Lainy Painter cold-emailed her way into Goldman Sachs from William & Mary by reaching out to an alum on a "Do Not Email" list, then gained operating experience at Gainsight where she watched a startup get built from scratch in the customer success software category. She focuses on founders with deep domain expertise in complex industries like logistics and transportation, asking two key questions: "Why you?" and "Why now?" to identify those with unusual market insight and clear timing advantages. Lainy Painter cold-emailed her way into Goldman Sachs from William & Mary by reaching out to an alum on a "Do Not Email" list, then gained operating experience at Gainsight where she watched a startup get built from scratch in the customer success software category. She focuses on founders with deep domain expertise in complex industries like logistics and transportation, asking two key questions: "Why you?" and "Why now?" to identify those with unusual market insight and clear timing advantages.