Paige Craig is an angel who loves to curse.

The 40-year-old former Marine might have a penchant for partying and swearing, but he’s also one of the county’s most prolific angel investors who has gone on to form a seed-stage venture capital firm.

Craig launched Venice’s Arena Ventures in January along with Jeffrey Lo, a former managing director at New York’s Fortress Investment Group, and has raised more than $27 million from 35 investors, according to a May 6 filing with the Securities and Exchange Commission.

Now working from Craig’s Venice living room, Arena will take office space in a West Hollywood office June 1, formalizing its position as an investor in mobile-video streaming app Meerkat, online denim retailer Dstld and digital interior design marketplace Laurel & Wolf, among several other startups. Angel investors put their own money in early stage companies while venture capitalists invest other people’s money as part of a firm.

Craig moved to Venice in 2008, about a year after selling his stake in Lincoln Group, a military contractor in Iraq and other Middle Eastern countries that was paid to generate pro-American news coverage in Arab media outlets.

Since then, Craig has invested between $50,000 and $100,000 in more than 100 early stage startups. Quite often, he’s one of the initial backers, if not the very first, to write a check.

“That’s the riskiest position in the world to be in,” he explained, since most startups fail. About a dozen of the companies in his portfolio have gone under so far, and he expects others will as well.

Failure is not unfamiliar to Craig.

In October 2010, he founded online platform BetterWorks that allowed companies to buy perks for their employees. Two years later, the company had gained little traction and folded.

“I built something that people didn’t actually want,” he said.

Risk, reward

While most startups struggle, the few that hit it big can make everything worthwhile for angel investors such as Craig.

Take San Francisco’s Wish, a mobile shopping platform Craig wrote a $110,000 check to during its seed round in 2010. The company is now reported to be raising a Series C round at a $3 billion valuation. Other bets that have paid off for him include ridesharing service Lyft, now valued at $2.5 billion, and social media analytics firm Klout, which was acquired by Lithium Technologies in March 2014 for $200 million.

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