Why Working Hard Will Keep You Poor - Earn Your Leisure + Larry Morrow + David Shands

What happens when four of the most influential forces in entrepreneurship, media, and culture sit down for a raw, unfiltered conversation at one of the country’s most disruptive Black-owned bookstore? You get a conversation that flips the script on success, reveals the ugly truths behind wealth-building, and shows you how to break generational curses in real-time. In this explosive dialogue moderated by David Shands at Baldwin & Co., Earn Your Leisure co-founders Troy Millings and Rashad Bilal sit alongside hospitality mogul Larry Morrow to break down how they went from kitchen tables and iPhones to multi-million-dollar brands—and why belief in self had to come before the checks ever did. They talk imposter syndrome, the lies we tell ourselves about “failure,” and how cultural capital can become financial power if you’re willing to bet on your own genius. If you've ever doubted your purpose or felt like you're building alone—this conversation will make you feel seen, charged up, and ready to pivot like a boss.

Larry Morrow is a New Orleans–based hospitality mogul, entrepreneur, and community builder known for creating some of the city’s most successful restaurants and nightlife experiences.

Rashad Bilal is the co-founder of Earn Your Leisure and a financial educator whose work breaks down wealth-building for everyday people.

Troy Millings is the co-founder of Earn Your Leisure and a former educator turned media entrepreneur dedicated to making financial literacy accessible and culturally relevant.

David Shands is an entrepreneur, author, and host of the Social Proof Podcast, known for spotlighting real stories of business success and practical lessons from top creators and founders.

This episode is part of the ongoing conversations hosted by Baldwin & Co., a Black-owned bookstore, café, and cultural institution based in New Orleans. Baldwin & Co. exists at the intersection of literature, ideas, and community—creating space for rigorous dialogue, storytelling, and intellectual exchange.

Through author talks, podcasts, live events, and community programming, Baldwin & Co. amplifies voices shaping how we understand culture, history, politics, faith, and the future.

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Website: www.baldwinandcobooks.com

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