Nick Halsey knows it can sound strange to an outsider: How is it possible for someone in Silicon Valley to have $10 million in the bank and still not feel rich?

So Mr. Halsey, 46, a veteran of a half-dozen technology start-up companies, walks a reporter through the financial realities of life near the top of the financial food chain. He made it clear he was not describing his own life so much as basing his estimates on what he knows about his peers, imagining he was the all-too-common type here who, despite the high quality of the area’s schools, sends his children to private schools and enjoys a penchant for free spending.

“I’m vastly amused by the flashy rich here,” Mr. Halsey said. “They’re mostly these techie guys with few social skills who don’t know what to do with their money.”

One former colleague, he said, spent $250,000 to buy a new a car, and then rarely drove it because taking it on the highway made him nervous. And when he did dare to get behind the wheel, “he’d park his car a mile from the entrance” because he was so worried about parking lot dings.