I’m Charles Holmes IV. Operator first. Strategist second.
Chicago-based. MBA. Years in marketing, operations, and applied AI — both inside companies and in businesses I’ve built myself. I work with founders who want systems that hold up after the engagement ends.
My story.
I’m based in Chicago. I have an MBA. I’ve spent years working in digital marketing, business operations, and AI implementation, both inside companies and in businesses I’ve built myself.
I didn’t get into AI consulting because it was trending. I got into it because I watched too many businesses leave real money on the table doing things manually that could be automated in a week.
My background covers a lot of ground. Performance marketing, operational systems, federal contracting compliance, and applied AI. What connects all of it is simple: building processes that work without requiring constant attention.
Why work with me.
I’ve been in the room.
I’ve been in the rooms where these decisions get made. I know what questions to ask and what answers actually matter for your bottom line.
I build systems, not tools.
I don’t sell you a tool. I build you a system that fits how your business actually operates, and that keeps working after the engagement ends.
I’m invested in the result.
I communicate like a normal person, not a consultant. And I’m invested in the result, not just the engagement. If it’s not working, I want to know.
What I’m building.
Di-Hy Digital
My AI implementation firm. We work directly with small and mid-size businesses to build and deploy AI systems tailored to how they actually operate.
Lunula Supply
A minority-owned government contracting firm with an active DFAS contract and real experience navigating federal procurement requirements.