In this episode, Jay Hill sits down with Chris Simon, a Baltimore-born entrepreneur and operator, to talk about what most motivated people never get taught: the rules of the game.

This isn’t about hype.

It’s not about quick money or shortcuts.

It’s about structure, exposure, relationships, and learning how to think like an owner — especially when you come from environments where hustle is praised but systems are never explained.

Chris breaks down how he went from creative hustles to building real businesses by learning:

how money actually flows

how to separate hustle from structure

how to build institutions instead of just personal brands

how to navigate grief, family, and responsibility while still growing

how exposure, relationships, and discipline changed his trajectory

This episode speaks directly to men who:

already believe in entrepreneurship

feel mentally cluttered or directionless

are tired of restarting every few years

come from inner-city environments like Baltimore, Atlanta, Houston, or NYC

want to build something that lasts

This is a reset conversation.

Advertising Inquiries: https://redcircle.com/brands

Privacy & Opt-Out: https://redcircle.com/privacy