Troy Millings and Rashad Bilal of Earn Your Leisure, Indya Davis, manager lead of multicultural marketing at Ally Financial, music executive and entrepreneur Dilla, and Grammy Award-winning poet J. Ivy judged the Earn Your Masters Pitch Competition in Chicago (Photo Credit: Ruler Images Media).
Financial literacy is a cornerstone of personal and professional success.
It empowers individuals to make informed decisions about budgeting, saving, investing and managing debt. Earlier this month, City Hall Restaurant, United Masters, Earn Your Leisure, and Ally Financial hosted the “Earn Your Masters” Pitch competition.
The Earn Your Masters pitch competition featured finalists who submitted online pitches. The selected finalists presented their business plans to the judges, and a winner was chosen to advance to the next stage later in the year. This final round primarily included businesses that are already up and running.
The audience heard detailed business plans, and entrepreneurs discussed their successes and areas for improvement. They also received real-time feedback from the judges. It was akin to a “Shark Tank” experience with added networking opportunities for participants and audience members.
Panel Discussion: Turning Creative Passion into Financial Success
Jason Weaver and J. Ivy at the Earn Your Masters Pitch Competition in Chicago (Photo Credit: Ruler Images Media).
The first session, “Creative Capital: Turning Creative Passion into Financial Success,” featured a distinguished panel that included media personality Kendra G, Chaucer Barnes (Chief Marketing Officer for United Masters), Traci Tolmaire (Head of Artist Operations at United Masters), and Chicago’s very own actor, entertainer, and singer Jason Weaver.
The panelists discussed their journeys to success, sharing insights on transforming their creative passions into financial success and maintaining it. They emphasized the importance of mindset, spirituality and surrounding oneself with the right people for effective networking.
After the panel discussion and a brief intermission, Kendra G invited audience members to promote their businesses and showcase their talents. This was followed by the pitch competition, judged by Troy Millings and Rashad Bilal of Earn Your Leisure; Indya Davis, manager lead, multicultural marketing at Ally Financial; Dilla, a music executive and entrepreneur and J. Ivy, a Grammy Award-winning poet.
Highlighting Chicago’s Entrepreneurial Spirit
Jeffrey Safo Darko of Mixplug won the competition (Photo Credit: Ruler Images Media).
Four Chicago entrepreneurs got to pitch their businesses to become finalists for the final competition in Florida, where they could win $50,000 for their business.
Robert Hatcher of Aurgin was the runner-up in the competition, while Jeffrey Safo Darko of Mixplug was the winner.
Judges’ Insights and Commitments
Davis expressed her profound honor and thrill at being a judge for the pitch competition.
“It’s always a privilege to support entrepreneurs by giving them a platform, resources, feedback, tools and opportunities to showcase their business ideas,” Davis said.
“I’m eager to hear all the innovative concepts emerging from such a vibrant market. Chicago is brimming with creators and entrepreneurs, and I can’t wait to see what they bring to the table.”
Davis also expressed that working with Bilal and Millings has been phenomenal. Their partnership (Ally and Earn Your Leisure) started three years ago, bridging the gap between culture and finance and providing financial education to our community.
Her goal in addressing diversity, equity and inclusion in marketing is to provide opportunities and representation. Ally excels in this area, ensuring that DEI is integral to our marketing strategies.
“We pride ourselves on our culture and employee resource groups that connect with diverse cultures,” she added.
The Journey of Earn Your Leisure
Rashad Bilal and Troy Millings of Earn Your Leisure (Photo Credit: Ruler Images Media).
Earn Your Leisure was rooted in education. Initially, Millings was a teacher, and Bilal was a financial advisor, and they both were dedicated to educating young adults about the importance of financial literacy.
The concept behind “Earn Your Leisure” began with a focus on financial education. Both noticed a widespread need for financial literacy across various demographics and recognized that financial education was necessary not just for young adults but also for people from all professions and backgrounds.
“This insight inspired us to create a social media campaign aimed at becoming a financial advisor to celebrities. We quickly saw the potential for something bigger,” said Millings.
“We used the hashtag #EarnYourLeisure to boost the campaign, and people began to assume it was the title of a show. This sparked the idea of creating a podcast. After deliberation, we used the hashtag as the show’s name.”
The podcast started with them exploring the backstories of sports, business and entertainment, but it quickly evolved into something more significant.
“However, we realized that we had an opportunity to shine a light on individuals from diverse careers, giving them the recognition they deserved. This shift in focus allowed us to provide value to a broader audience and became the foundation of our entrepreneurial journey.”
Upcoming Invest Fest 2024
“Invest Fest,” scheduled for later this month (Aug. 23-25), is set to be a landmark event where commerce and culture converge to empower our community. This event focuses on entrepreneurship, business and networking.
This year, Millings said that Earn Your Leisure is “introducing impactful opportunities, such as a $100,000 grant in collaboration with Microsoft and the Marathon Foundation and a $25,000 grant for a woman-owned health and wellness business led by Lauren London and partner HealthyMD.”
Invest Fest goes beyond mere entertainment; it offers education, networking, and honest business opportunities. The marketplace will showcase local businesses, providing exposure and potential investment opportunities.
“This year’s Invest Fest will provide significant grants and offer a marketplace where local businesses can showcase their products and services. We aim to foster a microcosm of investment and growth, reminiscent of the Black Wall Street era,” Millings said.
Essential Financial Advice
Bilal also emphasized the importance of foundational financial habits for those looking to enhance their financial literacy, especially in Chicago.
He calls for people to live below their means, develop disciplined financial habits, avoid unnecessary debt and focus on living within their means.
Bilal also recommends that people invest regularly to build a habit of investing, whether in stocks or other assets, which is essential for long-term financial growth and to have entrepreneurial insights when starting a business. They advise potential investors to consider industries with scalability and low overhead, choosing a venture they are passionate about that serves a clear need.
Millings added, “Educate yourself through various resources, whether podcasts, articles or mentorship. Be open to learning from anyone with valuable information, regardless of age or background. Building a strong educational foundation will help you apply your knowledge effectively and make informed decisions.”
Expanding Financial Education
Audience at the Earn Your Masters Pitch Competition (Photo Credit: Ruler Images Media).
In addition to Invest Fest, Bilal and Millings are rolling out a financial education curriculum, starting in New York City. They aim to expand this initiative to other cities, ensuring financial education is accessible nationwide.
There are no requirements for reaching out to Ally.
Davis also encourages everyone to connect with Ally on Instagram or explore its content hub, Conversationally, which offers educational articles on various money-related topics.
On behalf of the duo, Millings also expressed that Chicago is a beautiful city with a rich history, stunning architecture and incredible views. He and Bilal have enjoyed exploring the diverse cuisine and connecting with its genuine, down-to-earth people.
“Chicago’s entrepreneurial spirit and cultural vibrancy make it a special place for us,” Millings said.
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