Writing · AI
AI.
Operator-tier notes on the agent layer, foundation models, the procurement-side and deployment-side problems the trade press is mostly not surfacing.
174 pieces. All writing.
- April 22, 2026 · 3 min
When your AI becomes a design partner, the design-team org chart collapses the same way the dev team's did.
- April 21, 2026 · 3 min
Denial works because appealing is expensive. Claimable inverts that.
- April 17, 2026 · 2 min
Per-token pricing isn't a billing change. It's a product-architecture verdict.
- April 16, 2026 · 2 min
AI doesn't read your hotel brand. It reads your API.
- April 16, 2026 · 2 min
Opus 4.7 ships with design. Your B2B moat just got reshaped.
- April 14, 2026 · 2 min
Urgent care has a competitor with no CAC.
- April 13, 2026 · 2 min
The imaging RCTs are unimplemented. The LLMs without evidence are everywhere.
- April 8, 2026 · 2 min
OpenAI's S-1 is the governance doc. Read it before the next contract.
- April 8, 2026 · 8 min
UnitedHealth invested $1.5B in AI. No Canadian payer invested anything equivalent. That gap compounds.
- March 22, 2026 · 6 min
I have always been here. Just one layer up now.
- March 14, 2026 · 2 min
The NYT failed the blind test publicly. The trust stack failed privately.
- February 16, 2026 · 2 min
Expedia's 10-K named agentic AI. The board owns the threat now.
- February 14, 2026 · 7 min
Yegge burns $100 an hour in parallel. The unit economics are still the question.
- February 13, 2026 · 3 min
Canada tried again. The U.S. 2016 playbook now applies.
- February 3, 2026 · 6 min
The AI content problem is not misinformation. It is that operators cannot tell what is real anymore.
- January 27, 2026 · 6 min
I read the Claude Constitution so you don't have to. It's mostly fine.
- January 22, 2026 · 2 min
55% / $36.6B / six IPOs. The number every health-AI deck cites is the same number that calls the top.
- January 17, 2026 · 2 min
30% gone to AI Overviews. The OTA equity story repriced.
- January 16, 2026 · 8 min
The next wave of foundation models will get the deployment layer wrong. The capex cycle guarantees it.
- January 15, 2026 · 5 min
The fine-tune is dead. Long live the prompt engineer.
- January 14, 2026 · 2 min
Most enterprises can't build a clean thesis. Expedia builds 1,500 agents a year.
- January 12, 2026 · 3 min
Pick a substrate. The decade's moat is downstream.
- January 5, 2026 · 2 min
DMA and Google AI agree on one thing. The OTA is the spread to compress.
- December 17, 2025 · 3 min
Airbnb made AI the fourth pillar. Specialized beat general where trust was scarcest.
- December 15, 2025 · 8 min
What the open-weights community actually shipped in 2025.
- December 14, 2025 · 6 min
The open-source agents will win the long tail. EU GPAI enforcement will accelerate it.
- December 13, 2025 · 2 min
'Agents eat SaaS' is a clean thesis. Most enterprises can't build a clean thesis.
- December 11, 2025 · 3 min
AI Overviews don't kill clicks. They kill the attribution chain that monetized the click.
- December 9, 2025 · 2 min
Provider AI runs ahead. Payer AI lags. Their interop runs slowest.
- December 8, 2025 · 3 min
Famous or indispensable. Travel platforms have to pick one.
- December 2, 2025 · 3 min
Colorado AI enforcement is active. Three health-AI bills converged. The patchwork accelerated.
- November 18, 2025 · 3 min
NYC Local Law 144 enforcement exposed a compliance gap. Most hiring-AI vendors failed the audit.
- November 17, 2025 · 3 min
The unowned position is between the watch and the EHR.
- November 17, 2025 · 6 min
What the safety teams got right in 2024 shows up in the Claude Constitution and the 36-AG pushback.
- November 16, 2025 · 5 min
The OTA isn't a destination. It's a click-out tax.
- November 15, 2025 · 3 min
Why I cancelled my GitHub Copilot in 2025.
- November 14, 2025 · 2 min
Canada is 44 of 47. The number is the citation, not the country.
- November 14, 2025 · 3 min
The MCP gambit, two years in: Claude Cowork is the product built on the bet.
- November 13, 2025 · 6 min
Tool use is the only benchmark that matters after Claude 4 can code for hours unsupervised.
- November 12, 2025 · 12 min
The IDE was always a waiting room.
- November 11, 2025 · 3 min
I trust eval results from companies that do not sell the model being evaluated. The Texas AG settlement is why that matters.
- November 9, 2025 · 3 min
Local models are real. Local-models-as-product mostly are not. DeepSeek is the dividing line.
- November 8, 2025 · 3 min
Ambient scribes are the one healthcare-AI category where evidence and adoption moved together.
- November 5, 2025 · 2 min
Urgency-led conversion is a leading indicator. The retention haircut is the trailing one.
- November 4, 2025 · 3 min
Amazon cut 14,000 corporate roles and blamed culture. The receipts show it was the manager ratio math.
- November 3, 2025 · 2 min
AI deployment is a data-engineering problem in a model-engineering costume.
- November 3, 2025 · 6 min
The AI-for-prior-authorization pilots are the CMS mandate bet. Here is how to classify them.
- October 27, 2025 · 3 min
The system that caused overtourism is being asked to fix it.
- October 21, 2025 · 6 min
The AI-generated travel itinerary product was always going to be the booking funnel. Expedia's 10-K confirmed it.
- October 20, 2025 · 2 min
Healthcare AI adoption isn't a growth story. It's a redistribution schedule.
- October 19, 2025 · 2 min
AI pricing creates two consumer outcomes. Regulation only sees one.
- October 15, 2025 · 3 min
California AB 1018 is the automated-decisions safety act the hiring-AI vendors didn't see coming.
- September 23, 2025 · 11 min
We have not seen magic yet.
- September 17, 2025 · 2 min
Energy is the new chip. The grid is the four-year overhang.
- September 15, 2025 · 3 min
Agent deployment crossed 50%. The skills gap is the ceiling.
- September 14, 2025 · 2 min
Aschenbrenner cuts both ways now.
- September 13, 2025 · 2 min
MAI-DxO is the procurement question now. Where do physicians + tools beat it?
- September 5, 2025 · 6 min
The eval is the product. The Texas AG healthcare AI settlement is the consequence of ignoring that.
- September 1, 2025 · 8 min
The routing layer in healthcare AI is bigger than the diagnosis layer. Six million unattached Canadians prove it.
- August 15, 2025 · 2 min
Anthropic ships every two weeks now. Your eval window just got eaten.
- August 14, 2025 · 3 min
OpenEvidence is Nadler's second act. 1M physician questions a day.
- July 16, 2025 · 3 min
Four bolts went unrecorded. The CMES record-keeping was the safety control.
- July 15, 2025 · 3 min
MAI-DxO reset the room. Position your deck against it.
- July 14, 2025 · 2 min
AI travel-planning crossed 50%. The OTA is the checkout now.
- July 1, 2025 · 3 min
Illinois banned AI therapy. The prohibition names the liability every mental-health startup avoided naming.
- June 24, 2025 · 3 min
Texas passed TRAIGA. Three states now have comprehensive AI laws. The patchwork is the policy.
- June 17, 2025 · 3 min
IBM replaced hundreds of HR staff with AI and confirmed the back-office pattern is structural, not experimental.
- June 15, 2025 · 8 min
Why the agent layer skipped the orchestration startups.
- June 14, 2025 · 6 min
The AI-in-everything wave broke earlier than consensus expected. McDonald's and Klarna are the receipts.
- June 12, 2025 · 6 min
AI in claim adjudication is the under-discussed health-AI win the prior-auth mandate is about to mainstream.
- June 10, 2025 · 6 min
Canada just funded 10,000 AI scribes. The scribe is the wedge. The workflow layer is the business.
- June 9, 2025 · 2 min
The essay isn't a forecast. It's a discourse-shaping instrument.
- June 8, 2025 · 3 min
Software 3.0 is a mental model. Don't ship it as a roadmap.
- June 3, 2025 · 3 min
California SB 53 is what SB 1047 would have become. The operator compliance posture is the same.
- May 29, 2025 · 2 min
The travel hacker is now a vintage profession.
- May 16, 2025 · 5 min
Amodei skipped the deployment timeline.
- May 15, 2025 · 2 min
The "agents aren't production-ready" take aged badly. The 54% receipt.
- May 14, 2025 · 2 min
The OTA endgame is being the agent's vendor, not the user's.
- May 14, 2025 · 3 min
Cluely raised $5.3M for a posture. The posture became the category.
- May 13, 2025 · 3 min
Topol named the longitudinal-data wedge.
- May 8, 2025 · 3 min
United deployed AI to catch skiplaggers. The Texas jury said skiplagging is legal.
- April 15, 2025 · 3 min
Duolingo cut contractors in January 2024 and called it AI. The actual AI memo came 15 months later.
- April 14, 2025 · 5 min
Pick a calendar. Defend a budget. AI 2027 or Normal Tech.
- April 10, 2025 · 6 min
AI for hospital staffing is the only optimization that addresses both the burnout data and the org-design problem.
- April 1, 2025 · 3 min
The defensible asset isn't the drug, it's the dossier.
- March 31, 2025 · 6 min
The demo video died when Google AI Overviews recommended eating rocks. Here is what replaced it.
- March 28, 2025 · 6 min
What the year of vibes actually changed: vibe coding is a real productivity shift, not a discourse moment.
- March 25, 2025 · 3 min
The Deel/Rippling lawsuit is the first corporate espionage case where the evidence is AI-generated data trails.
- March 19, 2025 · 6 min
DOGE is the largest public-sector AI displacement test in history. The operator lessons are transferable.
- February 25, 2025 · 3 min
The 'multi-agent' marketing flag appears whenever Shopify-style memos run ahead of actual deployments.
- February 15, 2025 · 3 min
Vibe coding was real. The walkback is the lesson.
- February 12, 2025 · 3 min
LLMflation is good news for everyone except AI-health startups.
- February 11, 2025 · 6 min
Canada's AI regulatory vacuum is not a feature. It is a liability at the investor table.
- February 6, 2025 · 3 min
On the AGI-by-2027 claim: DeepSeek's $5M training run made the debate structural, not theatrical.
- February 4, 2025 · 3 min
US federal AI regulation is now a four-year on/off cycle. Operators who built for the EO are overspending.
- February 2, 2025 · 3 min
AI workers are unfortunately slowed down by law. At least in some domains.
- January 30, 2025 · 3 min
The agent-handoff failure mode Air Canada paid $650 to document publicly.
- January 28, 2025 · 6 min
OpenAI Operator is the demo of what every travel and healthcare booking flow needs in 18 months.
- January 15, 2025 · 3 min
The retraining-cycle question your AI vendor cannot answer, and what that tells you.
- January 14, 2025 · 2 min
Stargate is industrial policy. AI capex moved up a floor.
- January 12, 2025 · 2 min
The EHR bundling clock starts when the wedge works.
- January 9, 2025 · 8 min
Itinerary rebooking is the right shape of agentic travel. Expedia finally agrees in its 10-K.
- January 6, 2025 · 3 min
Long-stay travelers are an unbuilt platform tier.
- January 2, 2025 · 6 min
AI radiology is real. AI-in-radiology-as-product is mostly not. The FDA data explains the gap.
- December 16, 2024 · 2 min
Amodei's compressed century stops at deployment.
- December 14, 2024 · 2 min
Anthropic open-sourced the plumbing. Your roadmap just got shorter.
- December 12, 2024 · 6 min
The FDA just shifted from product approval to process approval. Your AI-cleared moat got drained.
- November 28, 2024 · 6 min
The agent stack did not collapse. The wrong prediction collapsed. Salesforce has the receipt.
- November 20, 2024 · 3 min
The next travel category is opacity-as-a-service.
- November 18, 2024 · 3 min
The Trump election reset the US AI regulatory calendar. Canadian operators should not breathe easy.
- November 13, 2024 · 3 min
When the model is free, the EHR is the moat.
- November 12, 2024 · 6 min
Healthcare-AI procurement is its own skill. The Texas AG settlement proved why.
- November 11, 2024 · 6 min
The Techno-Optimist Manifesto is the document that made every operator choose a side.
- November 10, 2024 · 2 min
DAX Copilot is a CFO product.
- October 29, 2024 · 6 min
The agent layer landed last quarter. The operator layer didn't.
- October 23, 2024 · 3 min
The model card no one reads is now the governance document everyone will require.
- October 19, 2024 · 3 min
Two travel companies are quietly shipping agentic features. One will call it existential.
- October 15, 2024 · 3 min
AI's capital gravity is pulling investment away from every adjacent tech sector.
- October 14, 2024 · 4 min
The wearables stack is now upstream of biology.
- October 9, 2024 · 3 min
Newsom vetoed SB 1047. California AI regulation will return and it will look different when it does.
- October 8, 2024 · 3 min
Founder Mode, Chesky version. Airbnb is the receipt.
- October 4, 2024 · 2 min
Zitron called it 'subprime AI'. File the receipt.
- October 3, 2024 · 2 min
AI slop is in your procurement pipeline. Audit before you debate.
- October 1, 2024 · 3 min
The Fed's 50bp cut changed the cost of capital for AI infrastructure. Here is what that means for your build-vs-buy math.
- September 30, 2024 · 4 min
Even the AGI bulls are quietly long adoption risk.
- September 28, 2024 · 4 min
The post-Stack Overflow developer exists.
- September 25, 2024 · 3 min
Intelligence got cheaper. Judgment didn't.
- September 24, 2024 · 6 min
OpenAI o1 introduced slow thinking. The operator question is where slow thinking earns its 4x premium.
- September 23, 2024 · 3 min
The Intelligence Age is the next round's pitch.
- September 20, 2024 · 5 min
The agent runtime will be the operating system, not the model alone.
- September 17, 2024 · 4 min
The cost-per-token graph is not the cost-per-task graph. The capex numbers prove it.
- September 16, 2024 · 6 min
Founder Mode is not a management style. It is a reaction to AI making middle management structurally visible.
- September 15, 2024 · 5 min
Microsoft leased a nuclear reactor. The grid became the new chip.
- August 27, 2024 · 2 min
Human-in-the-loop is the only AI promise that Klarna had to honor.
- August 19, 2024 · 3 min
AI triage in the ED keeps not landing. The deployment gap is the reason.
- August 15, 2024 · 4 min
Goldman published the bear case. Every AI deck answers to Covello now.
- August 14, 2024 · 4 min
Founder Mode is a permission slip. Manager Mode is a default.
- August 8, 2024 · 2 min
Ambient scribes were never going to be a product category.
- July 26, 2024 · 4 min
The first wave of agent failures will look like infrastructure failures.
- July 16, 2024 · 3 min
Copilot crossed 100M. Your TMC just became substitutable.
- July 15, 2024 · 5 min
The post-search internet, briefly.
- July 14, 2024 · 2 min
Aschenbrenner wrote a forecast. The market read a budget.
- July 9, 2024 · 6 min
Amazon is doing to healthcare access what Booking did to travel. Here is how it ends.
- June 26, 2024 · 3 min
On the morning routine I stopped having.
- June 25, 2024 · 6 min
What 'Claude for Education' tells us about Anthropic's roadmap.
- June 12, 2024 · 3 min
Colorado passed the first comprehensive US state AI law. Operators in travel and health need to read it.
- May 28, 2024 · 6 min
The AI-in-corporate-travel category is the second-most underbuilt.
- May 21, 2024 · 7 min
On Toronto winters, briefly.
- May 20, 2024 · 3 min
The drug commoditizes. The data doesn't.
- May 15, 2024 · 5 min
The 'rich agent / poor agent' divide is coming.
- May 9, 2024 · 6 min
AI in airline operations: where the unsexy money is.
- April 30, 2024 · 5 min
The 'we use [foundation model X] under the hood' admission.
- April 22, 2024 · 7 min
Revenue management is now an inputs problem.
- April 10, 2024 · 4 min
The 'long-context window' was always a transition primitive.
- April 9, 2024 · 3 min
The clinical-decision-support liability question.
- March 28, 2024 · 5 min
The agent is not the user. Stop building UIs that pretend it is.
- March 26, 2024 · 6 min
The post-app stack, sketched.
- March 24, 2024 · 4 min
Stop benchmarking on benchmarks the lab made.
- March 12, 2024 · 2 min
The cottage was already the office.
- March 5, 2024 · 7 min
The long tail is what an agent does that an agent can't.
- February 28, 2024 · 4 min
The synthetic-data debate is a distraction.
- February 27, 2024 · 4 min
Why the 'AI killed the search engine' framing is premature.
- February 15, 2024 · 2 min
The chatbot was an employee. Air Canada paid $650 for that ruling.
- February 5, 2024 · 5 min
The reasoning model wars are about evaluation, not capability.
- February 2, 2024 · 8 min
The single industry that's invisible to current AI tooling.
- January 23, 2024 · 6 min
Specs are the new prompt.
- January 12, 2024 · 5 min
The agent-to-agent commerce question.
- January 10, 2024 · 6 min
AI scribes and the documentation-burden question.
- January 8, 2024 · 7 min
I Have Always Been Here
A late new year's note about finally writing this stuff down.
- January 4, 2024 · 6 min
Booking became underwriting last winter.
- January 2, 2024 · 3 min
What the biotech foundation models will look like.
- January 2, 2024 · 4 min
AI for pharmacy operations is undersold.
- January 1, 2024 · 7 min
AI-driven 'patient journey' tools mostly aren't.
- September 3, 2007 · 55 min
Neo-nomads: Between 'Anyware' and 'Anyplace'
A 2007 master's thesis. Full text, figures, bibliography, and PDF.