The Path to AI-native

Most of AI is under the waterline

Eight levels from a chat window to a business that shapes itself, and the blockers on the way.

Eight levels from a chat window to a business that shapes itself, and the blockers on the way.

The escape

The biggest gap in the market isn’t a tool. People who don’t think like systems builders never escape the chat window, so their AI never starts to compound.

0ChattingWhat most people see of AIThe waterline: the escapeWhere systems thinking starts1ContextAgents start from a live memory2SystemsWorkflows run as skills and loops3TrustedAgents hold a task for hours4Running at volumeCost falls as volume grows5CompoundingEvery rep makes it better6AppliedAimed at one outcome, measured7Self-shapingThe system does the shaping
Chatting above the waterline, seven levels below it
The escapeSystems start to compoundBuilding systemsEvery run builds on the lastChattingEvery task starts from zeroSlower at first, while the systems are builtWeeks
Illustrative: the shape of the two paths, not a measurement.
  • Chatting

    Prompting back and forth gives back what you put in, one task at a time, and what comes out gets copied somewhere else. Nothing carries to the next task, so the value stays flat however good the model gets.

  • Building systems

    The business’s context in front of the agents, the work turned into skills and loops that act where the work lives, and every run building on the last. Slower at first, then it compounds.

You are here

Eight levels from a chat window to a business that shapes itself. Each starts with a challenge you’ll recognize, and the level is what it looks like solved. Each level opens below into its parts.

0

Chatting

AI as a chat window: useful in the moment, gone when the chat closes.

PartThe challengeSolved
Prompting

You type the same context into a chat window every time, and the good answers disappear when the chat closes.

What works is saved and reused.

This part is hard. Most don’t make it through because the context never leaves people’s heads, so each task starts from scratch.

Copy and paste

The chat ends as a brainstorm or a doc, and someone has to carry it to the place it is actually used.

Agents act where the work lives: they publish, update and shape it directly.

Tool hopping

A different AI tool for every task, none of them connected, with copying between them.

One place the work happens, connected to everything else.

The waterline: the escape. Most people stop above it.

1

Context

The company’s knowledge, live and permissioned, in front of every agent.

PartThe challengeSolved
Context engineering

Every task starts with explaining the business again, and the answer is only as good as what you remembered to say.

The right facts and tools are already in front of the agent.

The brain

What the company knows lives in people’s heads, inboxes and old threads, where no agent can reach it.

Every meeting, email and document becomes memory agents start from.

Live feeds

The AI only knows what someone pasted in, and by tomorrow it is out of date.

Meetings, email, chat and tool events stream in as they happen, so the brain stays current.

Connections

The data sits in a dozen tools, some with connectors, some only as exports or dumps.

One set of connections feeds the brain.

Access

Sharing the brain means everyone sees everything; locking it down means nobody gets the value.

What each person and each agent can see is set in one place, so the brain is shared safely.

This part is hard. Most don’t make it through because it feels all or nothing, and locking it down keeps the value from arriving.

Context rot

Old notes and outdated decisions sit beside new ones, and the AI can’t tell which is true.

Stale information is pruned, and the newest wins.

This part is hard. Most don’t make it through because the answers slowly get less reliable, and trust in the whole system fades.

What we built for itConnections, brains and mining

2

Systems

Workflows turned into skills, agents and loops that anyone can start.

PartThe challengeSolved
Building systems

The workflow lives in one person’s chat history, and nobody else can run it.

It becomes skills, agents and loops anyone can start.

This part is hard. Most don’t make it through because knowing how to build one the AI-native way is still rare.

Agent interaction

Working with agents means sitting in a chat, waiting on each step and babysitting it.

You start work, watch it run, and step in beside it.

Model lock-in

Everything is built around one vendor’s model, so a better or cheaper one means starting over.

The model is a swappable part.

This part is hard. Most don’t make it through because a change of model can mean a rebuild, so it feels safer to wait.

What we built for itConnections, brains and miningAgent interaction

3

Trusted

Agents that hold a task for hours and come back with work you can use.

PartThe challengeSolved
Length of work

Agents lose the thread after a few minutes, so someone has to restart and steer them.

They hold a task for hours.

Repeatability

The same request gives a different result each run, so nothing can be relied on.

The same method gives the same result.

This part is hard. Most don’t make it through because checking every run takes back much of the time it saved.

Counterbalance

All the effort goes into the agent that builds, and nothing checks its work before it ships.

Every maker has a checker.

This part is hard. Most don’t make it through because without a checker, a confident mistake can slip through and dent trust.

Voice

The output sounds like AI, not like you, and customers can tell.

It sounds like you.

This part is hard. Most don’t make it through because work that sounds and looks like AI is hard to put in front of customers.

Delivery

The work arrives as Markdown or a plain doc that has to be rebuilt before anyone sees it.

It arrives designed and ready to send.

This part is hard. Most don’t make it through because rebuilding each output by hand stops being worth it.

What we built for itAgent interactionSkill trainingContent and brand engines

4

Running at volume

More work through the same system, with the cost of each run falling as volume grows.

PartThe challengeSolved
Cost

Usage grows and the bill grows faster, until someone asks what it is really costing.

The cost of each run falls as volume grows.

This part is hard. Most don’t make it through because the cost of model spend grows faster than the value, and the pursuit gets reconsidered.

New use cases

Every new request turns into a new build from scratch.

It plugs into the system you have.

The feedback wave

A thousand agents produce work, and one person has to read and approve all of it.

A review layer shows what got done and takes approval in one pass.

This part is hard. Most don’t make it through because review becomes the bottleneck, and the work waits on one person.

Running the workflow

The work agents now do at volume is still tracked in spreadsheets and chats.

A system built for this part of the business runs it.

Engines

Every video, deck and campaign is still made by hand, one at a time.

Engines make them on brand, at volume.

Security

Agents can touch real data, and one wrong command can delete the only copy.

Data is protected, snapshotted and permissioned.

This part is hard. Most don’t make it through because one deletion or leak can be enough to end the experiment.

What we built for itSkill trainingContent and brand enginesThe review and system layerMarket maps and campaign infrastructureDeep research

5

Compounding

Every rep makes the system better and cheaper, and able to take on more.

PartThe challengeSolved
New problems

The system only does what it was first built for, and each new problem starts again.

Each rep unlocks problems it couldn’t take on before.

Hardening

Quality stops improving, because nothing feeds the results back into the method.

Every rep raises quality and hardens the method.

Skill chaining

Each skill works on its own, and a person still carries the work between them.

Solid skills become steps of bigger ones, up to whole outcomes.

Deep research at scale

What you need to know is scattered across thousands of sources nobody has time to read.

Missions run across all of it, and the data becomes leverage.

The software factory

Every internal tool you need becomes a software project with a queue behind it.

Specs go in, software comes out, and you watch the proof.

Sunk cost

Having built something, you defend it, even when something better has shipped.

You burn it down and rebuild when something better arrives.

This part is hard. Most don’t make it through because what they built three months ago is already behind, and rebuilding feels like starting over.

What we built for itMarket maps and campaign infrastructureDeep researchThe software factorySkill chaining

6

Applied

The loop aimed at one business outcome, with a number that moves.

PartThe challengeSolved
Theater

The systems are busy, but nobody can say what they earned or saved.

Every system ties to an outcome.

This part is hard. Most don’t make it through because the motion is easy to see and the results are hard to name, so support fades.

The bet

Everything is a priority, so nothing gets enough to move.

One gap on the wheel, one bet.

Measurement

There is no before and after, so nobody knows if a change worked.

An OKR tied to revenue or cost, tracked.

The team

One person gets ten times faster, and the rest of the company doesn’t.

The whole company runs on it.

This part is hard. Most don’t make it through because the gains stay with one person and are hard to spread.

What we built for itSkill chaining

7

Self-shaping

The system reads its own results and shapes the business, inside limits people set.

PartThe challengeSolved
What’s next

Every change waits on you to notice it, decide it and kick it off.

The system proposes and runs the next change.

Goal drift

Give agents room to act and they wander away from the goal.

Goals, limits and an off switch keep them on course.

This part is hard. Most don’t make it through because drift from the goal is hard to spot until a result comes back wrong.

Direction

With the system making changes, it is unclear who is steering.

People set the direction, and the system does the shaping.

What we built for itSkill chaining

The blockers you will run into

We ran into each of these building our own systems, and they are where we see people most often stall. You may meet some of them along the way, and knowing them early makes them easier to get through.

  1. You may find yourself re-explaining the business to a chat window, with each task starting from scratch.

    Stuck prompting
  2. The access question tends to come early: sharing the brain widely feels risky, and locking it down limits the value.

    All-or-nothing access
  3. Over time, older context can creep into newer answers and quietly make them less reliable.

    Context rot
  4. You’ll know it should be a system, and your team may not yet know how to build one the AI-native way.

    Building the system
  5. You may build around one model, then see a better or cheaper one ship a few months later.

    Model lock-in
  6. Results may vary from run to run, and checking each one can eat into the time it saves.

    Repeatability
  7. It’s natural to put most of the effort into the agent that builds, and less into one that checks its work.

    Counterbalance
  8. The output may sound and look like AI, and customers can often tell.

    Sound and look
  9. The work may arrive as Markdown in Obsidian or a plain doc, and need rebuilding before a client sees it.

    Markdown and plain docs
  10. As usage grows, the cost of model spend may make you reconsider the pursuit.

    Model spend
  11. Agents can produce more than one person can review, and the review can become the bottleneck.

    The feedback wave
  12. One wrong command might delete the only copy of something that mattered.

    Lost data
  13. You may struggle to keep up with the cutting edge when what you built is already three months old.

    Keeping up
  14. You’ll begin to see motion and productivity, and still be thirsty for results.

    Motion without results
  15. One person may get much faster while the rest of the team works the way it always has.

    One-person gains
  16. As agents get more room to act, they can drift from the goal in ways that are hard to spot.

    Goal drift

What we had to build

Nine core competencies the market hasn’t solved. Each takes a session to explain, and each is an exponential gain, not a fix for one blocker.

01Connections, brains and mining

Lifts levels 1 to 2
MeetingsEmailChatCRMFilesThe webThe brainAlways currentAgents start hereWho sees what

Everything the company knows, feeding in as it happens and mined into a memory every agent starts from.

Live feedsMeetings, email, chat and tool events stream in as they happen.
One memoryMined into people, decisions and quotes every agent searches first.
Who sees whatSet once per person and per agent, so access isn’t all or nothing.

02Agent interactionStarport

Lifts levels 2 to 3
ChatSteer, answer, approveAgents at workResearch 40 firmsBuild the review pageDraft the outreachLive preview

The layer where people and agents build together. Model providers solve about 90 percent of it, enough to sell more tokens, and almost every company lands on the rest unsolved.

Parallel lanesSeveral agents at once, each on its own task, on any vendor’s model.
Beside the workLive previews of what they are building, not a wall of chat.
Step inSteer, answer and approve in the moment, without stopping the run.

03Skill trainingOrbits

Lifts levels 3 to 4
SkillModel tierGradeCost per repFrontierAMid tierASmallAOpen weightAThe grade holds whileeach rep gets cheaper

Skills made repeatable and trained like an education, on frontier and open-weight models. It answers two risks at once: quality in execution, and the exponential cost of using AI.

Blind testsGraded on real past cases by an agent that can’t see the answers.
Grade heldTrusted only once it holds its grade, rep after rep.
Cheaper repsEach rep moves down a tier of model while the grade holds.

04Content and brand engines

Lifts levels 3 to 4
Brand kitColorTypeAaVoiceVideoASlidesAPostsACarouselsAPagesASoftwareA

Pipelines that make on-brand work at volume. We have built them for video, for slides, and even for software.

One brand kitColor, type and voice set once, read by every engine.
Every formatVideo, slides, posts, pages and software from the same kit.
Graded outputEvery piece checked against the brand before it ships.

05The review and system layerTerra

Lifts level 4
What the agents didApproveA system to run itDoingDone

When agents work, success arrives fast and brings two needs at once: a review layer to see and approve what got done, and a system built to run the workflow.

See it doneWhat every agent did, as a designed page, not a log.
Approve in one passHighlights, comments and approvals flow back into the work.
A system per wedgeA tool built for the workflow, tailored to the business.

06Market maps and campaign infrastructureHarvista

Lifts levels 4 to 5
The whole market, mappedFitsRanks highWork firstTo work this week010203040506A person sends every message

Every company and person in a market, mapped, ranked and worked from one place.

The whole marketBuilt by deep research, not bought as a list.
RankedScored on fit and timing, so this week’s list is short.
WorkedCampaigns run from the same map; a person sends every message.

07Deep research

Lifts levels 4 to 5
One missionEvery item gradedbefore it is keptABABBAFAAABAABABFAAABBAA

Missions sent far and wide across the fragmented web, running a complex skill on every item they find. It breaks data moats and turns data into leverage.

Far and wideMissions reach across thousands of scattered sources at once.
A skill per itemA full method runs on every item, not a summary of a few links.
Graded factsEvery finding graded before it is kept.

08The software factory

Lifts level 5
SpecBuildTestProofShipTheater mode1 Sign in2 Create3 Review4 ShipTied to the exact build

A spec goes in, and agents build, test and ship it. Ours keeps the lights on: you watch the proof play back instead of reading the code.

Spec inThe change is reviewed as a page before anything is built.
Built and testedAgents build it and record a test of every flow.
Watch the proofTheater mode plays the tests back, tied to the exact build.

09Skill chaining

Lifts levels 5 to 7
Deliver the auditAIngestPublishAudit an accountAFindWriteCheck a contractAReadCompareFlagOnce a skill holds its grade, it becomes one step of the skill above it

Once a skill is solid, with its own steps, it becomes a single step inside a bigger skill, and that skill a step inside a bigger one again. This is the work at the top of the market.

Solid firstA skill is trained on its own until it holds its grade.
Becomes a stepThen the whole skill is one step of the skill above it.
Whole outcomesSkills built of skills deliver a result, not a hand-off.

Up next

Back to The Jettison Method, 1 of 2

Run your transformation like a product

Read it now

Back to The Jettison Method, 1 of 2

The Transformation Wheel

Run your transformation like a product

Business is a loop. Map it on the wheel, find the weak wedge worth the most, and move one number.