Episode 13:

How Rashad and Troy of EYL Scaled Their Brand and Built The Biggest Business Podcast in the World

Do you ever wonder about the legend behind the business? Try legend(s). In this episode of WorkSmart, Morgan chats with Rashad Bilal and Troy Millings, the partners in crime behind the podcast and financial literacy company Earn Your Leisure. Rashad and Troy combined their respective skill sets to launch Earn Your Leisure, leaning on one another and tapping key hires as the company grew. Today, Rashad and Troy break down their journey to virality and why two is always better than one. 

Founders Squared

Let’s go back in time. Rashad was a financial advisor dipping his toes into social media, appearing on podcasts from time to time and posting clips to social whenever possible. Troy taught financial literacy. He knew about Rashad’s budding brand and suddenly found himself right beside him, brainstorming podcast names and running the brand’s general operations. 


Soon, the brand grew, always fueled by the mission of bringing financial literacy to young people in a way that’s unique, relevant, and entertaining.  

The First Hires

The pair hired a partner right off the bat. A friend from childhood who could see them through the ups and downs of building a business. Next, they hired an assistant and then help with tech and merch, always looking for people to do what they do best. For Rashad and Troy, the goal was to never do what others could do better. 


The right hire can make or break a business. Especially in the early days, there’s a lot of trust that goes into handing over the reins and counting on peers to develop as strong leaders. 

Revenue Streams Galore

Many look at podcasting as an easy gig. But building a media brand is far from it. With upwards of 10 streams of income, Rashad and Troy balance podcasting, YouTube, merch, educational courses, social media, affiliate programs, speaking, and events (pre-pandemic). They also don’t rely on outside funding to function and often say no to monetary offers. Because as Morgan reminds us, there’s no such thing as free money.

Advice For Young Entrepreneurs

Are you on the grind each and every day, posting and hustling online…but can’t seem to gain traction, growth, or real results? Rashad and Troy say, look at your messaging. Maybe something’s not resonating. And remember to stay consistent, test through trial and error, and check your ego at the door. Most importantly, don’t be a certified copycat. 

Homework Time

Find a great partner. There’s no need to exchange equity or capital just yet. It can be as simple as partnering on a social post or hopping on a joint Instagram Live. As black entrepreneurs, we’re stronger together.


Remember: work smarter, not harder.

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Deal Flow

The rate at which financial professionals like venture capitalists, angel investors, and private equity investors receive business proposals or investment offers. 


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