June 2024 → February 2026

From Executive Operator to AI-Native Strategist

Two years deep inside AI tools, automation, local models, and AI-assisted development. Not from the sidelines, by building, breaking, shipping, and comparing what works in real workflows.

10,000+
Hands-on AI Hours
7,260
Commits
across 28 repos
176k+
Lines Shipped
with AI assistance
70+
Tools Tested
6
Live Products
30K+ monthly users
Local LLMs
+ OpenClaw
in active use
Why this matters

Most AI advice comes from people who've either never operated a business or never built anything real with the tools.

I wanted both. I already knew sales, operations, enablement, incentives, customer experience, and executive strategy. The missing piece was understanding what AI could actually do when you push it hard.

This page is the receipts on that learning curve.

What I'm working on this month
How It Happened
Four phases. Twenty months. A lot of late nights.
Scroll horizontally to explore the journey
Phase 01

The Curious Beginner

June – August 2024

Understanding feasibility and breaking the "magic" barrier.

Commit Velocity ~5/week
First Questions
Asked Claude "Can you remember across chats?"
Started on a Windows machine with zero coding background. Struggled to differentiate between the Python shell and Command Prompt. Asked, "Can websites be coded in Python?"
First Automation
Birthday card pipeline with Make.com + GPT API
Built a birthday card automation pipeline using Handwrytten, Make.com, and GPT API. Early awareness of the tool ecosystem: "Could I use make.com for step 3?"
The Pivot to Code
No-code tools were limiting. Installed Python.
Realized no-code tools were limiting custom vision. Installed Wing Pro IDE and Python. First build: "Help me code a weather app with APIs." Learned that APIs are not magic, but structured contracts.
Python Make.com GPT API
Phase 02

The "Big Bang"

September 2024 – May 2025

Rapid experimentation. Learning by shipping. Breaking things.

Commit Velocity ~25/day (Oct)
6 Projects in One Month
todo-app, ZeroEffortAI, TheFinalsLoadout...
October 2024 explosion: todo-app (React practice), ZeroEffortAI (prompt library), TheFinalsLoadout (Vanilla JS), premium-response-generator, and Heritage Whisper V2 initialization.
763 Commits in October
~25 commits per day average
Heritage Whisper V2 initialization (Sept 30) followed by explosive development. State management bugs cascade lesson learned: "We went backwards. Now it's spinning the wrong direction."
The "Great Error Log"
18 errors in one terminal session
May 8, 2025: A massive multi-agent coding session (Claude + GPT pipeline) generated 18 recorded errors. Hit hard limits on context_length_exceeded and max_tokens. Learned to chunk tasks and "fail loud".
Next.js 14 React Supabase TypeScript Zustand
Phase 03

Architecting Heritage Whisper

August – October 2025

Production-grade architecture, security, and strategic constraint.

Commit Velocity ~10/day
Voice-First Strategy
"Seniors just talk, no typing"
Strategic pivot for elderly users. Prompt engineering breakthrough: "The long prompt is way worse than the short prompt." Zero-shot voice prompts outperformed elaborate instructions.
Security Architecture
Supabase Auth + RLS + WebAuthn
Implemented Row Level Security (RLS) to enforce tenant isolation. Added WebAuthn passkeys (TouchID/FaceID for seniors). Ethics decision: Rewrote public copy to avoid overpromising on compliance.
Stripe Integration
No "heroic wiring." Native integration.
Rejected manual API wiring in favor of Vercel's native Stripe integration. Forced webhooks to Node runtime (not Edge) because raw body verification failed in Edge environments.
Next.js 15 OpenAI Realtime WebAuthn Stripe Drizzle ORM
Phase 04

The AI-Native Operator

November 2025 – February 2026

Scale, SEO, advanced automation, and "AI Leader" operations.

Commit Velocity ~11/day
MCP Integration
Supabase + GitHub + Vercel MCPs
Connected Model Context Protocol servers for Supabase, GitHub, and Vercel. Discovered Claude Code's UI didn't support specific OAuth flows, requiring CLI configuration.
SEO Strategy Launch
4 content clusters defined
December 2025: Defined four SEO clusters (Memory Book, Legacy Book, Family Memory, Competitor Comparisons) to target high-intent traffic. Multi-tier personalization system designed.
PR Strategy & Soft Launch
Japanese American publications outreach
February 2026: Executed soft-launch messaging targeting Japanese American publications, leveraging the 442nd RCT family story. "Treat automation like production infrastructure."
Claude Code MCP Remotion React Native PDFShift
The Tuition

What it actually took to become AI-native.

No bootcamp, no CS degree, no playbook. 17 months of testing every frontier tool, burning through tokens, and building a local cluster to run it all.

10,000+
Hours
Hands-on AI work
70+
Tools Tested
17 months
$20K+
Tuition
Frontier subs & APIs
10B+
Tokens Burned
≈ 13M pages
Top Spend · 17 Months

Five tools over $2,000 each.

Where 17 months of frontier testing actually went.

ChatGPTOpenAI · Pro + API
$2,935
KlingAIVideo gen · Jan–May 2025
$2,689
GrokxAI · Active
$2,410
ClaudeAnthropic · Daily driver
$2,000+
CursorAI editor · Active
$2,000+
Breadth

Ten categories. One operator.

Most "AI users" live in one app. Real fluency means knowing when to reach for which tool, and which to leave behind.

Frontier LLMs
5
Claude · ChatGPT · Gemini · Grok · Perplexity
Local LLM
6
Qwen 3.5 397B · Qwen 3.6 35B · DeepSeek R1 · LM Studio · Ollama · Qwen 2.5
AI Coding
9
Claude Code · Cursor · Replit Agent · v0 · Factory AI · Copilot · Codex · Aider · Cline
Image Gen
7
Midjourney · DALL-E · Gemini · Flux · Stable Diffusion · Nano Banana · Promptchan
Video Gen
6
KlingAI · Runway · Sora · HeyGen · Beautiful.ai · Gamma
Voice / Audio
8
Wispr Flow · ElevenLabs · Auphonic · Suno · Whisper · AssemblyAI · Otter · Voicemod
Agent / Orchestration
4
OpenClaw · LiteLLM · Open WebUI · AnythingLLM
MCP / Search
6
Ref.Tools · Exa · SearXNG · Serper · Context7 · Brave
Build / Design
9
Google AI Studio · NotebookLM · Whimsical · Excalidraw+ · Mobbin · Canva · Aura · Lovable · Pompeli
Infrastructure
12
Vercel · Supabase · GitHub · Cloudflare · SendGrid · Adobe · Make.com · Resend · Notion · DocuSign · Wix · Firebase
Discernment

I keep what works. I drop what doesn't.

A 50/50 split between active and dropped tools isn't churn. It's how you learn what actually earns its place in a workflow.

Kept · Active Daily
35
ClaudePrimary thinking partner
ChatGPTPro + API
GeminiWorkspace + mobile
OpenClawCluster orchestrator
ElevenLabsVoice synthesis
Tried · Dropped
35
Otter.ai→ Whisper API
GammaQuick trial, didn't stick
HeyGenAvatar quality
Replit AgentHeavy use, then graduated
DeepSeek R1 671BBenchmarked, moved on

Volume isn't taste. The dropped column is where the taste lives.

The AI Rig

Four machines. One cluster.

$15K+ in hardware. Networked, orchestrated, running 24/7. Most AI users rent. This stack runs at home.

Online
Orchestrator
Mac Mini
Apple Silicon · Tailscale
Runs OpenClaw. Dispatches jobs across the cluster.
Online
Frontier LLM
Mac Studio
M3 Ultra · 512GB RAM
Runs Qwen 3.5 397B locally via LM Studio.
Online
Worker Node
Mac Studio
M4 Max · 64GB RAM
Second OpenClaw worker. Parallel agent execution.
Online
Image / Video
4090 PC
RTX 4090 · 24GB VRAM
Runs Stable Diffusion + a second local LLM.
Learning From the Best
The content creators who shaped my AI & vibe coding journey
Evolution of Thinking

The long prompt is way worse than the short prompt.

After testing Pearl AI. Complexity was hurting performance.

Pearl can not have any opinions. Is that clear in here?

Defining the AI as a "witness," not a therapist.

Let's stop the incremental patches. The system is fundamentally broken.

Recognizing architectural debt. The shift from "Help me make X" to systematic engineering.

If it runs 24/7, treat it like production infrastructure.

Feb 2026, while hardening OpenClaw automation.

The Journey Visualized

What I'm Building Now

Heritage Whisper is my current focus: a voice-first platform helping families preserve stories across generations.

If you have questions about this journey, want to share your own experience, or just want to connect, I'd love to hear from you.

See Heritage Whisper Connect on LinkedIn