourself. The revolution of financial empowerment is here, and we’re the architects,” said Rashad Bilal in a press statement.

Millings added, “Teaming up with the icon himself, Sean ‘Diddy’ Combs, to pour a million dollars into the heart of the Earn Your Leisure fund is nothing short of monumental. This partnership isn’t just about capital, it’s about a shared mission to light up pathways to prosperity. Picture this: a million-dollar torch igniting opportunities, sparking innovation, and dispelling the darkness of financial misinformation. Our collaboration with Diddy isn’t solely an investment—it’s an affirmation that the world is waking up to the importance of economic education.”