Your friendly AI helpdesk.

Think: vintage tech guy who actually listens. Bring the messy context; get calm, diagram-ready answers in return.

Across the OverKill Hill P³™ (the R&D studio behind AskJamie) stack, Jamie is your “phone a friend” for decision trees, tradeoffs, and “what should I do next?” moments.

Replatforming in progress

Custom GPTs were a valuable learning chapter. I am carrying that work forward into modular agent skills and tested plugin packages.

Read what is changing

Browse BrandGuard™ brand-voice protection case studies Explore the Lens System How AskJamie works Talk with Jamie
AskJamie™ avatar illustration

Fresh from the helpdesk build log

A quick pinboard for the newest drawers, diagrams and decisions Jamie is ready to show off.

From the GPT chapter

BFS: Framing Intelligent Futures 🔨🧠

A public-information BrandGuard™ case study (an AI brand-voice protection example) focused on Builders FirstSource. The original custom GPT prototype used public information about BFS, its market position, and its strategic priorities, demonstrating how AI-driven insights can align with a company’s unique vision and values. AskJamie™ architected the workflow and decision tree that guides users through the BrandGuard™ experience, ensuring clarity and confidence in every interaction.

Builders FirstSource BrandGuard™ GPT milestone illustration
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Inside the workshop

AskJamie Found-Ry

A place to turn useful thinking into an assistant specification, a decision guide, or a workflow you can revisit. Take a look at the private local workbench behind the next capability.

Explore the Found-Ry

Keep the helpdesk running

AskJamie™ is an independent R&D project — built in the open, one lens at a time. If this work has been useful, interesting, or made you think differently about AI, a Ko-fi contribution keeps the helpdesk running and the lenses coming.

Support on Ko-fi ☕

Where it fits

AskJamie™ is one of three sister sites in the OverKill Hill P³™ stack. Each one has a clear job; they don’t overlap, and they don’t pretend to be everything.

OverKill Hill P³™

The parent methodology — strategy, narrative architecture, and the long view across brands, careers, and ecosystems.

overkillhill.com →

Glee-fully Personalizable Tools™

The hands-on side: small, opinionated, interdependent tools for getting real work done — not a SaaS suite, a workshop.

glee-fully.tools →

AskJamie™ — you are here

The interpretive intelligence layer that sits above both: a warm, architected AI persona that translates between strategy and execution.

See the full universe →

What AskJamie™ is for

Not every question fits neatly in a form field. AskJamie™ exists for the “can we just think this through together?” kind of problems—where you need translation, not just information.

Explain it, don’t mystify it

Jamie breaks down concepts in plain language: diagrams when they help, analogies when they land, no jargon for its own sake.

Walkthroughs, not one-offs

Instead of dropping one answer and bailing, Jamie walks you through steps and branches: “If this is true, go here; if not, let’s pivot.”

Calm tone under pressure

Muted teals, paper grain, steady pacing—designed to make hard conversations navigable, not chaotic.

A note from Jamie

The ideas carry forward.

OpenAI is retiring custom GPTs. I am actively reworking the concepts, workflows, and solutions I built on that platform into modular agent skills and, after testing, plugin packages.

Custom GPTs were a valuable chapter in my learning. The next chapter builds on that work, with more room for useful methods to work together.

The GPT pages remain as case studies during the transition. A replacement is available only when its page provides a tested release and access instructions.

What is changing