Outlander VC’s Paige Craig on Investing Early and Identifying Intelligent Leaders

On this episode of the LA Venture Podcast, Outlander VC founder and Managing Partner Paige Craig discusses how he pivoted from working in the defense industry to investing early in major companies like Wish, Scale and Gusto.

Craig’s entrepreneurial journey is unique, to say the least.

Following his time in the Marine Corps and in national security, Craig said he saw an opportunity building capabilities for the U.S. following its 2003 invasion of Iraq. But with little fundraising success, he had to find his own way into the industry and his own competitive advantage. He traveled to the Middle East, posed as a CNN reporter and found his way into Baghdad.

“I can’t even tell you the shit we went through,” he said. During his time in Iraq, Craig said his Lincoln Group closed deals in the Middle East focused on gathering special intelligence, running unconventional operations aided by technology and creating other military capabilities.

“I endorsed every mission we took,” he said, “ and I can stand behind all of them if they ever get released and declassified someday.”

Craig eventually sold the company to multibillion-dollar defense contractor Constellis.

“I took my money, but more importantly, my lessons learned about how to create something from nothing and I started angel investing back in 2009,” Craig said.

His unique business background informs his approach to investing. Understanding company founders as people—particularly through his method of observing human characteristics linked to vision, intelligence, character and execution—helps investors understand their businesses.

“Everything comes down to identifying very unique people—the outlanders,” he said. “We are looking for extremely unique people who are highly inclined to build fast growing, highly scalable tech companies, when most of the world around them is saying, ‘fuck you’.”

Many investors mistakenly think they know how to run the companies they help fund, Craig said. But by identifying founders with both emotional and intellectual intelligence early on, he said he focuses instead on fostering leadership skills and developing the next generation of talent.

“These people reminded me of me several years back, where they're under-resourced [and] no one believes in them,” he said. “They're taking on huge missions that mean everything to them, and I just saw all these psychological parallels to what I went through. And I was like, ‘Look, I can't tell you how to develop a server farm, but what I can tell you how to do is how to lead people.’”

dot.LA Editorial Intern Kristin Snyder contributed to this post.

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