18 posts across Directing AI, Systems & Adoption, Work & Judgement, Supervising Agents
Four frontier-class models launched within days of each other, each strongest at a different kind of work. Here's how to match model to task without re-running the comparison every month.
4 min readOpenAI's CEO says AI security can't be patched into place. Anthropic's own IPO filing shows the business burning cash faster than it grows. Plan for both admissions instead of assuming they're already resolved.
4 min readAnthropic's draft IPO filing shows $16.3 billion in first-half revenue against an $80.7 billion net loss and $518 billion in compute commitments. The numbers are a vendor-risk planning problem for any team paying for AI, not just a headline about a funding round.
4 min readMost AI pilots don't fail loudly — they stop getting mentioned in standup while the subscription keeps renewing. Three questions that force the decision nobody schedules.
4 min readFour separate training commitments from Anthropic, OpenAI, and a joint industry fund over four months add up to more than $1 billion aimed at teaching people to use AI well. None of it bought a faster model — all of it bet that skill application is the bottleneck.
5 min readFour separate AI launches this year taught the same lesson from different angles: model choice matters less than task fit. Here are the three questions to ask before you pick a model for anything that matters.
4 min readEthan Mollick's research found the models best at doing your work alone score lower on helping you think it through, while a cheaper model does both well. Here's the three-question check for matching model to task.
4 min readMcKinsey's 2026 State of AI survey found only 6% of organizations see a measurable earnings return from AI. Its fix: for every dollar spent on the tool, spend five on the people using it.
4 min readA silent 40% token hike, a subsidized subscription, a budget built on sticker price, and an agent deployed where a prompt would do — four unrelated cost overruns from this year share one root cause. Here's the check that catches it before the invoice does.
5 min readOpenAI expanded ChatGPT Ads to roughly 40 countries this month, and only the Free and Go plans carry them. If your team never decided which ChatGPT tier people actually use, that gap just became a real cost.
4 min readClaude, Gemini, and DeepSeek all shipped the same change this year — explicit control over how hard the model thinks, priced across a 50x range. Here's the three-tier rule for matching effort to what a task actually needs.
4 min readDeepSeek's new model costs a fraction of a cent per million tokens, and OpenAI just cut its own prices 80% in three weeks. The tasks got cheaper — knowing which tier each one needs didn't.
4 min readWatching an agent work produces a specific reluctance to interrupt it, and that reluctance is expensive. Here are the four signals worth stopping on, and why the sunk cost is smaller than it feels.
5 min readUber exhausted its 2026 AI budget in four months. Sam Altman says enterprise cost complaints are now 'a meme.' The root cause isn't reckless spend — it's deploying always-on agents for tasks a single prompt could handle. Here's the three-tier framework that fixes it.
5 min readUber blew its annual AI budget in months. Simon Willison's $200 subscription runs $2,180 in compute. Anthropic's revenue went 5x in five months. If your team budgeted for AI tools in Q4, those numbers are already wrong — here's how to reset them.
4 min readClaude Pro subscribers consume $200–400 of compute per $20/month. OpenAI loses $1.22 for every $1 earned. GitHub Copilot switches to usage-based billing June 1. The price you pay for AI today is not the price it costs to run. Here's how to plan for when that changes.
5 min readLicences issued and hours saved are the two most common AI metrics and neither survives contact with reality. Four measures that tell you something, and one number worth having.
5 min readWhen Anthropic updated Claude to Opus 4.7, real-world token usage jumped roughly 40% — with no pricing announcement. Here's what that means for any team running AI workflows at any scale.
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