Paige Craig is a former U.S. Marine who bootstrapped a private military company from $10,000 to hundreds of millions in revenue after sneaking into Iraq dressed as a CNN reporter, bringing unusually hands-on operational experience to his role as a venture investor at Outlander VC. He has built a reputation for spotting diamonds in the rough by backing technically strong but under-networked founders very early, including writing one of the first checks into companies like Scale AI at extremely low valuations, and uses a disciplined, military-style framework for founder assessment that he has codified and speaks about publicly.

• Drawn to founders who demonstrate high intelligence, strong character, and a capacity for intense sacrifice. Believes that the ability to endure pain is a leading indicator of a startup achieving a massive valuation, and views leadership as a critical learned skill rather than just an innate talent. An example is the decision to invest in Blake Hall from the identity verification startup ID.me on the very same day they met because of his clear vision and execution potential.
• A strong passion for the military community and defense innovation. Frequently advocates for defense startups and strongly supports platforms that elevate military innovators. This military focus also ties into early investment successes, such as backing a military marketplace originally called TroopSwap that eventually evolved into the highly successful identity verification platform ID.me.
• Dedicated to providing the very first checks to early-stage startups that eventually grow into massive companies, particularly in the artificial intelligence and robotics sectors. Often highlights a track record of getting in on the ground floor with major tech successes like Scale AI, Lyft, and Gusto, while actively promoting current AI and robotics portfolio companies such as CocoRobotics and Vidrovr.
• Highly engaged with the Middle Eastern tech and investor ecosystem, specifically within the United Arab Emirates. Regularly travels to Abu Dhabi and Dubai for institutional investor summits, recognizing the region's strategic value in using artificial intelligence to overcome local labor gaps. This interest is personal as well, stemming from building a successful business in Dubai nearly two decades ago.