Every technological breakthrough requires capital to move from a prototype to scalable commercial product. The financial architecture of the New England tech sector evolved dynamically alongside the technologies it resourced, moving from informal networks of local wealth and risk-averse banks to the institutionalized venture capital firms of the late twentieth century. The oral histories collected here illuminate how early ideas secured vital funding. Practitioners describe the mechanical realities of early corporate finance: bootstrapping operations on personal savings, pitching complex software concepts to traditional bankers who only understood physical machinery, and negotiating with the region’s first specialized venture capitalists.