Technology, markets, policy, and the wider world.
Essays, operating notes, and observations from the archive.
All writing
20 essays · 2015–2026
2026
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Everyone's Inventing AI Ketchup
More people are writing than at any point in history, and somehow there is less to read. The reason is older than AI, and the fix is not the one most people reach for.
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The Agent Stack Is the New OS
Every conversation about agentic AI eventually lands on headcount reduction, because it is the one metric everyone in the room knows how to measure. That is an analogy problem, and the wrong analogy produces wrong decisions. The frame that fits is an operating system.
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Superhuman, Not Smaller
The dominant question in every operating conversation right now is how many roles an agent can absorb. I think the framing is wrong, and wrong in a way that leads operators into a mistake they cannot walk back.
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If Your AI Startup Is a Prompt, There Is a Problem
Roughly three-quarters of the AI startups launched in 2024 were essentially API wrappers, and the first wave of shutdowns is confirming it. The lesson is not that wrappers are dead. It is that the prompt is the cheapest, fastest-depreciating layer of the stack, and the companies that mistook the prompt for the product are discovering it the hard way.
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Forward-Deployed Didn't Start in Tech
Everyone is hiring forward-deployed engineers. The question fewer people are asking is where that skill was actually built. It wasn't invented in tech. It was the default mode of technical work in defense, heavy industry, and government for decades before Silicon Valley gave it a name.
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The Operator's Supercycle
Build cost on the periphery collapsed. The moats didn't. That asymmetry is the actual structure of this AI cycle, and it changes who is positioned to win.
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When Code Gets Cheap, Scarcity Moves
AI broke SaaS defensibility. The moats didn't disappear. They moved toward money movement, compliance, and infrastructure.
2025
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The AI That Built a Tool for Other AIs: A Collaboration Experiment
A collaboration experiment in which Claude and I built pr-vibe, a tool for triaging repetitive pull-request bot feedback.
2023
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3 Ways We’re Building a Championship Team at Leverage
Three characteristics we used to define a high-performing team: extreme ownership, proactive support, and rapid, precise accuracy.
2020
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Project N95: How Can I Help?
How a simple question became a national rapid-response effort to get personal protective equipment to frontline workers during COVID-19.
2019
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Startup Life, Chapter 17: Personal Growth == Startup Growth
On founder depression, finding balance, and why your company grows as fast as you do.
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Startup Life, Chapter 8: What to do when your Co-Founder almost dies?
When my co-founder needed emergency surgery eight months into our startup, every decision became personal.
2017
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Three discoveries from selling out to Corporate America
What I learned navigating Bank of America after the White House and startups.
2016
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Reflecting on my Tour of Duty
Three lessons from serving as Deputy Director of the Presidential Innovation Fellows.
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Selling to the federal government?
How to create pathways for emerging tech companies to enter the government market.
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DIY Wok Burner in an Hour
How a stainless steel mixing bowl became a high-heat wok burner in a little over an hour.
2015
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How Skynet will actually happen
A 2015 thought experiment about cloud robotics, shared intelligence, and the risks created when autonomous systems learn as one network.
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Discourse setup using AWS
An archived guide to deploying Discourse on AWS for a government program using FedRAMP-authorized infrastructure.
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PIF Knowledge Sharing and Transfer
On knowledge transfer and institutional memory in the Presidential Innovation Fellows program.
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Hello World
The obligatory first post.