Oscar Romero is at a crossroads. After 13 years as an in-house lawyer at Bridgestone Americas Inc. in Chicago, he’s leaving the company next year as it consolidates several offices into its Nashville headquarters. One idea he’s toying with: founding a consulting firm that helps companies determine their potential risks—compliance concerns, antitrust issues, weak trade-secrets protection, the potential for insider trading. “If I’m going to do something like this, it’s now or never,” Romero said.

Romero is in a rare position. Not many in-house counsel drop their training, expertise and job security to become entrepreneurs. The change from business partner to business runner is freeing, said several former attorneys, and it is similarly humbling. But it still goes against the risk-aversion ingrained in so many attorneys. And of the lawyer-originated companies out there, many are a safe bet—legal services consultancies and advice firms are common.

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