For five years, my parents told people I was the Harper family’s cautionary tale—the daughter who had abandoned Boston, run off to California, and never quite figured her life out. What they didn’t know was that while they were quietly mourning my “failure,” I was quietly building a health-tech company that would eventually be valued at $340 million.

By high school, the divide between James and me had widened into something permanent. He got into Phillips Exeter. I stayed at our local private school. Family dinners became rolling reports on his latest triumphs, interrupted only by tense discussions about my B in calculus despite the expensive tutor my parents had hired. The only person in the family who truly understood me was my aunt Meredith, my father’s younger sister and, in Harper lore, the other disappointment. She had gone to art school instead of medicine or law. Her studio smelled like turpentine and jasmine tea, and when I was sixteen and nearly in tears after another dinner spent listening to James’s future being praised while mine was described as “unclear,” she handed me tea and said, “They will never understand people like us. We see possibility where they only see approved routes. That is not a flaw. It is a gift.”