After serving in the Marine Corps, Paige combined his natural entrepreneurial instinct with his passion for national security and bootstrapped a private military company. Starting by driving solo into Iraq with $10k, he scaled his business to over $300M in revenue in four years, with programs across the Middle East, Africa, and Southeast Asia. He has used his experience from the first half of his career focused on national security and its success to form his approach to investing.

Paige spent the next six years angel investing and crafting his investing methodology. During this period more than ten percent of his seed investments have become unicorns, including Lyft, Wish, Gusto, Postmates, and Twitter. He credits this success to his life experiences, including many from his military service, that taught him the importance of the human element and the ability to be a contrarian thinker. Based on these beliefs and his early success, he created the 38-point Outlander Founder Framework that serves as the foundation of his institutional investing strategy today.

Since then Paige has led two funds, Outlander Archimedes (2015) and Outlander Edison (2020) implementing and refining his Founder Framework to find incredible founders and drive superior returns. Since investing, over the course of over 140+ investments, he has driven blended returns in the top 5% of VCs globally, including seed investments such as OpenDoor, ClassPass, Scale, and Andela.