C Street began with a broad promise and found its edge in a very narrow room: the room where lawyers, lenders and nervous executives decide what everyone else will hear. Its rise is a case study in turning lived expertise into a category of one.

He turned down Wall Street, backpacked through Kenya, and found his life’s work at two broken tables. Now Achieve’s co-founder is betting that AI can give ordinary households the sort of financial guidance once reserved for the wealthy.