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.”
The Business Blueprint
QUOTE: “I always kind of thought it would be big before we started. I always had the vision.” – Rashad Bilal During the first few episodes of Earn Your Leisure, Bilal and Millings used an iPhone to record themselves as they dissected business case studies like the launch and growth of Airbnb. Their consistent, authentic, and digestible delivery quickly resonated with listeners from the streets all the way to Wall Street. Within the first seven months, the podcast accumulated over 6,500 subscribers and an average of 20,000 plays per episode. It also began to rank on national podcast charts. “We were [ranking on] top 10 podcast charts by like episode 11. So, off the rip, we had a good following, and it just never really slowed down,” said Bilal. “It was a consistent build-up.” Bilal and Millings used the growing popularity of the podcast to secure interviews with high-profile entrepreneurs like billionaire Mark Cuban, NBA legend Shaquille O’Neal, and hip-hop mogul Dame Dash, who shared their personal blueprints for business success. Millings says he was surprised by the meteoric rise of EYL and the overwhelming response they received from listeners. “When I started seeing the numbers, I was like, ‘wait, we have 2,000 people listening?’ And every week, that number kept going up,” he said. On top of that, “our social media was exploding. The clips were going viral.” Not only did the hosts develop a global fan base, but they were changing people’s lives. We received “messages [from] people saying, ‘I’m in jail and I just listened to this episode. What y’all do is incredible, man! I wish I would have had this information. I probably wouldn’t be here,’” recalls Millings. Bilal, on the other hand, says he was confident in EYL’s ability to become a financial juggernaut from day one. “I always kind of thought it would be big before we started. I always had the vision.”From Classes to the Masses
By early 2020, Millings says he realized that EYL was making a greater impact than he ever could as a teacher.
“I’ll never forget on March 11, 2020, sitting at home, and I was just like, ‘this is going to change the world. I’m never going back to the school again,’” he said, recalling the day he resigned. By then, EYL was generating enough revenue to supplement his six-figure teacher salary through its YouTube channel, ad sales, merchandise, and live events.
By April 2021, the show boasted over 5 million downloads, a whopping 422,000 YouTube subscribers, and 702,000 Instagram followers. To satisfy their audience’s insatiable appetite for financial knowledge, the co-founders partnered with Matthew “MG The Mortgage Guy” Garland to launch “EYL University,” which includes dozens of online courses and webinars on a range of topics like real estate, cryptocurrency, credit, stocks, content creation, advertising, and e-commerce. They also launched the EYL podcast network, which produces and distributes shows like Inside The Vault with Ash Cash, Market Mondays with investor Ian Dunlap, and High Level Conversations hosted by thought leader 19 Keys. Furthermore, the duo secured a deal with iHeartMedia and Charlamagne Tha God’s The Black Effect Podcast Network that same year.
Media outlets couldn’t help but notice EYL’s viral celebrity interviews, podcast growth, and burgeoning social following. They were featured in national publications like Forbes and Black Enterprise and on Power 105.1 radio’s The Breakfast Club. In 2021, the co-founders landed a TV show called “Assets Over Liabilities,” where they interviewed hip-hop stars and influencers about business, on Sean “Diddy” Combs’ Revolt television and digital network. Later that year, they signed with United Talent Agency, a global talent agency based in Beverly Hills that represents the likes of Johnny Depp, Harrison Ford, and Charlize Theron.
EYL’s momentum continued in 2021 when over 4,000 people flocked to Atlanta to attend its inaugural economic empowerment conference, Invest Fest. The monumental event celebrated the marriage of culture and commerce, educating the next generation of Black investors and entrepreneurs on cryptocurrency, the stock market, real estate, insurance, and estate planning.
The number of Invest Fest attendees more than doubled to 14,000 people in 2022 and featured business titans like Tyler Perry, Rick Ross, and Chick-fil-a chairman Dan T. Cathy. It also marked the start of EYL’s partnership with Steve Harvey and Harvey Ventures to produce events.
In October 2022, Harvey and the co-founders took Invest Fest overseas, holding a three-day conference in London. The sold-out summit featured speakers like actor and host Terrence J and Black financial experts 19 Keys, Wall Street Trapper, Ian Dunlap, and Patricia Bright.
With no signs of slowing down, earlier this year the globetrotting pair launched the Market Mondays World Tour sponsored by Ally, which kicked off in Los Angeles in March, followed by a tour stop in Toronto in April. The tour is slated for London in June, Chicago in October, and Ghana in December. The financial powerhouses are also preparing to host the third annual Invest Fest in August, which promises to be their biggest and best event to date.
“This year we are expecting 20,000 people,” said an EYL rep in an email to BE. “Invest Fest 2023 will include an even larger vendor marketplace showcasing over 400 small businesses and live podcast stages with interviews from top entrepreneurs.”
Knowledge is Power
Outside of helping Black people around the diaspora achieve financial freedom, Millings and Bilal attest that the information they learn from their interviews has increased their financial prowess and business acumen.
“One of the benefits of sitting down with people, is we get to learn everything that they know,” said Millings. For example, he noted that episode 12, featuring celebrity mortgage broker Matthew Garland, changed his perspective on profiting from a multi-family home.
“I was living in one. I was like, ‘Why am I not thinking of this? Why am I not doing this?’” he said.
“Episode 11 is still probably one of my favorite episodes,” said Bilal. That episode featured restauranter Derrick Faulcon, who served five years in federal prison before opening Home Maid in Baltimore, and later Cloudy Donuts in Brooklyn, New York. Not only did Faulcon share his success story, but he gave a breakdown of his revenue model and strategy to secure profits.
“The way he looked at business from a holistic standpoint, getting the most out of the opportunity, as opposed to letting nothing go to waste and being very efficient, that was something that I still carry to this day.”
Economic Emancipation
Bilal and Millings agree that EYL is larger than them. It’s a movement that is breaking cyclical poverty and shifting wealth into the hands of Black Americans one show, event, and seminar at a time.
“Financial literacy is the essential tool that can create generational and sustainable wealth for our communities,” said Millings. “Without it, we’re likely to perpetuate the same mistakes, remain uneducated, and uninformed, and pass down the financial fears and traumas of the generations before us.”
Bilal, who describes himself and Millings as “financial liberators,” says their ultimate goal is to “be able to empower people. Be able to change people’s mindset and change people’s lives when it comes to finance. And also, just to inspire people to think bigger than their current circumstances and realize that anything is possible.”
He adds, “It would be great to be championed as the people that democratized business and made the playing field more equal for people who were disenfranchised when it came to financial literacy and business investing.”
“This is a world mission,” said Millings.