Autumn 2026

Considerations

Hard ideas, explained with things you already know. Pick a lane, or narrow by your industry, company size, practice or topic.

46 essays
· industry, size, practice, topic
A chef at the host stand seating guests while his cooks wait idle behind the pass
Cover story · Zero to OneThe founder is still the roadmapThe product sells, and every decision still waits on one person who never says why. What that cost one founder, and the two moves that change it.6 min readRead the essay
A recipe card pinned beside a working kitchen line with four cooks at their stations
Zero to OneA recipe is not a kitchenOne cook can prove a dish. A restaurant needs a kitchen. What happens when the leader never leaves the stove, and what a kitchen has that a recipe doesn't.6 min read
A builder handing a ring of keys to a real estate agent at the gate of a large new house while older neighbors watch from their porches
Small Business and StartupsEngineering and sales want different thingsA major feature reached GA and two people used it, because nobody asked sales until it was built. The questions to ask sales before you start.4 min read
A full water tower feeding a nearly closed pipe that drips into an empty bucket at a shop door
Small Business and StartupsCash is water, and timing is the pipeWhy a profitable month can still leave you short on Friday, and why the money you could raise today might not be there tomorrow.5 min read
A man in a saffron exoskeleton lifting a tall stack of file boxes in an open-plan office
Enterprise StrategyAI should be a supersuit, not a severance packageA suit on a rack lifts nothing. Build AI around what each person is great at and what drains them, and the headcount math stops being the whole plan.6 min read
Five different houses on one street, all fed by a single main pipe underground while a plumber works on a joint
Enterprise StrategyOne platform out of five acquisitionsAt Wiser, several products were pulling the same prices from the same sites, separately. Turning that into one platform meant treating the data as the product, and letting the roadmap do the moving.6 min read
Stalled traffic on a city boulevard beside a saffron bike lane with one cyclist, a man with a clipboard watching from the sidewalk
Enterprise StrategyTraffic was a stand-in for valueCount cars and a traffic jam looks like a great day. Visits are heading where impressions went, and the human visits that remain are worth more.6 min read
A wooden sailboat hauled out in dry dock, a worker scraping the hull
A Healthy Life in BusinessThe yearly dry dockOnce a year I end every recurring meeting and rebuild my time around what I want the next year to hold. Boats get hauled out for the same reason.4 min read
A man without his glasses squinting down a dim hallway toward a lit doorway, his glasses left folded on a side table behind him
Zero to OneUse fuzzy metrics until you get good onesNothing new has been measured before, so every early metric is a proxy. Admit it, declare success and failure up front, and sharpen the number as you go.5 min read
A nurse adjusting a dial on a neonatal incubator in a hospital ward at night, a nursery of empty cribs through the window behind her
Enterprise StrategyAn innovation lab is not an incubatorLabs are good at making new things. Incubators are good at keeping new things alive until they can breathe on their own. Big companies tend to build the first and skip the second.6 min read
A busy bakery and, through a doorway at the back, a baker hunched over a sewing machine in a cramped tailor's workroom
Small Business and StartupsThe AI trapA service company built itself a great AI dashboard and sold it to six owners it knew. What it ended up with was a tool, but not a product.5 min read
Schoolchildren all chasing one ball across a field while a coach with a clipboard watches the empty goal
Zero to OneFrom pickup game to teamIn a pickup game everyone runs to the ball. A team has positions. Who to sign first, and how to choose between duplicating yourself and firing yourself.5 min read
The whole restaurant staff crowded around one diner while a cook carries a single elaborate plate past tables of waiting guests
Zero to OneDon't become one customer's private chefYour biggest early customer keeps asking for "just one thing." A year later you're cooking for one table.5 min read
A builder pressing his hand into a freshly poured, roped-off square of sidewalk while a neighbor digs up a flower bed
Zero to OneWet cementSome early decisions set hard. Most stay soft for years. Knowing which is which tells you where to slow down.5 min read
A boy sitting against the school lockers with a box of candy on his knees, holding up one packet while classmates lean in and one offers a coin
Zero to OneYour first price is a guessIn middle school I sold gum for a quarter and imported candy for five dollars. The gum brought kids in. The candy taught me to price on value.6 min read
A long line waiting along a velvet rope in a credit union lobby while the branch manager switches on the lamp at an extra station
Small Business and StartupsOpen the lane where the line isA branch with a long line needs a station someone can open when the line forms. Why I stopped hiring for roles and started hiring people.5 min read
A small restaurant with a full parking lot and a line at the door, the owner sitting on an upturned crate by the kitchen door with a notebook
Small Business and StartupsThe full parking lotA restaurant doubled its customers in a year and still couldn't afford a second location. Busy hides what each customer costs you to serve.4 min read
A worker on a ladder rolling up the awning of an old department store beside a covered shopping arcade
Small Business and StartupsThe anchor tenantWhen a big client leaves, my first question is "How does this benefit you?" What a departing anchor frees up, and what to know before it happens.5 min read
A barber on a step stool repainting one panel of the price board above the mirrors while regulars wait with their newspapers
Small Business and StartupsNobody reads the menu boardOwners put off raising prices for years while costs climb. Most customers are reading the value, and the number matters less than you fear.5 min read
A row of office workers whispering down a long line of desks, the last man puzzling over a crumpled note
Enterprise StrategyThe game of telephoneStrategy said in the boardroom arrives at the team as something else, and nobody lied along the way. Pass the reason with the words, then go ask the far end of the line.4 min read
A pruner on a wooden ladder in a winter orchard, cut branches piled on the ground below
Enterprise StrategyPruning the orchardOld trees still bearing a little fruit take the sun from young ones. Before you plant again, get the full harvest from what's already growing, or cut it.5 min read
A family eating dinner under plastic sheeting among sawhorses and paint cans while a builder measures a stripped wall in the next room
Enterprise StrategyRenovating while you live in the houseTransformations stall when every room gets torn up at once. Stage change so people can still cook dinner, and move them into each finished room before you start the next.6 min read
A man in a cardigan pricing an old wall clock at a family yard sale on a suburban driveway
A Healthy Life in BusinessEverything on the drivewayYou only learn how much you own when it's all out on the driveway. Once a year I put my whole calendar out there by ending every recurring meeting.4 min read
A hiker resting at the top of a ridge, looking down at the trail winding through the valley below
A Healthy Life in BusinessThe trail from the ridgeOn the climb you see the next switchback. From the ridge you can see the whole trail. Mine turned out to be one question I keep getting handed.5 min read
An old cordless phone on its charging stand, battery gauge showing, on a desk under a crowded wall calendar
A Healthy Life in BusinessYour battery, not your calendarTwo hours on the calendar can cost you very differently. What charges me is perspective, and I go looking for it on purpose.4 min read
A pit crew working the wheels of a vintage race car while the chief mechanic signals to the driver
A Healthy Life in BusinessThe pit crewWithout a crew you're on the side of the road, lifting the car yourself. Keep people close who'll tell you your tires are bald.4 min read
An empty ballpark in winter, snow on the stands, a lone groundskeeper crossing the field with a shovel
A Healthy Life in BusinessThe off-seasonAthletes use the off-season to rest and prepare. Mine is where I check whether work has started leaking into the rest of my life.4 min read
An older sailor trimming the sail of a small boat heeling through the waves while two crew work beside him
Small Business and StartupsTitles are for pay. Roles are for Tuesday.On a sailboat, the best sailor isn't always at the helm. Split how senior someone is from what the work needs from them, then write the names down.5 min read
Two people writing behind folded screens at opposite ends of a long table, their two sheets overlapped on a light box between them
Small Business and StartupsGrading PMs without grading the graderMost PM reviews are a manager's story the PM hears at the end. Take both reads blind, lay them over each other, and let the gaps run the conversation.5 min read
A quiet gym with a pegboard of unused membership cards and one small group working out with a coach
Enterprise StrategyA gym membership isn't a workoutHanding out AI licenses changes almost nothing by itself. What got one design team further in three weeks than in the six months before.6 min read
A commuter driving at dawn with a tall milkshake in his hand, a banana and a bagel untouched on the passenger seat
Zero to OneJobs-to-be-done is misused. Here's how Christensen actually taught it.Jobs-to-be-done has turned into a sticky-note template. The real method is slower, done in the field, and in payments it turned up a job nobody writes on a sticky note: don't make me look foolish.5 min read
A college quad crossed by worn dirt paths, a groundskeeper paving the most worn one
Enterprise StrategyYour company is about to have a thousand apps nobody ownsYou told everyone to build with AI. They will. How to govern a thousand homemade internal apps without banning them or waiting for the first leak.5 min read
Two neighbors cutting up a storm-felled oak across the street while a man on the curb holds a hand-drawn map and points down the block
Enterprise StrategyShipping under constraintDuring COVID, the obvious move was to build our own contact-tracing app. We didn't. On deciding what not to build, and why coaching teams beat building expertise.5 min read
A coach in a dim film room, game footage on the wall, circling one play on the notepad on his knee
Small Business and StartupsA new product leader's first ninety daysA new coach watches film before touching the playbook. How founders should set up a new product leader's first ninety days, and how the leader should spend them, starting with the calendar.6 min read
A country doctor watching a patient limp across worn floorboards, a clipboard ignored at his hip
Small Business and StartupsWhat thirty days inside a company turns upA questionnaire finds what it asks about. A month in the standups, customer calls and code reviews finds what's actually going on. A composite of what that month tends to show, and the questions to start with.4 min read
A harbor weather station at dawn, storm flags on the signal mast, a brass barometer by the hut door and a slate board chalked with forecast marks
Enterprise StrategyPlan like a weather forecastNobody calls the forecaster a liar when the ten-day outlook changes. Plan in three horizons, say how sure you are about each, and update them on a schedule.5 min read
A cook working through one dish at a plain counter, a recipe card propped up beside him and a small bell hanging from the shelf above the stove
Enterprise StrategyG.I.V.E. on one real decisionFrameworks are easy to explain and hard to use. Here's one concept run all the way through G.I.V.E. (goal, insight, value, expectations), failure criteria included.6 min read
A switchboard operator moving one cord to a new jack on an old telephone switchboard
Enterprise StrategyLet them change how they payAt Meta, a business chose how it paid for ads on day one and couldn't change it without starting over. Fixing that had a ten-figure impact.4 min read
A desk stacked with ledgers and statements, a mobile phone lying on the open ledger and a long receipt curling to the floor
Enterprise StrategyOutsourcing is a loanOutsourcing gets you the capability now. You pay interest on it for as long as you don't own it. At PenFed, the interest was a mobile app that shipped about once every 14 months.5 min read
A restaurant with a busy lamplit kitchen and a blank sign above the door, its tables empty while passers-by walk on
Enterprise StrategyThe brand is the product's first screenPenFed's old name told most of the people it wanted to serve that it wasn't for them. A year as interim CMO: a new name, year-round campaigns, and analytics that turned marketing into an investment.5 min read
A worried homeowner at his garden gate holding an empty leash while a mail carrier points down the block toward a gap in the hedge
Zero to OneA week to write the rulesDuring COVID I had about a week to write contact-tracing app guidelines for the CDC. Some of the most useful thinking came from a company that finds cars.4 min read
A machinist at a lathe holding a micrometer to a freshly cut part
Zero to OneLook for the driftMost product failure is drift: quiet and slow, and invisible until the parts stop fitting. Watch behavior first, and watch the meetings.5 min read
A desk covered in small folders tied up with string, one thick folder lying open in the lamplight
Enterprise StrategyTwo out of three should failA fund where every bet pays off is taking no risk. Declare how each AI pilot will succeed and how it will fail before it starts, then review them as a portfolio.5 min read
A carpenter on a ladder fitting a heavy timber beam through a half-demolished wall while a worker with a sledgehammer pauses to watch
Enterprise StrategyCut the layer, keep the decisionsAI can take over a lot of what management layers relay. It can't take the decisions they hold. Find those before you cut, or they land on someone by accident.5 min read
A half-built backyard deck, a carpenter drilling post holes with an auger while the homeowner watches from the back steps with a rolled-up plan
Small Business and StartupsStop funding teams by headcountA team gets eight people because it had seven last year. Nobody says what the eight are supposed to make true. Fund the problem instead, and let the team shape follow.5 min read
A cook finishing a plated dish at a butcher-block counter as a smiling guest steps in from the hall with his coat over one arm
Enterprise StrategySixty, twenty, twentySixty percent of any experience should be the pattern people already know. Twenty is yours. Twenty is the moment. Where to follow the pattern, and where to break it on purpose.5 min read

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FinTechPayments, data, access, riskRead the brief →HealthcareSystems, payers, digital healthRead the brief →Digital agenciesPricing, consolidation, owned IPRead the brief →PlatformsConsolidation, pricing, agentsRead the brief →AIFrom pilots to P&LRead the brief →

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