The experience did not make him hate expensive clothes. It made him distrust what people believed expensive clothes proved. He wore navy polos, soft button-down shirts, plain watches, and shoes in which he could walk all day. He could buy any suit he wanted, but he disliked the idea of dressing as a different person to make someone else recognize his intelligence. More important, his appearance allowed him to observe how potential partners treated a man before they knew how much power he possessed.
His investment firm, Cole Ventures, managed three billion eight hundred million dollars on behalf of institutions, families, and foundations. The number represented assets entrusted to the firm, not money stacked in Darien's personal accounts, a distinction he insisted his staff maintain. Its investments ranged from healthcare systems to industrial software and logistics businesses. Darien evaluated opportunities through financial models, engineering reviews, customer interviews, and an unusually careful study of leadership behavior. A compelling product could survive an imperfect founder. A toxic founder could destroy a compelling product.
That concern made Ashford Technologies interesting and troubling in equal measure. Its software performed well in independent tests. Several hospital groups had achieved measurable reductions in costly equipment failures, and one major utility had used its warnings to prevent an extended outage. But employee interviews suggested a company where speaking candidly felt dangerous. Customer service teams complained that senior management sold promises they could not deliver, then blamed the teams when customers grew angry.
On the evening before his meeting with Victoria, Darien sat in a rented apartment in San Francisco with his head of research, Maya Bennett, on a video call from New York. He had flown in after a meeting in Seattle, choosing to spend an extra night reviewing the diligence package before facing Ashford's leadership. Beyond the apartment windows, the city lights rose and fell over hills washed in cool fog. On his desk lay an annotated report nearly an inch thick.
"The technology is absolutely worth saving," Maya said. Her screen displayed a chart showing successful predictions at three pilot customers. "But this is a company that has grown faster than its internal controls. There are risks they barely seem willing to acknowledge."
"What about the workforce?" Darien asked.
Maya hesitated. "I've spoken with former employees who don't want their names in a report. They describe different standards for different people. Women of color say they were praised for doing the work and passed over when the promotions came. Latino managers say they were accused of aggression for disagreements that earned their white colleagues compliments."
"Did they bring complaints to human resources?"