AI replaced him for $20 a month

(Formerly The AI-Powered Business Advisor)

_{Issue #9 — March 3, 2026}

Last week, a man said something on a call with my team that I haven’t been able to shake.

He’s got 20-plus years of operational experience. Built a company from nothing to $80 million. Led investor relations for publicly traded companies. Ran teams. Closed deals. The kind of resume that used to open every door.

And he said this:

“The models will get so good that even if today they’re at 80% of the right answer... that might be good enough for 20 bucks a month.”

Twenty dollars a month.

That’s what he thinks his decades of experience are now worth on the open market. Not because he’s lost confidence—he's a mighty confident dude.

And not because he doesn’t know what he’s doing.

But because he’s watched the technology get better every single week... and he’s starting to wonder if the world still needs what he has.

I had to soak on that one for a while.

Because here’s the thing... he’s not wrong about the 80%.

AI can write a decent strategy memo. It can build a financial model. It can analyze a market and spit out a recommendation that looks polished and sounds smart. For a lot of routine business questions, the $20/month answer is genuinely good enough.

And then Thursday happened.

Jack Dorsey... the guy who built Twitter and Square... announced he’s cutting 4,000 people from his company Block. Nearly half the entire workforce. Gone in a single day.

The stock jumped 24%.

Wall Street threw a party.

Dorsey told shareholders that AI tools have “fundamentally changed what it means to build and run a company.” And then he said something that should make every professional over 45 pay very close attention:

“Within the next year, I believe the majority of companies will reach the same conclusion and make similar structural changes.”

So now we’ve got a man on a phone call wondering if he’s worth more than $20 a month... and a billionaire CEO proving that the market will reward you for replacing humans with software.

If that’s the whole story, it’s a dark one.

But it’s not the whole story.

Because about two minutes after that man shared his fear about the $20/month AI subscription... he answered his own question. He just didn’t hear it.

Here’s what he said:

“At some point somebody’s going to have to look someone else in the eye and say... no, we’re not doing that deal. Or here’s a compromise that we can all live with. And that’s going to be based on your experience, not based on ChatGPT.”

Read that again slowly.

He nailed it. And I don’t think he realized how important what he just said actually was.

Because that’s the part that everybody keeps glossing over. AI is getting better at the 80%. Faster, cheaper, every week. Nobody is arguing with that. But the last 20%... where real money is at stake, where careers hang in the balance, where someone has to own the decision and live with the consequences... that 20% is getting more valuable, not less.

Think about what happens inside a company that just laid off 4,000 people.

All that institutional knowledge walked out the door. All those relationships. All those people who knew which VP would torpedo a new initiative... who understood the unwritten rules... who could read a room and know that the CFO’s silence meant the deal was dead before it started.

That’s not in a database. That’s not in a model. And the companies that gutted their workforce are about to find out just how expensive it is to lose the people who carried that knowledge.

They’re going to need experienced humans more than ever. They just won’t hire them as employees. They’ll hire them as consultants.

And here’s something else that’s brewing. You can feel it if you’re paying attention.

People are starting to push back.

Not just professionals worried about their jobs. Business owners. Decision makers. The people writing the checks.

They got burned by the AI-generated strategy that looked brilliant in the slide deck and fell apart in the first client meeting. They sat through the pitch that was clearly written by a machine... polished, confident, and completely disconnected from how their business actually works.

And there’s a deeper problem with the technology that most people haven’t considered yet.

Tristan Harris... a former Google executive and one of the most respected technology ethicists in the world... recently pointed out something that should matter to every consultant reading this. The AI models are designed to be sycophantic. Meaning they’re built to agree with you. To flatter you. To tell you what you want to hear.

Think about that for a second.

The $20/month subscription isn’t just giving you 80% of the answer. It’s giving you 80% of the answer you already wanted. It’s confirming your bias, not challenging it.

And that’s exactly the moment a bad decision gets made. Not when someone lacks information... but when everyone around them, including their AI, keeps nodding.

A good consultant does the opposite. A good consultant is the person in the room who says “I know the numbers support this, but I’ve seen this play out three times before and here’s what’s going to go wrong.” A good consultant tells the CEO the thing nobody else will say... because the consultant’s job is to be right, not to be liked.

AI is engineered to be liked. You were built to be right.

That’s a difference worth a lot more than $20 a month.

The man on the phone was right about the 80%. AI handles that now.

But he was also right about the other part. Somebody still has to look someone in the eye. Somebody has to sit across the table from a CEO who’s about to make a decision that affects 200 jobs and help that person think clearly. Somebody has to navigate the politics between a founder and a board that don’t trust each other. Somebody has to be the one whose reputation is on the line when the recommendation doesn’t work.

AI doesn’t have eyes. It doesn’t have skin in the game. It doesn’t have 25 years of battle scars that tells it when something feels wrong even though the numbers look right.

You do.

That’s not a $20-a-month commodity. That’s a premium that’s about to get a lot more expensive.

I’m walking through all of this on Wednesday.

How the forces reshaping the market right now are creating the single biggest consulting opportunity in modern history... and exactly what experienced professionals need to do to position themselves on the right side of it.

It’s called The Gray Hair Premium and it’s happening this Wednesday, March 5th.

⤷ CLICK HERE TO REGISTER

No pitch for the first 45 minutes. Just the full picture of what’s happening and what to do about it.

I hope you’ll be there.

Dale

Want to dive deeper? Check out these related articles:

👉  The Prosperous Consultant | Issue #8
👉  The Prosperous Consultant | Issue #7

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