Tagged: Engineering Management

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The Org Chart Is the Product

For most of my career I believed I was building products but looking back, I was mostly building org charts. Every real scaling problem I hit — Weedmaps…

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Radical Uncertainty Is the Job

Most advice about building a company is the answer to a puzzle. The hardest parts were never puzzles. In 1921, the economist Frank Knight drew a line that…

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The Marginal Return of Intelligence (And the Marginal Return to It)

One week ago I announced Grazier Ventures and Aqen.ai. Since then I’ve been asked a version of the same question about a dozen times: how are you actually going…

The Org Chart Is Flattening & Nobody Has a Replacement

Two things happened last week that look unrelated but aren’t. JPMorgan told its 65,000 engineers and technologists that AI tool usage is now part of their performance reviews.…

“Tokenmaxxing” Is Lines-of-Code Thinking for the Agentic Era

Silicon Valley has a new competitive sport, and it’s exactly the mistake you think it is. The New York Times reported last week that engineers at Meta, OpenAI,…

Your AI Notetaker Is the Biggest Security Decision You’re Not Making

Every engineering leader I know is running at least one AI meeting recorder. Fathom, Otter, Fireflies, Granola — they show up in your Zoom call, they transcribe everything,…

Minutes Added To Workforce

Every company I’ve talked to in the last two quarters is asking the same question about AI: what’s the ROI? The instinct is to measure AI value in cost…

Block Just Cut 3,500 Jobs. You’re Reading It Wrong.

Jack Dorsey announced this week that Block is cutting roughly 3,500 people — about 40% of its workforce. The stock has been sliding for years. The headlines are…

Are You Managing Your Manager? (The Agentic Update)

In 2015, I stood in front of a room full of engineers at Code Driven NYC and laid out a formula for how individual contributors could take charge…

The Next Platform Giant Is Hiding in Plain Sight

Every major era of software development has produced a defining platform company. The one that quietly became the infrastructure everyone depends on. GitHub didn’t win because git was…

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The notebook, in your inbox. Every Tuesday, one essay on AI implementation, engineering leadership, or the operator-to-founder transition. No digests, no roundups, no AI-generated news — just the ideas I'm actually working through.