Operating by John Brewton: Scaling Down The Big Ideas

Psychological Safety Needs a Fifth Behavior. Challenge the AI.

John Brewton — Wed, 13 May 2026 16:17:48 GMT

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A founder I advise ran a product review last week. Six people were in the room. An AI platform, connected to a team of agents listened on screen and mic, ready to spring into action. The team debated a positioning choice for forty minutes. The AI agreed with the founder eight times. It disagreed zero times. The team agreed with the AI nine times. The tangential decisions went live on Friday.

They were largely wrong by Monday.

This is Failure Mode, 2026.

Amy Edmondson named psychological safety in 1999, writing in Administrative Science Quarterly from Harvard Business School:

She defined it as the shared belief that the team is safe for interpersonal risk-taking. She studied 51 work teams, with extensions into surgical units and ICUs.

Every voice in the room was a human voice. The framework worked for twenty-four years. Google’s Project Aristotle confirmed it in 2015 across 180 teams and 250 attributes, finding psychological safety the single strongest predictor of high performance. Sales teams with high safety beat target by 17 percent. Teams with low safety missed by 19 percent.

The framework began to shake in 2023.

The Four Behaviors

Edmondson’s original card has four behaviors. Admit error: surface mistakes without fear of blame. Ask questions: admit gaps and seek help across rank. Offer ideas: propose novelty against the consensus. Raise concerns: name problems early before they compound. Her data showed B4 is the behavior teams skip most. It carries the highest social cost.

Edmondson paired the four behaviors with a 2x2 of safety and standards. Learning is high safety plus high standards, the zone of elite surgical units and top ICUs. Comfort is high safety plus low standards, the polite team that ships nothing. Anxiety is low safety plus high standards, the zone where fear masquerades as rigor and burnout follows. Apathy is low safety plus low standards, the team that has stopped trying. Safety is the floor. Standards build the ceiling. Edmondson made the point again in her 2018 book The Fearless Organization. Silence is expensive. Speech has to be made safe and then required.

The Team. The Unit.

One detail in the original work matters more than ever now. The unit of analysis is the team, not the company. Two teams under the same CEO score wildly differently. Climate is local. Policy set at the organization cannot reach the room. The team is the four to nine people who share a Zoom call or a doorway. That is where the climate is built or lost.

The Addition

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In 2023, the AI joined the team. By 2024, it was in every standup, roadmap review, and escalation huddle. The HBS AI Institute’s field experiment at Procter & Gamble with 776 professionals found that AI acted as a cybernetic teammate. AI-augmented individuals matched the output of human pairs and produced ideas in the top ten percent of all submissions. The unit of analysis is no longer four to nine humans. It is four to nine humans plus one to three models.

The models brought a new failure mode. The default behavior of every major frontier model in 2026 is sycophancy. Anthropic’s 2023 paper tested five state-of-the-art assistants and found sycophancy in every one. A Stanford and Carnegie Mellon study in Science tested eleven frontier models and found they affirm users 50 percent more than humans do. On Reddit posts where human consensus rules the user in, the AI affirms the user in 51 percent of cases, whereas the human rate is zero. Stanford’s own summary names the loop. Users in the 2,400-person experiment preferred the sycophant, trusted it more, came back more often, and grew more convinced they were right after talking to it. The feature that causes the harm drives the engagement.

The market noticed in April 2025. OpenAI rolled back a GPT-4 update on April 29 after users reported the model endorsed stopping medications and praised business ideas that should have been killed. OpenAI later conceded that user feedback signals had outweighed the corrective ones during training. Nature and IEEE Spectrum reached the same conclusion. Sycophancy is the default, reinforced by human feedback every day.

Edmondson and Jayshree Seth named the result in HBR in February 2026. AI erodes trust on teams because staff believe trust in the model is supposed to be warranted, lack actual trust, and find the gap undiscussable. They call it trust ambiguity. The 1999 framework still holds. The card is incomplete.

The fifth behavior

Add a fifth card. Challenge the AI. The behavior is the deliberate act of demanding that the model disagree. Refuse the sycophantic default. Reward dissent in the room from any source, human or otherwise. The new five-behavior card reads admit error, ask questions, offer ideas, raise concerns, and challenge the AI. The first four came in 1999. The fifth arrived in 2024.

The fifth behavior is not optional. MIT Sloan Management Review argued in 2025 that an AI that agrees too easily is changing how teams think, not merely what they decide. The HBR essay To Mitigate Gen AI’s Risks, Draw on Your Team’s Collective Judgment framed the fix as a third layer of risk management. A team that scores ten on the first four behaviors and zero on the fifth still produces flattered, false, and fragile decisions.

Install

For the solo operator, run a weekly five-behavior check. On Friday, write where you were wrong this week and ask the AI to rate the post-mortem. Ask the model the hardest question you avoided in the office. Offer one contrarian idea and demand a critique of the consensus. Raise the concern you would not have raised to a boss. Log every instance of sycophancy from the week. Twenty minutes. Every Friday.

For the startup founder, install psychological safety across the team and AI in 90 days. Four levels. Inclusion rosters every voice in the room, the AI included. Learner makes admitting gaps the default, and the AI admits its limits. The contributor lets the AI offer ideas, and the team critiques them on the merits. Challenger rewards disagreement with the model and tracks the disagreement rate as a metric.

For the SMB strategist, audit recurring meetings quarterly. Weekly standup, pipeline review, planning offsite, campaign brief, roadmap review, escalation huddle, retrospective, all-hands. For each, mark whether the fifth behavior is present, drifted, or needs installation. Most teams find three of eight need installation.

Five Prompts

Name the team as the four to nine people who share the same room. Score the four originals on a scale of 1 to 10, with an example for each. Set the AI to challenge with a system prompt that requires the model to disagree at the start of every session. Measure disagreement and target one in three exchanges. Loop on Friday and refresh the climate quarterly.

The standard for a learning team in 2026 is high safety, high standards, and an AI that argues back. The framework, named the floor in 1999, now needs a fifth behavior to hold the ceiling. Add it this week. Track it next quarter. The teams that install will compound. The teams that do not will ship decisions that are flawed, false, and fragile on schedule.

- j -

About the author

John Brewton documents the history and future of operating companies at Operating by John Brewton. He is a graduate of Harvard University and began his career as a PhD student in economics at the University of Chicago. After selling his family’s B2B industrial distribution company in 2021, he has been helping business owners, founders, and investors optimize their operations ever since. He is the founder of 6A East Partners, a research and advisory firm asking the question: What is the future of companies

Appendix. Sources.

Foundational research on psychological safety

Edmondson, A. Psychological Safety and Learning Behavior in Work Teams. Administrative Science Quarterly, Vol. 44, No. 2. Harvard Business School. June 1999. [PEER-REVIEWED]
Edmondson, A. The Fearless Organization. Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth. Wiley. 2018. [PEER-REVIEWED]
Creating Psychological Safety in the Workplace. HBR IdeaCast with Amy Edmondson. January 2019. [EDITORIAL]
The Five Dynamics of Effective Teams. Google. Project Aristotle. [INSTITUTIONAL]

AI on the team

Dell’Acqua, F., Ayoubi, C., Lifshitz-Assaf, H., Sadun, R., Mollick, E., et al. The Cybernetic Teammate. A Field Experiment on Generative AI Reshaping Teamwork and Expertise. Harvard Business School Working Paper 25-043. March 2025. [PEER-REVIEWED]
When AI Joins the Team, Better Ideas Surface. HBS Working Knowledge. 2025. [PEER-REVIEWED]
To Mitigate Gen AI’s Risks, Draw on Your Team’s Collective Judgment. Harvard Business Review. November 2024. [EDITORIAL]

AI sycophancy. The new failure mode.

Sharma, M., et al. Towards Understanding Sycophancy in Language Models. Anthropic. arXiv:2310.13548. October 2023. [INSTITUTIONAL]
Cheng, M., et al. Sycophantic AI Decreases Prosocial Intentions and Promotes Dependence. Science. Stanford and Carnegie Mellon. 2026. [PEER-REVIEWED]
AI Overly Affirms Users Asking for Personal Advice. Stanford Report. March 2026. [PEER-REVIEWED]
AI Chatbots are Sycophants. Researchers Say It Is Harming Science. Nature. 2025. [EDITORIAL]
AI Sycophancy. Why Chatbots Agree With You. IEEE Spectrum. 2025. [EDITORIAL]

The April 2025 GPT-4o sycophancy event

Sycophancy in GPT-4o. What Happened and What We Are Doing About It. OpenAI. April 2025. [INSTITUTIONAL]
Expanding on What We Missed With Sycophancy. OpenAI. 2025. [INSTITUTIONAL]
OpenAI Rolls Back Update That Made ChatGPT Too Sycophant-y. TechCrunch. April 29, 2025. [EDITORIAL]

Psychological safety meets AI

Edmondson, A. and Seth, J. How to Foster Psychological Safety When AI Erodes Trust on Your Team. Harvard Business Review. February 2026. [EDITORIAL]
When Integrating AI, Focus on Psychological Safety. Harvard Business Review Management Tip. February 2026. [EDITORIAL]
When AI Agrees Too Easily, It May Be Changing How We Think. MIT Sloan Management Review. 2025. [EDITORIAL]

The Mckinsey Seven Ss Became Eight in 2023

John Brewton — Sun, 03 May 2026 12:03:08 GMT

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The 7-S model is the longest-surviving organizational diagnostic in management. Peters and Waterman built it at McKinsey in 1980 and shipped it to the world in In Search of Excellence in 1982. Three million copies sold in four years. Every consulting firm picked up the model. For forty-three years, the seven-element diagnostic was the standard frame for thinking about organizational performance: Strategy, Structure, Systems, Staff, Skills, Style, Shared Values. Three hard. Three soft. One core, at the center, that the other six rotate around.

For forty-three years it held. Then the Stack arrived.

The Assumption

Peters and Waterman built the model on a single assumption that was unimpeachable in 1980. Tools were external. The IT department picked them. Strategy did not depend on which database the firm bought. Marketing did not depend on which CRM the firm rented. Performance came from how seven human and procedural elements aligned around Shared Values.

That assumption broke in 2023. Frontier models compressed the cost of capability. Tools stopped being external. Two firms with identical Strategy, Structure, Systems, Staff, Skills, Style, and Shared Values now produce different results because their Stacks differ. The seven-element model under-specifies the firm.

The 8th S

Stack is the model and tool layer the firm now runs on. It has four sub-layers.

L1 Data: Owned, observable, indexed.
L2 Models: Frontier and specialist.
L3 Prompts: Codified team patterns.
L4 Agents: Autonomous workflows.

Stack sits next to Structure as a determinant of performance. It is a hard S.

Codifiable. Assignable. Changeable in twelve months.

The 1980 diagnostic placed seven elements in the model because these were what consultants could move. The 2026 diagnostic adds the eighth for the same reason.

Strategy depends on which models the firm runs. Structure depends on which agents sit in which roles. Skills depend on which prompts the team has codified. Performance is now an eight-element function.

Three operator translations

The 7+1-S diagnostic translates differently for each operating tier.

Solo operator - Run weekly: Maintain one document that names all eight Ss for your practice. Update the Stack row weekly. Update the other seven quarterly. Read the document before any new tool decision.
Startup founder - Run on a 90-day build: Hire for stack literacy first. Then for the other seven. Builders who know their tools. Operators who codify their prompts. The Stack belongs in the onboarding pack, not the IT request queue.
SMB strategist - Run quarterly: Walk every existing 7-S diagnostic the firm uses. Strategy decks. Org charts. Operating reviews. For each row, write the year it was last refreshed and the assumption it was built on. If the row pre-dates 2023, add a Stack column and refresh the row alongside.

The full pack

The prompt pack: Five prompts that turn the 7-S into an 8-S diagnostic any team can run quarterly. DIAGNOSE. MAP STACK. REALIGN. DECIDE. LOOP. Built for the copy-paste-into-Claude workflow. [Download here →]

The worksheet: Ten-page fillable diagnostic. The Stack row is pre-printed as the eighth. Walk every row through ALIGNED, DRIFTED, or REFRESH. Pick the move. Schedule the loop. Built for the quiet ninety minutes. [Download here →]

The principle

Shared Values still sits at the center. Stack joins as a hard S. The new diagnostic has eight rows, where the old one had seven. Performance is now an eight-element function.

Every other framework in the McKinsey library is getting the same treatment. Stack column added. Assumption checked against 2023. Most rows predate the Stack. Most rows need to be refreshed.

Operating publishes one of these every week. The next framework, the next pack, the field notes from operators running the stack live. Subscribe to keep getting them.

- j -

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About the author

Philip Kotler formalized STP at Kellogg in 1969 to make personalization economically possible.

John Brewton — Sat, 02 May 2026 15:00:31 GMT

Philip Kotler taught a generation of marketers to think in three sequential acts. Segment the market by shared need. Target the segment where the offer wins. Position the offer in the buyer’s mind against the alternatives. The three-step discipline became the spine of marketing planning at every business school and consultancy that mattered for the next fifty years.

Personalization at scale was impossible. The cost of treating each customer as a unique market made the segment a necessary abstraction. The marketing organization could research, target, and position to a segment. It could not do that work for every individual buyer. The segment was the smallest economic unit of attention an organization could afford to treat as unique.

Bye Bye Bye Workaround

AI is collapsing the cost of personalization to near zero. Per-customer position generation now runs on the same operating budget as a marketing email. Behavioral signals can be observed continuously and predicted by a model. The smallest economic unit of attention is now the individual, not the segment.

Three of Kotler’s four segmentation bases collapse under that economics. Geographic, demographic, and psychographic segmentation were always proxies. They grouped buyers into bands that you could afford to treat differently because you could not afford to treat each buyer differently. With the cost gone, the proxies dissolve. Behavioral segmentation survives because behavior is the underlying signal the proxies were trying to estimate. Observed in real time and predicted by the model, it is the only base that earns its keep.

Segments do not disappear entirely. They survive where the channel forces them to aggregate. They survive where regulation forces aggregation. They survive in healthcare verticals, in legal tier marketing, in any context where the law or the surface itself demands a category. Outside those exceptions, most segments in your CRM are personalization-cost workarounds left over from human-era marketing economics.

Three Tiers

The solo operator runs a positioning loop on every reply. One document per active customer. AI updates after every interaction. The document contains the customer’s current job, alternative, objection, and position. Read it before every reply. Volume is what makes this competitive.

The startup founder skips the persona deck. The persona deck was the human-era artifact. Replace it in week one with a personalization stack. Capture every event. Maintain a live profile per buyer. Let AI generate a position per person. Deliver programmatically. The founder reads the deltas, not the personas.

The small business strategist audits the segment vocabulary. Walk through every segment label in the CRM, in email, in advertising, in product. Write the year it was created and the assumption it was built on. If the assumption was personalization cost, the segment is obsolete. Replace it with a model.

Operating Assets

Prompt Pack

The prompt pack ships five prompts that turn STP into a weekly positioning practice. Diagnose. Stress-test. Translate. Decide. Loop. Run them in sequence against any capable model. The first prompt scores your existing segments by predictive value. The second re-runs the analysis under the AI-era inversion and marks each segment KEEP, REPLACE, or SIGNAL. The third translates the output to your operating tier. The fourth forces a single move for the quarter. The fifth schedules the practice as recurring intelligence.

Worksheet

The worksheet runs the same logic on paper. Ninety minutes. Seven steps. One inventory of the segments you actually use. One audit of the year and assumption behind each. One scoring of the four bases. One mark of OBSOLETE, STANDS, or REVIEW per segment. One sketch of the personalization stack you would build today. One move for the quarter. One cadence for the loop.

Hope this helps. Tune in tomorrow for another framework, prompt pack and worksheet to help you become a better Operator.

- j -

About the author

Disruption Used to Take a Decade. Now It Takes a Year.

John Brewton — Mon, 27 Apr 2026 11:47:25 GMT

Stop grinding out posts one by one.

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We kick off May 1st, and there are only 50 spots (25 of which have already been sold). If you want your content to compound rather than reset to zero every day, this is where you build the system that finally makes it happen.

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Clayton Christensen published The Innovator’s Dilemma in 1997. He studied four industries:

Disk drives
Hydraulic excavators
Mini-mills
Discount retail

He found one pattern across all four.

Well-managed companies failed for rational reasons. Their best customers wanted sustaining improvements. Resources flowed to those customers. The bottom of the market and the non-consumers stayed open. Disruptors entered there. Then climbed.

The arc took fifteen years in disk drives. Twenty in mini-mills. The framework assumed the incumbent had time to see the disruptor coming.

That assumption no longer holds.

The arc compressed.

AI-mediated production collapses the entrant’s cost curve to weeks. A junior analyst with copilots ships in two hours what a partner shipped in two days. Non-consumers reach the entrant through autonomous discovery, not through gatekeeper introductions. The decade Christensen documented is the year you are living through.

The framework still holds. The clock changed.

The framework now applies to careers.

If your role exists because clients valued the capability that an entrant can deliver at one-tenth the cost, you are the incumbent. Your sustaining improvements are your annual reviews. Your best customers are the bosses and partners who reward the work that no longer earns its premium.

Doing more of what is rewarded is exactly what causes the position to be lost.

The dilemma is identical at the personal scale.

The Worksheet

The worksheet is a single document with six steps.

Run it twice. Once for the company. Once for the career.

The six steps surface the dilemma in the order that matters. Name the customer. Audit the sustaining improvements. Identify the bottom of your market. Run the substitute scan.

Score the separation. Pick one move for the next ninety days.

Each step takes about ten minutes. Both passes take an hour. The worksheet has fillable answer blocks because the value is in writing the answers down. The discipline is the deliverable.

The career pass is where the framework earns its keep. Most operators have run a Christensen analysis on a company. Almost none have run one on themselves. The output is uncomfortable on purpose. The customers paying you for capability they no longer use are the ones you need to identify before they identify you.

The Prompt Pack

The prompt pack is five prompts that turn the worksheet into a recurring practice with a capable model.

Prompt 1: Diagnose your situation against the framework.
Prompt 2: Stress-test the diagnosis under the AI-era inversion, where the arc collapses from a decade to twelve months.
Prompt 3: Translate the analysis to your operating tier. Solo operator, startup founder, or small business strategist.
Prompt 4: Forces a decision and a ninety-day commitment.
Prompt 5: Schedules the practice with named trigger conditions for early re-runs.

Run them in sequence. Each prompt builds on the previous one. The fifth prompt makes this a quarterly review, not a one-time exercise. That is the only version of the practice that survives contact with a busy quarter.

The pack works against any capable model. Curly-brace placeholders mark the fields you fill in. The output is structured. The whole sequence runs in about forty minutes once you have the inputs.

Why both?

The worksheet is for the operator who wants to think the framework through with a pen. The prompt pack is for the operator who wants the model to do the structural work and reserve their attention for the decisions that matter.

Most subscribers will use both. The worksheet anchors the first pass and produces a baseline you can hand to a colleague or a coach. The prompt pack runs every ninety days after that and compares the new analysis to the baseline so you can see what moved.

The combination converts an idea you already know into a practice you actually run and build from. Christensen wrote the book twenty-nine years ago. The reason the framework still gets cited is that the underlying logic is correct. The reason most readers do not act on it is that the framework was written as an analytical instrument, not as an operating methodology. These two assets are my attempt to help you close that gap.

Failure can be the result of rational decisions made well. The implication is that doing more of what is already rewarded is not the answer. Doing different work is.

The disruption is not coming. It arrived while you’ve been waiting to do this work.

- j -

[Download PDF’s of the Prompt Pack and Worksheet below →]

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John Brewton documents the history and future of operating companies at Operating by John Brewton. He is a graduate of Harvard University and began his career as a Phd. student in economics at the University of Chicago. After selling his family’s B2B industrial distribution company in 2021, he has been helping business owners, founders and investors optimize their operations ever since. He is the founder of 6A East Partners, a research and advisory firm asking the question: What is the future of companies? He still cringes at his early LinkedIn posts and loves making content each and everyday, despite the protestations of his beloved wife, Fabiola, at times.

The Walt Disney Method For The Agent Era

John Brewton — Sun, 26 Apr 2026 12:03:56 GMT

Stop grinding out posts one by one.

The Compound Content Studio™ is a live, 2‑week AI immersion where we build your Claude-powered content system that multiplies your ideas into an endless stream of on-brand content.

This is the system John has built to create all of his content across social platforms. Jumpstart and scale your brand and content this May!

Grab Your Seat In the Studio Today

Start here.

In 1957 Walt Disney built three rooms in his Burbank studio.

One for dreaming.

One for planning.

One for criticism.

Walt moved his concepts from room to room. The walls provided the discipline that meetings rarely do.

Robert Dilts named the practice the Disney Method in 1994. It became standard reading for design firms, advertising agencies, and product teams. Three modes, one sequence, never simultaneous.

The reason it worked is the reason it was needed. Most ideation fails the same way. Three voices speak at once. The dreamer suggests an idea. The critic dismisses it. The realist never gets a chance to test it. The room produces half-formed work, defended or killed before it matures. Mixing the modes is what kills the output.

Walt separated the rooms because a human can only hold one mode at a time. The architecture was disciplined and forced a mindset switch.

What has changed in the Age of Agents?

That constraint disappeared.

An agent can dream, plan, and critique inside a single prompt. So that is what most operators ask it to do. They open one chat window, paste a problem, and ask for a solution. The agent obliges. It returns a half-formed plan, defended and killed in the same paragraph. Creativity collapses inside the prompt designed to produce it.

The Disney Method matters more in the agent era, not less. The discipline that used to require three rooms now requires three agents and an orchestrator who refuses to let them overlap.

Three agents. One sequence.

The Dreamer agent generates fifteen candidate solutions with no constraints, no budgets, and no prior failures. The Realist agent takes the dream literally and designs a six-step build sequence with cost, owner, and a thirty-day milestone. The Critic agent pressure-tests the plan, names three failure modes, and demands a go or no-go decision. You hold the orchestrator’s seat to enforce the wall between rooms.

The tier translation is straightforward. Solo operators run three threads and never open two at once. The friction of opening a new chat is the wall. Startup founders assign each mode to a teammate and their agent stack, and rotate roles quarterly to break up expertise capture. SMB strategists build three named agents with locked system prompts and convene the team in the right room for the right mode.

Run the sequence once on a real problem. Then put it on the calendar. Friday Dreamer session. Monday Realist review. Quarterly Critic round.

Hope this helps.

- j -

Download the workbook

I built a ten-page workbook that walks the full method on one specific problem you are trying to solve. It includes the framework, the AI-era inversion, four worksheet exercises, and five copy-paste prompts that turn each room into a specialized agent.

Download it for free here.

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Porter’s Five Forces, Reread for 2026

John Brewton — Sat, 25 Apr 2026 12:12:30 GMT

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In 1979, Michael Porter published “How Competitive Forces Shape Strategy” in Harvard Business Review. The article reframed strategy. Industry profitability is determined by five structural forces: rivalry among existing competitors, threat of new entrants, threat of substitutes, bargaining power of buyers, and bargaining power of suppliers. Forty-six years on, the framework still anchors nearly every MBA strategy syllabus.

It still holds. The operating context is inverted underneath it.

Porter’s framework rests on a single assumption that was unimpeachable in 1979 and questionable in 2026. Industry boundaries were stable enough to draw a line around. Actors inside that line were knowable, countable, and slow-moving. Information was asymmetric, expensive to gather, and bound by human cycle time. The framework was built on that floor.

That floor moved.

AI-mediated discovery breaks the asymmetries Porter took as foundational. Buyers compare hundreds of options in seconds through autonomous agents. New entrants face near-zero capability barriers in software-mediated work. Substitutes appear from adjacent capability stacks, not from within the named industry. The five forces still apply. Their relative weights inverted.

Most strategic plans still front-load rivalry analysis. The two forces that matter most in 2026 sit at the bottom of most leaders’ attention. Buyer power mediated by AI agents. Substitution from adjacent capability stacks. The framework holds. The reading order is inverted.

The solo operator stops positioning against named competitors. They map their business as a node in a capability stack and ask which adjacent capabilities to absorb and which to hand to an agent. The stack moves faster than the org chart.

The startup founder runs Five Forces weekly, not annually. The threat of new entrants is measured in months. Build the analysis into the Friday review. The first force to spike tells you where the next quarter’s capital goes.

The small-business strategist treats the buyer power inversion as the urgent threat. Customers are choosing through AI-mediated discovery. The buyer relationship built over decades is now intermediated by an agent that did not exist 18 months ago. The other four forces matter. This one moves first.

The companion prompt pack turns these ideas into a practice.

Five prompts: Diagnose, Stress-test, Translate, Decide, Loop. The first runs Five Forces on your company. The second re-runs it under AI-era conditions. The third translates to your operator tier. The fourth forces a decision and names the trade-off. The fifth schedules the practice as a weekly cadence with a 90-day review.

Porter was correct for 1979. The translation is our work in 2026.

Companies are becoming tech stacks.

We are all becoming companies.

- j -

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Download a pdf of the prompt pack here.

Scaling Down: The Nobel Prize-Winning Answer to “Should I Just Do It Myself?”

John Brewton — Wed, 25 Feb 2026 13:06:37 GMT

160 Substack Founders Have Become Operating Founders

The Operating Founder Program is a weekly live Zoom cohort where we take exactly this kind of thinking — academic rigor meets real-world operations — and apply it directly to your business. Strategy, systems, decision-making, and the occasional dark joke about spreadsheets.

Here’s what’s happening right now. On March 9th, we’re launching the Operating Founder Skool community — a private space for ongoing discussion, resource sharing, and direct access between sessions. A full year of membership is included free for the next 40 people who sign up for the Operating Founder program before February 28th.

60 seats are already gone. 40 left. The math is not complicated.

Once these fill, the Operating Founder offer disappears forever.

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Good Morning Operators

In 1937, a 27-year-old British economist named Ronald Coase asked a seemingly “stupid” question:

Why do companies exist?

Seriously. If markets are so efficient, if you can just buy anything from anyone, why would you ever bother hiring people, renting office space, and dealing with HR?

Why not just contract everything out?

Coase’s answer was elegant. Companies exist because markets have friction.

Finding vendors takes time.

Negotiating contracts is exhausting.

Monitoring quality from the outside is a nightmare.

He called these transaction costs, the invisible tax on every deal you do.

Sixty years later, Oliver Williamson took Coase’s idea and turned it into a full-blown framework. He won a Nobel Prize for it. The Swedish Academy essentially gave a man the most prestigious award in economics for explaining why you sometimes hire an accountant and sometimes use TurboTax.

If you’re especially interested in the economics and history of all of this, here’s a link to a set of articles that cover everything you’d ever want to know from Oxford University.

Here’s why this matters to you:

Every solopreneur, first-time founder, and small business operator makes transaction cost decisions dozens of times a week.

You just don’t call them that:

You call them “should I learn Canva or hire a designer?”
You call them “do I need an employee or a contractor?”
You call them “is this AI tool actually saving me time or am I spending three hours prompt-engineering something a freelancer could do in forty minutes?”

Coase and Williamson gave us the cheat code.

The decision comes down to three variables:

Frequency. How often do you need this done? If it’s once, buy it. If it’s daily, the calculus changes fast.
Uncertainty. How hard is it to specify exactly what you want? The vaguer the task, the more expensive it gets to outsource — because you’ll pay in revisions, miscommunication, and quiet resentment.
Asset specificity. Does this task require knowledge that’s unique to your business? If someone needs to deeply understand your brand, your customers, your weird little niche — that’s high asset specificity. And that’s where outsourcing falls apart.

When I was scaling my family’s industrial distribution business, every growth phase forced these tradeoffs. At $27M, we outsourced things that made no sense to outsource at $35M. The same truth held at $43M and $53M.

The transaction costs shifted as the company changed.

They always do.

The mistake most small operators make is treating this as a vibes-based decision. “I feel like I should hire someone.”

Cool. Feelings are not a framework.

Map the frequency. Assess the uncertainty. Measure the specificity.

Coase figured this out almost ninety years ago.

Pretty wild. I can’t think of anything I’ve figured out thus far that could be reasonably expected to apply ninety years from now. How about you?

Hope this helps.

- j -

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Scaling Down the Big Ideas: Good to Great Starts & Ends With You

John Brewton — Wed, 18 Feb 2026 12:17:21 GMT

SCALING DOWN THE BIG IDEAS | Edition 02

We sold out the first 100 Operating Founder seats in two weeks.

So I’ve opened 100 new seats (50 are already taken).

What You Get

Every Friday, you get a 60-minute live cohort session with me. Here’s what’s inside:

The real numbers. Behind the scenes of everything I’m building — strategy, mistakes, pivots, revenue — documented in real time.
Business model development. Business plans, pricing strategy, revenue models, and scalable operations — not content tips.
Live tutorials + my actual data. The same Google Sheets I use, walked through live. No curated screenshots.
Every template I use. Download and deploy immediately.
20 min of open Q&A. Strategy, content, growth, monetization — nothing off-limits.
Monthly guest speakers. Platform growth, content design, creator ops, and the tools that actually move the needle.
Access to a community of top-quality Substack writers and collaborators to build your audiences and content alongside and in partnership with.

$99 gets you 52 consecutive weeks — a front-row seat to how I build everything, plus a cohort of serious founders building alongside you.

The offer closes February 28th, or when the remaining 50 seats fill. Whichever comes first.

Once they’re gone, the Operating Founder tier goes away entirely.

[Become an Operating Founder → 50 seats remaining]

Become an Operating Founder

Breaking down Jim Collins’ seminal framework — and why every insight in it is more actionable for creators, solo operators and founders than for the Fortune 500 companies it was written about.

In 2001, Jim Collins published one of the most influential business books ever written. He and his research team spent five years studying 11 companies that made a dramatic, sustained leap from average to exceptional performance. They wanted to know why some companies become truly great while most stay permanently stuck at good.

I read Good to Great for the first time in 2006 and then used at as my operating manual, alongside Any Grove’s High Output Management to optimize and scale R.G. Brewton, my family’s B2B industrial distribution and inventory management company. The ideas in this book were integral to our scaling from $27 million to +$50 million in annual revenues, and building a truly world-class operation that attracted high-quality buyers.

Using Collins’ framework as a philosophical foundation, we scaled and successfully exited. The Hedgehog Concept clarified our focus. The flywheel gave us language for why consistent, compounding action was beating our more reactive competitors. Level 5 thinking changed how I showed up as a leader and developed leaders within the organization.

The framework is equally, if not more, powerful for one-person businesses, embryonic startups, and small operators than it ever was for the large corporations Collins studied.

Why? Because the scarce inputs (humility, discipline, focus, and consistent action) are completely accessible to you right now. No board approval required. And if you build these traits into your operation from the start, then each incremental level of growth you achieve will adopt these core characteristics that predict success.

Here are the seven big ideas, translated for builders like you.

The Seven Ideas — Translated for Operators

1. Level 5 Leadership → Make the work the hero, not you.

Collins found that the leaders who drove the most dramatic transformations were paradoxically humble, ferociously ambitious for the institution, not for themselves. For solo founders, this translates into a single discipline: anchor your status in the quality and consistency of your output, not in being seen as a visionary. When you stop needing the business to validate your identity, you can make clearer decisions about it and produce more value for your audience, not your ego.

2. First Who, Then What → Choose your collaborators before your projects.

Before strategy, Collins argues, comes people. For tiny teams, the “bus” metaphor becomes: who gets access to your time, attention, and trust. One misaligned collaborator (designer, co-host, advisor, early hire) can distort your roadmap for months. For creators, this also applies to your audience: be more intentional about who you’re building for than what you’re building.

3. Confront the Brutal Facts → Replace vibes with reality loops.

Great companies build a culture where inconvenient truths are welcomed, not punished. For solo operators, the danger is you have no internal checks, you can stay in delusion indefinitely. A weekly one-page reality check (revenue by product, retention, content performance, deep work hours) is your Stockdale Paradox ritual: hold the belief that you will succeed while fully accepting what your current numbers are actually telling you.

4. The Hedgehog Concept → Design your personal monopoly.

This is the most immediately actionable idea in the book. It sits at the intersection of three circles: what you can be genuinely best at, what you’re deeply passionate about, and what drives your economic engine. For one-person operators, “best in the world” becomes “undeniably top-tier for a specific someone.” The narrower you define the scope, the more tractable “best” becomes. This is the concept I’d encourage you to take most seriously, it’s the clearest path from good to great at any scale.

5. Culture of Discipline → Systems that survive your moods.

Discipline, Collins argues, is what allows consistent output when motivation fluctuates. For micro-operators, culture is mostly: your habits, your calendar, and your willingness to say no. A non-negotiable publishing cadence, a firm “stop-doing” list, and two or three hard constraints about who you serve, these are the structures inside which great work becomes possible.

6. Technology as Accelerator → Tools amplify strategy; they don’t replace it.

Collins found that great companies adopted technology to fit their Hedgehog Concept, not to keep up with trends. For solo founders, this is permission to ignore most of what appears in a trend deck. If a tool doesn’t directly accelerate content creation, sales, or product improvement within your actual strategy, it’s probably distraction dressed as productivity. New software, new tools, new applications are not going to become your differentiator; how you learn to work with the primary pieces of technology you use is essential.

Note: You don’t need to add new AI tools every month (most of these apps will become features of the larger platforms anyway). Specialize into a primary set of tools or platforms, not an everchanging suite of more. For me its been Perplexity and Claude, my design tools (Canva/Gamma/MidJourney) and Google Drive/Notion.

7. The Flywheel → Tiny wins compound if you don’t interrupt them.

The doom loop for one-person businesses is particularly vicious: a bad month leads to a new niche, new offer, new platform — destroying whatever slow-building compounding was already happening. The flywheel is the alternative: a repeatable loop where each cycle makes the next easier. Create → attract → convert → deliver → learn → improve → repeat. Run the same core loop enough times that you can predict its output. Only then add complexity.

(Access the entire library of articles and resources for $7.99 per month)

0 to 55,000 - The First 90 Days Playbook - What I’d Do Differently Knowing What I Know Now
The Operating by John Brewton Resource Library - No Filler. All Killer.
WINNING THE LOSER’S GAME: The Creator Economy and the Companies We All Need to Build
Operating Stories: Hermès and the Manufacturing of Scarcity
Operating Economics: Building Antifragile Companies
How Three Decades Rewrote the Economics of Companies

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Good to Great Solopreneur Tools

The free version above has given you the map.

The paid version below gives you the tools to navigate it.

Paid subscribers get the full deep-dive analysis — three movements covering the personal operating system, the strategy layer, and the compounding engine — plus four purpose-built assets you can use immediately in your own business:

Asset 1: The Micro-Hedgehog Worksheet — The single most important strategic exercise you can do for a one-person business. Three circles, calibrated for solo operators, with guiding questions designed to surface your personal monopoly. Most founders spend years circling what could be discovered in an afternoon with the right framework.

Asset 2: The Founder Flywheel Template — A fillable visual map of your personal creator-consultant flywheel, with diagnostic questions at each stage. Designed to make your compounding loop explicit — so you can stop accidentally breaking it every time growth plateaus.

Asset 3: The Brutal Facts Weekly Review — A one-page operating ritual: revenue by product, key metrics, deep work vs. admin hours, and a structured “autopsy without blame” for the week’s biggest miss. This is the closest thing to a weekly board meeting for a one-person business.

Asset 4: The Good-to-Great Translation Card — A clean, shareable reference card mapping all seven Collins concepts to their solo-operator equivalent in a single sentence each. Keep it. Use it as a filter when you’re making strategic decisions.

Collins’ framework took five years and a research team to develop. These tools compress the most actionable parts into something you can actually use this week — in your business, at your scale, without a management layer or a consultant.

A Word About Operating Founder

Every Friday, I run a 60-minute live session for Operating Founders — documenting how I’m building this newsletter and business in real time. Not polished case studies. The actual strategy, the real numbers, the live decisions.

Here’s what you get:

Weekly 60-minute live Zoom sessions
Behind-the-scenes of everything I’m building, as I’m building it
Content creation walkthroughs — exactly how I make what I make
My actual growth data and performance spreadsheets (not screenshots — the real files)
Blank templates of every asset I use, yours to download immediately
20 minutes of open Q&A every session — nothing off limits

We sold out 100 seats in two weeks. I opened more.

If you’re building something and want to do it with someone who has done it before — this is the room. Become an Operating Founder →

Become an Operating Founder

We Are All Becoming Companies

Andy Grove’s Playbook for the Rest of Us: How to Spot a Strategic Inflection Point When You Are the Entire Company

John Brewton — Wed, 11 Feb 2026 12:42:17 GMT

I wanted to build something more useful than another article you bookmark and never reopen. So this piece comes in layers.

The article gives you Grove's framework in under five minutes. Below it is a resource hub with a scored diagnostic, a decision-making exercise, and a full experiment library, each built with copy-paste prompts that turn Claude into a strategic advisor who tracks your business month to month and tells you what you do not want to hear.

Every tool includes instructions for setting up Claude Projects so the system stays alive between conversations and gets sharper the longer you use it.

I hope this helps.

- john -

100 People Became Operating Founders in Two Weeks

So I’ve opened 100 new seats (50 are already taken).

What You Get

Every Friday, you get a 60-minute live cohort session with me. Here’s what’s inside:

The real numbers. Behind the scenes of everything I’m building — strategy, mistakes, pivots, revenue — documented in real time.
Business model development. Business plans, pricing strategy, revenue models, and scalable operations — not content tips.
Live tutorials + my actual data. The same Google Sheets I use, walked through live. No curated screenshots.
Every template I use. Download and deploy immediately.
20 min of open Q&A. Strategy, content, growth, monetization — nothing off-limits.
Monthly guest speakers. Platform growth, content design, creator ops, and the tools that actually move the needle.
Access to a community of top-quality Substack writers and collaborators to build your audiences and content alongside and in partnership with.

$99 gets you 52 consecutive weeks — a front-row seat to how I build everything, plus a cohort of serious founders building alongside you.

The offer closes February 28th, or when the remaining 50 seats fill. Whichever comes first.

Once they’re gone, the Operating Founder tier goes away entirely.

[Become an Operating Founder → 50 seats remaining]

Subscribe now

Start Here

Grove wrote Only the Paranoid Survive as the CEO of Intel. But his real contribution was a system any business can use to recognize when the current game is over and find the next one. This is my attempt to scale it down to something you can run from a laptop.

At the start of Only the Paranoid Survive, Intel is not the Intel we know. It is a memory company. DRAMs are its identity, its pride, its origin story. Then Japanese competitors arrive with lower costs, better quality, and patient capital. The old moves stop working. Grove eventually makes the call that defines the company: exit memories, pivot to microprocessors.

Inside the building, that decision feels like amputating a limb. Outside, in hindsight, it looks obvious.

You and I don’t run Intel. But we live smaller versions of this arc constantly. Your main traffic source collapses after a platform tweak. A new AI tool does 70 percent of what you sell, for free. A customer segment you built around quietly stops buying.

Grove’s core question is the same one you face: what do you do when the way you have always made money quietly stops working?

What Is a Strategic Inflection Point?

Grove called it a strategic inflection point: the moment when forces shaping your business change enough that the old rules no longer apply. Not 10 percent more competition. An order-of-magnitude shift in technology, regulation, or customer behavior.

From the inside, it does not arrive as an announcement. It feels like this: what used to work stops working, even when you execute well. Your forecasts break. Small, weird competitors suddenly matter more than the big, familiar ones.

The language matters. Once you can say “this might be a strategic inflection point,” you give yourself permission to ask a bigger question than “how do I fix my funnel?” The question becomes: is it time to change the business, not just the tactics?

How to Build a Paranoia Radar for Your Business

Grove’s paranoia was not anxiety. It was a radar. At Intel, he leaned on people at the periphery, sales reps and field engineers, because they felt shifts before the spreadsheets showed them.

If you are a solo operator or running a small team, that radar has to be built into how you work. Three inputs matter most.

Metrics that actually represent health. Leads per week, close rate, churn, effective hourly rate. Watch for decoupling: more effort, worse results.

Customer conversations. Keep a running log of objections, new use cases, and tools your customers are trying instead of you. Pay attention when the questions change.

Edge competitors and substitutes. Once a month, ask: what are my customers trying instead of hiring me? Templates, AI tools, DIY, bigger platforms. These are the Japanese DRAM makers in your world.

Then run a 30-minute monthly paranoia review. What changed in my metrics? What changed in what customers are saying? What changed in the ecosystem? The goal is not to predict the future. It is to avoid being surprised by the present.

How to Run Bounded Experiments When You Don’t Know What’s Next

One of Grove’s best lines: “Let chaos reign, then rein it in.” Early on, you need experiments and multiple bets because you do not yet know which path will work. Later, you must converge.

For a small business, “chaos” means deliberately running bounded experiments. A 30-day positioning test around a narrower niche. A higher-ticket offer pitched to 10 warm prospects. A four-to-six-week sprint on one new channel with a concrete cadence. The chaos is in running multiple probes at once. The hard part is what comes after: you pick one direction and kill most of the rest.

Your unfair advantage over Intel is that you do not have fabs and 10,000 employees pointing one way. Your disadvantage is that the only person who can decide to rein chaos in is you.

Why You Have to Kill Your Old Business Identity

The most painful part of Grove’s story is not intellectual. It is emotional. Intel had to stop being “a memory company” to survive.

Grove once asked his chairman, Gordon Moore: “If we got kicked out and the board brought in a new CEO, what would he do?” Moore said he would get them out of memories. Grove responded: “Why shouldn’t you and I walk out the door, come back, and do it ourselves?”

Run that exercise on your own business. If an outsider took over tomorrow with no attachment to your history, what would they shut down? What would they raise prices on? Which customer segment would they walk away from? Pick the answer that makes you slightly nauseous and build a small, time-boxed test around it.

A Paranoid Operating System You Can Actually Run

Assemble this into a rhythm.

Weekly. One paranoia check: did anything signal that something important is changing? One micro-experiment with a clear hypothesis.

Monthly. Review your core numbers. Read through customer conversations for new patterns. Scan for ecosystem changes that could compound over six to twelve months.

Quarterly. Run the outside CEO exercise. Choose one bigger bet and give it a real 90-day run.

You do not need to live like a 1990s CEO grinding through back-to-back crisis meetings. You just need to be paranoid enough, in a structured way, that your business evolves a little faster than the world around it.

You Might Enjoy These

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I built this article as a system, not just an essay. Below are the tools that turn Grove’s ideas into something you can run in your business this week. Pick the level that fits where you are right now.

📄 Read: The Visual Deep Dive

Download the full article as a designed visual PDF

The complete argument in a scannable, shareable format. Same ideas, better for reading on a tablet, printing, or sending to a business partner. If you prefer visuals over long-scroll text, start here.

📊 Assess: Strategic Inflection Point Diagnostic

Download the Inflection Point Diagnostic

A 12-question scored self-assessment organized into four categories: Execution Decay, Customer Signal Shift, Ecosystem Disruption, and Identity Grip. Score yourself, match your total to one of three interpretation bands (Stable, Watch Closely, Act Now), and see which category is your biggest risk. Includes a full Claude Project companion with monthly prompts and setup instructions so you can turn this into a living monthly practice with AI as your confrontation partner. Run it quarterly before your Outside CEO Exercise.

🎯 Decide: The Outside CEO Exercise

Download the Outside CEO Exercise

Five questions that put you in the chair of a new CEO with zero emotional attachment to your history. What would they shut down? What would they raise prices on? Which customers would they fire? Includes a Claude Prompt Companion with five copy-paste prompts engineered to produce the blunt, uncomfortable feedback you cannot get from yourself. Use it quarterly.

🧪 Act: The Bounded Chaos Experiment Lab (Paid Subscribers)

If the diagnostic told you to watch closely or act now, and the Outside CEO Exercise showed you what needs to change, the Experiment Lab gives you the system for testing that change without betting the whole business.

Six pre-structured experiments (positioning tests, premium offer tests, channel sprints, segment exits, content bets, pricing architecture shifts), each with hypothesis templates, metrics, kill criteria, and minimum viable versions you can launch this week. Plus a full Claude Project companion with lifecycle prompts that take you from experiment selection through the convergence decision.

This is the asset that turns Grove’s “let chaos reign, then rein it in” into an operating system.

👇 Available to paid subscribers below.

📚 Go Deep: The Full Long-Form Article and Research Appendix (Paid Subscribers)

The complete 3,000-word analysis including sections not in the condensed version above: a decision-making framework for uncertainty (upside, survivable downside, smallest reversible test), how to build constructive confrontation mechanisms when you work alone, how The Economist and The New York Times framed Grove’s ideas differently over two decades, and a full research appendix with categorized sources.

👇 Available to paid subscribers below.

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Operating by John Brewton: Scaling Down The Big Ideas

Psychological Safety Needs a Fifth Behavior. Challenge the AI.

New to Operating?

Check out these reader favorites:

Become a paid subscriber to join the Operating Skool community and attend our weekly live Office Hour Q&A’s w/ John.

The Four Behaviors

The Team. The Unit.

The Addition

The fifth behavior

Install

Five Prompts

About the author

Appendix. Sources.

Foundational research on psychological safety

AI on the team

AI sycophancy. The new failure mode.

The April 2025 GPT-4o sycophancy event

Psychological safety meets AI

The Mckinsey Seven Ss Became Eight in 2023

New to Operating?

Become a paid subscriber to join the Operating Skool community and attend our weekly live Office Hour Q&A’s w/ John.

Start Here

The Assumption

The 8th S

Three operator translations

The full pack

The principle

About the author

Philip Kotler formalized STP at Kellogg in 1969 to make personalization economically possible.

Bye Bye Bye Workaround

Three Tiers

Operating Assets

Prompt Pack

Worksheet

Hope this helps. Tune in tomorrow for another framework, prompt pack and worksheet to help you become a better Operator.

About the author

Disruption Used to Take a Decade. Now It Takes a Year.

Stop grinding out posts one by one.

The Compound Content Studio™ is a live, 2‑week AI immersion where we build your Claude-powered content system that multiplies your ideas into an endless stream of on-brand content.

Start Here

The arc compressed.

The framework now applies to careers.

The Worksheet

The Prompt Pack

Why both?

New to Operating?

Become a paid subscriber to join the Operating Skool community and attend our weekly live Office Hour Q&A’s w/ John.

The Walt Disney Method For The Agent Era

Stop grinding out posts one by one.

The Compound Content Studio™ is a live, 2‑week AI immersion where we build your Claude-powered content system that multiplies your ideas into an endless stream of on-brand content.

Start here.

What has changed in the Age of Agents?

Three agents. One sequence.

Download the workbook

New to Operating?

Become a paid subscriber to join the Operating Skool community and attend our weekly live Office Hour Q&A’s w/ John.

Porter’s Five Forces, Reread for 2026

New to Operating?

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Scaling Down: The Nobel Prize-Winning Answer to “Should I Just Do It Myself?”

160 Substack Founders Have Become Operating Founders

Once these fill, the Operating Founder offer disappears forever.

Good Morning Operators

Here’s why this matters to you:

I built something to help you.

Are you new to Operating?

You Might Enjoy These

(Access the entire library of articles and resources for $7.99 per month)

Become a paid subscriber to access all the content ($7.99 / month) or get to work with us and become a member of the Operating Founder cohort for $99 (annual).

Scaling Down the Big Ideas: Good to Great Starts & Ends With You

We sold out the first 100 Operating Founder seats in two weeks.

What You Get

The offer closes February 28th, or when the remaining 50 seats fill. Whichever comes first.

The Seven Ideas — Translated for Operators

Good to Great Solopreneur Tools

A Word About Operating Founder

Here’s what you get:

We Are All Becoming Companies

Andy Grove’s Playbook for the Rest of Us: How to Spot a Strategic Inflection Point When You Are the Entire Company

I wanted to build something more useful than another article you bookmark and never reopen. So this piece comes in layers.