co-founders of PIH. He remembered encountering a child with big eyes and a memorable smile who was living in a dirt-floored hovel, and saying, “For Christ’s sake, put a tin roof on and pour a concrete floor. I’ll give you the money. Holy shit!” Speaking of his donations to Partners In Health, he told Paul much the same thing as he later wrote down: “I can’t say that I never had a few qualms about giving but they were very few and as I went along I realized what great joy there was in seeing a child half dead and six months later seeing him running around having a good time with the other kids.”
Paul didn’t give away a great deal of the $8 million he got from Boston Light. After meeting Tom, he started writing $10,000 and $20,000 checks, mostly to organizations that Tom supported, mainly homeless shelters and Partners In Health. Later, after the founding of Kayak, the size of Paul’s checks grew, however. PIH’s chief fundraiser remembered the day in 2005 when Paul asked him to come over for breakfast, appeared at the door disheveled, and said, “I’ve been thinking things over and talking to Tom, and I’m going to give you a million bucks.”
Over the next few years, Paul started running low on cash—he spent more than $2 million remodeling his house—but he borrowed against his shares in Kayak and went on donating money to his own and Tom’s favorite causes.
Tom, meanwhile, was busy enacting a plan for self-impoverishment. He would say he didn’t believe in “wearing a hair shirt” but had come to realize that stockpiling money was the equivalent of burying it, as a servant does in the parable of the talents. “I feel sorry for people that are wealthy and sitting there with millions—some of them billions—just making more money. I ask myself, ‘For what?’ Why don’t they take a few million and give it to the very poor and marginalized people all over the world who suffer so much, in great part because of the greed of the wealthy?”
When Tom sold his Cambridge apartment and moved to a house in Newton, Paul felt bereft. He called Tom from Kayak and said, “Don’t think you’re going to get away without serving me gin and tonics. I’m gonna hunt you down and figure out where to get my drinks.” An hour later, one of Paul’s team came to his desk and told him there was someone at the door asking for him. It was a burly man in workingman’s clothes, a tough-looking guy with a huge brown paper bag in his arms. He growled, “I’m lookin’ for Paul English.” He handed over the bag. In it Paul found seven bottles of gin, bottles of all sizes, from a nip to a gallon jug.
Tom was the person who made gifts. It could be hard to talk him into receiving one. One winter day, Tom’s wife remarked to Paul that Tom would like to go to Florida but felt too old for all the rigamarole of a commercial flight. The next day Paul called Tom and said, “I went to this fundraiser and there was an auction and I won time on a corporate jet, but it’s about to expire. Do you know anyone who could use it?”
Tom said, “You’re full of shit,” and hung up.
Paul redialed. “Tom, I didn’t win it at a corporate auction, that may have been an exaggeration, but please will you let me fly you two to Florida?”
It took a while, but Tom eventually agreed. Then Paul called a friend in the aviation business, who told him he could rent a really nice jet for $18,000. Paul was aghast. He had entered his period of borrowing money. But he rented the jet and also a limo to take Tom to the airport, and just for the sake of Tom’s company, he flew with him to Florida, returning the next day.
Tom had told Paul, among others, that once he had provided for his family’s future, he would give the rest of his possessions away to worthy causes and die without a nickel of his own. By around 2009, Tom had been enacting this plan for most of a decade. He had grown very thin and frail, and full of worries. When he
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