AI is already inside your organization. Frequently without policy, oversight, or approval.

Red Boot LLC helps mid-market leaders build AI governance frameworks before shadow AI becomes a board-level crisis.

THE PROBLEM

The risk is already inside your walls.

Employees are using AI tools — ChatGPT, Copilot, Gemini — to make decisions, draft communications, analyze data, and interact with customers. Most executives don’t know the extent of it. Most organizations have no policy governing it.

Data exposure. Compliance liability. Decision accountability. These aren’t future risks. They’re happening right now in companies exactly like yours.

The organizations that get ahead of this will lead. The ones that don’t will manage incidents.

Services

AI Governance Diagnostic

A focused assessment of where AI is being used across your organization, what risks exist, and what governance infrastructure you need. Delivered in 2–3 weeks as a clear, actionable brief.

Implementation Blueprint

A custom AI governance roadmap built for your organization — policies, oversight structures, accountability frameworks, and a phased rollout plan your team can execute without external dependency.

Ongoing Advisory & Program Management

Fractional AI governance leadership on a retainer basis. Red Boot stays engaged as your AI footprint grows and regulations evolve — keeping your framework current, your leadership informed, and your risk managed.

Built by a practitioner. Not a theorist.

Jonathan Mickles founded Red Boot LLC with one conviction: AI governance isn’t a technology problem — it’s a leadership and accountability problem.

With over 20 years of experience in program management, GRC, and technology delivery across government and commercial sectors, Jonathan brings the frameworks, the credentials, and the real-world judgment that mid-market organizations need right now.

M.S. Computer Science, NC A&T State University · PMP · CSM · CSPO

Author: AI Adoption Is a Governance Problem: A Field Manual for Organizational Leaders

Jonathan Mickles

Your AI Governance Journey Starts Here

Most mid-market organizations are already using AI — without policy, oversight, or executive accountability. The question isn’t whether you have an AI governance problem. It’s whether you know it yet.

AI Adoption Is a Governance Problem: A Field Manual for Organizational Leaders gives you the frameworks, tools, and decision-making language to get ahead of the risk before it becomes a crisis.

What People Are Saying

I've worked with Jonathan in the past, as we shadow-partnered on some work together. The combination of his creativity and his connections allowed some opportunities to successfully manifest, which I don't believe would have otherwise. It was a pleasure to work with him, and I'd do so again.

Claude Labbe

Realtor and Investor

Jonathan asked me better and more detailed questions than most of the podcasts I’ve been interviewed on. He brought the conversation to very important topics. He doesn’t just interview in a way where you’ve heard the answers before. Fantastic show!

Adrian Smude

Podcast Guest / Mobile Home Investor

Jonathan created a software program for our logistics company 20 years ago. This software is the platform for the daily operations and is integral to our operation. He was easy to work with and very receptive to suggestions. I would hire him again with no hesitation.

Karl Robinson

R and R Tranportation, Founder

Sovereign Systems Podcast

The Sovereign Systems Podcast explores how leaders design systems that produce durable outcomes — in business, technology, and personal sovereignty.

Hosted by Jonathan Mickles, the show examines the intersection of:

• AI governance
• operational systems design
• strategic investing
• decision-making under uncertainty

Earlier episodes explored strategic multifamily investing and capital deployment. The current direction expands that conversation toward systems that produce lasting leverage — financially, operationally, and organizationally.