American · ASEAN · Global Markets

Building businesses
that run themselves.

I’m Kenn Crook. I build AI-orchestrated ventures across software, music merch, and the post-labor economy.

Who I Am

30+ years of enterprise tech.
Builder-level execution.

I’m a senior IT and security architect who combines Fortune 100 consulting experience, enterprise leadership, software development, AI workflow engineering, and real-world operational execution. I don’t just advise — I build, secure, automate, optimize, and deploy.

Background
  • 20 years · Indiana University, Kelley School of Business
    Associate Director of IT · Chief Security Officer · Enterprise Cloud Administrator
  • 9 years · PwC
    Global Application Security Architect — designed and led enterprise application security architecture initiatives and developer security education programs used across global teams
Today

AI integration, autonomous workflows, infrastructure automation, cloud systems, cybersecurity strategy, and modern application ecosystems.

Hands-on with the same emerging AI tooling I architect: orchestration systems, autonomous agent frameworks, multi-agent workflows, advanced prompt architectures, media automation pipelines, and intelligent business systems running in production.

I bridge the gap between
Enterprise architecture & rapid AI-era innovation
Security & usability
Strategy & execution
Legacy infra & cloud-native
Human workflows & intelligent automation
Expertise
• AI system architecture & orchestration
• Multi-agent AI workflows & autonomous systems
• LLM integration & prompt/system architecture
• Application security architecture
• Cloud infrastructure & automation
• DevSecOps & secure SDLC implementation
• Security reviews & threat analysis
• VPS/server deployment & optimization
• Linux infrastructure & self-hosted AI tooling
• Python development & automation
• API integration & workflow engineering
• Enterprise IT strategy & modernization
• Identity, access, & security governance
• Technical product strategy
• Systems integration & operational scaling
• AI-assisted content & media pipelines
• Automation-first business infrastructure
I’m strong at
  • • Rapidly understanding complex systems
  • • Identifying hidden operational or security risks
  • • Designing scalable architectures
  • • Translating business goals into technical execution
  • • Building practical AI-enabled workflows that actually work in production
I value
• Accuracy
• Clear communication
• Real-world practicality
• Security-first design
• Long-term maintainability
• Fast iteration without reckless shortcuts

Whether you need a security architect, AI systems consultant, infrastructure strategist, automation engineer, technical advisor, DevSecOps specialist, solution architect — or someone who can connect all of those together coherently — I bring enterprise-level thinking with builder-level execution.

If your project involves AI, automation, security, cloud systems, scalable architecture, or integrating complex technologies into something usable and resilient — I can help.

Start a conversation →
About the Stack

A solo operator with an
AI-native team.

I run a portfolio of small ventures that would normally need a 20-person company. Instead I have Kenn’s Angels — three AI collaborators — wired into my real infrastructure (SQLite agent bus, memory graph, MCP servers): Chloe (Claude Opus 4.7 via Cowork mode + Claude Code), Ava (OpenAI Codex), and Heather (Google Gemini).

What ships out of this setup: a LINE translation bot serving real users, the merch store and storefront for the band I Moan Style (the Angels run the store — the music itself is mine, written and produced by a human), and the studio I run for clients at Angel IT Studio.

The thread connecting all of it: figuring out how a single human plus an AI team can outproduce a small company, ethically, with margin, and without burning out.

Currently Shipping

Projects in production

Live ventures, not pitch decks. Each one is generating data, paying its own bills, or close to it.

Merch Store (AI-run)

I Moan Style — Merch

The Angels run the merch operation: 14 album-art designs across 48 live products on Shopify, fulfilled by Printify, with image pipelines, mockup generation, and shop-page regeneration fully automated. The music itself is human-written and human-produced.

Shopify Printify Higgsfield
Services · Studio

Angel IT Studio

A US-based studio that ships fast: AI workflow automation, LINE bot launches, spreadsheet dashboards, and checkout path wiring. American, ASEAN, global markets.

LINE Stripe Workflow Automation
SaaS · LINE Bot

Translate 4 Me

Real-time chat translation for LINE groups. Free tier on a self-hosted NLLB-200 model, premium on Google Cloud Translation. 130+ languages on the Pro tier.

Node.js NLLB-200 LINE Messaging API
iOS App

Universal Anomaly Photographer

Swift 6 / SwiftUI iOS app for anomaly detection and motion-triggered photography. Advanced camera controls, frame-by-frame review, time-lapse capture.

Swift 6 SwiftUI CoreMotion
Tracker · Etsy

Retire Abroad Tracker

Excel + Google Sheets master template for tracking the path to retirement abroad. Multi-currency, country comparisons, sold via Etsy & PB4U Shopify storefront.

Excel Etsy Multi-currency
AI Infrastructure

Kenn’s Angels Stack

SQLite-backed agent bus, MemPalace knowledge graph, MCP servers, and three AI collaborators: Chloe (Claude Opus 4.7 via Cowork + Code), Ava (OpenAI Codex), and Heather (Google Gemini). The plumbing that makes the rest of the portfolio possible.

SQLite MCP MemPalace
Ventures & Brands

The full portfolio

Angel IT Studio
angelitstudio.com
I Moan Style
imoanstyle.com
GitHub
github.com/kenncrook
Bone Chilling Bites
YouTube
How it’s built

The everyday stack

Claude Opus 4.7 (Cowork + Code)
OpenAI Codex
Google Gemini
MCP Servers
React / Tailwind
Node / Python / Swift
Shopify · Printify · Stripe
Hostinger VPS · Cloudflare
Get in touch

Have a project?
Let’s build it.

Best path for client work is the studio. For everything else — collaboration, partnerships, just-saying-hi — the address below.

hello@kenn.ai Hire the studio →