Earn Your Leisure:
Leaders of a Financial Revolution
Earn Your Leisure Co-founders Rashad Bilal and Troy Millings have triggered a paradigm shift that has raised the financial consciousness of Black America
WRITTEN BY: SELENA HILL | COVER IMAGE: TY DAVIS | COVER VIDEO BY: EDWIAN STOKES | DIGITAL LAYOUT: DEVEN ROBINSON
On a cool Saturday morning in mid-March, Rashad Bilal and Troy Millings entered a swanky hotel lobby in downtown Austin, Texas, exhibiting a confident, subtle New York swagger that commands the room. Donning dapper streetwear while standing at 6’3” and 6’2”, respectively, it’s easy to mistake them for professional athletes or, perhaps, rappers or hip-hop music executives. Nonetheless, even those who don’t recognize them can tell they’re a big deal.
We sat down at the Diner Bar inside The Thompson Austin Hotel, where they both ordered oatmeal. Bilal’s bowl is topped with walnuts and blueberries and comes with a side of fruit. The 39-year-old says he tries to eat healthy as much as possible, while Millings, 41, prefers a light meal ahead of their big day. Later that afternoon, they’ll be taking the stage at South by Southwest (SXSW), one of the world’s largest music, tech, and culture festivals. Their demeanor, however, is calm and self-assured. But that’s not surprising. After sharing stages with Steve Harvey, Tyler Perry, and Floyd Mayweather at arenas like Madison Square Garden in New York and the Royal Hall in London, this is just another day at work for the dynamic duo.
Hours later, Bilal and Millings are greeted with loud cheers and applause when they step on stage at SXSW to moderate a live conversation with rap veteran Jadakiss, Grammy-nominated artist and producer Ryan Leslie, and rising indie artist LaRussell. The focus of the discussion, however, is not on the artists’ music careers but rather on their journeys into entrepreneurship and wealth creation. The panel discussion published on YouTube the following week as another episode of Earn Your Leisure (EYL), the wildly popular financial literacy podcast Bilal and Millings launched in 2019. The YouTube video has since racked up over 88,000 views – a mere drop in the bucket for EYL, which has amassed more than 50 million downloads and is consistently ranked in the Top 20 Business Podcasts in the U.S., peaking at No. 1 on the Apple Podcast charts.
Bilal and Millings created EYL to enlighten underserved populations starved for economic empowerment. They carved their own lane, explaining sophisticated finance principles and economic trends through the lens of hip-hop, sports, and entertainment. Their unique approach—which feels like a college business course being taught in a barbershop—has helped EYL accrue a cult-like following that includes over 2 million social media followers. It has also turned EYL into a multifaceted platform that includes an online university, a podcast network, a TV show, live events, and a world tour. Furthermore, it has cemented Earn Your Leisure as the culture’s go-to source for financial knowledge and transformed how urban communities think about money.
Bilal and Millings created EYL to enlighten underserved populations starved for economic empowerment. They carved their own lane, explaining sophisticated finance principles and economic trends through the lens of hip-hop, sports, and entertainment. Their unique approach—which feels like a college business course being taught in a barbershop—has helped EYL accrue a cult-like following that includes over 2 million social media followers. It has also turned EYL into a multifaceted platform that includes an online university, a podcast network, a TV show, live events, and a world tour. Furthermore, it has cemented Earn Your Leisure as the culture’s go-to source for financial knowledge and transformed how urban communities think about money.
Bilal and Millings created EYL to enlighten underserved populations starved for economic empowerment. They carved their own lane, explaining sophisticated finance principles and economic trends through the lens of hip-hop, sports, and entertainment. Their unique approach—which feels like a college business course being taught in a barbershop—has helped EYL accrue a cult-like following that includes over 2 million social media followers. It has also turned EYL into a multifaceted platform that includes an online university, a podcast network, a TV show, live events, and a world tour. Furthermore, it has cemented Earn Your Leisure as the culture’s go-to source for financial knowledge and transformed how urban communities think about money.
LESSONS IN BUSINESS
Four years ago, before EYL was conceptualized, Millings worked as an educator at a public school in The Bronx, New York, while Bilal was a financial adviser. As lifelong friends who grew up in a small working-class community in Westchester just 20 minutes outside New York City, they understood the importance of creating multiple revenue streams. “We knew that we could not save our way to wealth,”
Millings told BLACK ENTERPRISE. So, the friends set out to create a business together. Their first venture was a blog called Fashion Wavve circa 2015. An early student of social media, Bilal’s goal for the fashion blog was simple: “Build it up, get a following, and then have people pay us to promote their brands,” he said. “I’ve been studying social media for a long time,” he continued. “I saw social media as a business opportunity before there was a term called ‘influencer.’”
The plan worked. “We got the [Instagram] page up to 10,000 followers, but we didn’t really have a strong passion for it, so it kind of died off,” he admits.
Later, Bilal and Millings partnered with two friends to launch an innovative app called Jock Drive that used technology to enhance a DJ’s performance and allowed them to store their records in a cloud service rather than carrying physical records. They outsourced a company in India to build the app, but that “didn’t go well” due to the time difference and cultural differences.
“Apps can be very expensive and can take a lot of time to get done,” said Millings. As a result, the four friends lost $30,000 and an unaccounted amount of time that they had invested into the app. Yet, the lessons they learned about business operations were invaluable.
“We kind of learned the hard way,” says Millings. “It was a business lesson that had to be learned. Sometimes it’s better to pay more to get the job done correctly or have it built in an area that you have access to,” he said. “We saw the idea. We saw that it could be lucrative, and we were like, let’s just go after it. I’m not sure how much we studied the space. I’m pretty sure we could have been more diligent about that.”
Likewise, Bilal says Jock Drive taught him the significance of “understanding what you’re actually doing [and] being knowledgeable, that’s important—and being hands-on.”
Most importantly, “it didn’t discourage us,” Millings added. “There are no failures. There are only lessons.”
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Financial literacy is the essential tool that can create generational and sustainable wealth for our communities
– Troy Millings
CLASS IS IN SESSION
Meanwhile, while working for the New York City Department of Education, Millings felt compelled to offer students taking summer school classes practical information. He began incorporating financial literacy into his lesson plans and asked Bilal to lecture his students about money. Eventually, the longtime friends created a complete curriculum on finance for the students. They also began recording the lectures and sharing the videos on social media. “Spend, saving, sharing. That’s pretty much the three things you can do with your money,” Bilal told a classroom of 14-year-olds in a recording dated July 15, 2017. “No matter how much money you make, if you spend everything that you make, how much money are you going to have after that? Nothing.”His videos teaching financial literacy to teens became popular on his Instagram page, where he regularly shared money tips with his 40,000 followers. Wanting to expand his reach, he decided to create the Earn Your Leisure podcast to discuss the money plays behind sports, entertainment, and business. Naturally, he asked Millings to be his co-host and partnered with longtime friend Michael MacDonald, the third co-founder of EYL, to launch a revolutionary podcast focused on equipping Black communities with the tools, information, and resources needed to acquire wealth.
“Financial freedom is the root of empowerment,” he said. “When you look at mass incarceration, health issues, poor education, violence, these are all issues that stem from a lack of financial resources. Achieving financial stability and financial freedom is our only chance at changing our condition in America and in the world.”
The timing of the podcast launch in January 2019 was perfect. Nipsey Hussle and Jay-Z’s music had ignited a new generation of hip-hop lovers to take an interest in financial literacy. Plus, Dame Dash’s viral interview on The Breakfast Club in 2015 about the importance of entrepreneurship and ownership also signaled that the culture was hungry for financial knowledge.
“It helped make the ground fertile,” said Bilal. “A lot of different factors came into play. COVID definitely helped accelerate [our growth]. Even hip-hop, different people putting messages in their music from Nip to Jay to Rick Ross.” That set the stage for EYL’s success. “A lot of different ingredients made the meal. We didn’t plan it, but it was definitely good timing.”