EP 100 — Outlander VC's Paige Craig On Funding Defense's Black Sheep Before Anyone Else Will

Paige Craig built his first company by sneaking into Baghdad as a private citizen with a fake CNN badge, no government backing, and no contacts, starting with a $5,000 DARPA task and scaling to a $30M program within months. He sold that company and took everything he learned about operating in chaos into Outlander VC, where he writes the first check into founders before revenue, customers, or a real business model exists. His 38-principle framework for evaluating founders, developed after conversations with roughly 4,000 of them, is how he consistently finds the people tier-one funds pass on and turns them into multibillion-dollar outcomes

Paige is a former Marine intel officer who built a private military company from scratch in a war zone, and he now invests at a stage most VCs won't touch. His views on what makes founders succeed and what most investors get wrong are grounded in a track record most people in this space will never have.

Topics discussed:

• The 38-principle founder evaluation framework across vision, intelligence, character, and execution
• Why character and perseverance outrank strategy, speed, and technical ability at pre-seed
• Fast execution loops as a primary investment signal before any revenue exists
• Why pedigree is a poor predictor and how non-standard founders generate outsized returns
• The veteran founder trap: command-and-control conditioning versus self-directed leadership
• Why pitch decks and financial forecasts are useless signals at formation stage
• Pushing defense contract authority to unit level as a fix for the valley of death
• Unmanned ground vehicles as the most underfunded category in defense tech right now

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