Four More Capital

Four More Capital is a Chicago-based private investment group that makes direct equity investments across various emerging technology sectors, maintaining a specific strategic focus on artificial intelligence applications and insurtech platforms. The firm utilizes a highly hands-on direct investment model to build long-term ownership stakes in early-stage enterprises, actively supporting executive management teams through operational scaling and strategic market expansion initiatives. Rather than operating through a traditional venture capital fund structure, the organization deploys proprietary capital to back technology-enabled businesses that require flexible financing solutions. To date, the firm has executed exactly nine direct investments across its target sectors, which notably includes backing the artificial intelligence-driven workplace safety and commercial insurtech software platform CompScience. The investment group Four More Capital was officially founded in 2021 by sibling investment partners Toni Crown and W. Andrew Crown.