Earlier this year, I was in the plush boardroom of the wealth-management division of a major Canadian bank, on a floor high above the branch where everyday transactions take place. The investment manager handling my account wasn’t happy. The strategy I’d recommended, she explained, could result in me paying quite a bit more money to the CRA. “That’s okay,” I responded. “I’m comfortable paying more in taxes.” She laughed nervously. “Well, that is the first time I have ever heard that.”

I’m rich. At 30, I sold my small Canadian technology company Dabble DB—an early online-database tool—to Twitter, and my family moved to San Francisco. For the next decade, I worked in senior technical roles at Silicon Valley startups, sometimes in person but mostly remotely from Galiano Island in B.C. I retired at 40 with enough wealth to do pretty much anything I wanted for the rest of my life. When I confided my financial status to a good friend from high school, she looked puzzled. “I’m sure you’re good at what you do,” she said, “but why would they pay you that much? It’s not like you’re a basketball star.” The truth is, I got lucky. After leaving Twitter, I was an early hire at Stripe—at that time, a small, unknown payment processing company. Tech startups pay their employees partly in stock options, so when Stripe unexpectedly grew to hundreds of times its initial size, my equity grew in value along with it.

I’d lucked out from the start, though: I was born in Canada. People in my situation often talk about being self-made, but I don’t see it that way. I think about my parents, who moved here from the U.S. in the 1970s and lived in a Vancouver housing co-op built by the city and the federal government. I think about their stable jobs at the University of British Columbia, and the education I got in Vancouver’s public schools—and later, at UBC myself, with a scholarship from public money. I also think about starting Dabble DB with investment capital from a public pension plan, along with Canadian R&D tax credits that reimbursed large parts of our payroll. In Canada, I could take........

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