If you think making money is hard, just try giving it away. That’s one lesson evident in A Truck Full of Money, Tracy Kidder’s new book about Paul English, the now millionaire cofounder of the travel website Kayak.com. Kidder, having chronicled the hardware revolution in his 1981 book The Soul of a New Machine, wanted to return to the topic of computing. He set his sights on English, a coding prodigy who was in the midst of selling his remarkably successful travel-booking site for billions of dollars. English is an interesting character—possibly bipolar, certainly driven—who succeeded beyond his wildest dreams. You see, he never aimed to become a millionaire. He just wanted a site that worked well, a happy user base that kept coming back, and a team that hummed and thrummed and had fun. The money was a by-product. But after the sale of Kayak, English did in fact have great wealth—he’d been, in the words of one of his colleagues, hit by that “truck full of money” (a memorable phrase that became the title of Kidder’s book). How, though, to recover? What does one do for a second act? English is hardly alone. Once today’s millionaires and billionaires hit it big, they’re chased by the expectation that they, like the philanthropists of the past—the Carnegies and Rockefellers, who endowed some of the United States’ great universities and other public institutions—will give away at least some of their fortune to make the world a better place. Bill Gates, for instance, established a foundation for that purpose. But other efforts, like Mark Zuckerberg’s attempts to reform the Newark, New Jersey, school system, have failed miserably—although the Facebook founder and his wife, Priscilla Chan, are trying to bounce back with the Chan Zuckerberg Initiative, an organization that recently announced that it will give away $3 billion to “cure, prevent, or manage” all disease by the end of this century. For his part, English set out to follow the example of his friend and quasi mentor, Thomas J. White, another accidental millionaire who donated most of his fortune to Partners in Health (PIH), a nonprofit that supports health missions in Haiti, Mexico, Russia, and other countries around the world. (PIH was cofounded by Paul Farmer, the subject of another Kidder book, Mountains Beyond Mountains. ) In the end, however, despite an exploratory visit to a homeless community in his hometown of Boston, the Kayak founder had less interest in doling out dollars than in creating another venture-backed tech start-up—not for the money, necessarily, but for the action. Philanthropy didn’t have nearly the same luster as building something from scratch, so his nascent charitable efforts soon faded. English did have other options. He could have decided to donate a significant sum to some well-established charity organization, one that appears to be doing God’s work in eradicating global poverty. But even in that direction lie hidden dangers, exposed by a 2014 documentary, Poverty, Inc., that explores the equilibrium that the international aid community and social entrepreneurship have created in the developing world. Director Michael Matheson Miller reviews the situation in Haiti in particular and in some sub-Saharan African countries, and finds that the perfectly legitimate desire to help, which often manifests itself in the form of cash and in-kind donations, keeps the developing world in its developing state. Gifts from individual philanthropists, nonprofits, governments, and socially conscious businesses have created a state of dependence. When a country is awash in free money, free clothes, and free food from the developed world, it’s nearly impossible for local farmers and entrepreneurs, even formerly successful ones, to compete. Industry dries up, but the residents can’t always rely on specific kinds of aid, since it’s inconsistently delivered. That’s not to condemn any person or organization with good intentions—the filmmakers are very careful on this point. No one is ungracious about the aid offered. But the single most important message to come out of Poverty, Inc. is from aid recipients themselves: Stop. Stop giving us free stuff and help us figure out how to build sustainable businesses that will have positive and long-lasting impact on our communities. The free shoes sure were nice for a while, but we’d really like to build our own shoe factories instead. So what’s a modern philanthropist to do, especially one not grand enough to endow a foundation or initiative in the style of Gates and Zuckerberg? One option—turn to The Robin Hood Rules for Smart Giving, by Michael M. Weinstein and Ralph M. Bradburd. Based on the methods developed by Weinstein and others at the Robin Hood Foundation, the book bills itself as a guide “for making choices among philanthropic options when resources are limited”—which they always are, even for billionaires. The foundation, established in 1988, calls its methodology “relentless monetization,” a formula that allows the donor to evaluate different choices using the same criteria—a kind of fancy-pants cost-benefit analysis. The method is simple on its face: Adopt a mission statement, translate that mission into well-defined goals, identify a specific intervention to try along with the relevant outcomes, and then analyze and score the results. Repeat. Simple, perhaps, but not easy, which is why the authors provide detailed guidance on how to make choices that have real, positive impact in the world. Whatever one’s approach—whether Robin Hood’s quant-driven methodology or Tom White’s all-in style—it’s clear that giving away money must be as disciplined a process as making it in the first place. One cannot simply donate millions willy-nilly and expect to change the state of the world for the better. If philanthropy worked that way, we’d be done by now.
