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.

“It worked really well, and it was extremely popular,” Ratcliffe says. “I thought the records management software thing was going to take off.”