More! Faster! Now! Forever?

The Relentless CEO in the Age of AI

This post has been sitting in my drafts for a while. Rather than perfect it, I’ll honor an earlier post and share as it is. Thanks for your grace and I would love to hear your thoughts.

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I keep noticing a pattern with some of the best performing CEOs I work with. The words people use to describe them are almost always the same: relentless, 24/7, hungry, unreasonable. They want more, faster, now.

They don’t operate with a traditional hierarchy. They live in the weeds, with a massive context window that takes in every detail about the business, the customer, the numbers. Speed is their killer feature. They accelerate at every single opportunity.

They make unreasonable asks of their teams, things that feel impossible in the moment but somehow get delivered. The people who thrive around them are stretched, pushed, and often transformed. Not everyone lasts forever, but the right ones show up for the right chapter.

I don’t think this is something they learned. It’s how they’ve always been wired. Founder mode is their default operating system, not something they switch on at work.

At the same time, we’re watching AI shrink, reorder, and accelerate the jobs of every part of their companies — developers, marketers, product managers, finance, sales, etc. Every part of the organization is being rewired.

Matan-Paul Shetrit

of Writer.com recently wrote about this shift in a piece on The Orchestration Graph. His argument is that execution is quickly becoming free, but supervision is expensive. The real job of the firm, and its leaders, is moving from doing the work to orchestrating how the work gets done across people, agents, and systems.

That makes me wonder if what used to look like micromanagement, this relentless appetite for detail, speed, and unreasonable asks, might actually be the right operating system for the AI era. A CEO with a near-infinite context window isn’t just driving their team, they’re supervising a hybrid network of humans and machines. Think of a product manager who used to need a team of five, now running a swarm of agents that prioritize bugs, draft specs, and run simulations. The leverage is huge, but the oversight is everything.

If execution is abundant, maybe the scarce resource is orchestration. And maybe these CEOs are showing us what that looks like. Or maybe it’s just a faster way to burn through people and systems.

Here’s where I say, “I’m not sure of the right answer yet, but it is something I’ve been thinking a lot about.”

What are your thoughts?

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