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Illustration by Matthew Daley

In most contexts, the story of Silicon Valley’s Venture Law Group is a cautionary tale. Founded in 1993 by Craig Johnson, previously a leading partner at Wilson Sonsini Goodrich & Rosati, VLG made a meteoric rise representing and investing in the likes of Yahoo, Cerent, Hotmail and plenty of other long-forgotten dot-com darlings. The firm scratched at a place in the Am Law 200 a mere seven years into its existence. Three years later, it merged into Heller Ehrman, its fortunes having faded when the dot-com bubble burst.

Among the innovations that did not hasten the firm’s decline, however, was a client-facing software suite and deals database developed in-house by a team led by Jackson Ratcliffe. A computer scientist with a degree from Duke University, Ratcliffe arrived at VLG by way of what would become a familiar loop in his professional career: After working at a law firm, Simpson Thacher & Bartlett, from 1988 to 1993, he spent two years in a technology consultant role before being drawn back to a law firm. What he built was branded “the VLG Advantage.” It amounted to an online data repository for a company’s contracts and legal documents, accessible by client and firm alike.

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