Writing API documentation at a fast-growing startup is hard. Small writing teams need to pick their battles and balance keeping pace with the product while elevating the developer experience. But a stale developer portal can erode confidence in your documentation just as quickly as outdated content. When a startup grows into an enterprise, it’s easy for past choices that made so much sense at the time—a great hire or the perfect tool—to come back and haunt you. How do you know when it’s time to reset? And how do you deliver your documentation’s next giant leap forward? This talk will describe the unique origin of Marqeta’s API documentation, explain some of our missteps along the way, and provide a framework for fixing your biggest documentation pain points.