Craig Cummings is a former Army intelligence officer and Bronze Star recipient who co-founded and served as COO of RideScout, a mobility startup acquired by Daimler, and now uses his battlefield experience to evaluate leadership under pressure in founders at Moonshots Capital. He focuses on investing in extraordinary leaders rather than specific sectors, particularly veteran founders, and coaches military operators on career transitions while maintaining a lead with love approach that connects combat-zone camaraderie to how he supports his portfolio companies.

• A strong investment focus on dual-use technology, specifically software that serves both commercial markets and national security interests. He frequently highlights portfolio companies that help the government avoid rebuilding solutions from scratch, such as Transmute meeting security standards for Customs and Border Protection.
• Prioritizes supporting and funding military veteran entrepreneurs, viewing military service as a strong foundation for business leadership. This is evidenced by his participation as a judge in veteran pitch competitions and his pride in data showing a significant portion of his firm's investments are in veteran-led startups.
• Evaluation of startups based heavily on the quality of leadership, often hosting events and summits specifically centered on this trait. He frequently praises founders, such as the CEO of Cart.com or Red 6, not just for business metrics but for their personal ability to lead and execute under pressure.
• Offers tactical, granular advice on the mechanics of fundraising and networking. He shares specific strategies for founders, such as how to craft the perfect forwardable introduction email to get a VC's attention or how to generate excitement and fear of missing out during a raise to secure better terms.
• Interest in modernizing critical infrastructure through AI, supply chain digitization, and digital identity verification. He points to investments like ID.me helping the IRS or Gretel.ai working with Microsoft Azure as examples of meaningful technology that solves large-scale institutional problems.