The moment Jenny Jackson typed ‘the end’, she knew that she had a hit on her hands. ‘I’m trying to think of a way to say this that doesn’t sound insane,’ says the debut author from her home in Brooklyn, New York.
‘Oh God! Forgive me, I’m just gonna say it. Like, you know how when Tiger Woods hits the ball, he knows if it’s going in?’
If a first-time novelist comparing herself to the greatest ever exponent of his sport strikes you as a shade immodest, rest assured, Jackson’s instincts have proved 100 per cent correct.
Her book Pineapple Street – a sparkling social comedy about the prenups, tablescapes, real-estate deals and tennis partnerships of the uber-rich Stockton family – is the literary equivalent of a hole in one.
The manuscript, which Jackson wrote while living on the eponymous Pineapple Street with her husband and two children during the coronavirus pandemic, sold for a reported seven-figure sum in April 2021. A TV adaptation is already lined up.
The moment Jenny Jackson typed ‘the end’, she knew that she had a hit on her hands. Jacket and dress, Veronica Beard. Earrings, Mignone Gavigan. Boots, Gianvito Rossi
Day-trippers are heading to the waterfront neighbourhood of Brooklyn Heights to survey the historic mansions featured in the novel and sample the almond croissants of Le French Tart. The reviewers (mostly) love it, too.
‘Not only does she succeed in getting us not to loathe the Stocktons,’ gushed The New York Times, ‘she even succeeds in persuading us to love them.
A little bit.’ The author Chris Bohjalian wrote, ‘It’s the novel Jane Austen would have written, if Jane Austen lived in Brooklyn Heights in the 21st century.’
But then, he would say that; Jackson is, in a manner of speaking, his boss. The literary phenomenon of the year also happens to be a vice-president and executive editor at Alfred A Knopf (part of Penguin Random House).
The person who paid that huge advance? The publisher Pamela Dorman (also part of Penguin Random House). Jackson is someone who knows the market extremely well: ‘I’ve done this for 20 years. I think it would be falsely modest for me to say, “I finished the book and didn’t know if it was good or not”. That’s my job!’
Jackson, 43, has the glossy blonde hair and ready supply of gossip of one of New York’s winners. She stresses that the elite world of the novel – in which people say things like: ‘Oh no! I left my bracelet in Lena’s BMW and she’s leaving soon for her grandmother’s house in Southampton!’ – is not her world.
However, her father was a software engineer who ended his career at Google, so clearly her own family didn’t do too badly. She grew up in Ipswich, a picturesque coastal town in Massachusetts, which inspired the hometown of Sasha, the middle-class character who marries into the Stockton family in the novel.
Jackson’s husband Torrey is a film producer and they have two children: Waverley, seven, and Sawyer, four. The book advance immediately improved prospects for the family – they have moved a few streets away from Pineapple Street, but still within the same neighbourhood.
However, Jackson is not giving up her editing job any time soon and her day-to-day life is much the same: marketing meetings, sensitivity reads, line edits. ‘I’m just treating myself like another author that I work for right now,’ she says.
Her book Pineapple Street – a sparkling social comedy about the prenups, tablescapes, real-estate deals and tennis partnerships of the uber-rich Stockton family – is the literary equivalent of a hole in one. Suit, Veronica Beard. Sandals, Gianvito Rossi
Still, her bridesmaid-turned-bride status has given her fresh insights into what her authors have been going through all of these years. ‘I used to think that the reason people wanted their book published was because they wanted to be celebrated,’ she says. Really, she now thinks, it’s all about being read.
‘It is so insanely gratifying to hear from people I went to high school with who are reading it. It’s had this incredible effect of letting me have deep, honest and unexpected conversations with people about their personal lives. And I’ve talked to people about money in a way that I’ve never done before.’
That’s not so surprising, since the novel lays bare all the intricacies of trust funds, prenups and tax-efficient investments that the extremely wealthy usually prefer to keep quiet. The Stocktons are Wasps (white Anglo-Saxon Protestants) who made their fortune in New York real estate but live according to an intricate social code regarding what one is and isn’t supposed to spend money on (elite schools, tennis clubs and charity auctions, good; fast cars and flashy watches, bad).
I’m just treating myself like another author that I work for
Sasha and her easygoing husband Cord have taken up residence in his family’s ancestral mansion on Pineapple Street, surrounded by Cord’s family’s heirlooms. Sasha isn’t delighted about this.
The antique sofa gives her a rash. And ‘it was extremely hard for Sasha to achieve orgasm while the mahogany headboard that probably belonged to a congressman or secretary of transportation banged against the wall’.
Despite these misgivings, Cord’s sisters, Darley and Georgiana, both assume Sasha is after the family wealth and call her ‘the GD’ – gold-digger – behind her back. But both have their own anxieties. Darley has put her corporate career on hold to raise her two children – a decision she regrets when her husband loses his banking job.
The novel arrives at a time when the appetite for tales of the super-rich seems to be endless – see Succession, Fleishman is in Trouble, The White Lotus, Triangle of Sadness. And it helps that the prose slips down like unoaked chardonnay.
Still, many have already taken objection to the warmly indulgent tone that Jackson takes towards the Stocktons, and have questioned whether a novel about quirky, rich, white people is really what the world needs.
It’s a criticism she has pre-empted. ‘I feel like the books that I truly love are the ones that engage your empathy on the deepest level and make you see things differently,’ she says.
‘I love The White Lotus. I love Succession. But there is something a little bit cheap and dismissive about being like, “rich people are morally bankrupt”, right?’ She thinks it’s more interesting to assume that rich people want to be good but are blind to the realities of the world. ‘Unexamined privilege is probably a lot more common than total diva-monster privilege.’
While it is the first novel that Jackson has published, it is not the first she has written. As a teenager, she dreamed of being a writer but gravitated towards publishing as a steady career, which gave her the chance to hone her editing skills.
Her successes as editor include Cormac McCarthy’s The Passenger, Kevin Kwan’s Crazy Rich Asians, Gabrielle Zevin’s Tomorrow and Tomorrow and Tomorrow, as well as books by our own Dolly Alderton and Helen Fielding.
‘They say never meet your heroes, but literally, working with her when we were both highly caffeinated and woefully hungover was the most fun of my entire life,’ she says of Fielding. Jackson’s authors tend to praise her sense of fun as well as her commercial instincts.
Her own literary ambitions finally came spilling out after what sounds like a painful period of her life following a bereavement
in 2019. She is reluctant to give details but confirms that ‘someone who I love died’. When the coronavirus lockdown arrived, she found herself waking at 4.30am each day, her head squirming with thoughts. Eventually, she decided that she may as well try to get these down on the page. ‘It was really a psychological thing I needed to work through.’
In the end, the project consumed her. And if you’re wondering how a person with a full-time job produces a novel while confined to a small apartment with two young children, the answer is ‘benign neglect’.
While it is the first novel that Jackson has published, it is not the first she has written. As a teenager, she dreamed of being a writer but gravitated towards publishing as a steady career, which gave her the chance to hone her editing skills
When Waverley and Sawyer woke up, she would throw granola bars at them, switch on Netflix and carry on writing until they pleaded for real food. In the evenings, she would perch on the loo, typing away on her laptop as their bathwater went cold.
Once they were in bed, she’d work at the kitchen table, often with a ‘big, healthy pour’ of white wine. After six weeks she had a novel – but it was one that she would never be able to show to anyone as it was far too personal.
‘As I said, the writing process isn’t complete without readers,’ she says. ‘I knew I couldn’t share this book, and it’s impossible for me to explain how sad that made me. I was emotionally wrecked about it.’
This made her determined that the next thing she wrote would be different. ‘From day one, I was trying to write something sellable. It sounds cynical, but I wanted people to be able to read it. So I wrote Pineapple Street as something that nobody would be hurt by and that nobody would be able to tell me I couldn’t share.’
She took inspiration from two sources. One was a New York Times article about rich 20-something heirs who had decided to give away their inheritance. And the other was the experience of living under the same roof as in-laws during the pandemic. Torrey’s family are, she admits, ‘a bit Wasp-y’.
It’s insanely gratifying that people I went to school with are reading it
But she assures me that the Stocktons are not based on them and no offence has been taken. Crucially, her mother-in-law does not ‘tablescape’, though she does play tennis. ‘Yes, tennis is our family love language. That is how we communicate.’
So, a big commercial bestseller was always what she was aiming for. Does she worry about how it looks, though? The publishing industry is currently falling over itself to check its privilege and showcase its own diversity.
And yet the phenomenon of the year is a book about privileged white people written by a privileged white woman who happens to work in publishing.
‘Definitely!’ she says. ‘I mean, that’s one of the tricky things about writing a family story – you’re pretty hemmed in in terms of diversity, because you’re working within one gene pool.
Also, I think that books satirising the wealthy land better when you’re satirising rich white people. I’m not interested in satirising a rich person of colour because that’s not my place.’
Still, I couldn’t help wondering why the family’s housekeeper Berta didn’t get a line or two. She is constantly in the background, cooking, cleaning, caring, but we have no hint of her opinions. She does confirm that the book had a ‘sensitivity read’ to check that the Korean-American character Malcolm was plausible.
‘I wouldn’t have felt comfortable publishing it without that read.’ But other than Malcolm, she says she didn’t necessarily have the right to create a more diverse cast. ‘We’re at this really interesting place in publishing where we want diverse characters, but we also want to be mindful of who has the right to tell what story.
And so I think my feeling is, I’m going to write what I know. But I’m going to try and publish interesting stories that are different from mine.’
The book is, by her own admission, a social comedy rather than a satire. But she would like readers to take away a message: ‘It’s wrong for people to be born into such great fortune – and it’s wrong for people to be born into such poverty.’ So would she raise inheritance tax?
‘Oh, my God, that I don’t have an answer for… I was actually just thinking about it last night. What is the answer? Is it nothing? Is it a little bit? I’ve been wrestling with that same question.’
I wonder how her former neighbours in Pineapple Street are taking their newfound fame. A recent New York Times style article about Brooklyn Heights hasn’t delighted locals. ‘Everyone was grumbling about this, saying, “We’re not a tourist destination. We’re just a neighbourhood.” And I’m like: “Guys, if you own your apartment, all I did was raise your property values. You’re welcome!”’
But what if you don’t own your apartment? What if your landlord decides to double your rent? ‘I do apologise!’ She concedes that she did take some artistic licence. ‘I mean, it’s really a normal neighbourhood that just has some rich people. But for the sake of fiction, it’s fun to pump up the volume, you know?’ Residents of Ipswich, Massachusetts be warned: her next novel is set there.
Pineapple Street by Jenny Jackson will be published by Cornerstone on 13 April, £14.99*