He once told me the most important quality of an entrepreneur is “delusional optimism,” a statement that cut one way when I thought about myself and my novel and another way when I thought about my friend, his start-up company and his wife.Ī few months later we visited them in Oakland, where they lived in a wood-shingled cottage with rosemary hedges and a lemon tree. My old roommate and his girlfriend were married at a California courthouse. Katie didn’t care if I became a lawyer or not she just wanted me to have a job and a plan. Then I had started over on my novel and gone part-time at work. A few months earlier, I had renounced writing and applied to law school. We were living in Iowa then, where I wrote fashion copy by day and labored at a broken novel by night. Lately we had been fighting about the future. My fiancée, Katie, and I shared what we called “real love,” which meant we were past giddy romance and we fought, though we knew we’d never break up. He had met his girlfriend one weekend in Madrid and taken her on a second date in Sweden. He was an entrepreneur in Silicon Valley who, by his mid-20s, had already sold one company for millions and attracted a lot of funding for his new online venture. When my old college roommate told me he was dating a woman in Europe, I kept my response neutral.
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