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CEO Dinner Insights

An intimate forum for friends of the CEO Dinner to exchange entrepreneurial experiences and discuss technology trends.

ceodinner.substack.comSource feed ↗15 episodes

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CEO Dinner Insights July 2026: Cognoscere et Cognosci

To know and be known: why knowing about someone isn’t knowing them — and why the real risk is “not that AI knows me, but that it becomes me.”

CEO Dinner Insights June 2026: The View From Your Window

A roomful of windows onto one world -- and not a single pessimist in the room.

CEO Dinner Insights May 2026: Please refrain from mentioning our future overlords

Third spaces, things that used to be better, and what we improved until we ruined it.

CEO Dinner Insights: April 2026: The Ghost in the Shopping Cart -- On Agent Adoption, Echo Chambers, and the Last Mile of Human Choice

When agents will handle our purchases -- and why we can’t agree.

CEO Dinner Insights: March 2026: Banging Rocks -- On Chip Concentration, Foot-Dragging Institutions, and the Last Things Humans Do Best

What could slow AI -- and what it still can't replace

The White Space Around AI: Where Human Value Lives

First mile intention and last mile perfection

CEO Dinner Insights: February 2026 - SaaS-mageddon: Mirage or Metamorphosis?

How AI Is Repricing Software, Expanding Its Addressable Market Into Payroll, and Shifting Moats From Interfaces to Institutions

Why IQ and EQ Aren't Enough Anymore. The Age of AI Demands AQ.

Intelligence and social savvy are necessary but not sufficient. What separates those who ship from those who stall is having high agency (AQ).

CEO Dinner Insights: January 2026

What Tech Leaders Are Really Thinking About The Year of AI Backlash, The Phases of AI Transformation and The Skills That Matter to Entrepreneurs

CEO Dinner Insights: December 2025

Claude, Gemini and ChatGPT Grade Last Year’s Predictions and Place Odds on 2026

CEO Dinner Insights: November 2025

What 18 Tech Leaders Are Really Thinking About Who They Are Long and Who They are Short.

The AI Wildfire Is Coming. It's Going to Be Very Painful and Incredibly Healthy.

AI won’t crash—it will burn. Like every tech cycle, the fire will clear the brush, redistribute talent, and leave infrastructure to power what comes next. The question is: what kind of plant are you?

CEO Dinner Insights: October 2025

What 12 Tech Leaders Are Really Thinking About Poly-Intelligence, The AI Investment Bubble, and Breaking Down Knowledge Silos

CEO Dinner Insights: September 2025

What 12 Tech Leaders Are Really Thinking About Board Governance, The AI Hype Cycle and Coming Shakeout.

CEO Dinner Insights: August 2025

What 15 Tech Leaders Are Really Thinking About AI, Leadership, and the Future