Ep. 9 - The Secret To Having It All with Craig Cummings | Moonshots Capital

What happens when a West Point graduate, Army intelligence officer, startup founder, and venture capitalist realizes that success was never about the destination?In this episode of 50 Chairs, I sit down with my longtime friend and mentor, Craig Cummings, Co-Founder and General Partner at Moonshots Capital.Craig’s journey spans U.S. Military Academy at West Point, the National Security Agency, building and selling RideScout to Daimler Mercedes-Benz, and now investing in some of the country’s most ambitious founders across defense tech, AI, biotech, and national security.But this conversation goes deeper than resumes and exits.We talk about:Why “the climb is the joy”The loneliness of entrepreneurshipLeaving the military three years before retirementBuilding startups while facing personal adversityHow Moonshots evaluates founders and leadershipWhat authenticity actually means in leadershipThe emotional reality of acquisitionsWhy founders must know when to keep going and when to stopThe secret to “having it all”This is a conversation about ambition, identity, leadership, friendship, and learning to appreciate the journey before the summit.If you’re building something, questioning your next move, or chasing a version of success that still feels out of reach, this episode is for you.🎧 Listen on Spotify, Apple Podcasts, and YouTube 🌐 More episodes and founder playbooks at www.50chairs.com@50chairs For the 50chairs Playbook from every episode go to www.50chairs.com