The Win-Win Fallacy

Entrepreneurs say they’re trying to help others while also helping themselves—but that claim may be hope masquerading as description.

The last open piece of land in Silicon Valley is now zoned for Cisco headquarters
The last open piece of land in Silicon Valley is now zoned for Cisco headquarters (Bob Sacha / Getty)

Justin Rosenstein was largely unknown to the broader world, but he was a star in Silicon Valley. He had been instrumental in inventing several of its seminal technologies. A programming and product design phenom, he helped start Google Drive and was the co-inventor of Gmail chat. Then he moved to Facebook, where he was the co-inventor of Pages and the “like” button. More than a billion people were regularly using tools that Rosenstein crafted. He had been rewarded with stock said to be worth tens of millions of dollars. He wasn’t yet 30.

Rosenstein now faced a dilemma not uncommon among young entrepreneurs who have found early success: what to do with his money and his remaining decades on earth. He knew he wanted to improve the world, and he was guided by one of the reigning mantras of the age — that of the “win-win.” He decided that his method of bettering things would be to start a company, Asana, which sold work-collaboration software to companies like Uber, Airbnb, and Dropbox. He believed that Asana’s software could be his most forceful way of improving the human condition. “If we really could build a universal piece of software that could make everyone in the world who’s trying to do positive things 5 percent faster, right?—I guess we’ll also make terrorists 5 percent faster—but on the whole, we think that that’s going to be really, really net-positive.”

Rosenstein’s desire to improve people’s lives by making everyone a little more productive was noble. But one of the central economic challenges now facing his country is the remarkable stagnation in wages for half of Americans despite the remarkable growth in productivity. The increasingly extractive financial sector is in part responsible. That sector could be arranged in other ways, including tighter regulations on trading, higher taxes on financiers, stronger labor protections to protect workers from layoffs and pension raiding by private equity owners, and incentives favoring job-creating investment over mere speculation. Such measures could help to solve the underlying problem by preventing the capture of the gains from growing productivity. Absent such measures, an initiative like Rosenstein’s wouldn’t bring the change it promised. It would serve to further increase an abundant thing likely to be hoarded by elites (productivity), instead of a scarce thing that millions need more of (wages).

But Rosenstein had almost religious faith in the win-win. “What’s amazing about tech is—and there’s other industries like this, but I think it’s something that is particularly common in tech—is that there are so many opportunities to have your cake and eat it, too, right?” he said. “There are a significant number of opportunities—Google search being the most massive example of all time—where we simultaneously are doing something lucrative and really good for the world. And, in fact, I think that a lot of times you can get in situations where they’re all aligned, where the bigger the reach of the good you’re doing, the more money you’ll make.” It was a vision in which social justice and the concentration of power would somehow increase in tandem, ad infinitum.

Behind Rosenstein’s Asana and countless other similarly minded initiatives, there stands a radical theory: win-win-ism. It is a new twist on an old idea about the beneficial side effects of self-interest. The long-standing idea took root in the emerging commercial societies of urban Europe a few centuries ago. Its most famous statement is Adam Smith’s declaration about the social benefits of human selfishness:

It is not from the benevolence of the butcher, the brewer, or the baker that we expect our dinner, but from their regard to their own interest. We address ourselves, not to their humanity but to their self-love, and never talk to them of our own necessities but of their advantages.

This idea that self-love trickles down to others is an early ancestor of win-win-ism. In his Theory of Moral Sentiments, Smith elaborates on the idea with his famous metaphor of the “invisible hand.” The rich, he writes,

in spite of their natural selfishness and rapacity, though they mean only their own conveniency, though the sole end which they propose from the labours of all the thousands whom they employ, be the gratification of their own vain and insatiable desires, they divide with the poor the produce of all their improvements. They are led by an invisible hand to make nearly the same distribution of the necessaries of life, which would have been made, had the earth been divided into equal portions among all its inhabitants, and thus without intending it, without knowing it, advance the interest of the society.

The selfish pursuit of prosperity, Smith is arguing, takes care of everyone just as well as actually attempting to take care of everyone. From this general idea familiar theories derive. Trickle-down economics. A rising tide lifts all boats. Entrepreneurs expand the pie. Smith tells the rich man to focus on running his business on the assumption that positive social consequences will occur automatically, as a happy by-product of his selfishness. Through the magic of the “free market”—an oxymoron ever since the first regulation was imposed on it—he unwittingly arranges for the common good.

The kind of win-win represented by Asana—as well as the new impact investment funds pledging to combine strong returns with poverty alleviation, and the new social enterprises, and the bottom-of-the-pyramid retail plays—innovated on this tradition by turning it upside down. The winners of commerce were no longer told to ignore the social good and keep their contribution to it indirect and unintentional. They were to focus on social improvement directly and intentionally. Rosenstein shouldn’t just start a software company, but one he thought most likely to improve the condition of humankind.

The new win-win-ism is arguably a far more radical theory than the “invisible hand.” That old idea merely implied that capitalists should not be excessively regulated, lest the happy by-products of their greed not reach the poor. The new idea goes further, in suggesting that capitalists are more capable than any government could ever be of solving the underdogs’ problems.

An influential statement of this new creed is found in the book Philanthrocapitalism: How the Rich Can Save the World. Published in the autumn of 2008, as millions of people watched the economies around them collapse and could have been excused for feeling that the rich were ruining the world, the book made the case for the wealthy as saviors. The authors, Matthew Bishop and Michael Green, stress that this salvation comes not in the old, happy-by-product way, but directly, when the winners assume leadership of social change:

Today’s philanthrocapitalists see a world full of big problems that they, and perhaps only they, can and must put right. Surely, they say, we can save the lives of millions of children who die each year in poor countries from poverty or diseases that have been eradicated in the rich world. And back home in the United States or Europe, it is we who must find ways to make our education systems work for every child.

While Adam Smith’s ideas were based on an analysis of how markets work, this new idea is based on a view of the moneyed themselves. Bishop and Green write that the “self-made” people who built their fortunes amid “the surge in entrepreneurial wealth in the last thirty years” are different from winners past, and not just because of their willingness to help others by parting with wealth they only just acquired. “Entrepreneurs are also, by nature, problem-solvers and relish the challenge of taking on tough issues,” Bishop and Green write.

Under the new theory, entrepreneurship can become synonymous with humanitarianism—a humanitarianism that greases the wheels of entrepreneurship. A charitable interpretation of this idea is that the world deserves to benefit from flourishing business. A more sinister interpretation is that business deserves to benefit from any attempt to better the condition of the world.

Nowhere is this idea of entrepreneurship-as-humanitarianism more entrenched than in Silicon Valley, where company founders regularly speak of themselves as liberators of mankind and of their technologies as intrinsically utopian. After all, even a workplace software company like Rosenstein’s Asana could claim on its website that “we’ll improve the lives of every person on the planet.” A friend of Rosenstein, Greg Ferenstein, set out years ago to chronicle these grand claims and make sense of this new mentality radiating from the Valley. He was a reporter in the Bay Area who had written for various outlets, notably TechCrunch, the booster newsletter of Silicon Valley. He had become interested in the bigger ideas animating the people he covered—what win-win-ism imagines for the world and what, at times, it obscures.

Ferenstein interviewed many technology founders and distilled their ideas into a working philosophy. He calls this philosophy Optimism, though it seems to be just a slightly tech-inflected version of standard-issue neoliberalism. The ideology’s central thrust, he said, is a belief in the possibility of the win-win and the harmony of human interests. “The basis of old government is the notion of a zero-sum relationship between different classes—economic classes, between citizens and the government, between the United States and other countries,” Ferenstein said. “If you assume that inherent conflict, you worry about disparities in wealth. You want labor unions to protect workers from corporations. You want a smaller government to get out of the way of business. If you don’t make that assumption, and you believe that every institution needs to do well, and they all work with each other, you don’t want unions or regulation or sovereignty or any of the other things that protect people from each other.”

There is no discounting the audacity of this idea. It rejects the notion that there are different social classes with different interests who must fight for their needs and rights. Instead, we get what we deserve through marketplace arrangements—whether office software to make everyone more productive or the sale of toothpaste to the poor in ways that increase shareholder value. This win-win doctrine took on a great deal more than Adam Smith ever had, in claiming that the winners were specially qualified to look after the losers. But what do they have to show for their efforts, given that the age of the win-win is also, across much of the West, the age of historic, gaping inequality?

In a country that is losing its middle class, in a wider world racked by anxiety about globalization and technology and displacement, what is the win-win theory’s response to the problem of suffering? “It’s not an emphasis of this ideology,” Ferenstein said. Suffering can be innovated away. Let the innovators do their start-ups and suffering will be reduced. Each entrepreneurial venture could take on a different social problem. “In the case of Airbnb, the way you alleviate housing suffering is by allowing people to share their homes,” Ferenstein said. An Airbnb ad campaign along these lines featured older black women thriving now that the entrepreneurs had helped them to rent out rooms and make extra money. Of course, many poor people don’t own homes or have a surplus of space to rent out. And many African Americans find it difficult to rent on the platform—hotels can no longer easily discriminate by race, but spare-room hoteliers often do. But what was even more striking than these blind spots was the notion, implied in Ferenstein’s idea, that the winners should receive a kickback from social change.

Indeed, in the case of Airbnb and other so-called win-wins, the claim of a harmony of interests is hope masquerading as description. There are still winners and losers, the powerful and the powerless, and the claim that everyone is in it together is an eraser of the inconvenient realities of others. “This ideology radically overestimates who will benefit from change,” Ferenstein admitted. Then what will happen as believers in win-win change amass ever more power—and not only economic power but also the power to guide the pursuit of societal betterment, one start-up at a time? “People will be left behind,” Ferenstein said. This seemed to contradict the whole premise of Optimism—that we are all invested in each other’s success and will prosper together. In fact, Ferenstein now seemed to be saying that the better the Optimists did, the more people would be beached. This claim jibed with what actually was going on in the world—the benefits of progress flowing primarily to the already fortunate; the widespread cutting loose of those on the wrong side of change.

It is fine for winners to see their own success as inextricable from that of others. But there will always be situations in which people’s preferences and needs do not overlap, and in fact conflict. And what happens to the losers then? Who is to protect their interests? What if the elites simply need to part with more of their money in order for every American to have, say, a semi-decent public school?

The win-win vision reflects a bitter truth: Often, when people set out to do the thing they are already doing and love to do and know how to do, and they promise grand civilizational benefits as a spillover effect, the solution is oriented around the solver’s needs more than the world’s—the win-wins, purporting to be about others, are really about you.