From bootstrapping a defense intelligence startup with five credit cards to backing some of the most ambitious robotics and autonomy companies in the world, Paige Craig has built his career around one core belief: exceptional people matter more than polished ideas.

In this conversation, Paige Craig, founder and managing partner of Outlander VC, joins Greg to unpack how his unconventional path through the Marine Corps, intelligence work, and entrepreneurship shaped his philosophy as an investor. Paige shares why he spends more time analyzing founders than products, how his team evaluates leadership under chaos, and why physical AI and robotics will define the next two decades of innovation.

The discussion also dives deep into the realities of robotics deployment, the hidden complexity behind autonomy, and what separates founders who can survive the brutal transition from prototype to real-world scale.

Highlights:

• Paige’s journey from a difficult childhood and military service to building and bootstrapping a multi-hundred-million-dollar intelligence company
• Why Outlander VC invests at the “pre-conception” stage, backing founders before products or customers exist
• The 38-point founder framework Outlander uses to evaluate vision, intelligence, character, and execution
• Why great founders often emerge from hardship, high agency, and an obsession with solving problems
• The loneliness of leadership and why Paige believes the best investors act as true problem-solving partners
• How Outlander structures conviction-driven investing, including single-partner authority to write early checks
• Why physical AI, robotics, and automation are entering a massive growth cycle driven by AI, manufacturing reshoring, and falling hardware costs
• The biggest differences between investing in robotics versus pure software startups
• Why cheap, rapidly deployable robots often outperform “exquisite” high-cost systems in the race toward autonomy
• Lessons from backing Coco Robotics and Havoc AI, including the realities of deploying robots into unpredictable real-world environments
• The overlooked operational challenges of robotics businesses: supply chains, government relations, field operations, and human oversight
• Why many robotics founders underestimate the difficulty of scaling hardware systems outside the lab
• Paige’s perspective on defense tech investing, the influx of “tourist VCs,” and what founders should look for in strategic investors
• The leadership gaps technical founders often face as companies scale, and how mentorship can help engineering leaders grow into organizational leadership roles
• Why AI may fundamentally reshape the future role of engineering leadership and startup team structures

Connect with Paige Craig on LinkedIn: https://www.linkedin.com/in/paigecraig/

Learn more about Outlander VC: https://outlander.vc/

Connect with Greg Toroosian on LinkedIn: https://www.linkedin.com/in/gregtoroosian/