ai-native-law-firm
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Casey O'Grady Is Teaching an AI Law Firm to Pick Up the Phone
The Harvard-trained lawyer left consulting, started Blueshoe in a Boston-area coffee shop, and kept changing the product until one stubborn problem came into focus: legal help moves much slower than the question that starts it.
Blueshoe
Blueshoe is an AI-native law firm that pairs licensed attorneys with proprietary legal reasoning software to make quality legal help affordable and always-on for individuals and small businesses. Founded in 2025 by Harvard Law graduate Casey O'Grady and MIT-trained engineer Kai Yee Wan, the Y Combinator-backed company started as a legal-reasoning research platform piloted at Harvard, Yale, and Columbia law schools, then extended into a full-stack firm covering employment, housing, consumer, personal injury, and product-liability matters without billable hours.
Manifest OS
Manifest OS is a New York-based legal technology company building the operating system for AI-native law firms. It powers a unified law-firm brand, Manifest Law, with an end-to-end AI platform and centralized back office, replacing the billable hour with flat, outcome-based pricing. Starting in business immigration, the company raised a $60M Series A at a $750M valuation in April 2026, reported as the largest Series A in legal-tech history.
Monica Desai Weiss
Monica Desai Weiss is the Chief Business Officer of Manifest OS, the New York startup building an AI-native law firm model that raised a $60M Series A in April 2026 at a $750M valuation. A former bond trader at JPMorgan, she ran Operations & Strategy at Blockchain.com, then spent years as a Principal at Kleiner Perkins backing fintech, crypto and consumer companies including Settle, Propel and Nova Credit. She is also a writer whose 'Bits' essays dissected the early DeFi and NFT waves.