James and the Giant Pitch

A classic British tale sums up the modern American Dream

A startup founder: “I’m building this company to get insanely rich.”

I didn’t believe him then, and I didn’t believe him after the business went under. Avarice alone just can’t explain the startup impulse. Founding a company is an unreasonable amount of work, with unreasonable odds against success, even if you’re talented. I’m convinced that wealth is only an acceptable cover for what entrepreneurs are truly seeking when they start building. But what is it?

Roald Dahl’s James and the Giant Peach [Viking Books for Young Readers; $6] might have the answer. It’s a tale about an orphan who has a stroke of luck, digs into the opportunity, and rides it through hyper-growth to world fame. Though written half a century before YCombinator accepted its first cohort, James embodies the “CEO at Stealth” types who seek meaning in the startup world.

Dahl’s message is clear: entrepreneurs crave friendship. They are damaged people, and modern commercial success is an expedient path to filling the team-shaped holes in their hearts.

A quick recap will be useful for most readers: James & The Giant Peach begins when James’s parents are eaten by an angry rhinoceros. The orphaned boy is sent to live with his cruel Aunties Spiker and Sponge, stand-ins for your standard capitalists. His life is toil, toil, toil until an old man hands him a paper bag full of magical “little green things”. On accident, this seed round is spilled into the soil near a dead peach tree. A fresh peach appears, then grows, and grows, and grows until it’s the size of a blimp. The power of an investment.

Aunts Spiker and Sponge step in to capitalize on the opportunity. “There’s a pile of money to be made out of this if only we can handle it right. You wait and see,” Customers come from far and wide to see the peach. James hustles while his aunts lounge. But one night, James spots a hole in the peach and crawls in.

Inside, he meets his team: enlarged bugs that keep the peach rolling, then afloat, and finally aloft. Working together, they fend off hungry sharks, harness a twitter of seagulls, and evade cloud infrastructure engineers. Finally, James and co. plop down in downtown Manhattan, mere blocks from the stock exchange. Within hours, they’ve issued shares of the peach to the general public. The children of the city go wild, and James becomes a celebrity.

The progression is familiar: from unseen toil to miraculous investment to product-market fit. Then, a treacherous march towards IPO and the diffusion of control to nameless crowds. Mansions, interviews, books. The American dream.

But this is the external story of the fruits of hustle. That doesn’t explain James’ motives; it just gives shape to the action. The internal story is what we’re after.

And James Henry Trotter, who once, if you remember, had been the saddest and loneliest little boy that you could find, now had all the friends and playmates in the world. And because so many of them were always begging him to tell and tell again the story of his adventures on the peach, he thought it would be nice if one day he sat down and wrote it as a book.

What drives James forward is loneliness. And what better way to fix that than to trap six other humanoids in a floating peach?

Dahl makes clear that James’ did not win the lottery, but was chosen, hand-selected, because of his pain. The old man, telling James what the bag of green things — crocodile tongues, monkey fingers, pig gizzards, parrot beaks, and sugar, it’s explained — will do for him: “Marvelous things will start happening to you, fabulous, unbelievable things — and you will never be miserable again in your life. Because you are miserable, aren’t you?” James is so cosmically sad that he warrants supernatural investment.

Whatever criticism we might levy against this inequitable distribution of capital, the business of the peach does its job. It brings joy to James. Each teammates contributes according to their talents: the centipede brings his jaws, the spider her craft, the grasshopper his wisdom, the ladybird her warmth, the earthworm its caution, and the glow worm her light. And James brings his iron will to keep them together, thick or thin, good or bad.

The question, though, is whether loneliness can ever be cured through these professional relationships, which are fundamentally utilitarian, and therefore not friendships per se. His childhood trauma leaves him only with the idea of kids — “the little friends whom he used to know would be down by the seaside, playing in the wet sand and splashing around in the water…”

We might well wonder whether James — holed up inside his Peach Seed in the center of Central Park, writing his autobiography, besieged by children — is living his dream, or trapped in it. The insectoid teammates he makes in the peach are not-quite-human; the humans fans who adore him at the end are not-quite-friends. Is he happy?

I think so, but for one reason only: he spills the magic things.

He wasn’t supposed to. He was instructed to put them in some water, add some of his hair — “That sets them off!” — and drink the jugful. “And then, my dear, you will feel it churning and boiling in your stomach, and steam will start coming out of your mouth, and after that… you will never be miserable again in your life.” Instead, James trips, and he dumps the magic into the peach tree.

Had he kept it to himself, perhaps he may have become less miserable, and in doing so, lost his drive to explore. May have found the magic in himself, rather than in others. May have dreamed of money, rather than friends.