A brisk wind is mussing up
Vanity Fair editor Graydon Carter's curious pageboy hairdo. It's a sunny autumn morning in San Francisco, with the U.S. election a few weeks off, and Carter is loitering behind a small downtown theatre, the venue for an annual gathering the magazine calls, with some justification, its New Establishment Summit. A senior female aide approaches him, and the editor sits down next to her on a ledge around a planter and, with pens in hand, they go through printouts of seating plans, analog people in a digital era.
Many of the conference's featured speakers have been caricatured by a cartoonist on a scrim out front. They're all members of the coastal elite that Vanity Fair likes to feature in its glossy pages. Amazon CEO and Washington Post owner Jeff Bezos fraternizes with artist Jeff Koons and CBS head Les Moonves, while Facebook founder Mark Zuckerberg and his pediatrician wife, Priscilla Chan, rub shoulders with late-night host Conan O'Brien and wit Fran Lebowitz.
There's another, less recognizable face on the scrim: that of venture capitalist Chamath Palihapitiya, who's been invited to speak at the conference for the first time. The Canadian expat is known in Silicon Valley primarily for three things: helping Zuckerberg to grow Facebook from big to supersized; buying a share in the then-hapless Golden State Warriors NBA team; and his willingness, from time to time, to break ranks with his adopted community. Indeed, he's been so ready to criticize his peers that The Wall Street Journal recently called him, in a headline, "the venture capitalist whom venture capitalists love to hate."
Before heading into the theatre, Palihapitiya does a brief TV interview with a Bloomberg reporter. He sits easily in a tall director's chair, his lanky form clad in the requisite tech-exec mufti of black blazer, blue button-down and jeans. He tends to favour clothes in muted colours cut to fit his slender form—casual but not sloppy, and never the fleecies and gadget-lumpy khakis worn by some of his fellow tech travellers.
His caricature on the scrim accentuates his prominent nose, but in person, it's the eyes that have it, darting about, scrutinizing. In his leisure time, Palihapitiya plays high-stakes poker, and he's someone who looks, always, for the tell.
He talks fluently to the Bloomberg reporter about global warming and, more specifically, about a company that is building ocean-going sailboat drones to measure the effects of climate change. It's one of many projects funded by his venture capital firm, Social Capital, to which the Waterloo University-trained engineer has directed much of the wealth he acquired as one of Facebook's earliest employees. His net worth is reputed to be around $1 billion (all currency in U.S. dollars).
The seating plans annotated, Carter smooths his silver hair back into place and rushes, like the White Rabbit, through the theatre's back door. Soon, Palihapitiya follows—he's part of the day's first panel, on the state of Silicon Valley.
Tech writer Nick Bilton starts by pitching a softball to Palihapitiya and two fellow panelists. What would he need to know to do their jobs, to earn the keys, he jokes, to their private jets?
Kleiner Perkins Caufield & Byers VC Mary Meeker says she looks to see if start-up heads are willing to surround themselves with people better than they are. Aaron Levie, CEO of the fast-growing cloud-storage company Box, says he is constantly thinking about the consequences of the industrial world going digital. These are safe, woolly answers, swimming in the tech community's mainstream.
As is his custom, Palihapitiya goes his own way. "The most important thing in my job is to write down what you believe in," he tells Bilton, "and to use money to amplify your moral and ethical perspective."
From this standpoint, the Vanity Fair conference looks like the last gasp of a more heedless time.
Palihapitiya has been something of a naysayer for a few years now, sober when so many in the Valley have giddily watched the tech market, with a few blips, rise and rise again. He has declined to invest in many of the projects that have made those around him say yes, absolutely.
Instead, he and Social Capital have invested heavily in start-ups trying to make headway in the risky health and education spheres, where the payoffs come later, if at all, and aren't purely financial. "If life were a race, it's fair to say that the starting lines at birth are unevenly distributed," Social Capital's vision statement reads. "And when people are deprived of an opportunity to excel and contribute, we all lose."
Palihapitiya himself started well behind many of his Valley peers. Certainly, he's a singular creature in the boardrooms he frequents: the Sri Lankan-born, Canadian-bred son of refugees whose socialist father instilled in him a strong belief in the social safety net. But, a contrarian by nature, he also has a strong libertarian streak and has expressed disdain for the problem-solving capacities of government. He's a bro's bro, to be sure—a fast-car-driving, poker-playing lad—but he has also called out the Valley's sexism so hard that a female tech CEO has labelled him the best feminist she knows.
As Silicon Valley struggles to position itself in the Trump era, Palihapitiya finds himself with well-placed friends on both sides of the nation's great, gaping divide. With his long-standing willingness to speak his often complicated truth, this means Palihapitiya is about to hit his moment of peak influence—and he is determined to use that influence. Not to make billions backing the next Uber, but to build a legacy based on his own version of what's right. "Do you know who was the richest person 100 years ago? No. If you want to be remembered, it's because you created a religion, you figured out gravity, you came up with a unified theory." Given the long odds and setbacks Palihapitiya has already overcome, why shouldn't he think big?
Palihapitiya wasn't born rich. His father, Gamage Palihapitiya, was originally a civil servant in Sri Lanka's health ministry. He brought his wife, Srima, and his young family, including six-year-old Chamath, to Ottawa so he could take an entry-level job at the High Commission in the 1980s. When insurgents unseated the government back home, he sought asylum.
Chamath's father eventually found a job as a data entry clerk; the mother worked as a housekeeper and nurse's aide. But the Palihapitiyas often relied on public assistance, with the five of them (Chamath has two younger sisters) sharing a one-bedroom apartment over a laundromat.
For all its privations, Palihapitiya remembers his upbringing, and his father, with fondness. "I absorbed a lot of his world view," he says, "though I didn't end up anywhere near as leftist as he is." His interest in business began early: He remembers reading a business magazine's rich list, fantasizing that, one day, he'd be on it.
Palihapitiya is unusually tight-lipped about his school days. "I was a bit closed in. I didn't have many friends." But that changed when he got to the University of Waterloo to study electrical engineering in 1994. In the hurly-burly of frosh week, he made a close friend, only to lose him later that year to a rare form of cancer. Palihapitiya is still reluctant to speak of the loss, giving up his friend's first name—Amit—only when pressed.
It was during Amit's illness that he grew close to Brigette Lau, a Waterloo computer engineering student who is now his wife. "Chamath was a character," recalls Lau, "someone who gave people a hard time." Through the process of losing their mutual friend, Lau got behind his formidable wall. "Under the hard exterior, there was this big heart."
Looking back on his time at Waterloo, Palihapitiya is particularly glad the co-op program allowed him to alternate study and work terms. "I was only a marginal-to-decent student, but I realized in the work terms that I was a good practical problem-solver." (In a payback to his alma mater, he arranges for some 20 Waterloo students a year to do lucrative work terms in the Valley.)
After graduation in 1999, Lau joined a big accounting firm's San Francisco office, and Palihapitiya landed a job trading derivatives at BMO Nesbitt Burns in Toronto. "My boss gave me a zero bonus at Christmas, which hurt my ego but woke me up, because I was losing myself in that job. I might still be there otherwise."
Palihapitiya followed Lau to California. The millennium was turning, and the Internet boom was speeding toward a bust. Though the Valley was in a shaky state, Palihapitiya soon found his footing with two early digital music sites. One of them had fewer than 10 employees—all, like Palihapitiya, in their early 20s.
That's when he met (and impressed) Sean Parker, the piratical founder of Napster, who would go on to become president of Facebook.
In 2000, AOL swallowed both the music sites Palihapitiya was working for. He soon found himself running AOL's music division, and then its rudimentary instant-messaging platform. Palihapitiya credits his mentor at AOL, Kevin Conroy—now a top executive at MGM—for plucking him out of the crowd. "He basically was like, 'This kid is really smart, and we pay him next to nothing, and everybody else around him is a bozo.'" At 26, he became AOL's youngest VP, with 200 employees under him.
He has vivid memories of his first meeting with Mark Zuckerberg, in the fall of 2005. "Parker set up some meetings with me and Zuck," Palihapitiya says. The social network was young—maybe 15 employees, and open only to university students, even though Zuckerberg had dropped out of Harvard and moved to Palo Alto. "Zuck didn't say much," recalls Palihapitiya. "It was very cold, it was raining, and he had the famous North Face fleece on, Adidas flip-flops."
Palihapitiya recommended to his superiors that AOL buy the social network. He couldn't get the go-ahead to make an offer, so instead, he proposed a deal to integrate AOL's chat function into the product. "We did a lopsided deal, in favour of AOL," he says. Within a few months, they decided to unwind the partnership, and Zuckerberg and Palihapitiya became friends in the process.
In 2006, with AOL treading water, Palihapitiya joined the venerable Mayfield venture fund, under Silicon Valley legend Yogen Dalal, who'd helped his Stanford professor Vint Cerf come up with the Internet's lingua franca, the TCP/IP protocol.
It was during this time that Palihapitiya started hosting what has since become Palo Alto's top high-stakes poker game, with 14-time World Series of Poker champion Phil Hellmuth. A who's who of founders and VCs became regulars. (Poker wasn't his first card obsession: "I started out with bridge, but these old ladies you think are so respectable, they cheat!") When told that Wikipedia pegs his poker winnings at $175,000, Palihapitiya scoffs, "That's just tournaments."
Dalal laughs when I repeat a story from the AOL period, published in The New York Times, of Palihapitiya, after an all-night poker game, taking his $50,000 in winnings to a BMW dealership, where the salesman refused even to let the unkempt young man test-drive a vehicle. Palihapitiya crossed the street to a Mercedes dealer, bought a sedan, and drove it back to show the Bimmer salesman.
Wasn't this kid a bit hard to handle? If so, the courtly Dalal isn't saying: "Chamath was everything a young man should be."
He was also an able pupil. But when Zuckerberg came calling in 2006, "I said it was too good for him to resist," says Dalal. "You can always be a VC. I told him, 'Go, make great things happen.' And that's what he did."
After the Vanity Fair panel, Palihapitiya climbs into a black SUV and heads across town for another speaking engagement. In a room in an old Spanish Mission-style army building with views of Alcatraz, he addresses a gathering hosted by the C100, a group of top Canadian tech execs based in the Valley. He is asked—of course he is—about Facebook, and he gives a fairly jokey thumbnail sketch of his time there.
He joined in 2007, as vice-president of growth, mobile and international. As such, he led one of the teams charged with generating revenue—which it did, he says, without reinventing the wheel. "Google copied Yahoo, and we copied Google. I'd go see the team and check in. 'Are we still copying Google? Good. Keep doing that.'"
But in our interviews, he talks seriously about what it was like being part of one of the greatest growth stories of all time.
At first, he had difficulty adjusting to Zuckerberg's valourization of coding, as reflected in the now-massive campus's address, 1 Hacker Way. "I had a chip on my shoulder. I was, I am, an engineer. I felt superior to the people who were just, as I thought then, coders. I had earned this big ring."
He says this is part of what Zuckerberg had to teach him: the insignificance of status. "He doesn't care about labels," says Palihapitiya, a vestige of awe in his voice. "It must be hard to drop out of any university, but to drop out of Harvard? What matters to him is not what car you drive. What matters is, are you a good person, a smart person, an ambitious person? It's hard, but you should want to do the things you want to do, independent of how society judges you."
Now, he says, "I work with people, and I don't even know where they went to school, or if they did." He also says that by placing a high value on coding—for a long time considered the grunt-work of tech—Zuckerberg kept Facebook nimble, a place with the organizational intelligence to readily implement new ideas.
Palihapitiya duly adjusted his attitude on this front and took charge of getting the social network from 50 million users to over the 100-million hump.
One of his early hires, Stanford-trained engineer Ray Ko, is still with him, as a partner and head of growth at Social Capital. "We worked together to figure out how to use data to help the growth team make better decisions," Ko says. "What product should we build, what features should we embed? A team with this focus had never existed in the Valley before. The idea before that was that if you build a great product, they will come."
Ko says, for instance, that they learned how critical it was for a new Facebook user to land a certain number of friends within the first week, and so a function that suggested friends for new users, and nudged existing users to befriend new arrivals, was added. Retention increased dramatically.
Within a couple of years, Facebook had blown past 100 million and was on its way to achieving the impossible-seeming dream of topping a billion users. Facebook's growth seems inevitable in hindsight, but Palihapitiya points to MySpace and Friendster, two early social networks that drew millions of users, then hit walls, declined and ultimately fell.
Facebook's growth was a big win for Palihapitiya. Another was his push for Zuckerberg to hire Sheryl Sandberg from Google, where she was head of global online sales. Palihapitiya knew her in part because he played poker with Sandberg's husband, Dave Goldberg, best known for his stint as CEO of SurveyMonkey, and thought she'd make a good chief operating officer. She is now one of the Valley's most respected executives, having managed Facebook's exponential growth and still found time to write Lean In, the influential book of career advice for women.
At the same time, Palihapitiya suffered a loss of face. As the person in charge of Facebook's mobile division, he'd helped pioneer apps for the first iPhone and its competitors. In 2009, he proposed that Facebook launch its own smartphone, and worked with Swiss industrial designer Yves Béhar, Intel and AT&T to devise a prototype. The phone, he says, was beautiful. But Zuckerberg nixed the project, which would have cost an estimated $1 billion—money the pre-IPO company didn't have.
"I made it hard for Zuck to say yes," Palihapitiya says now. "I wasn't wrong to push for the phone, but I let my ego get in the way."
You're no one in Silicon Valley until you've had an exit e-mail go viral, and, when Palihapitiya left Facebook in 2011, his duly made the rounds. It is remembered now mainly for its most abrasive piece of advice: "Don't be a douchebag." But it also has gentler, more nuanced points to make. "Speak the truth," he wrote. "It's too easy to 'manage'—upwards, sideways, downwards—and be rewarded for it. This is death….Respect the person, but don't let bad ideas go unchallenged."
The phone setback notwithstanding, he left Facebook on good terms. "I had done most of what I came there to do. The team I built, they've all gone on to great things. They run a lot of Facebook, and are top people at Uber, Pinterest, Airbnb."
He and Lau—who married in 2005 and now have three children—remain friends with Zuckerberg and his wife. And though Palihapitiya has not confirmed (or, for that matter, denied) the estimates of his post-Facebook net worth, he is not beholden to anyone. Which means he can afford to cultivate the same independence he so admired in Zuckerberg—to take his commitment to truth-telling to the next level.
Social Capital is as one-off as Palihapitiya himself. He and Lau wanted to find market solutions for problems traditionally addressed by charities. "We felt the discipline of the market was important," Lau says. Their firm would invest primarily in three sectors in particular need, Palihapitiya felt, of reform: financial services, health care and education. Most of his peers, meanwhile, were investing in social media—an area that no longer holds any interest for him. "After I left Facebook, I had people pitch me social networks of all kinds, for people who love fish, people who are more than six feet tall, people who have only travelled within a certain area of the world."
Instead, he's going after much larger problems—how education fails smart kids who grow up poor, the long-term management of chronic diseases. "There are other VCs in the Valley who go at these things sporadically," says Yogen Dalal, "but not in such a systematic way. The risks are big. These are highly regulated areas, with many existing players."
To help him in his quest, Palihapitiya has lined up what Bloomberg has called a "League of Extraordinarily Rich Gentlemen" as backers, among them billionaires like Hong Kong's Li Ka-shing, Germany's Nicolas Berggruen, Brazil's Jorge Paulo Lemann and America's Eli Broad. Palihapitiya also put a chunk of his own money—"hundreds of millions," he says—into Social Capital, as did early partners Mamoon Hamid and Ted Maidenberg. (Lau is co-founder and a partner specializing in education.) And he worked his Valley network to get top technologists and thinkers to provide not just money but advice to young entrepreneurs. Why not sit a newbie with a good idea down with Sean Parker or LinkedIn founder Reid Hoffman, and see what happens?
Although the Valley has been good to him, Palihapitiya set up Social Capital because he felt the tech community was losing its way. He agreed with PayPal founder and Facebook backer Peter Thiel that Silicon Valley has too often preferred trivial pursuits to tough ones, giving us 140 characters instead of flying cars. This differing vision has sometimes set him at loggerheads with those around him. He's become, deliberately or not, the Valley's conscience.
His public set-to with home-stay network Airbnb is just one example of Palihapitiya publicly breaking ranks, at the cost of what might have been a hugely lucrative deal.
In 2011, he e-mailed Airbnb's CEO and some of its backers, criticizing its founders for taking $21 million from an early investment in the company for themselves. Their decision, he said, made him reluctant to invest. "My basic principle on this stuff is that if you want liquidity, that's fine," he wrote, "but you should make it available to everyone."
To the annoyance of Airbnb's investors, the e-mail went public. Palihapitiya justifies his criticism, contrasting the way the Airbnb founders handled money with the way Zuckerberg did.
"Zuck shared with his employees and, at the time, I was a young father, working hard, and we didn't have that much," he tells the C100 crowd. The stock and compensation packages were "all the money in the world to us. It was right, but it also seeds something important in the business, a competitive advantage, when you do that."
Airbnb is now valued at $30 billion, but Palihapitiya appears not to regret the e-mail. Instead, he backed the office-communication app Slack Technologies, run by fellow Canadian Stewart Butterfield. Slack is one of the Valley's so-called unicorns, start-ups whose market valuation reaches $1 billion, and its employment practices and benefits have earned raves from employees. "Butterfield's is a beautiful, fair and inclusive world-view," says Palihapitiya. "I would fucking murder people to make his way of doing things successful."
As his first answer at the Vanity Fair event suggests, Palihapitiya believes businesses become more competitive, not less, when ethics play a role in decision-making at the top. On similar grounds, he has criticized the tech industry's lack of diversity. He and his firm collaborated with a respected tech publication, The Information, to quantify the extent of the problem on the investment side. The findings of the 2015 study: More than 92% of senior investors at top venture firms were male, and 78% of them were white.
His own Palo Alto-based firm is the United Nations in comparison to most of his competitors. "I want to be surrounded by people who have a shared set of values, but who manifest those values differently, and so it helps when there are men, women, people who are gay, straight, Jewish, Muslim, Catholic, Buddhist, tall, short, underweight, overweight."
He takes the argument one step further. "Women invest differently than men. Your investment decisions are stronger if you have different people at the table."
He has also pushed for big tech to help mitigate the effects of skyrocketing housing costs in the Bay Area, where a one-bedroom will set you back $3,500 a month. He's proposed that San Francisco take a per-cent share in start-ups—to which the city gives significant tax breaks—and use the revenue to build affordable housing.
This position landed him in hot water with Ron Conway, an early backer of Google and PayPal. A video of the senior VC publicly berating Palihapitiya, a resident of Palo Alto, for daring to criticize San Francisco mayor Ed Lee, went viral in 2014. Palihapitiya, in a pink V-neck sweater, remained calm. "Ron, all I was saying is that there's all these people in the city who feel frustrated. There's a ton of people who feel like they're getting pushed out."
The to-and-fro went on, with Conway screaming at the end: "You don't know what you're talking about."
Palihapitiya doesn't back away from his position. "I tend to be, generally, mostly right," he says. "When I said that, nobody wanted to hear it. 'Why are you being a downer? Why are you raining on our parade?'"
Frank discussions of tech's social responsibilities were rarer then. But in the wake of Donald Trump's election, that's all most Valley-dwellers can talk about. Can social media minimize the circulation of false news? Is there some way of encouraging engagement across divides, rather than accentuating the bubble effect? What can be done about unemployed and underemployed Americans in the heartland and elsewhere?
Palihapitiya is likely to play a central role in the tech community's engagement with the incoming administration. He has known Peter Thiel, Trump's tech consigliere, for years and backed his digital security firm, Palantir. Thiel, in turn, is a limited partner in one of Social Capital's funds.
Like Thiel, Palihapitiya has been known to voice Ayn Randian ideals. He once reportedly dismissed the U.S. federal government as "completely useless," and he tends to put more stock in the ability of business, especially the tech business, to solve difficult problems. This way of thinking, of course, animated the Trump campaign, which promoted his lack of government experience as an asset, not a shortcoming.
That said, Palihapitiya is no fan of Trump. At the Vanity Fair event, the moderator asked the panel members whether Facebook should remove Thiel from its board, after reports that he'd contributed $1.25 million to the Trump campaign. Remember, this was several weeks before the election, and few of those present could contemplate a Trump presidency.
Of the three panelists, only Palihapitiya endorsed a purge. "Absolutely, I would [remove him]….Trump is repudiating all the things that make America awesome." (Zuckerberg kept Thiel on the board.)
After the election, Palihapitiya spoke at a panel organized by Wired and berated himself for not foreseeing a Trump victory. "My job as an investor is to see these things coming," he said. "You can't look at data any more. Polls are worthless, pundits are worthless, the unemployment rate that we use is probably worthless."
He goes one step further, chastising himself and his community for failing to ease the problems that led so many to vote for Trump. "We were complacent," he said. "We're all complicit in this. There was an underappreciation of the economic malaise that exists in this country. As a person who grew up in a really difficult economic situation, I look at a lot of these people as my people. I feel like I completely let those people down."
And so, while he doesn't propose collaborating with Trump, he does suggest that Silicon Valley try to solve the problems that got him elected.
That is just one of the legacy projects Palihapitiya has set for himself.
Having recently lost his father to complications from diabetes, Palihapitiya has joined a consortium that backs cutting-edge software to help manage the chronic condition, which afflicts an estimated 420 million people worldwide and is particularly pervasive among South Asians. (Dalal, who was diagnosed with diabetes himself, is another backer and sits on the board.)
Glooko, as the company is called, has worked with the major makers of insulin monitors to develop software to collect patient data. Its system enables any blood-sugar monitor on the market to communicate the patient's levels directly to the doctor. "That data, when aggregated, can give the company all kinds of information about how best to manage this condition," says Palihapitiya. In a remarkably short time, it has become a global force in diabetes management.
The grail for Palihapitiya is the development of a smart, artificial pancreas to help regulate the digestion of sugar. He is not involved in the day-to-day management of Glooko. But still, inventing the smart pancreas—now that's the sort of contribution that tends to get remembered.
On the education side, he has poured money into an app that identifies geniuses—an investment made based on Lau's advice. Brilliant is an online game that rewards mathematical aptitude and aims to help universities identify super-bright students. It brought a young woman of prodigious intellect in Juarez, Mexico, to Palihapitiya's attention, and the couple has enrolled her, at their own expense, at Waterloo. "There are lots of Steve Jobses out there who aren't getting their shot," he says.
These investments aren't likely to generate quick returns. Still, Social Capital is certainly not averse to making money. Besides backing Slack and Box, it made an early $25-million investment in Yammer, an enterprise communication tool run by Palihapitiya's poker buddy David Sacks. When Microsoft bought the start-up in 2012 for $1.2 billion, Social Capital made a profit of $80 million.
These days, Palihapitiya seems driven to make more long-shot bets, if the ultimate aim is a good one. With Ray Ko's help, he has developed an approach to managing and encouraging growth that he thinks is likely to increase the odds of success—applying the lessons they learned at Facebook to other companies. In the industry, it's become known as growth-hacking, a term Palihapitiya hates, since it suggests there is a set of facile rules that guarantee success.
After the election, Palihapitiya contributed a state-of-the-Valley op-ed piece to The Information. "The last decade," he wrote, "could be summarized as follows: easy money, easy decisions, easy growth, and easy markups resulting in more easy money, more easy decisions…and so on. The problem is that the cost of these decisions now outweighs the benefits."
Palihapitiya says a lot of surprising things for someone who's done as well as he has. He talks about the corrupting influence of money—"our kids are basically screwed"—and gives a nod to his father's socialist views. "Capitalism, as it's been practised, is not working."
Although Social Capital's approach has been market-driven so far, Palihapitiya has floated the idea of working, in the future, with non-profits. And recently, he returned to his native Sri Lanka to suggest ways in which the government might improve the nation's spotty Internet access and make it free, to boot.
His father would surely have approved. After his dad died in 2014, the son reportedly went into counselling to help manage his grief. When asked now what his father thought of his pretty fabulous success, he says: "He was proud, for sure. But I don't think he ever really understood it. He'd have been happy enough if I became a professional and got a nice house in an Ottawa subdivision. With Zuck, I saw his father visit, and take in and appreciate what he had built. My dad and I, we never got that moment."