@HarvardHBS MBA | Angel Investor in AI Infrastructure | Engineer turned operator and now investor! Substack - https://teapawt.org/t.co/0takhGyUki
Toronto 🇨🇦
Joined March 2017
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Keith Rabois's most famous framework: barrels vs. ammunition. PayPal had 254 people, 12-17 barrels. Most companies have two. The framework is a decade old and was built for a world where execution was hard. AI is rewriting the ratio. 🧵
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AI does the work. The barrel decides what work is worth doing. The question is not whether we will have enough barrels. It is whether they will aim at the problems that matter.
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Full essay with Drucker and Prussian military parallels, the fake barrel problem, three solutions for coordinating barrels without hierarchy, and what this means for founders, PMs, and investors. Building on @rabois x @lennysan.
chiponmyshoulder.substack.co…
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AI is not replacing workers. It is promoting ammunition into barrels.
@rabois's barrels vs. ammunition framework is a decade old. It was built for a world where execution was hard.
That world is dying. Here is what changes:
Inspired by @rabois x @lennysan
chiponmyshoulder.substack.co…
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Switching a stateless provider is a weekend project.
Switching a stateful provider means losing months of accumulated optimization. Rebuilding observability baselines. Weeks of degraded performance.
This does not look like swapping cloud providers. This looks like migrating off Salesforce.
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The company that wins on cost attracts customers who leave for a lower cost.
The company that wins on trust attracts customers who stay.
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Everyone is optimizing for cost. The winners are optimizing for switching costs.
Full essay with three counterarguments honestly addressed:
chiponmyshoulder.substack.co…
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Everyone assumes inference commoditizes.
Multiple providers. Declining costs. Easy switching. Race to the bottom.
I think the opposite is more likely. Inference will concentrate.
Here is why. 🧵
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I am angel investing in AI. Pre-seed. $5-10K checks.
Two areas:
- AI infrastructure (dev tools, inference, compute orchestration)
- AI-enabled services (selling the work, not the tool)
Shipped inference APIs on custom silicon (acquired by AMD). Evaluated 200+ companies. I invest as a former customer.
DMs open.
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Interesting framework. But the biggest test case in AI says otherwise.
Google had 4 billion users. OpenAI had zero. ChatGPT holds 70% market share. Gemini holds 20%.
Distribution gets you in the room. Taste gets you invited back.
chiponmyshoulder.substack.co…
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