About

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.

01 — Story
My background

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.

I’m not a vendor. I’m an operator who also happens to be really good at this.
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02The Quick Read
Education
MBA
Specialty
AI Strategy
Operations
2 Active Ventures
Based In
Chicago, IL
03How I Think

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.

04Ventures

What I’m building.

AI Implementation Active

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.

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Est. 2024 · Chicago, IL
Government Contracting Federal Contract

Lunula Supply

A minority-owned government contracting firm with an active DFAS contract and real experience navigating federal procurement requirements.

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Est. 2024 · CAGE 9GWP3
05Connect

Find me elsewhere.

06Let’s Talk

Let’s see if it’s a fit.

No pressure. 30 minutes. If it’s not the right time, I’ll tell you.

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