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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What happens when a decorated Army intelligence officer, Truman Scholar, and PhD becomes a venture capitalist? You get Craig Cummings — a man whose entire journey has been shaped by leadership, heart, and a deep commitment to service.
In this episode, Craig sits down with Keira to share stories from his time at West Point and 17 years in the military, including how he helped bring the first cellular network to the battlefield. He opens up about meeting his wife at the Truman Scholarship ceremony, the lessons he learned from both leading and following, and how he now uses those insights to back exceptional founders at Moonshots Capital.
This is a conversation about purpose, grit, and the power of leading with love — whether in uniform or in business.
We talk about:
Expectations vs. reality in the military
Leadership that starts with heart
Navigating transitions and reinvention
What he looks for in the founders he invests in
The advice he’d give to his 8-year-old self
If you've ever wondered how to turn discipline into compassion, and success into service — this one’s for you.
16 episodes
