The grind looks different now, but the rules haven’t changed. Jeremiah sits down with creative entrepreneur and Walmart pre-media manager Jeremy Bobo to map the path from burning 5,000 CDs by hand to building brands that travel on algorithms. Jeremy unpacks why face-to-face hustle still matters, how to handle rejection without losing momentum, and the exact moments to choose free value over fast monetization to grow your audience and revenue.

We start with Jeremy’s Little Rock roots and the soccer scholarship that opened his world, then move through a decade in music where he learned to create demand when the internet was more MySpace than For You Page. From there, Jeremy breaks down his three-part growth framework: sharpen the idea, lock the brand image, and aim with intent at the right demographic. He shares lessons from agency work on global kids’ brands like Hello Kitty and Paw Patrol, where consistent visuals and category cues drive sales, and he explains how to benchmark top competitors without becoming a copy.

The conversation gets practical fast: guerrilla marketing versus today’s virality, how subscriptions and free content can coexist, and why nonprofits often out-execute for-profit teams on marketing discipline. We talk team culture and incentives, the microagency model behind District 21, and why sourcing the right partners can 10x speed to market. Jeremy also dives into Walmart’s tech-forward shift and what it signals for retail, automation, and media in the next five years. Plus, a powerful reminder to evolve, using Jelly Roll’s reinvention as a blueprint for staying relevant while widening your impact.

If you’re a creator, founder, or marketer asking when to monetize, where to focus, and how to stand out without burning out, this conversation gives you a lean, repeatable playbook. Subscribe, share with a friend who needs the push, and tell us: which platform will you double down on this quarter?