In 2017, Core Innovation Capital invested $725,000 in Hugo Insurance, a pay-as-you-drive auto insurance startup targeting the non-standard market. Core followed with $300,000 in 2019 during a Seed II round. By 2022, Hugo founder, David Bergendahl, sought $10 million in Series A funding at a $30 million valuation, inviting Core to lead with a $5 million investment. Despite early promise, Hugo faced state licensure delays, high customer acquisition costs, technical issues, churn, and the loss of a key carrier partner. While Bergendahl expressed optimism about progress, Core's managing partner, Arjan Sch tte, had to weigh the firm's stricter follow-on investment criteria against the risk of diluting ownership if Hugo succeeded.