Insights
Writing on AI, startups,
and what it takes to ship.
Essays on the production gap, startup strategy, and the founder’s inner operating system. The weekly playbooks live in the AI-Native Founder newsletter, and the running LinkedIn series lives in Field Notes.
Fresh from the newsletter
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How the Two Loops Run — And Where They Break
Both loops running on the substrate from last week — and, honestly, the four places they break. The finale of the AI-Native Startup Architecture series.
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The Shared Repository: What an AI-Native Startup Writes Down, and Where
The substrate has a shape: four kinds of file, in one place agents and humans both read. Here's a repo you can clone. Article 3 of 4 in the AI-Native Startup Architecture series.
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The Architecture: Two Loops on One Substrate
Diana Hu and Andrej Karpathy each described one half of the same machine. Here's the whole architecture. Article 2 of 4 in the AI-Native Startup Architecture series.
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What Makes a Startup AI-Native
The defining feature of an AI-native startup isn't its tools — it's the shape of its operating loop. Article 1 of 4 in the AI-Native Startup Architecture series.
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From the archive
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The Entrepreneur Extinction Event (And How to Be the Asteroid)
The entrepreneur extinction event: GPU scarcity isn't killing startups, it's rewriting the rules so solo founders outbuild teams with 50x their res…
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Economic Trends
A speaking topic on reading economic, credit, and technology cycles — and how founders and investors can position for the shifts ahead.
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Entrepreneurial Mindset
A talk drawn from The Inside-Out Entrepreneur on building the mental resiliency, clarity, and purpose founders need to last the journey.
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Tech & AI Innovation
A talk on where AI is taking startups: how generative tools collapse costs, reshape competition, and hand small teams enterprise-scale leverage.
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Startup Leadership
A talk on leading early-stage teams: hiring A+ people, giving real ownership, telling one clear story, and pacing the company to the market.
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Are We Heading Off Of A Cliff?
From Microsoft Azure to AWS to Climate Corp: why infrastructure automation keeps going obsolete, and why infrastructure as code won't save us.
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There Has To Be A Different Way
We saved millions automating cloud infrastructure, then watched the gains regress in weeks. Why I founded Magalix to rethink DevOps with AI.
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Looking Ahead – Episode #1 With Timothy Chen
My conversation with Essence VC's Timothy Chen on cloud complexity, Kubernetes, and whether AI can take infrastructure operations to the next wave.
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Early-stage startup CEO 2020 learned lessons
Five lessons from leading a startup through 2020: hire A+ people, let the team own problems, tell one clear story, match your velocity to the market.
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Prioritize Impact and Maximize Energy
Stop optimizing your to-do list. Use the 5-WHYs to find the one milestone that matters, then build an environment that makes you work on it daily.
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Entrepreneurs, Don’t Start Without a Strategy
Strategy is getting desirable ends with available means. Why founders need one before day one, and why it doesn't conflict with moving fast.
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The Art of War and Strategy for Entrepreneurs – Situational Awareness
Using Sun Tzu's five factors to build situational awareness: how founders read macro trends and micro signals before committing to a strategy.
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8 Pitch Deck Slides Must Have In Your Startup Fundraising
The eight slides every fundraising deck needs, from opportunity to ask — drawn from my own pitches and the many NOs before the YES.
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Top 3 Critical Slides in Your Startup Pitch Deck
Traction, team, and market are the three slides that actually land funding. What belongs in each and the metrics VCs want to see.
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The Impact of Economic Cycles on Venture Funding
The impact of economic cycles on venture funding: how expansions inflate startup valuations, downturns reset them, and what investors should ask at…