People Are Scared to Commit

I’ve been noticing something in leadership conversations lately. Everyone agrees AI matters. No one serious is dismissing it anymore. It’s “strategic.” It’s “inevitable.” It’s “a priority.” But the tone shifts the moment the conversation moves from interest to commitment. At first, it’s confident. We’re investing or we’re exploring.

Then you ask a harder question. What are you willing to change because of it? What are you willing to stop doing? What part of your operating model are you actually prepared to rewrite? That’s when it gets quiet.

And I get it. AI isn’t just a new tool. It forces tradeoffs and it challenges headcount models. It exposes inefficiencies we’ve normalized. Once you commit, you’re accountable to outcomes, not curiosity. So a lot of teams hover in the middle with pilots and experiments. Enough to say they’re moving, not enough to fundamentally change anything. The hesitation isn’t really about whether AI works. It’s about what happens if it does. Because belief doesn’t show up in slide decks. It shows up in the pipeline. In the org chart. In the bets you’re willing to make publicly. So before we argue about hype or revolution, let’s talk about proof.

Let’s start there.

I booked 101 sales meetings in two weeks with the help of my AI Cloud Employee, Sloane.

Don’t believe me? Check the calendar:

The best part?

I hired an AI Cloud Employee, trained her, and watched the meetings roll in.

Here’s how it went down:

She’s calling. Emailing. Chatting. Texting. I’m watching our pipeline fill and asking myself, “Who the hell is this woman?” This is the difference between an AI Agent and a Cloud Employee. One hacks workflows. The other just does the damn job.

See how Sloane works.

Now I know what some of you are thinking. “Yeah Gabe… but AI makes mistakes.”. And you’re not wrong, but doesn't everyone?

Your employees aren’t perfect. So why does your AI need to be? I don't get it.

We’ve tolerated human error for decades. Missed numbers. Bad emails. “Updated” forecasts that somehow round up every quarter. Nobody called it a hallucination. We called it Tuesday. Now the AI makes a mistake and everyone acts like it committed a felony.

Relax.

It’s an AI agent. Not a prophet. You already review everything your team touches. The intern’s word salad. The freelancer’s recycled deck. The rep who swears this deal is “definitely closing.”

No one on payroll is batting a thousand. The only difference? AI makes mistakes faster. Costs less. Doesn’t ask for PTO. And it improves. You’ve never hired perfection. Stop pretending you require it now.

Everyone’s obsessing over whether AI is perfect, almost no one is asking whether the product is.

Most AI startups don’t have PRODUCT-MARKET FIT. They have PRODUCT-MESSAGE FIT. Big difference.

Product-message fit gets you nods. But product-market fit means they don’t churn.

Right now? Most AI companies are just good at the pitch. They say they’ve got traction. What they really have is curiosity at scale.

Why? Because buyers are cornered.

So they say yes to the first call. The demo. The pilot. But then? Crickets. Pilot ends. Results are meh. And your champion’s already flirting with another AI vendor.

Why? Because most AI companies are built to win the room, not the renewal. The pitch lands but the product doesn’t. Message fit might get you in the door, but only real impact keeps you in the org.

So...stop selling demos and start owning outcomes and maybe, just maybe, you’ll make it past $3M ARR before flaming out like the rest of your AI friends.

And when companies know deep down they don’t have real product-market fit…they hide.

“Stealth startups” bug me. I think it's because I hate hiding dressed up as a strategy.

I feel like stealth is for billion-dollar labs and defense contracts. Not for two founders with a deck and a logo.

If you’re early and hiding, it’s usually one of three things:

Nobody is waiting to steal your half-baked idea. We're all too busy trying to survive our own.

You gotta understand this:

You gotta get going. Launch. Sell. Get punched in the face. Iterate. I gotta say, pressure makes real companies and silence makes fragile ones. So come out of stealth or admit you’re just protecting your ego.

This is where leadership comes in. Because AI doesn’t fix weak ownership.

I’m sorry, but you’re not a real CRO if all you do is babysit the sales team and whine about pipeline like it’s someone else’s problem.

If you’re not owning the whole number, call yourself whatever fancy title you want, but I’m calling you what you are… a sales leader. A real CRO owns their fate, runs the show, and takes control of the entire revenue engine.

This isn’t about one CRO. Or one startup. Or one tool. It's bigger than that.

80 million people don’t read the same AI article by accident. This is one of those articles you forward to everyone you know… especially the friend who still thinks ChatGPT is just a better version of Siri :)

So that’s the thread this week.

Individually, they’re hot takes. Together, they’re a pattern. AI is making motion cheap. Really cheap. You can generate more activity in a week than teams used to produce in a quarter. But ownership didn’t get automated. Judgment didn’t get outsourced. The number didn’t get any less real.

That’s the tension. We’re watching roles stretch, compress, and blur. The timeline between idea and execution is basically gone. You can test distribution in a day. You can spin up outbound in an hour. You can fake traction in a weekend. What you can’t fake for long is outcomes.

I’ll be over here training Cloud Employees and still owning outcomes. Because AI replaces motion. It doesn’t replace responsibility.

That’s it for today. Connect with me on Linkedin if you actually want to understand what an Autonomous Organization looks like in the real world.