In fall 2021, Aliana Piñeiro, impact director at Boston Impact Initiative (BII) discovered that an entrepreneur the organization was considering for an investment had failed to disclose pre-existing debt with another lender. Although the business scored highly on BII's criteria for investment, Piñeiro and her colleagues had to reevaluate its risk profile in light of the additional debt. They also had to decide how to manage their relationship with the entrepreneur. The BII team determined an entrepreneur's creditworthiness through a series of in-depth conversations rather than using a one-size-fits-all application form. They also did not perform criminal background checks or credit checks. Nevertheless, they were disappointed that the entrepreneur had not disclosed his previous debt, and wondered why he had failed to bring it up in their previous conversations. At the conclusion of the case, Piñeiro and her team must decide whether to move forward with the investment and if so, how to address the issue with the entrepreneur.