Craig Cummings

Craig Cummings, co-founder and general partner at Moonshots Capital, joined the Next Round Ready podcast to talk about his path from military service to venture capital. He shared his background, including his West Point education, early work in cyber warfare, and his decision to leave the Army after 17 years of service. He also described how his military experience shaped his view of pressure, which he framed as a privilege in high-stakes environments.

On the show, Craig covered the qualities that make startups investable, such as leadership, technical acumen, and market opportunity. He discussed what investors look for in pitch decks, the value of warm introductions, and the importance of effective investor updates. He also explained how technical and non-technical founders can partner successfully and why choosing the right investors matters for long-term success.

The conversation also touched on the Ride Scout story, which traced a path from battlefield technology to mobility solutions, and on the realities of deal flow, where investors triage thousands of pitches to make a handful of investments.