The "Passive Income" trap ate a generation of entrepreneurs

The anecdote that says it all

It has been reported that Joan Westenberg’s new essay paints a bleak, funny, and a little sad portrait of what she calls "Passive Income Brain." The opener is sharp: a man who thought he was “building a business” was dropshipping jade face rollers he’d never used, never understood, and never bothered to support—five months in and $800 in the hole. Westenberg bought him coffee. You can feel the embarrassment and the pity in that small, humane moment; it’s the emotional hook of the piece.

Big numbers, thin margins

It has been reported that between 2019 and 2021 roughly 700,000 new Shopify stores opened, taking the platform from about one million merchants to 1.7 million. Many of those shops were set up in the service of a single promise: build a system, make money while you sleep, quit your day job. The essay alleges that the real winners were the people selling courses about how to get rich passively—an ouroboros of advice that fed itself.

Why it matters

Westenberg argues that optimizing for “passivity” warped priorities: care and customer work were treated as bugs, not features. Who wouldn’t want money that shows up while you sleep? But when passivity becomes the goal, you stop caring about what customers actually need. The piece lands as part cautionary tale, part cultural diagnosis—an indictment of a trend that turned entrepreneurship into a lottery ticket rather than a craft. The essay, discussed on Hacker News and published on Joan Westenberg’s site, is a reminder that systems without care are often just scaffolding for failure.

Sources: joanwestenberg.com, Hacker News