LA Venture Podcast


Paige Craig — Outlander VC

June 22, 2022


Paige Craig shares his amazing story of sneaking into Iraq dressed as a CNN reporter, how he built a private military from scratch inside Baghdad and then how he parlayed that exit into an incredible investing career that includes Wish, Scale, Gusto, AngelList and many others.

Full transcript

Today's guest Paige Craig was one of the big players in the early days establishing LA tech. He invests super early in people. He has an amazing list of early stage investments that include the Lyft, Wish, Gusto, Postmates, AngeleList, and many more. We're going to talk about his amazing track record, but I'm going to ask if we can first start with his entrepreneurial journey because it is truly unlike any other VC story I've heard.

Hello Paige.  Thank you for showing me the guns in the backgrounds.

I think I have 13 in this room and I think six actual ones next door.

Are these not actual ones?

No, these are, these are photographs of weapons.

Okay, but the actual guns are in the gun room?

Yeah. I mean, I have, I have my actual guns locked up like a responsible gun owner

Okay, great.

And I know guns are not politically correct right now, but that's a different discussion.

Well, but they're a core part of your entrepreneurial journey. And I thought we could jump in and you could tell us about what you did and how you got started driving into Iraq with $10,000. I really don't know the story, but I'm dying to hear it.