Meet Michael MacDonald, One of the Forces Behind the Earn Your Leisure Business Empire

The Earn Your Leisure (EYL) founders took the world by storm with a different approach, combining business, financial literacy, and entertainment to build a business empire. 

The company started in 2019 with what is now a Top 40 business podcast and has since expanded into a media organization; an online education platform, Earn Your Leisure University; and a one-of-a-kind festival, Invest Fest.

When discussing financial literacy, it is hard to miss Rashad Bilal and Troy Millings, co-founders of Earn Your Leisure. But, Michael MacDonald, the third co-founder of EYL, has been working quietly behind the scenes from day one to build the EYL brand and turn it into the success it is today.

Bilal, Millings, and MacDonald all grew up in New York City and have known each other since elementary school. Today, they are business partners in multiple ventures and have grown Earn Your Leisure to eight figures in revenue. It all started with a dream. Now these founders are taking Invest Fest to Europe, with plans to turn EYL and EYL University into publicly traded companies in the future.

I sat with MacDonald to discuss his journey as the third Founder of Earn Your Leisure. He shared the incredible odds he overcame to get to where he is today. “I grew up in the projects, on welfare, with a single mom and five siblings. I was in special education. I wasn’t supposed to make it,” MacDonald told BLACK ENTERPRISE.

MacDonald’s story is a testament to the belief that your start doesn’t have to determine how far you go in life. Here are my key takeaways from our conversation.

       Photo Credit: North 13th and Create

Overnight success takes 10 years

For many people, Earn Your Leisure blew up out of nowhere. But, for years, Bilal and Millings were in classrooms teaching the youth about financial literacy. MacDonald, the brain behind the visuals and EYL’s early content strategy, had been practicing his craft for years.

“I started making flyers for promoters in my neighborhood, getting $50 a flyer at 14 years old. I was doing graphic design throughout high school.

One of my friends and mentor taught me photography, and I was a photographer for ten years. Before Earn Your Leisure. I worked with DJs, influencers, and models to help them get off the ground and build their brands,” MacDonald said.

The three friends found success with Earn Your Leisure, but it wasn’t the first business they started together. “We started investing in real estate in 2008, but that didn’t work out. We tried a cloud business for DJs. We had a couple of small businesses.”

Years later, the trio started EYL without investing much money upfront. “We started the podcast with no money. We just invested our time.”

Photo Credit: North 13 and Create

Have a Clear Vision, Build the Right Team, and Get To Work

According to MacDonald, in 2017, when Bilal had around 300 followers, he shared his desire to build a financial literacy brand on social media. “He told me he wanted to build his Instagram to be the biggest financial literacy platform on the internet. I said, let’s do it and plugged him into different tools, doing photoshoots and videography work with him and building content. He started posting financial clips, and it was catching attention.”

When Bilal reached 40,000 followers on Instagram, people kept telling him to start a podcast.

“When Rashad (Bilal) asked me about it. I told him it was a good opportunity and how we could monetize it. So, we set up the podcast, and he was looking for a co-host. He thought, who better than Troy (Milling)? He talked to Troy every day. It made sense, and Troy was down with it.”

So MacDonald created the LLC, set up the podcast, the YouTube, and the trio got to work. In less than four months, the podcast had 5,000 listeners.

                                                                     Photo Credit:Jaylon “Quality” Cooper

Invest in Your Vision and Let Everyone Play Their Role

In the early days, MacDonald said, everyone had to sacrifice time and resources to make the vision happen. “I knew I was losing money on some other clients because I was dedicated so much time to Earn Your Leisure. But, I believed it wasn’t just about Rashad, Troy, or Michael, but that what we were doing would change the world, and financially our lives would change too.”

After the podcast’s success, MacDonald thought about launching Earn Your Leisure University and selling EYL merchandise. For the first 18 months, they didn’t take a dollar out of the company. Instead, they put all the money they earned back into the business.

They started selling EYL merchandise and built the ecosystem for EYL University. EYL University got to 4,000 members in less than a year.

Bilal, Millings, and MacDonald partnered with MG The Mortgage Guy on EYL University, and he handled everything real estate on the platform to further expand the EYL organization. Eventually, they started hiring people to help expand the company. Today, Earn Your Leisure employs 15 people. MacDonald shared that Earn Your Leisure went from earning $100,000 in its first year in business to Earn Your Leisure and EYL University being on track to hit eight figures in 2022, excluding Invest Fest, which is a monster in itself.

It is clear that the co-founders understand and respect each others’ roles on the EYL Team. “You need the talent. But you also need the systems and the machine behind the talent. Everybody has a role to play,” MacDonald said.


Be Consistent

MacDonald recalled the challenges, especially the first 18 months, when they were pouring all their time and energy but were not receiving any income from EYL. They had to remain consistent, regardless. Building a business empire like Earn Your Leisure requires consistency and sacrifice. MacDonald remembers wanting to go out on Friday night or to watch football on Sunday, but not being able to do those things for a long period. Instead, along with Millings and Bilal, he dedicated that time to Earn Your Leisure and turning their vision into reality.

“You can’t give up on your dream. It’s going to be ups and downs. There were times when I didn’t think I could do it anymore. But I kept going because I knew it would be bigger than anything we had ever done.”

Anne-Lyse Wealth is a certified public accountant, a financial literacy advocate, and a communications strategist for business leaders.

She is the founder of The ALW Communications Agency, which helps leaders amplify their brand through storytelling and PR, and the Plutus Awards-nominated, a platform dedicated to inspiring millennials to build wealth with purpose.

Anne-Lyse is a freelance writer for Fortune Magazine, Business Insider, and Harvard Business Review Ascend, among other publications. She is the author of Dream of Legacy, Raising Strong and Financially Secure Black Kids, and the host of The Dreamers Podcast.