750 Words: Buster Benson's private journaling side project becomes a $20k/month business

750 Words is a private journaling site that asks you to write 750 words every day — roughly the daily practice known as morning pages — and nothing about it was designed to scale. Buster Benson, who earned a creative-writing degree before learning to code at Amazon, launched it as one more plate in a life of spinning projects: he co-founded the Robot Co-op behind 43things, built an early iPhone app, ran a Seattle art gallery and bar, and later co-founded Habit Labs, whose healthmonth.com raised venture money. A decade on, the unglamorous writing site was the project that worked.

The product's discipline was subtraction. For over ten years the core idea did not change: one habit done well, minimal features, no pivots. It grew entirely through word of mouth — no ads, no SEO tricks — and its stickiness came from streaks, with badges Benson says he never expected to need at 2,000 or 3,000 days. His own rules, repeated by readers years later, were 'intentional unoptimization' and a warning that the biggest requirement was not to try to do other things at the same time.

Monetization was a conversation with users, not a decision imposed on them. The site ran free, moved to donations, and then to a subscription the discussion put at about $5 a month; when Benson had to make it pay or shut it down, he brought the community into the choice. That transparency built trust that lasted, while he kept taking demanding full-time roles — commenters from his Slack years noted he was head of product for the Slack platform — and shut down the venture-backed health startup around him. As one reader summarised the interview: the writing site was actually the better business.

The numbers stayed modest for years — commenters reading the article's revenue chart put monthly revenue around $2,000 in 2012 — before the interview title's roughly $20,000 a month in 2019, which Benson said was enough for a family of four almost anywhere outside the Bay Area. The Hacker News discussion of the interview drew 355 points and 136 comments, most of them about what a deliberately small business can teach.