Home Blog ‘Earn Your Leisure’ Podcast Hosts Talk Finance, Celebrity And Scale – Forbes

‘Earn Your Leisure’ Podcast Hosts Talk Finance, Celebrity And Scale – Forbes

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Rashad Bilal and Troy Millings of Earn Your Leisure attend the 2022 InvestFest at Georgia World … [+] Congress Center. (Photo by Paras Griffin/Getty Images)
“But, how do you scale it?”
That’s the business question usually following any acknowledgement of a good idea, whether at work, at play, at school or even at church. How do you take a really great idea and make it work for hundreds, thousands or even millions of people?
The co-founders of popular podcast Earn Your Leisure are working their way toward an answer, and so far this involves going outside, visiting cities and interacting in a music-festival style with listeners via its global and in-person Invest Fest, traveling to numerous cities for Market Mondays live chats and posting no-frills, nearly daily Earn your Leisure podcast tips for navigating the stock market.
“A lot of [financial] conferences have taken place over [in] the last couple of years, and become pretty popular,” explains Earn Your Leisure co-founder Rashad Bilal, in an interview just a few days before recording the live-in-Chicago session of the global tour for Market Mondays, a podcast offshoot of Earn Your Leisure. “We thought: ‘How can we be different and how can we add our own spin to it and do something that nobody was currently doing?’ So the idea of a festival came into play and the word festival was important because that separated it from conferences or summits.”
The tour had two sold-out dates in Toronto and is headed to Ghana next. In Chicago, hey rented out a popular facility- the Atheneum Center for Thought and Culture, that can hold hundreds, has a stage and a theatre and is built for performance and education. There, fans – or listeners – gathered to talk stocks, bonds, investments, artificial intelligence, real estate, loans and credit — all topics of intense interest to the American black community, which is the target market for the podcast. At the same time, many of these events showcase music, celebrity, athletes and interviews with people held in high esteem with the black community.
Pair that with the fact that African-Americans have historically and systemically been suppressed from accessing many wealth-building conversations and opportunities afforded to other populations. If an event offers financial intelligence and access that was once hidden from the community, it’s no surprise that EYL events tend to sell out.
In fact, the Journal of Financial Therapy in 2018 cited a study that said the racial wealth gap in American is in part due to African-Americans not investing in the stock market. The Center for American Progress in 2021 issued a report detailing the reasons for the black-white wealth gap, but also provided ideas for closing said gap. [“On average, Black households had 14.5 percent of the wealth of white households, with an absolute dollar gap of $838,220.” – Center for American Progress ]
Until more wealth correction policies are implemented, EYL hopes to provide information that might close and bridge this wealth gap – at scale. And that’s where culturally-relevant training and conversations come in. The duo has interviewed everyone from Van Jones to Jemele Hill to Rick Ross to billionaire Robert Smith. Learning from the rich, pairing that with finacial market information and sharing the information in an authentic, no-frills manner is what makes the podcast work.
Being a trained educator who is familiar with and welcoming to black culture also helps, explains co-founder Troy Millings, who created the Earn Your Leisure brand with Bilal after having worked as a 6th grade health and physical education teacher in the New York public school system.
“A lot of people just think, ‘all right, I’ll get into this space ’cause it looks cool’ — Not knowing that there’s an actual process and a skill to giving information to somebody where they can hold it and then apply it,” explains Millings. “I think it’s one of the unique skills that we’ve been able to possess. And that starts from early days with me and him being in the classroom, me not knowing about finance, him being new to the classroom environment and learning from each other. People get to see that every day now because that’s something we were practicing eight to 10 years [ago].”
Original episodes featured the duo only talking about financial tips. But the turning point came in 2019 when former Bad Boy executive Derek Ferguson came to the show and explained how he attained his position. From then on, the duo included stories of success – the blueprint, if you will – to their offerings.
Some of that advice still sticks.
“Robert Smith, the wealthiest black person in American history, was just giving us some information and his advice on our business model,” says Bilal. “He was telling us that you just gotta always think bigger? In scale, right? And it’s not necessarily about doing everything manually, but having systems in place to free up your time to actually be able to scale, to do a variety of different things at a quicker and faster level.”
And Tyler Perry, who attended the second Invest Fest, offered this gem: “He looked at the scale of it and said, ‘well, what’s next?’,” remembers Millings. “We’re thinking to ourselves: ‘this is pretty grand. We’re doing pretty well.’ He was like, ‘nah, you gotta dream bigger.’ And it was a lesson that he learned from listening to Sidney Poitier, after Oprah had brought him to an event and he told [Poitier] about his vision and they looked at him like, ‘that’s great, but can you dream bigger? Can you scare yourself with your dreams?’”
To that point, the first Invest Fest had 4,500 attendees. The second had 14,000 and this year’s – created in partnership with Diddy and Steve Harvey – had 20,000, say the founders. As far as Market Mondays and Earn Your Leisure, any guests are booked directly by the duo, who keep wrangling costs low by leaning on their network to secure interviews.
The duo are also careful to remind listeners and attendees to do their own research and to remain in control and up to date on where they spend, save or invest money. Not to sound cliche, but knowledge is power. And also, especially with the holidays approaching, their biggest tip is to listen and learn before doing anything.
“In order to understand something, you need to be educated. And so we always encourage people to educate themselves, right?” Bilal says.
But back to the question of scale. With thousands of listeners happily logging in and connecting digitally, why would the guys put themselves through the grind of traveling cross country and across continents? After all, late December sees Ghana as the next stop.
“How do we impact more people? How do we add more value?”says Millings. “That’s always been in our mindset: how do we scale bigger?”
Listen to season Two: Assets Over Liabilities here.

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