# I Almost Made an Anti-AI Guy the CTO of One of My Companies. Dodged a Bullet.

I run a group of companies. I co-founded them. I set the technical direction.

Last week, I was about to promote someone to CTO of one of them. Senior Director of Engineering first. Clear path to CTO. Equity. Full technical ownership.

Then he told me: “I don’t like the AI stuff. I want a real team.”

A real team.

In 2026.

The guy I was handing the keys to — doesn’t believe in AI.

That’s like appointing a head of transport in 1908 who says “I don’t trust cars. Get me more horses.”

Took me about 4 seconds to wish him well.

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Here’s why this is insane.

Across my companies, AI-native operations isn’t a nice-to-have. It’s the thesis. Small teams with AI agents outperforming traditional orgs 10 to 1. Multi-agent workflows handling bookkeeping, contract generation, client-facing bots, code shipping daily — all with AI deeply in the loop.

This isn’t experimental. This is how we operate. This is how we win.

This guy looked at all of it and said: nah, hire me 5 engineers.

Meanwhile — Anthropic, the company that literally BUILDS the AI, uses AI to write their own code. The smartest AI company on the planet doesn’t ship without AI in the loop.

But my almost-CTO thinks humans typing everything by hand is the move.

Brother.

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This is the split happening at the leadership level right now and it’s scarier than people realize.

It’s not junior devs resisting AI anymore. It’s senior leaders. Directors. CTO candidates. The people supposed to see around corners — staring directly at the wall.

**Camp A:** AI is the biggest leverage multiplier since the internet. Tiny teams. Massive output. Ship fast, iterate faster.

**Camp B:** “Real engineering” means big headcount, manual everything, building from scratch like it’s 2019. AI is a shortcut, not a superpower.

I was about to put a Camp B leader in charge of a Camp A company.

That’s not a disagreement on tools. That’s a disagreement on the future.

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**Alignment on vision beats talent every single day.**

If my CTO doesn’t believe in the core thesis — we’re dead on day one. Every architecture decision, every hire, every sprint becomes a fight over whether we should even be doing what we’re doing.

Early breakup is better than a bad relationship. Always.

And honestly? I’m grateful. Imagine 6 months in — full team hired, culture baked — and THEN I discover my CTO has been quietly building against the thesis the whole time.

He saved me a catastrophe by showing me who he was early.

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**The uncomfortable question:**

Do you have someone in a leadership position right now who secretly thinks your core bet is wrong?

That’s not a disagreement. That’s a time bomb.

Find out now. Not in 6 months.

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*I’m a group chairman co-founding AI-native companies. My Telegram bots have more productive arguments at 3am than most engineering teams do in a full sprint. Follow along for the ride.*