Like many entrepreneurs, Gebbia faced numerous challenges in the early stages. One significant obstacle was gaining the trust of users. To address this, the founders focused on creating a robust trust and safety system, including user profiles, reviews, and secure payment methods. Additionally, they faced skepticism from investors. Gebbia and his team persevered by bootstrapping and even resorting to selling custom-made cereal boxes to fund their venture. Their resilience paid off when they finally secured seed funding from Y Combinator.