I have bought strategy the way most small brands buy it: in pieces, from whoever seemed to know the part I didn't. An agency deck at one brand. A consultant's audit at another, which turned into a longer engagement. Market research I paid for, read closely, and filed. Across the brands I've run it adds up to tens of thousands of dollars, and maybe it got actioned and maybe it didn't.
- An agency deck at one brand.
- A consultant’s audit at another, which turned into a longer engagement.
- Market research I paid for, read closely, and filed.
I want to be careful with "maybe it didn't," because the easy version of this story is that the work was bad. Mostly it wasn't. Some of it was very good. The problem sat somewhere else, and it took me years and a different job to see where.
Strategy is near and dear to my heart. I wanted to be in all of it, at every brand, every decision about where we were going and why. But you can't have expertise everywhere, and a small team doesn't get to pretend otherwise, so you buy the piece you're missing. What you're buying is knowledge, and knowledge has a property that makes it unlike anything else on the invoice. You don't know if it's good or useful until you hear it. You pay first and find out after. For my whole operating career, hearing it was gated and expensive.
You don't know if it's good or useful until you hear it.
What the frameworks can't carry
I got my MBA at Kellogg, which is a marketing school, and a ton of what I learned there is folded into how I operate. Positioning, segmentation, the way you take a category apart to find where you fit. This is not the piece where the MBA sneers at the MBA. The frameworks are real and I still reach for them.
What the classroom can't give you is the context to apply them. There is no substitute for experience. All the frameworks in the world are hard to use without knowing which one fits the situation in front of you, and that knowing comes from having lived through situations. A positioning that's correct on paper and wrong on the shelf. A retailer who wants something the framework doesn't have a box for. An operator who has had things not work out carries something the framework doesn't. Put the two together and you have a strategist. Put a system around both that actually understands the brand and you have something I never had while I was running brands.
Someone who has had things not work out carries what the framework does not: a positioning that was correct on paper and wrong on the shelf, a retailer who wanted something no box accounted for.
Positioning, segmentation, the way you take a category apart to find where you fit. They are real, and they are hard to use without knowing which one fits the situation in front of you.
One that already holds the brand record, so the framework gets applied to your situation on the first pass, with your claims, your audiences and your competitors already in the room.
"Understands the brand" is doing real work in that sentence. Any strategy engagement starts with discovery, the stretch where the consultant learns what the operator already knows. You pay for that stretch like any other, and it always felt to me like the part that should have been free. The context was the costly part of every engagement and the least valuable, because it was mine to begin with. That problem has its own piece, *The Context No Hire Can Carry*. For strategy the consequence is direct. When the system writing the recommendation already holds the brand record, the money that used to buy discovery buys the recommendation, and the framework gets applied to your situation on the first pass, with your claims, your audiences, and your competitors already in the room.
There's a sharper version of this point, and it's the one I'd want a founder to sit with. The frameworks that worked ten or fifteen years ago might not work anymore in an agent-based world. When the buyer is sometimes a model, when the shelf is an answer in a chat window, when the channel mix rewrites itself every quarter, a framework built for a world of humans reading packaging is a starting point at best. Every leader, regardless of education or experience, has to stay current and adapt, and what I learned in school is no exception.
Thousands of companies, one pattern
For three years I was a Director at Techstars. I saw thousands of pitches, did diligence, and talked with hundreds of entrepreneurs about where they were going. If you want to know what that many strategy documents teach you, it's pattern recognition. After enough of them you stop reading the plan and start reading the gap between the plan and the company.
| The plan | The company | |
|---|---|---|
| What each one held | The deck was often right, and the founders were often smart. The strategy lived in the document. | The business went on doing the things it already knew how to do, and nothing connected it to the plan. |
The pattern that showed up more than any other: people can have a great strategy, and if they can't execute, it doesn't matter. The deck was often right. The founders were often smart. The business stalled anyway, because the strategy lived in a document and the company lived somewhere else, and nothing connected the two. I'd watched the same thing from the inside at my own brands. The audit I paid for was correct. Then it sat in a folder while we did the things we already knew how to do, because the thing we knew how to do was the thing we could execute on a Tuesday.
The business stalled anyway, because the strategy lived in a document and the company lived somewhere else, and nothing connected the two.
Somewhere in those years my own standard for what counts as strategy changed. Building brands on Amazon had already shown me that a lot of what I'd been calling judgment was statistically provable as right or wrong; that story belongs to *The Fourth Shelf*, and the short version is that once you've seen a decision proven with numbers you lose your taste for decisions that can't be. I still believe in judgment. I stopped believing in judgment that wouldn't show its work.
Where the gate moved
What AI changed is the gate. Strategy can now be cheaper and faster, possibly better, and it can be written from your brand rather than from a template. A template with someone else's name barely scrubbed out is the fear, whether or not it was ever the fact. Everyone can see the cheaper-and-faster part. The part that mattered to me is quieter. You can hear it before it costs you tens of thousands of dollars. The knowledge is in front of you first. If it's wrong, it's wrong cheaply. If it's right, you've spent an afternoon getting up to speed on what's possible for your brand, which used to take months of time, tons of thinking, a roster of experts, and a long stretch of indecisiveness while everyone waited for somebody to be sure.
| Where the gate used to sit | Where the gate sits now | |
|---|---|---|
| The order things happen in | Pay, then hear it. Whether the knowledge was any good was a question you could only answer after the invoice. | Hear it, then decide, then execute. If it is wrong, it is wrong cheaply, and the deciding is still yours. |
You can hear it before it costs you tens of thousands of dollars.
Pattern recognition, the thing three years of pitches gave me, is also the part of a good strategist that got cheap. A model has read more strategy than any one strategist has, and it can recognize a category pattern quickly and say where the white space is. Knowing which pattern is yours, and which recommendation your team can actually carry on a Tuesday, stays with the operator. I don't think that part gets automated, and I wouldn't want it to.
Then you can execute it, which is the half of the Techstars pattern the deck never solved. The reason Chart lives inside Jinn is that a strategy which can't reach the hands doing the work is one more audit in a folder, the same folder mine sat in. Chart gets you up to speed on the market, the competitors, the white space, and how the brand reads to each of its audiences. The rest of the system, the writer and the ad studio and the visibility audit, works from the same brand record and executes according to what you believe and where you've decided the opportunities lie. You make the decisions to chart your path, and the system carries them out to the surfaces.
It is slower than asking a chatbot, and I'd rather say that here than have you find it. For the research-backed reports, the sources are retrieved and stored before a word is written, and a second, independent AI reads every claim against the source's actual text before the claim is allowed to become a sentence. That takes time, and *40 Minutes on Purpose* makes the case for the wait: why we treat it as part of the work, and why a strategy that arrives in three seconds worries me more than one that takes forty minutes.
What I'd have done with it
What Chart does, in the plainest words I have: let's understand what's going on in the market, with competitors, where there's white space, what we're doing well, how this reads, and who the different audiences are. Let's really look at those pieces of the puzzle and put together the best picture. Then let's grade the brand as it is, honestly, write the roadmap to fix it, and show the sources.
Every brand I've run would have used that, and every one of them paid for a partial version of it, from people who each saw one piece. Most brands would love to be able to do this. Now they can.
One thread I'd rather leave hanging than tie off. A grade is a verdict, and I've come to believe a verdict without a cure is a product failure, which is why every grade Chart gives comes with what to do about it. But a roadmap is still a document, and the pattern I watched for three years at Techstars doesn't care how good the document is. Execution is still yours. What's different is that the strategy and the hands carrying it out now read from the same page, and the moment you find out whether the strategy was any good comes first, before the money.
Hearing it used to be the gated part. Now it's where you start.
Why doesn't good strategy get executed?
Because the strategy lives in a document and the company lives somewhere else, and nothing connects the two. The deck is often right and the founders are often smart, and the business stalls anyway while the team keeps doing the things it already knows how to do.
What can't a framework give you?
Context. There is no substitute for experience: all the frameworks in the world are hard to use without knowing which one fits the situation in front of you, and that knowing comes from having lived through situations.
What actually changed about buying strategy?
The gate moved. It used to sit before the knowledge, so you paid and then heard it. Now you can hear it before it costs you tens of thousands of dollars, which means that if it is wrong, it is wrong cheaply.
Chart is in private beta.