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Angel Q&A Series: Paige Craig

Paige Craig is Managing Partner at Arena VC. As an LA-based angel investor he has invested in over 100 startup companies including Lyft, Postmates, Plated, Laurel & Wolf, Zen Payroll, Caarbon, and many more. Paige is actively involved with startup communities around the world, and through Arena Ventures runs a syndicate on Angellist. Paige spoke with us a bit about his experience as an angel:

SA: How did you get your start?
PC: I grew up in a very poor family but hustled to earn a spot at West Point. I went into the Marine Corp afterward and the US intelligence community after that. In 2003 I bootstrapped and launched my own company, a private military business and scaled it across the Middle East, African and Asia. After selling the business I decided to become an angel investor and help founders in their earliest days.

SA: Why do you invest in startups?
PC: Given my background, I’m very good at reading people and at recognizing the types of people who thrive in chaos and can build massive companies. I focus on risky, wildly ambitious endeavors, so seed stage startups are the natural fit as an investor. I’m not a finance expert or from a traditional tech background but I’m very good at recognizing exceptional founders and great ideas before anyone else.

SA: How did you feel when you made your first investment? What went through your head when you signed the check?
PC: I remember thinking along the lines of “I can’t wait to be part of the team and get my hands dirty.” I love helping founders so I tend to invest in businesses that personally excite me and where I add value.

SA: You’ve decided to start your own venture fund, what prompted that?
PC: Both (my business partner) Jeff Lo and I had been successful angel investors and close friends for several years. We collaborated on numerous deals and talked about someday formalizing that collaboration into something.

Last year our discussions about crowdfunding and the evolution of the venture capital industry led us to realize how powerful an entirely new, hybrid model of VC firm could be – in December we decided to go build it ourselves.

SA: Do you think it’s important for more veterans to become entrepreneurs or angel investors? How can we better nurture that?
PC: Veterans are uniquely positioned to participate in both. There are tons of amazing men and women who’ve led their teams through chaos and I wish we had more of them on the front lines of venture and startups. They understand the value of leadership, teams and execution. They know what it means to get shit done.

The two downsides I frequently see are (1) most veterans are used to working in very hierarchical organizations and startups are the complete opposite and (2) they’re used to following the rules … Most startups break rules and make up their own. That said I’d love to have more warriors in our industry.

SA: What’s the worst move or decision you’ve seen any early stage investor make?
PC: Investing because something is “Hot” – every day I get deals sent my way where a fellow investor encourages me to invest because “so and so” is investing, or the founder is connected to some amazing leader or celebrity. Honestly I just don’t give a crap about social proof. Investors should invest because they personally believe in the team, the vision and the market as a total package and not rely on others or social proof.

SA: What’s your preferred way to bond with your founders?
PC: Tequila, racquetball, or outdoor adventure.

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