The dynamic duo behind Earn Your Leisure have built a financial movement for the culture, proving education is the ultimate asset.
Troy Millings, a former educator, and Rashad Bilal, a financial advisor and entrepreneur, are the co-founders of Earn Your Leisure (EYL), a groundbreaking media company. Their journey began with a shared passion for empowering their community with financial literacy, a topic often overlooked in traditional education. Through EYL, they have created a platform that demystifies complex financial concepts and makes them accessible to everyone. By blending business acumen with pop culture, they have cultivated a loyal following and built an empire that includes a top-ranked podcast, live events, and an online educational community.
Invest Fest: The Pinnacle of Business Conferences
Q: Tell us about the early days of Invest Fest and how it’s grown. A: Invest Fest is the pinnacle of business conferences, not just in America but in the world. The idea came to us in 2021 when we realized nobody had successfully blended festivals with business. We wanted to merge culture and commerce, speaking a language nobody else was. We had already built our community, so the demand for an in-person event was there. The goal was to combine entertainment with learning, bringing topics like cryptocurrency, real estate, and entrepreneurship to the main stage. We also created a marketplace that now highlights over 400 businesses, giving new entrepreneurs an opportunity to showcase their products. Invest Fest has grown into a three-day event drawing over 40,000 to 50,000 people. It’s a place where like-minded individuals can come together, network, and be inspired by their favorite celebrities and business leaders.
Q: What was the moment you both realized Earn Your Leisure was more than just a podcast? A: Troy: Early on, when we started in 2019, people were already gravitating toward the financial education content we were creating. They forced us into the media space by demanding a podcast where they could get more information. We saw that guys like us weren’t talking about finance. When we looked at our analytics and saw listeners in South Africa, Kuwait, and Tokyo, we knew this was a global message. We realized finances and business education are a universal language, but the education around it isn’t. We found that weak spot and built a place to create, which led to networking events, Invest Fest, a New York Times bestseller, and even a curriculum.
A: Rashad: For me, it was our first networking event in Los Angeles. We were coming from New York, and to have a hundred people show up in less than 24 hours was incredible. That’s when I knew this was something special that would grow beyond what we could imagine.
Troy and Rashad: A Perfectly Balanced Yin and Yang
Q: How has your childhood friendship and individual career paths shaped your dynamic as co-founders? A: Troy: It’s fascinating how our paths in life led to this. My background is in education, and Rashad’s has always been in finance and entrepreneurship. As best friends since middle school, I know his strengths and weaknesses, and he knows mine. People often see us as the perfect yin and yang. I’m more outgoing, and he’s more reserved in public. We know where one of us is weak, the other has to be strong. The level of trust and respect we have for each other goes beyond business, but it’s essential for our success. We also have a third partner, Mike, who we grew up with. Having that loyalty and trust from a lifelong brotherhood is crucial for building a global brand.
A: Rashad: Everything Troy said is true, especially the ability to communicate without speaking. You can’t replicate that. We just always understand there’s more work to do, and we can never be complacent. That mindset is what helps the mission and the partnership.
The Deeper Meaning of Earn Your Leisure
Q: Earn Your Leisure has a deeper meaning. What does that represent to you? A: Troy: It started as a hashtag in the early 2010s. We grew up in New York, but not in the city, and people often assumed we had it easy. They never saw the hard work—Rashad studying for his Series 7, me working three jobs to pay for college. They only saw the vacations and the nice cars. The name came from the idea that everything we had was earned. It was a message that if people realized they had to work for everything they received, it would change their lives. Now, it means something different to everyone, but the core message remains the same: you have to earn your freedoms, your luxuries, and your time.
A: Rashad: It’s about not skipping steps. On social media, people see the highlights—the vacations, the houses, the cars—and they want to jump to the end result without doing the work. The most important part is earning your luck and understanding that you have to earn your leisure.
Conversations That Left a Lasting Mark
Q: What conversations at Invest Fest left the deepest mark on you personally? A: Troy: Tyler Perry’s conversation was very timely for me. He talked about the evolution of success and how, as you climb the mountain, you must be mindful of who you bring with you. He said you can do a disservice to others by bringing them to a place where they’re not meant to be, where the air is thin. That advice resonated deeply, and it made me rethink how we approach bringing others into our mission.
A: Rashad: For me, it was Robert F. Smith. I had studied him for years and even wrote about him before Earn Your Leisure existed. To have him give us personal advice was memorable. He told us to always think about scaling—if you have 10,000 people, how do you scale to 20,000 without doing more work? He’s all about having systems and a mindset built on scaling efficiently.
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