CAIO / COACH
23 essays publishedMonthly

Field
notes.

Frameworks, case studies, and hard-earned insights for leaders navigating the 50/50 era of human + AI work.

All essays

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023May 30, 2026

The Other 50% Just Got Bigger

The most automated companies are hiring more expert humans, not fewer. The five-step engine that turns cheap automation into more human work, and why the leader who sets the goals is the half that grows.

AI Leadership6 min read
022May 20, 2026

Everyone Is Selling Easy. I'm Selling Hard.

A private AI retreat for non-technical founders. Tracy shipped fairpay.website by Day 2. Maureen built a marketing agent team. James returned for a second retreat and is launching Janet.Care in 30 days. Real capability built by your hands.

AI Leadership5 min read
021May 3, 2026

Everybody Needs a Coach (Including Me)

Every leader you admire is being coached. Most of them by several people. Often for decades. Here is what coaching actually looks like, and what to do about the moments between.

AI Leadership6 min read
020May 2, 2026

How a Founder Built His Product in 5 Days Instead of 3 Months

James, the founder of Janet.Care, was quoted $300,000 AUD and three to six months for the next phase of his longevity platform. He flew to Vietnam instead. Five days later he was 70% done. He coded it himself.

AI Leadership6 min read
019Apr 18, 2026

You Don't Need to Become Technical You Need a Stack

You've been nodding in meetings about AI, code, and MVPs for years. You're not going to learn Python this quarter. You don't need to. You need a stack.

AI Leadership5 min read
018Apr 12, 2026

How I Built a Content Studio With Claude Code in One Conversation

I built a multi-brand content production system using Claude Code in a single session. The three-layer framework of context, instructions, and workflow that makes AI content actually sound like you.

Claude Code5 min read
017Apr 7, 2026

FAST Goals: How to Build a Goal System That Doesn't Fade

FAST goals keep OKRs alive. Frequently discussed, Ambitious, Specific, Transparent: the MIT Sloan framework that makes team goals drive behavior past week three.

AI Leadership6 min read
016Apr 3, 2026

Your Team Needs This Skill

Leadership used to be 100% people. Now half of your team is AI. Two skills unlock the other 50%: ABC (Always Be Cataloguing) and AI workflow design for business.

AI Leadership5 min read
015Apr 2, 2026

I Raised $9.5M and Still Couldn't Read My Own Codebase Then AI Happened

TINYpulse raised $9.5M with top investors. The founder still couldn't read the codebase. Here's what changed when AI collapsed the wall between founders and engineering.

AI Leadership5 min read
014Apr 1, 2026

The CMS Is Dead AI Killed It

AI replaced the CMS. Here is the 4-step system non-technical founders use to control their content and ship like engineers. No code required.

Claude Code5 min read
013Mar 30, 2026

Using AI Was 2025 Leading AI Is 2026

The 50/50 Era is here: teams now manage 50% people, 50% AI. Leaders who lead AI--not just use it--will define the next generation of leadership.

AI Leadership5 min read
012Mar 30, 2026

The Hotel AI Personalization Gap

Hotels collect guest data but fail to activate it. The AI Personalization Flywheel explains how hotel AI personalization creates real competitive advantage through data-driven experiences.

AI Leadership4 min read
011Mar 30, 2026

18 Entrepreneurial Learnings from a Founder Who Built in the World's Toughest Markets

Paul Chu spent 26 years building businesses across six countries. One slide, 18 entrepreneurial learnings, and what each one means for leading in the AI era.

AI Leadership7 min read
010Mar 19, 2026

The Four Offices of the Future: Why Your Org Chart Is the Reason AI Isn't Working

95% of companies see no ROI from AI. Not because the technology doesn't work. The Four Offices framework diagnoses where AI should create value and why it currently isn't.

AI Leadership8 min read
009Mar 13, 2026

How to Build a Talent System That Actually Scales

A step-by-step framework for building AI-ready talent systems that scale from hiring to retention. Structured interviewing, culture design, and AI tools that work.

AI Leadership7 min read
008Mar 10, 2026

Iteration Is the Secret Weapon of AI Power Users

85.7% of high-fluency AI users iterate on outputs. Anthropic's research reveals iteration as the primary difference between marginal and exponential AI value.

AI Leadership6 min read
007Feb 27, 2026

Jack Dorsey Layoffs: What 4,000 Cuts Reveal About AI and SaaS

Block cut 40% of its workforce while profitable. Stock jumped 20%. What Jack Dorsey understands about AI disruption that other CEOs are missing about SaaS and workforce strategy.

AI Leadership8 min read
006Feb 4, 2026

8 Marketing Trends for 2026 That Actually Matter

Eight marketing trends reshaping how organizations reach and convert customers in 2026. From vibe marketing and digital twins to answer engines and collapsed funnels.

AI Leadership10 min read
005Jan 29, 2026

The Leadership Brand You Already Have

Your leadership brand is not what you aspire to be. It is what your team predicts about you under pressure. Learn how to discover, own, and build guardrails around it.

AI Leadership7 min read
004Jan 20, 2026

Custom GPTs: How to Build Role-Based AI Assistants

Step-by-step guide to building purpose-built AI assistants with Custom GPTs. Create cognitive infrastructure that scales consistency across your team without engineering.

Claude Code8 min read
003Jan 13, 2026

7 AI Dictation Tools That Actually Work in 2026

Professional AI dictation tools compared: Wispr Flow, Monologue, Superwhisper, and more. Seven reliable speech-to-text tools for technical professional work in 2026.

Claude Code10 min read
002Jan 6, 2026

Google AI Studio and the Hidden Ecosystem

Discover Google's AI Studio ecosystem: NotebookLM, Gemini Gems, Nano Banana, Imagen 3, Whisk, and Opal. Six tools reshaping how AI Officers work and manage complexity.

Claude Code9 min read
001Dec 31, 2025

Interactive AI Avatars for Business

Scale your expertise with interactive AI avatars. Build conversational AI that handles customer support, onboarding, sales, and operations around the clock.

Claude Code11 min read
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