Ideo realized there was a big opportunity in death. There are currently 76 million American baby boomers inching reticently in its direction. “We’re a generation that’s used to radicalizing things,” Bennett explains. Now, as many boomers watch their parents die just as Bennett had, accepting the soulless, one-size-fits-all deaths that society deals them, they seem to be rebelling one last time. Everywhere Bennett looked — New York Times opinion pieces and Frontline specials; assisted-suicide laws; the grassroots Death Café movement, where folks get together for tea and cake and talk about their mortality; a campaign in La Crosse, Wisconsin, that got 96 percent of the entire town to fill out advance directives, spelling out their wishes for end-of-life care — he saw his generation striving to make death more palatable, more expressive. And at the far extreme is the crop of phenomenally well-capitalized biotech startups working to get around the insufferable inconvenience of death altogether, either through science-fictionesque “radical life extension” treatments or by uploading your consciousness to the cloud. (These include Calico — Google’s so-called “Immortality Project” — and J. Craig Venter’s company Human Longevity, Inc. The founder of Oracle, Larry Ellison, who set up the Ellison Medical Foundation to defeat death, has explained his motivation succinctly: “Death has never made any sense to me.”) One way or another, Bennett told me, “We’re all holding hands and saying, ‘Forget that shit. Not going to happen.’”
I followed Bennett’s work over the past year — a journey that, in the end, may reveal less about the death of people than it does about the life of ideas, particularly the brand of Big Idea that distinctly Californian institutions like Ideo send careening through the culture. Right away, Bennett understood it would take years to see the sort of wholesale shift he was imagining — a generation or more. There was so much to do, he could really start anywhere. He just needed to find a few suitable clients, to locate a few fissures through which a genuinely different conversation about death could begin to flow. And because he was looking in San Francisco, in the year 2014, the first one he found was a startup building an app.
The app was called After I Go. The president and ceo of the company building it, Paul Gaffney, had founded two other startups but had spent most of his career working near the top of large corporations such as Charles Schwab, Office Depot, Staples, and aaa, primarily helping them find their footing online. He was 47, a loose and affable guy despite being excruciatingly analytic at his core. Once, when I asked Gaffney about himself, he explained that his “personal value proposition” is “establishing a vision for a new outcome particularly in consumer-related spaces enabled by the novel use of technology” — but he managed to sound human when he said it, even warm.
Gaffney described After I Go as TurboTax for death: a straightforward app that would allow people to write wills or advance directives and, in general, preemptively smooth out the many ancillary miseries that can ripple through a family when someone dies. Bank accounts, life-insurance policy numbers, user names and passwords, what night the garbage goes out — all of it could be seamlessly passed on. Whatever fear or despair people feel about death is only heightened by the fear that, because they never got around to making the necessary preparations, their death might burden the people they love. Gaffney assumed there’d be a big market for an app that eliminated that risk. “Simply providing people with that sense of organization would be a huge emotional payoff,” he said. But he was spectacularly wrong. Bouncing his ideas off potential investors, he quickly understood that no one welcomed a chance to prepare for death. It’s thankless drudgery — plus, it reminds you you’re going to die.
Gaffney realized he couldn’t just build the right tool; he also had to build the motivation to do the job in the first place. That’s what people would pay for. Suddenly, the work After I Go needed to do was no longer rational but emotional — which is to say, far outside Gaffney’s personal value proposition. (“I learned a long time ago that I’m not a good test case for how human beings respond,” he explains.) And so he hired Ideo to help.