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Vol. II — No. 184Remarkable People · Exceptional CompaniesToday's Edition

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Legend
Casey O'Grady Is Teaching an AI Law Firm to Pick Up the Phone
Founder · Operator · Executive

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.

casey-ogrady · blueshoeRead →
Legend
Monica Desai Weiss
Investor · Operator · Executive

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.

monica-desai-weiss · manifest-osRead →