At a party at the True[x] offices on Wilshire, three dudes have just finished pitching an app. They look like design students, with black vests and matching haircuts. One of them boasts that the founder had a chance to be the sixth employee at Instagram. But when the founder starts talking, he says he would have actually been the fifth.
"That's the one regret I have," he says.
The app is called Unvael, which they describe as "Instagram for music." They're trying hard to be mysterious about it. If you want to know more, they say, you need to come with us to Mexico.
"Spotify and Pandora — they're all fucking retards," the founder says. "Soundcloud — that's a lot of shit. A fuckload of shit."
The trio had been pitching Paige Craig, an angel investor who's still standing nearby, wearing a "Pray for Surf" T-shirt and spitting tobacco juice into a Tecate can. Craig shot them down with three words: "Music? I'm out."
Craig is just back from San Francisco, where he met with the founders of Caarbon, a startup that aspires to be the Uber of valet parking. He was hooked by the concept: No more circling the block looking for a spot — just open an app and arrange for a valet to meet you wherever you want. When you want your car back, they'll bring it to you.
Craig was sold when he met the Caarbon team. The CEO grew up in Detroit and sold books door-to-door before getting into Harvard. Craig also grew up poor, so he likes founders who have shown "grit."
Craig also has a rule that he will invest only in ideas that could change the world. Caarbon won't cure cancer, but he thinks it could disrupt the valet business — maybe the whole parking industry. He talks about Caarbon like it's a woman he just started dating and hasn't slept with yet.
As he extols the company to a small cluster of friends, Craig's enthusiasm spreads. One guy says the app could help him avoid parking tickets, which have cost him nearly $1,000 in the nine months since he moved to L.A.
But then another guy pricks the mood with a practical question. What happens when the bars close at 2 a.m. and everyone wants their car at the same time?
"No idea," Craig says. But, he adds, "It's a great team."
Six years after arriving in L.A., Paige Craig has become one of the city's top angel investors. Some think of him as L.A.'s version of Ron Conway, the prominent Silicon Valley tech booster. Others call him the mayor of Silicon Beach.
"He's probably the most connected guy in L.A.," says Mark Mullen, who runs L.A.-based venture fund Double M Partners.
Angel investors tend to be entrepreneurs who, having built and sold a business, find themselves wealthy and idle. Instead of retiring to the beach, they bet their own money on fledgling companies.
Because they're using their own funds, angels can take risks that professional investors won't, and they provide mentorship and support. For a certain kind of person, the risk is thrilling.
At 39, Craig looks more like a surfer than a professional investor. He's compact and muscular, with the bearing of a Marine. Usually clad in a T-shirt, cargo shorts and flip-flops, he always carries an iPhone 5 and a tin of Copenhagen snuff. He is blunt and often profane, especially when shooting down a pitch.
"A lot of people are gonna sugarcoat things," entrepreneur Josh Payne says. "Paige is the type of guy who's like, 'Your idea is shit.' "
Craig moved to L.A. knowing almost no one. He began throwing parties at a rented beach house in Venice, which became a place for entrepreneurs to do shots with investors while hashing over term sheets.
He has become one of the city's most prolific investors. Since coming to L.A. in 2008, he has invested in 90 tech companies, including ridesharing app Lyft and Burstly, which just sold to Apple.
His decisions are largely based on gut instinct. When he likes something, he doesn't wait to pull the trigger.
Most startups fail. But Craig says his biggest regrets are not about losing money but rather about failing to act on his instincts: "It's the same regret you feel if you see some girl in the train station, and there's something about her that you want, and you choose not to take action on it."
Startup investing is a social phenomenon. If one investor likes a company, that makes it more attractive to others. The hard part is getting the first investor to say yes. Craig is often that person.
"When it comes to L.A., a lot of people look at whether he's made an investment as an indication as to whether this is a legit L.A. company," entrepreneur Micah Baldwin says.
L.A.'s tech scene is small — just a fraction of Silicon Valley's. Craig is squarely at the center of it. His life is a blur of startup founders pitching apps, entrepreneurs seeking advice and other investors prowling for a scrap of intelligence that could lead to a deal. With 90 companies to oversee, he doesn't have time for much else.
"Anytime something eats too much of my life, I kill it," he says. "Girlfriends, video games..."
Every few months, he skips town on some adventure. Craig likes scuba diving and rock climbing — anything that involves the risk of serious injury. Last year, he broke his shoulder and tore two knee ligaments in a snowboarding accident.
He has cultivated a reckless image, but friends say that's deceptive. After taking 200 startup pitches in the last three months, he invested in only five companies, and he carefully structured those deals to his advantage.
Niko Cunningham, the CEO of Caarbon, calls him "pseudo-swashbuckling yet highly disciplined."
"He appears to be a regular Joe," Cunningham says, "but that mind is working 1,000 miles a minute."
It's fashionable for tech entrepreneurs to drop out of Harvard or Stanford. Craig is the rare example of someone who went into tech after dropping out of West Point.
He grew up in Sacramento, where his father, Charles, ran a framing business out of the family home. They barely had enough to live on. As a child, Craig wanted to become an artist, or maybe Indiana Jones.
He ended up as a West Point cadet but chafed under the Army's bureaucracy. After three years, he dropped out. He ended up enlisting in the Marines, which he found more agreeable. If the Army was IBM, the Marines were a scrappy startup — small groups solving problems on their own. Working in intelligence, Craig finished his undergraduate degree, earned an MBA and was promoted to sergeant before leaving the service in 2000.
The invasion of Iraq three years later presented a unique opportunity. Craig knew private investment would flood into the country and someone would make a fortune. That summer, he took out a home equity loan on his place in Washington, D.C., maxed out his credit cards and flew to Amman, Jordan. There, he posed as a journalist and ultimately persuaded a driver to take him to Baghdad. He was carrying $10,000 in a camera bag.
"I'm sitting there like, 'Holy shit, if this doesn't work out, I'm fucking bankrupt,' " Craig says.
He and his business partner, Christian Bailey, spent a year hustling before they started winning Pentagon contracts to assist with "psychological operations."
"In this war, the space you had to dominate and win in was really the mind," Craig says. "Thoughts, perceptions, ideas, stories — these things had much more power, especially in an age when information is being transmitted faster and anyone can create the news."
Their company, the Lincoln Group, was awarded contracts worth as much as $130 million. At one point, the company had 40 employees in the United States and another 200 in Iraq. Those employees were tasked with placing pro-American TV spots and news articles in Iraqi media, without disclosing that they originated with the U.S. military.
In the tech world, this would be called native advertising. In the context of a war, the term is propaganda.
The military could not do this work itself, creating an opportunity for a fledgling contractor.
"There were private contractors operating in the Middle East, but none of them could do PR and media stuff," Bailey says. "And there were PR and media companies in the U.S., but none of them could deploy to a war zone."
It was lucrative work, often absurdly so. In a later tell-all account for Harpers, a Lincoln Group intern reported that the company was paid $1 million for TV spots that cost just $12,000 to produce.
It was also dangerous. Craig prided himself on taking risks that more established companies would not. He drove around in unarmored cars and met with Iraqis whose allegiances were not always certain.
The work was most perilous for the Iraqi staff. According to The New York Times, one of the company's Iraqi workers was killed by gunmen after going door-to-door in Anbar Province to administer a poll.
When the first story about the Lincoln Group's efforts broke in the L.A. Times in late 2005, it created a stir on Capitol Hill. A Pentagon inquiry eventually cleared the company of wrongdoing, but the firm was passed over for a $250 million contract the following year.
For Craig, it was a stressful period.
"Guys are getting killed," he says. "I got reporters up my ass about this shit. I got politics — I got the White House interfering with our projects. I got people on both sides — some people hate the Iraq War, some people are fucking right-wing crazies. And I'm just trying to do a job and get shit done."
Now, when Craig evaluates startups, he sometimes thinks about whether he would take the founder into a combat zone. He sees his experiences in Iraq as a more intense version of what every startup goes through.
"It's a lonely, lonely, lonely business," he says. "When you're doing a startup, life is not all roses and rainbows like you see on Instagram, and killing it."
After four years in the Middle East, Craig sold his share of the Lincoln Group and left war zones behind. He needed to decompress, and was drawn to L.A.'s laid-back lifestyle.
He also needed some risk, something that would get his adrenaline pumping. Eventually, he stumbled into angel investing.
It's 6:45 a.m. on a Thursday, and Craig is sweating and grunting through a game of racquetball at the Santa Monica YMCA. His opponent, Eric, is fresh out of college (and asked that his real name not be used to avoid causing problems with his employer).
Eric works at a tech company, biding his time before he launches a messaging app. Craig acts as his mentor — offering advice, making introductions and helping him refine his ideas. Eric is eager to learn.
Craig has been sick since he got back from San Francisco. Eric is fit and forces Craig to chase the ball all over the court, the squeak of sneakers echoing off the walls.
"I can't breathe today," Craig says.
At one point, Craig winces and reaches for his back. Eric asks if he's OK. He's fine, Craig says, and they play on. When Craig loses the first game, he slams the ball in frustration.
Toweling off between games, they talk about the sex-harassment suit that was recently filed against Tinder, the L.A.-based dating app. Craig knew the CEO back when he was pitching a find-your-dog app. He also used to play poker with the co-founder, who allegedly sent abusive texts to his ex-girlfriend.
"What a fucking idiot," Craig says.
Craig comes back and handily wins the second game. He streaks around the court, pivoting backward to slam the ball off the rear wall. His T-shirt is soaked in sweat.
At the break, he mentions a guy who has put off starting a company out of financial considerations. "He's too addicted to that paycheck," Craig says.
It's a message he wants to drive home. Being an entrepreneur may require living on a modest income for years. If you get comfortable in a well-paying job, you'll never do it.
In the third game, Eric takes an early lead but Craig finds another gear and guts it out in the end. Eric stalks off the court and throws his racket to the floor.
They get breakfast at Huckleberry Cafe, brainstorming features for the app over huevos rancheros.
"If people make a lot of introductions, should they get recognized for it?" Craig asks. "I've never seen a score showing who's a good connector. That'd be useful, right?"
Many of Craig's ideas seem to come from his own life. An excellent connector, he would rank highly within this hypothetical app. He argues that attracting connectors would help build out the network, which is the biggest challenge in launching a messaging platform.
Conceptually, it's reminiscent of Klout, the service that aggregates social media data to rank people by their influence, then sells that information to brands.
A lot of people hate Klout, but Craig was an early believer, investing $180,000 in its first seed round. At one time, Klout promised to become as essential to ranking social media profiles as Google is to ranking websites. It didn't work out that way, but Klout nevertheless did well by its investors. The company sold earlier this year for a reported $200 million. If that's accurate, that means the earliest backers saw a 67-fold return. (Craig can't disclose the details, saying only, "It was a great return.")
Eric is not totally sold on the idea of rewarding connectors with points, and that's fine by Craig. It's Eric's app.
They part ways in the parking lot. Just before Craig gets into his Range Rover, he calls out to Eric.
"Quit soon," he says.
Craig arrived on the L.A. tech scene as a wild man with money. Alec Shankman remembers going to Craig's house to pitch him on an investment in 2009, and finding him hosting a beach party and doing shots of Patrón. A few drinks in, they decided to forget about business. Shankman came back to pitch the next day, and Craig ended up investing $50,000.
"He's just kind of notorious — in a good way — for having a drink in one hand and a checkbook in the other," Shankman says.
Jameson Detweiler met Craig at Summit at Sea, a Caribbean cruise for the tech industry. After a few minutes of talking about his company, Craig offered to write Detweiler a $50,000 check.
"I thought, 'Who is this guy?' " Detweiler says. " 'He's crazy. Where is his money coming from?' "
Craig's friend Michael Schneider recalls Craig getting into a conversation at South by Southwest with the CEO of Foodspotting.
"He pulled out a checkbook from his back pocket and started writing a $100,000 check," Schneider says. "I looked at him, like, 'Are you sure? You've been drinking all day.' He's like, 'No, no. I like what I hear. I'm in.' "
Foodspotting later sold to OpenTable, but not every deal was a winner. Craig also backed MogoTix, a ticketing app that was destroyed by Eventbrite; GameCrush, a social gaming site that got overrun by masturbators; and Ecomom, whose founder bankrupted the company and shot himself in the head.
Many others live on in limbo, with little prospect of generating a return.
And then there was Craig's own company, BetterWorks, which he launched in 2010.
At the time, big tech companies were getting buzz for using lavish perks to attract and retain employees. Workers were provided catered meals, dry-cleaning service, gym memberships and yoga classes.
BetterWorks sought to help smaller companies create a similar office culture. Discounts also were hot, thanks to the success of Groupon. BetterWorks combined the two ideas, offering discounted perks to incentivize employee performance. The sales pitch: "Google perks at Costco prices."
As Craig recruited his team, his enthusiasm was hard to resist.
"He gave me a call and said, 'I got a billion-dollar idea,' " says Robyn Ward, who became BetterWorks' director of business development. "When Paige is trying to sell you an idea, there's nobody better."
Craig brought in big-name co-founders, including Zao Yang, who created Farmville, and George Ishii, an early PayPal employee. On the strength of their reputations, they raised $10.5 million in venture capital. With a valuation close to $100 million, BetterWorks became one of the marquee companies of Silicon Beach.
"It was an intense valuation," Craig says. "I negotiated the shit out of people."
The concept was an easy sell for tech companies that wanted to mimic Google's workplace culture. But as the sales team tried to branch out to more traditional companies, it met resistance.
"We started getting responses from HR departments and hiring teams that were, like, 'Hey, that's a nice idea, but our employees are lucky to have a job,' " Craig says. "The lead time to close a deal was getting longer and longer." Sales sputtered, and tensions arose between the sales team and the product team, as well as between the co-founders.
"It was amazing the quickness with which things went from skyrocketing to not working," Ward says.
Craig believes a much smaller company could have succeeded by focusing on tech clients. But with very thin margins, BetterWorks needed broad adoption in the non-tech economy to generate the returns sought by venture capitalists.
"The reality is, we were building something people didn't need," Craig says. "What I really fucked up on was basically mistaking perks and company culture as a medicine rather than a vitamin. Medicine, you have to take it. A vitamin is nice to have but, honestly, you can skip it."
After just 18 months in business, BetterWorks shut down.
Craig returned money to his investors and spent a couple of months trying to get jobs for his employees. Then he left for Africa and Europe to clear his head. The experience gave him a much more critical eye as an investor.
"I think I crush a lot more dreams these days," he says. "There are things we want the world to have, and sometimes the world just isn't going to get those things."
Craig now lives a few blocks from the beach in Venice, in a modernist condo decorated with Pop Art photographs of guns. It's a short walk from Amplify.LA, the tech accelerator where he spends much of his time when he's in town.
Craig, an investor in Amplify, keeps a desk there, but it's empty except for a stack of snuff tins and a bottle of tequila — a gift from a deal closing.
He takes most of his meetings on the couches in a communal area. This afternoon, he gets a visit from Andrew Dudley. A British anti-deforestation activist, Dudley is best known for running on the field during sporting events to draw attention to his cause. He prefers to be called Jungle Bird.
Dudley is here with a serious idea. He's pitching an app that would allow lumber companies to prove that they are harvesting legal timber, helping customs officials crack down on illegal deforestation.
The concept sounds promising and, unlike a lot of other apps, it could actually change the world for the better. But as Craig digs in, he concludes that Dudley's activist zeal will be incompatible with future stockholders' need for massive returns.
"Every tech investor you talk to, they have to have outsized returns to pay for the 95 percent of companies that we invest in that go to zero," he explains.
Angel investors might look like cowboys of capitalism, taking wild bets on little more than gut instinct. In reality, they are at the bottom of the investment food chain. Craig invests only in companies that he thinks can be sold to venture capitalists. And venture firms will invest only in companies that could go public or be bought by a public company.
In a sense, Craig is scouting for venture firms, so he has to think as they do.
"I want to do good, but I also have to invest in things that are going to have outsized returns," he says. "The way you're running the company, it's probably not going to happen."
"Thank you for your honesty," Jungle Bird says.
Craig can be even more blunt with his friends. Earlier that afternoon, he and a friend spend an hour going over an idea for an e-commerce platform. The friend then asks how to approach angel investors, and whether Craig would be interested in writing a check.
Craig responds sharply. "You're going to raise with no product, and no work?"
"I don't know," the friend says. "Let's talk about it."
"I'd say fuck off," Craig says. "You want [to get] funded for nothing but thinking? No one does that." No one good, anyway: "You can find a high-net-worth individual to do that, i.e., an idiot."
Craig suggests the friend put together a rudimentary version of the product, which means finding an engineer to build it.
"Which, I'm not a fucking tech dude," the friend says. "I mean, I'm a tech dude" — but, like most tech entrepreneurs, he doesn't know how to code.
"You do that, you can raise a respectable seed round," Craig says. "Versus, right now if you try to raise a quarter-million, half-million, you're going to take it in the ass."
He suggests applying to several tech accelerators.
The checkbook has been put away. These days, Craig is doling out tough love.
Investors try to read industry trends the way surfers try to read waves. Most trends will fizzle out — like Groupon's daily deals — but others will become massive, altering the culture and generating billion-dollar companies.
At the moment, Craig is most excited about three big trends. The first is labor disruption, otherwise known as the rise of freelancing. He's an investor in Lyft and Postmates, two apps that facilitate part-time work for drivers. He takes Lyft when he can, and is downright evangelical about Postmates, an app that promises to deliver anything. For lunch, he often opens the app and orders chicken skewers.
He's also big on virtual reality, which he thinks could supersede mobile phones as a hardware platform. On a visit to Wemolab, a Venice company that makes virtual reality software, Craig straps on an Oculus Rift headset. Watching Craig tour an underwater world, his head swaying side to side, an engineer whispers, "He's in the Blue."
After being eaten by a virtual shark, Craig takes off the Oculus and starts riffing on the future of virtual reality. It could be used to broadcast live sporting events and concerts, or to create virtual shopping malls.
Wemolab will end up being one of the handful of companies Craig invests in before leaving for Europe.
A third theme is crowd-funding, or what Craig calls "the disintermediation of capital." He believes that gatekeepers — banks, professional investors — prevent good people from getting funded. But with online platforms, investors can go around the traditional channels.
He's an investor in AngelList, which is sort of like Kickstarter for startups, allowing entrepreneurs to seek investments online. As Craig sees it, AngelList removes the gatekeepers, giving everyday people access to promising startup deals.
It also happens to be great for angel investors such as Craig.
Angel investing involves a fair amount of work — finding deals, evaluating them, checking backgrounds. Other investors then come along and piggyback.
AngelList lets the lead investor charge other investors for that work. First, angels pool capital from a group of investors into a "syndicate." The angel charges those investors "carry" — a percentage of the growth of an investment — for the privilege of getting into a deal.
"It's basically taking what we've all been doing for years and rewarding us for doing it," Craig says.
With enough investors behind him, he could make far more in carry than on his own investment. In other words, Craig will be operating like a freelance fund manager — not just risking his own money but getting paid to risk other people's as well.
Craig thinks crowd-funding could be revolutionary, much in the way that Twitter and Facebook helped stir the Arab Spring.
"I think some day we're going to see a crowd-sourced conflict," he says. "If nation states can't agree on what to do, maybe you crowd-source the Iranian revolution."
The vision of investors waging proxy wars on literal battlefields is not without practical concerns. If someone else offered it, it would come with a wink. But Craig is deadly serious.
"That's the broader trend humanity is moving to, allowing citizens to decide what they want to do," he says. "Say we decide the MEND rebels in Nigeria should get financing to overthrow the northern Nigerians. Right now we have to rely on politicians. Maybe we should rely on consumers to make those choices."
Caarbon allows Craig to combine two of his passions — labor disruption and crowd-funding — in a way that takes full advantage of his skills as an investor.
Caarbon wants to disrupt the valet industry just as Uber is disrupting cab companies. Craig argues it will be good for consumers, who will be able to park anywhere for a couple dollars above meter rates, and good for valets, who will earn more and have more autonomy.
Whether it will work out that way in reality is hard to say; Caarbon doesn't have a product yet. But it's a good story, and that's the key to fundraising.
To build the product and launch it, Caarbon is looking to raise a seed round of $1.5 million. Bay Area venture capital firms are putting in about $1 million. Craig is investing $50,000, and he wants to fund the rest of the deal as a syndicate through AngelList.
If he can pull that off, it will work to his advantage. Other investors will pay a 20 percent carry to be part of his group.
The bigger the syndicate, the more the carry. If his syndicate puts in $200,000, and Caarbon eventually sells for 10 times its current valuation, then Craig will end up making $360,000. But if his syndicate puts in $500,000, Craig will make $900,000 — for doing the same amount of work.
In either scenario, Craig's $50,000 investment also will return $450,000 in profit. But in the latter case, he will end up making twice that amount from the other investors.
It's not a bad deal for the investors, who will still see their money go up eightfold, but it's a great deal for Paige Craig.
It's up to Niko Cunningham, Caarbon's CEO, to decide how much money to take, and from whom.
Cunningham met Craig only a month ago, but he's impressed. He likes Craig's scrappiness and his military background. They hit it off right away. Caarbon is based in San Francisco, and Cunningham will need help when he expands to L.A.
"He wants to be known as the guy you go to in L.A. when you're building a consumer-facing company," Cunningham says of Craig.
After pitching his idea for months to disbelieving investors, Cunningham suddenly finds himself in demand. Craig, who's competing with other investors for the biggest possible slice of the deal, finds it's in his interest to make himself useful. He begins by gathering intelligence on a potential competitor.
As it turns out, Caarbon is not the only company that wants to be Uber for valet parking. CurbStand has quietly launched with about 70 valet stands in L.A., and plans to roll out in other cities this fall.
Based in Beverly Hills, CurbStand supplied valets to a Malibu Fourth of July party hosted by Paris Hilton, who posted about it on Instagram.
"There's a lot of buzz," CurbStand CEO Serge Gojkovich tells the Weekly. "You're gonna hear a lot about CurbStand in the next couple months."
CurbStand's business model is different from Caarbon's. It's essentially a cashless payment system for valet operators, while Caarbon wants to disrupt valet operators. But they're both tackling the same market.
CurbStand has the advantage of being first to launch. Caarbon has not delivered a product yet — which is why it needs financing — and when it does, it will be only in San Francisco.
Craig believes that Caarbon also should be in L.A., the valet capital of the world. He's urging Cunningham to launch here as soon as possible.
"Everyone is so San Francisco–centric," Craig grumbles to a friend. "It would do 50 times here what it would do in San Francisco."
When Craig gets wind of CurbStand, he calls up Gojkovich, says he's an investor and starts asking questions. Gojkovich explains the CurbStand business plan and shares details about the investors and the team. Craig then calls Cunningham to relay what he's learned.
"It's fucked up," he tells Cunningham by phone. "I wouldn't be concerned at all."
CurbStand is funded by guys in the parking industry, he says. The investors do not come from the tech world — a major liability, in Craig's eyes.
"I see this all the time," he says. "There's not a single smart investor in the deal."
Craig also is not impressed with Gojkovich, who comes from Grindr and ParkMe. He didn't know who Craig was, and didn't seem to have a sure grasp on his metrics.
"When they fail, and they will fail ... " Craig pauses. He's about to suggest hiring away some of CurbStand's team but thinks better of it. "I don't think that's the kind of talent you want to go steal."
Craig has been doing this sort of thing for his companies for years, only now, with AngelList, he has figured out how to get paid for it.
Before hanging up, Craig brings up financing. He wants Cunningham to take as much as possible from his AngelList syndicate.
"The minimum is $200K," he says, then suggests he can push it to $400,000. "Take the weekend to think about it, and let's lock in by Monday what that amount's going to be. You have enough commitments from venture guys."
On a Wednesday morning, the Caarbon syndicate launches on AngelList. Craig has convinced Cunningham to take $300,000. Within 30 minutes, the syndicate is oversubscribed.
Craig then goes to work on Cunningham, pressing him to let the syndicate invest more. He doesn't want to dilute the founders' stake too much, he says. That would be bad for the company.
So he suggests that some non–syndicate investors should be forced to buy in to the deal at a significantly higher valuation — paying more for a smaller slice of the company. Amazingly, everyone agrees to this.
Cunningham bumps Craig's syndicate up to $500,000 and ends up taking about $2 million in total.
Remarkably, some of the investors in the syndicate are seasoned, Silicon Valley angels who are quite capable of finding deals on their own.
But they're willing to pay a premium to Craig, either out of courtesy and respect or in the expectation that he will some day return the favor.
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Cunningham is both exhausted and exhilarated.
"When Paige gets involved," he says, "it's a whirlwind."
Craig is about to leave town for Utah. From there, he's headed to tech events in Iceland, Sweden and Berlin.
Before he goes, he offers Cunningham suggestions on who to hire when Caarbon launches in L.A.