This chapter delves into the dynamic landscape of venture capital (VC) investment in Nigerian fintech companies, examining the legal and regulatory considerations that shape these transactions. Acknowledging the transformative impact of technology and innovation on global commerce, the chapter begins by exploring the profound disruption of the financial services industry in Nigeria, leading to the birth of fintech. Drawing on available data, the chapter provides a comprehensive overview of VC investment trends over the last five years, spotlighting leading VC firms and their engagements within the Nigerian fintech sector. It explores the funding sources unique to fintech, highlighting the prevalence of VC over traditional finance channels; ticket sizes, deal structures, focusing on equity deals, and the distinction between direct and indirect investments (considering the peculiarities of offshore holding companies and Nigerian operating companies). Critically, the chapter details the funding cycle, from pre-seed to Series A–D while exploring the transaction cycle, from the term Sheet to completion, and outlines potential VC exit options, such as IPOs and sell-downs. Importantly and considering that most Nigerian fintech companies are regulated, the chapter explores the core legal and regulatory issues, encompassing licensing requirements, approval processes, and other corporate matters arising from VC deals. In conclusion, the chapter reflects on the future trajectory of VC investments in Nigerian fintech, considering recent interventions by key regulators including potential impact on market participation, alongside growing investments in other industries such as healthtech, and artificial intelligence, raising questions about the sustainability of fintech’s dominance in attracting VC funding.