The Kurty D Show

049- Diamonds in the Rough with Paige Craig

Episode Summary

This week, I'm excited to share my conversation with my friend, Paige Craig- the Founder and General Partner at Outlander VC- which is launching its third early-stage VC fund. Paige has one of the most incredible stories of any of my friends- from growing up dirt poor outside of Sacramento, California, to getting to Westpoint, then becoming a Marine, and starting the Lincoln Group- a Private Military Company operating across the Middle East, Africa, SE Asia that he grew to 1,000 full-time headcount. After Paige sold the Lincoln Group, he transitioned into an angel investor and has 17 unicorns from early-stage investments, including Postmates, Lyft, AngelList, Gusto, Wish, and more. Paige and the team at Outlander are finding diamonds in the rough- founders who have what it takes to win but aren’t part of the elite networks of the top schools, top cities, or social networks. Paige’s background all comes together to deliver returns that put him in the top 1% of tech investors, and I’m excited to share this honest and inspired conversation with one of the most interesting people I know.

Episode Notes

Key Takeaways:

Paige Craig’s remarkable story of growing up.
Paige’s experience at Westpoint
What spurred Paige to enter and serve in the Marine Corps
What it was like trying to start a business without access to money.
The origin story of the Lincoln Group, and when Paige sold it.
The lessons Paige learned from working alongside people from poorer countries.
Why and how analyzing people forms a core pillar and differentiator in Paige’s business.
The importance of establishing trust and understanding with your investors.
Why a startup’s success lies in its founders.
When the true value of a business shows itself.

Tweetable Quotes:

“My job is to find incredibly special people who can create incredible value and create profitable companies eventually that change the world.” – Paige Craig
“It's about finding out who is your ideal customer. Are you serving them?” – Paige Craig
“I love learning, but even more than learning, I've always really enjoyed doing.” – Paige Craig
“When I look at founders now, I understand how hard it is when you don't have access to money.” – Paige Craig
“The most incredible value typically takes a decade or longer to find and build.” – Paige Craig
"If you build incredible value for customers and you run your business right, you will get revenue." – Paige Craig
“If you're going to go after certain types of people, you have to understand them; you have to understand why they perform or outperform in certain environments.” – Paige Craig
“The very basic pillar of our business is to analyze people and realize that our mandate is picking exceptional, rare type of Founders.” – Paige Craig
“I think too much money corrupts founders early. And there's great value created when there are restrictions on the money given to them.” – Paige Craig
If you want to be a great investor, particularly at the early stage, the number one most deterministic thing in a startup's success is its founders.” – Paige Craig
“But that's one of the great benefits of being in the military. I fully utilized all my education benefits in the Marine Corps.” – Paige Craig
“As a company gets later on in life, you can analyze the product and the customers, and there's lots of different ways to become a great investor.” – Paige Craig

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