Despite significant needs, most urban areas face considerable barriers in accessing finance for resilience building. As a result, urban areas can be acting as “involuntary pioneers” in the development and deployment of financing mechanisms. Lessons are being learned and shared from pioneer practices. We argue that investment remains over-reliant on funding sources that are conceived and directed externally to urban actors. This chapter makes the case for a pivot away from this reliance towards greater levels of endogenous finance that is developed and controlled by governments, businesses and households within cities. This pivot requires greater attention to supportive enabling environments, upscaling of innovative financing tools, recognition of informality and equity, and a focus on developing business cases that recognise and capture the dividends from the multiple benefit streams of resilience building in urban areas.