July 2, 2026
Giddy-up, the comments got ugly
Cowboys, Frontiersmen, Settlers, Townspeople, Cityfolk
Startup ‘cowboys’ spark a wild comment war over labels, history, and office astrology
TLDR: The article says companies move from chaotic startup mode to orderly big-business mode, and different personalities fit different stages. Commenters turned that into a fight over whether the idea is insightful, cringe corporate labeling, or a history-blind love letter to "cowboys" and "settlers."
A post trying to explain how companies grow — from scrappy "Cowboys" who survive daily chaos to process-loving "Cityfolk" in giant, stable businesses — absolutely lit up the comments. The basic idea is simple: different people thrive at different stages. Some love the messy, anything-goes phase of a young company; others shine once rules, routines, and scale kick in. Easy enough, right? Not according to the crowd.
The biggest split was over whether this is a smart way to describe work life or just corporate fan fiction. One camp said the model is useful because it captures something real: some people truly do have different appetites for disorder, and a person who thrives in a garage-startup vibe may be miserable in a big, polished company. Others instantly dragged it as "horoscopes for MBA people," mocking the whole thing as yet another personality-labeling obsession dressed up in business clothes.
Then the thread swerved into full-on cultural controversy. Several commenters blasted the frontier/cowboy/settler language as awkward at best and offensive at worst, arguing it romanticizes violence and erases the ugly history behind those words. One pointed to Simon Wardley’s alternative framing, Explorer-Settler-Villager-Town Planner, as a less loaded option. And yes, there was nostalgia too: older programmers fondly recalled the era of "cowboy coding" — reckless, legendary, chaotic, and apparently way more fun in memory than in practice.
Key Points
- •The article defines five organizational archetypes tied to company stage: Cowboys, Frontiersmen, Settlers, Townspeople, and Cityfolk.
- •Cowboys represent the earliest phase, where survival and adaptability matter more than durable process because the organization is highly chaotic.
- •Frontiersmen and Settlers describe the shift from ad hoc work toward stable products, product-market fit, and repeatable processes.
- •Townspeople and Cityfolk represent later stages where process refinement, mechanization, and organizational efficiency dominate.
- •The article says people tend to be more effective and satisfied at certain levels of organizational chaos, and can become mismatched as a company evolves or regresses.