Pineapple Street author Jenny Jackson: ‘There should not be 25-year-old billionaires, it makes no sense’

Jenny Jackson’s novel has just come out and everyone is tagging her on Instagram. “I see that the post says, like, ‘this was such an easy read!’,” the Pineapple Street author tells me, before jokingly lowering her voice into a slightly threatening tone. “I’m like, ‘Easy? Easy read? Don’t you mean wonderfully sophisticated and deeply moving and thought-provoking?’ But then” – she lights up – “a huge part of me is like… ‘yes!’”

Having been a hotshot book editor for the past two decades – Gabrielle Zevin, Katherine Heiny, Kevin Kwan and Emily St John Mandel are among her authors – Jackson knows it takes “a certain kind of artistry” to craft a novel that people want to inhale in one sitting. Pineapple Street neatly slots into the space previously occupied by Sorrow and Bliss, Such a Fun Age and Fleishman Is in Trouble as this year’s essential smart summer read. But it will also – brace yourselves, British people – have us all talking about money. It charts the (quite vast) fortunes of the Stockton family, who live in Brooklyn Heights and probably own quite a lot of it. At the heart of the novel are three women: Darley, who has given up access to her trust fund so that her husband won’t have to sign a romance-killing prenup; Sasha, privately referred to as “the gold-digger” by the family she has married into; and Gen Z-er Georgiana, a charity worker beginning to think her inheritance might be obscene.

Jackson wrote the novel during the pandemic; unable to see her authors in person, she had nowhere to put her “sparkly energy”. That energy is tangible today, as she bounces into the Penguin offices in a bright green mac, wearing a pair of silver clogs so fabulous that they warrant serious pre- and post-interview discussion. Jackson has that unself-conscious American confidence. She talks in flowing paragraphs, punctuated by jokes and funny voices. Every so often, she leans forward and speaks as though she’s confiding a secret. In London to juggle Pineapple Street press commitments with work meetings for her day job (she’s launching Dolly Alderton’s books in the US), she tells me her husband has joined her on the trip. “Which is, like, in some ways,” she says, with one of her sly leans, “I feel like such a dork.”

But before you ask, no, Jackson is not a one percenter. She was raised in a small village in Massachusetts, in a “solidly middle class” family – her father worked for software companies, her mother for an environmental engineering company, and her brother, brilliantly, is an “octopus farmer in Hawaii”. When she was growing up, Jackson didn’t think a lot about money – “which I recognise is a privilege in and of itself” – until she got to New York and “I just felt like I had arrived on another planet”. Now vice president and executive editor at Knopf, a division of Penguin Random House in the US, Jackson started her publishing career in 2002 as a lowly paid assistant. Her flatmates then – three investment bankers – subsidised her rent because they needed to fill the room, and they liked her.

Writing a novel, she suggests, was “like a dream suppressed”. Throughout high school and college, she had wanted to be a writer, but “as I mentioned, no trust fund”. Working in publishing, she decided, would at least give her proximity to the thing she loved: books. “How hilarious am I, that I was like, ‘I need to make money, I’m going to work in book publishing’, like, oh my god, Jenny, let’s think about this,” she jokes.

Pineapple Street is already being adapted into a TV show – but Jackson had actually written another novel just before it – one that was deeply personal, prompted by the loss of someone close to her. The project was all-consuming and helped her find her own voice as a writer, but she realised it was too private to publish. “It still eats at me,” she says. For her next idea, started in earnest at the end of 2020, she “just wanted to write something that would be like a happy escape”. It was inspired, in part, by an article in The New York Times, “The Rich Kids Who Want to Tear Down Capitalism”, “about socially minded millennial heirs who feel like their inheritance is at odds with their morality”.

In a culture that has become deeply sceptical about inherited privilege, some might say it was a bold move to write a novel that humanises one percenters. “I think we’ve explored pretty well the ‘rich people are culturally, emotionally vacant’ strain,” Jackson says. “And I also think you catch more flies with honey. I thought it was interesting to operate from a theory that everyone on some level wants to be good, but that our ability to see ourselves is the thing that prohibits us from often being good.” The fact that the Stocktons will never not have money changes the stakes for the characters, too: because economic security is not an issue, it “forces you to go somewhere deeper, and more emotional interior”. It’s something we’ve seen throughout Succession, Jackson observes – “the way that each of those characters is trying to buy love”.

Jenny Jackson

Although the issue of gross personal wealth preys on the minds of some of her characters, Jackson doesn’t think such inequality can be solved simply by benevolent, rich individuals setting up foundations. “It’s a much bigger problem,” she says, while pointing out that a novel about tax policy would have been pretty dry. “We need to abolish the kind of inheritances structures that we have. It’s insane. There should not be 25-year-old billionaires, it makes no sense. People should not inherit that level of wealth when we’re living in an age of such gross income inequality.”

With its multi-generational cast, Pineapple Street astutely observes the quirks and tensions between boomers, millennials and Gen Z. “I know it’s popular to s*** on generations younger than yours, but I am, like, all in on Gen Z. I think they just have a much greater social conscience than Gen X, and I don’t think they’re going to stand for income inequality. I have a lot of hope they’re going to even the playing field at some point,” she says. In her long career in book publishing, Jackson has seen a few playing fields shaken up. “When I first started out, there was such a sexist attitude towards literary fiction, you know; we were living in the age of the Jonathans. It was all about Franzen and Lethem and Safran Foer, and Jennifer Weiner was making a big stink about chick lit and women’s fiction being taken seriously. And now, the New York Times Book Review put my book on the cover. Holy moly. That wouldn’t have happened,” she explains.

Right now, Jackson feels in “my happiest heyday”. That’s because “the Venn diagram of what’s selling” – books by women, further bolstered by projects like Reese Witherspoon’s Book Club – “is absolutely overlapping with what I love”. But publishing, she knows, goes in cycles. Much was recently made of the fact that Granta’s Young British Novelists only included four male authors on a list of 20. “I’ve had some funny conversations with agents lately saying I think male fiction is what we need next, and so I’m actively looking for those writers. But it’s funny because I don’t see publishers leading that charge,” she tells me. “It’s a chicken and egg thing with publishing: are we trying to publish to meet the needs of readers? Or are we tastemakers telling readers what they need? Honestly – some of both, right? Like on a good day, I like to think I’m a tastemaker, on a bad day it’s like we’re all chasing the ‘if that, then this’.”

Despite Jackson’s buoyant attitude about the fiction market, I wonder if there’s anything about the publishing industry – currently in a febrile mood, divided by debates about representation, censorship and cancel culture – that depresses her. It is, she suggests, “in a tricky growing pains moment, as we try and figure out who’s allowed to write what”. (Jackson tells me that a sensitivity reader gave her useful feedback for Pineapple Street’s American-Korean character, Malcolm). She’s also concerned by “the Twitter mob mentality”. “I’ve seen people on Twitter invent scandals that are just not based in reality, and it can be so damaging to a writer’s reputation,” she says. “It’s not conducive to creativity to feel that a Twitter mob is sitting on your shoulder ready to tear you down for having said something outrageous in your book. Characters in novels should be allowed to say outrageous things.”

The atmosphere in publishing is the first topic in our conversation that Jackson slows down for, pausing for a while to think. I get the impression she operates at a breakneck pace, neatly illustrated by an anecdote she tells me about time, motherhood – she has a five-year-old and a seven-year-old – and being a runner. “Before, I would be like, ‘okay, I’m gonna go for a run at 5pm, so at 3.30 I’m gonna have a small amount of protein and a carbohydrate so that I’m in perfect running form’. And then I had kids, and my schedule just went crazy, and I’d be like, ‘oh man, I just ate a giant croissant and an orange, but I suddenly have half an hour and I’m gonna have a stomach cramp, but this is my only chance to run. So here I go!’” She has learnt not to be precious about her time. After all, this is how she wrote Pineapple Street – by telling herself, “I’m going to sit on the closed toilet lid and write while my kids are in the bath.”

Clearly the process works. Jackson is writing a second novel – time to turn on the tap.

Pineapple Street is out now, published by Cornerstone