The concept of *unlearning* in Chapter 48 and the Y Combinator (YC) model represent two fundamentally opposing approaches to action, leadership, and success. While C emphasizes accumulation, urgency, and overcoming obstacles to "win," Ursula K. Le Guin’s translation of the Tao Te Ching argues that true power comes from "shrinking," "not doing," and flowing like water to avoid obstacles entirely.

Chapter 48 of the Tao Te Ching draws a sharp distinction between conventional learning and the Way. Le Guin translates this as: "Studying and learning daily you grow larger. / Following the Way daily you shrink".

Y Combinator exemplifies "growing larger." It describes a process where founders "work intensively," "compress months of growth into weeks," and strive to build companies into massive entities like OpenAI ($500B) and Airbnb ($100B). This aligns with the worldly pursuit of accumulation and "being bright" or "keen," which Le Guin notes leads to the "greatest evil: wanting more".

Le Guin argues that to follow the Way, one must "get smaller and smaller" until arriving at "not doing". This "unlearning" is the removal of the "fuss," desire, and intellectual rigidity that creates resistance.

The relationship between Unlearning and Not Doing is that unlearning strips away the ego-driven need to force outcomes. The YC text quotes Paul Graham defining a formidable founder as "one who seems like they’ll get what they want, regardless of whatever obstacles are in the way." This defines success as the imposition of will upon the world—an act of force. In contrast, Le Guin’s commentary states that wei wu wei (Action by Inaction) is "power that is not force". A Taoist leader does not overcome obstacles by crashing through them; rather, like water, they go "right / to the low loathsome places, / and so finds the way". To the Taoist, the "formidable" approach of forcefully removing obstacles is dangerous because "Those who think to win the world / by doing something to it, / I see them come to grief".

The YC website highlights that "the sense of urgency is so infectious among founders" that it creates maximum productivity. Le Guin’s translation warns explicitly against this state—she writes: "Racing, chasing, hunting, / drives people crazy". Le Guin notes that "To run things, / don't fuss with them," and that "Nobody who fusses / is fit to run things". The "fuss" (or shi) is interpreted by Le Guin as "diplomacy" or "meddling"—essentially, the intense activity and "doing" that YC celebrates.

Instead of infectious urgency, the Taoist relies on "doing without doing," which Le Guin describes as "uncompetitive, unworried, trustful accomplishment".

The YC website describes "formidable founders" who do—they build, pivot, and acquire vast valuations through intense effort. Le Guin’s Tao Te Ching suggests that this is the path of "growing larger". In the Taoist view, these founders are "doing something to" the world, which is a "sacred object" that should not be seized. While YC founders "get what they want," Le Guin observes that "the ever-wanting soul / sees only what it wants," blinding them to the "mystery" and the true nature of the Way. Unlearning, therefore, leads to not doing by dismantling the very ambition that drives a founder to become "formidable" in the first place.

Edit: TBH, IMHO, "the low loathsome places" are not dissimilar from the indignities which a founder should be prepared to suffer, and so maybe startups aren't completely anathema to the Dao.