This paper examines the investment analyses and contractual terms of 67 portfolio investments by 11 venture capital (VC) firms. The authors analyze the attractiveness, risks, and deal terms of the investments, as well as the expected post-investment monitoring activities. They find that greater internal and external risks are associated with more VC cash flow rights and control rights. Greater internal risk is also linked to more contingent compensation for the entrepreneur. The complexity of the venture is associated with less contingent compensation. The results are interpreted in the context of financial contracting theories, such as principal-agent theories and control theories. The paper also discusses the relationship between VC actions and contractual terms, finding that VCs are more likely to strengthen management teams as VC control increases and to provide value-added services as VC cash flow rights increase. The findings contribute to the understanding of how VCs choose and structure their investments, providing insights into the role of information collection and financial contracts in mitigating conflicts of interest.This paper examines the investment analyses and contractual terms of 67 portfolio investments by 11 venture capital (VC) firms. The authors analyze the attractiveness, risks, and deal terms of the investments, as well as the expected post-investment monitoring activities. They find that greater internal and external risks are associated with more VC cash flow rights and control rights. Greater internal risk is also linked to more contingent compensation for the entrepreneur. The complexity of the venture is associated with less contingent compensation. The results are interpreted in the context of financial contracting theories, such as principal-agent theories and control theories. The paper also discusses the relationship between VC actions and contractual terms, finding that VCs are more likely to strengthen management teams as VC control increases and to provide value-added services as VC cash flow rights increase. The findings contribute to the understanding of how VCs choose and structure their investments, providing insights into the role of information collection and financial contracts in mitigating conflicts of interest.