Chinat · September 1, 2026

The org chart adopts last

The org chart adopts last. Someone who runs a whole office in Menlo Park told me she wants to try the tools herself before she brings anything to her firm. Not a pilot, not a committee, not a rollout plan. Her, alone, seeing for herself whether it actually saves her time.

Six months ago I would have treated that as a stall. Now I think it is the whole game.

For a long time I believed that selling AI transformation meant selling to the organization. You build the enterprise case, you find the champion, you get the budget approved, and the capability rolls downhill. It is a clean story. It is also mostly fiction. The clients who have actually paid me lately mostly started as one curious person. Not a logo, not a department. A person who had felt the tools work on their own workflow and wanted more of that feeling. If the organization adopts at all, it does so after the individual.

Once you believe that, your go-to-market changes, because the question is no longer how do I get in front of the company but how do I get in front of the individual before anyone has approved anything. My answer turned out to be a class.

I teach a course on operating in the modern age of AI. The students are almost exactly the people I would otherwise be cold-emailing for months with no reply. Except instead of me chasing them, they show up for two hours and put their real problems on the table. A course inverts the sales motion. By the end of a session I do not have a lead I need to qualify. I have a diagnosis. I have watched someone struggle with a specific task and I know what I could build for them. The class is not the product. It is the best lead generation I run, and people pay to attend it, so the top of my funnel is profitable instead of a cost.

I want to be honest about the size of this. The people paying me right now are mostly individuals and small teams, not enterprises writing six-figure checks. The transformation budget everyone talks about is imaginary until one human being has personally felt the work get easier. So you sell to that human being first. You make them the hero inside their own company, and you let them carry you in. The enterprise contract, if it comes, comes later and comes because of them.

The person I run these weekly sessions with is building the opposite way. Research first, revenue whenever. He is comfortable making nothing for now because he believes the product is downstream of the research being right. That is a legitimate path, and for his work it may be correct. But for the work I am doing, money is the forcing function I trust most. It tells me which of my many ideas someone will actually pay to keep alive. These last couple of weeks of actually selling taught me more about what people want than months of building things I found interesting.

There is a version of this that sounds cynical, like I am dressing up sales as education. It is the reverse. The class has to be genuinely good or nobody comes back and nobody refers me, and a room full of sharp people notices immediately if you are wasting their afternoon. The teaching is the quality bar. The lead generation is the byproduct of teaching well. That is the part I did not expect: the most commercial thing I do is also the most generous.

So here is where I have landed. Sell to the individual, not the org. Teach, because teaching is how you meet the individual with their real problem visible. Treat revenue as feedback, not the goal. And stay suspicious of the clean enterprise story, because the messy individual one is the one that pays. The business starts with the individual.

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