Life in the Singularity

Life in the Singularity

Context Engineering Dethrones Prompt Engineering

Matt McDonagh's avatar
Matt McDonagh
Jul 27, 2025
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I spent the first part of my career on Wall Street, first in the I-banking grinder and then co-founding a hedge fund. You learn a few things in that world. You learn to spot the difference between a good story and a good business.

You learn that the real, durable alpha isn’t in the shiny new thing itself, but in the unglamorous, complex plumbing that makes it work reliably. The guy who sold the first exotic credit default swap made a mint; the guys who built the systems to price and manage the risk on a trillion dollars of them built entire empires.

When I moved into tech investing, I brought that mindset with me. For the last 15 years, I’ve been elbows-deep in data and machine learning engineering, building the systems that turn raw data into predictable growth.

I don’t just write checks; I get in there and help companies wire up their revenue engines and business operations with AI. And let me tell you, the current frenzy around LLMs feels a lot like 2007. There’s a world-changing te…

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