In 2017, Arjan Sch tte, founder of Core Innovation Capital, faced a decision on whether to invest in Hugo Insurance, an auto insurance startup. Core, an early-stage social impact VC firm, focused on "fintech for good," by investing in financial services for low- to middle-income consumers. Since 2010, Core had raised $120 million across two funds and backed nearly 50 companies, including Ripple Labs and NerdWallet. Core was deeply committed to measuring its social impact and had developed a written set of impact criteria that it used to annually measure impact. Hugo, founded in 2016 by David Bergendahl, developed a "pay-as-you-drive" insurance product for the $33 to $40 billion non-standard auto insurance market. By offering flexible, incremental payments, Hugo aimed to address the 13% of U.S. drivers who did not have insurance due to high upfront costs. While Sch tte admired Bergendahl's passion and early testing, he questioned Hugo's scalability and profitability. Concerns about unproven demand, high acquisition costs, and operational complexity loomed large as Sch tte deliberated whether Hugo could meet Core's dual goals of social impact and financial success.