Bill, at that time, heads a Bay Area start-up with his friend Josh, developing software to make medical records available across hospital networks. The work has been especially demanding the last year, after the tech bubble collapsed and investor funding dried up. In its struggle to remain afloat, the company needed to downsize, and Bill is now its entire legal team, as well as its chief operating officer. He should be working today, to put together a presentation for a prospective client that could underwrite the costs of future development. Instead he’s here, chanting with the group he’s fallen in with, shouting his throat hoarse.

Bill has never taken part in such demonstrations before. There are blue-uniformed riot police everywhere—on foot, mounted on horseback, seated on motorbikes—all armed with lethal-looking batons, geared in shields and helmets. Placing himself in any situation that invited the attention of the police was high on the list of activities that displeased his grandmother. He can almost feel Mame’s fingernails pinching into his earlobes, showing her disapproval.

But he’d chosen to march after all.

Bill doesn’t consider himself a pacifist—he supported the first Gulf War, the rooting out of the Taliban from Afghanistan, and the broad outlines of “The War on Terror”—or an activist. Until now, he’s never joined any political or politically inclined organization, not even the Black Student Union at Stanford, where he got his undergraduate and law degrees.

Bill has always believed what his grandparents spent their life impressing on him—that his life is what he makes of it. That if he stays out of trouble and works hard, he’s bound to succeed. That there’s nothing stopping him, not the color of his skin, not his race, not his background, only the powers he lets control him.

His life has borne this out. Years of hard work in a mostly White and Asian high school pay off. He graduates from Stanford with distinction, and without debt, cobbling together a slew of scholarships. A phenomenal LSAT score enables him to enroll in Stanford Law School, allowing him to remain close to Mame after his grandfather’s death during his sophomore year. His success at his first job, at a large firm in San Francisco, allows him to quickly clear his law school loans. This positions him well to make the switch when the dot-com boom takes off, joining his best friend, Josh, also from Stanford, to start a company that angel investors salivate over as a probable emerging market leader in healthcare software.

But when the dot-com bubble bursts, it also unfairly devastates their start-up. The last two years have been a series of setbacks, with their VCs pulling out and their flagship product floundering, despite all their efforts to turn the tide.

Bill, for the first time in his life, is facing the certainty of failure, of all his hard work of the past few years coming to nought. Many of his friends cashed out before the bust, selling their half-baked start-ups at the first opportunity, as though they understood something he didn’t—that knowing how to ride the wave and knowing when to get off was more important than hard work.