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Confessions of a Venture Capital-Backed Startup Founder

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Sometime in the second half of the past decade, I decided to found a start-up. I was in my 20s and working at a mid-size tech company, and I didn’t yet have an idea, or even a general sense of where I wanted to focus. But I was convinced becoming a founder was the right thing to do next. In college, I had majored in a discipline within the liberal arts. I would have liked to become a philosopher or a writer but lacked the intestinal fortitude to risk being poor, a perpetual worry in spite of — or because of — having enjoyed a solid upper-middle-class upbringing. My desire to be a capitalist may have crystallized a few years after graduation, when I attended a reading by a former professor, a lecturer from my alma mater, on tour for his new book. Seeing me in the audience, he invited me to a sumptuous dinner with several eminent literary types: an award-winning author, the proprietor of a cherished bookstore, a leading critic. We spent a great evening gossiping about famous writers, but

Illustration: Tim Bouckley This article was featured in One Great Story , New York ’s reading recommendation newsletter. Sign up here to get it nightly. Sometime in the second half of the past decade, I decided to found a start-up. I was in my 20s and working at a mid-size tech company, and I didn’t yet have an idea, or even a general sense of where I wanted to focus. But I was convinced becoming a founder was the right thing to do next. In college, I had majored in a discipline within the liberal arts. I would have liked to become a philosopher or a writer but lacked the intestinal fortitude

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