What if you could do it all over?

Once, in another life, I was a tech founder. It was the late nineties, when the Web was young, and everyone was trying to cash in on the dot-com boom. In college, two of my dorm mates and I discovered that we’d each started an Internet company in high school, and we merged them to form a single, teen-age megacorp. For around six hundred dollars a month, we rented office space in the basement of a building in town. We made Web sites and software for an early dating service, an insurance-claims-processing firm, and an online store where customers could “bargain” with a cartoon avatar for overstock goods. I lived large, spending the money I made on tuition, food, and a stereo. In 1999—our sophomore year—we hit it big. A company that wired mid-tier office buildings with high-speed Internet hired us to build a collaborative work environment for its customers: Slack, avant la lettre. It was a huge project, entrusted to a few college students through some combination of recklessness and char ... Read full article.