This tutorial focused on many competing aims, challenges, and trade-offs involved in leading and doing Requirements Engineering (RE) in a highly dynamic and uncertain environment of a venture-capital-backed New York City startup Fr8Hub (https://www.fr8hub.com) which runs a marketplace for over-the-road logistics services across North America. How to set up RE roles, responsibilities, and processes in such an environment? How and why did these change during the first 1000 days of this business? Which concepts, methods, and tools from RE research worked, and why? Which ones we tried and failed to get results from? How does RE - representations, models, and elicitation, representation, validation, verification methods - interface with corporate strategy, finance, product design, engineering, marketing, sales, and business intelligence? How do the priorities of speed and scale influence how RE is organized and done? Which research questions did this fieldwork lead to? I discussed these questions together with the audience during the tutorial, while showing actually applied RE methods, processes, and artifacts; I described actual situations, and found potential courses of action with the audience, described actual choices we made and their outcomes. Beyond the role of RE in those situations, the aim is to stimulate discussion about the use of long term fieldwork in RE research, what can be gained through it, and how this one worked out.