As Pippa Middleton and her high-flying husband James Matthews finally call it quits on their £1.3million petting zoo, one wonders what could possibly be next in store for the sister of the Princess of Wales.
She become an overnight sensation due to her figure-hugging dress at Kate’s wedding to Prince William in 2011, but the socialite has struggled to truly escape her sister’s royal shadow.
According to royal expert Richard Fitzwilliams, Pippa’s trajectory ‘echoes’ the experience of Prince Harry, who has often complained about his upbringing as a royal ‘Spare’.
Mr Fitzwilliams told the Daily Mail: ‘Life’s lottery can be very cruel. No one can influence when they are born. Yet if your eldest sibling becomes famous, the spotlight often falls on you as well. If you lack talent, the obstacles can be insuperable.
‘Despite the temptation, it can be unwise to try to cash in on this peripheral fame. The pity is that, like Harry and Meghan, she seems to want to prove something.’
While Pippa, 42, has dabbled in the world of books, fitness columns and even a brief television stint, none of these ventures have ever materialised. Instead, she has been subject to financial loss, public ridicule, and quickly cancelled deals.
Most recently, her big plan was to convert 72-acre Bucklebury Farm into a thriving business and family attraction with her husband James.
However, it was hit by six-figure losses every year, resulting in a debt of £807,543 in 2025.
Their plans to expand the site were routinely criticised by the local highways authority, while one nearby resident called the venture a ‘snooty cash grab’ that had become a ‘place of snobbery and middle-class inclusivity.’
Yet while many locals may welcome the downfall of Bucklebury Farm – it marks the latest in a long list of ‘unhappy business experiences’ for Pippa spanning more than two decades.
Pippa Middleton become an overnight sensation due to her figure-hugging dress at Prince William and Kate Middleton’s 2011 wedding, but the socialite has since failed to truly escape her sister’s royal shadow
While Pippa, 42, has dabbled in the world of books, fitness columns and even a brief television stint, none of these ventures have ever materialised. Instead, she has been subject to financial loss, public ridicule and quickly cancelled deals
After amassing attention across the globe in 2011 due to her figure-hugging bridesmaid dress at the royal wedding of Kate and Prince William, Pippa was quick to enter into the world of celebrity and embrace lucrative deals.
In 2012, it was announced Pippa had landed a deal from publishing house Penguin worth £400,000 for a book on party planning.
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But, her party planning book, Celebrate, was not well received and sales were poor.
Mr Fitzwilliams explained: ‘There are echoes here of Harry, whose ill-advised memoir Spare made all too clear that the supposedly inseparable brothers were far from being close.
‘Meghan’s much touted cookery series for Netflix, With Love, Meghan met a similar fate with reviewers to Pippa’s book and viewing figures were low.’
Launched with much fanfare in October 2012, reviewer Jan Moir, writing in the Daily Mail at the time, pointed to her less than original ideas and her lack of any obvious qualifications beyond penning the blog on her parents’ Party Pieces website.
‘From the moment she appeared in butter satin at her sister’s wedding, Pippa has struck absolutely no one as the kind of girl you would always find in the kitchen at parties,’ continued Moir.
‘And would she really have gained a lucrative publishing contract to write about something she calls “simple, creative entertaining” if her sister were not married to a member of the Royal Family?’
Less-than-profound advice in the book included having a bonfire on Bonfire Night and serving pumpkin soup in a hollowed-out pumpkin at Halloween.
Other tips included telling her readers to prepare ice for drinks by ‘filling trays with water well before your party’.
Two weeks after it was released, the glossy tome sank to number 180 in Amazon’s list of bestsellers, and the internet retailer slashed the price of the book in a bid to shift copies.
Despite jetting to New York to promote her book, Pippa’s efforts fared even worse on the other side of the pond, with Celebrate at 308 on Amazon’s U.S. bestseller list in the month after its release.
According to royal expert Richard Fitzwilliams, Pippa’s trajectory ‘echoes’ the experience of Prince Harry , who has often complained about his upbringing as a royal ‘Spare’
According to the Daily News, Pippa was in talks with NBC for a new job after she was interviewed by Matt Lauer. However the deal never materialised. According to reports at the time, talks over a £40,000 contact ‘stalled’
Meanwhile Pippatips, a spoof Twitter account mocking the ‘banal’ party hints contained in Celebrate, quickly gained 20,000 followers.
Reflecting on the unsuccessful venture in a 2016 interview, Pippa said that she felt ‘she hadn’t earned the right’ to author such a book, ridiculed for being a list of blindingly obvious tips.
‘I believed in it and I can’t blame anyone else, but maybe it might have been better if I had waited a bit longer before doing it.’
Yet she remained undeterred by the bleak sales and public ridicule, and in 2012, Pippa became a regular columnist for several publications and contributed several articles to The Spectator magazine.
She started a food column in the supermarket magazine Waitrose Kitchen beginning in the spring of 2013.
However, established chefs were left appalled that a woman with no obvious cooking experience had been hired and accused Waitrose of publicity seeking, while Pippa was once again charged with capitalising on her royal connections.
In March 2013, she was dropped by her literary agent David Godwin who had helped her launch Celebrate!
Speaking after the news broke, he said: ‘I am very sorry it has happened, but yes, it is true: I no longer represent Pippa and I wish her every good luck.’
Then, with lacklustre sales uppermost in publisher’s minds, plans for a follow up to Celebrate! were quietly shelved.
In 2012, it was announced Pippa had landed a deal from publishing house Penguin worth £400,000 for a book on party planning. But, her party planning book, Celebrate, was not well received and sales were poor
Nonetheless, in June of that year, she was named a contributing editor of Vanity Fair and wrote a series of columns for the magazine.
Pippa also began writing a fortnightly sports and social column for The Sunday Telegraph.
In January 2014, her US publisher Viking dropped her altogether having sold just 18,000 copies of the book, with a source telling the Sunday Times that ‘Pippa’s Celebrate sales are nothing to celebrate.
‘She was a superstar after the wedding, and everybody thought it would be a success. Even Sarah Ferguson sold more books when she started her writing career.’
According to the Daily News, Pippa was in talks with NBC for a new job after she was interviewed by Matt Lauer.
NBC News previously denied that a deal was in the works but the network was reportedly in serious talks with Pippa for months about becoming a lifestyle and health correspondent.
However the deal never materialised. According to reports at the time, talks over a £40,000 contact ‘stalled’ – with sources describing how one particular scene featuring Wild West Dancing had been ‘cringeworthy’.
Meanwhile, Pippa’s Telegraph column, only six articles old, was axed after the paper discovered that its readers ‘just weren’t into it’.
A source, speaking at the time, added: ‘There was a lot of negative mail coming in after each column and there were too many off-limit subjects for her. They ran out of ideas.’
Her Vanity Fair column, meanwhile, was laughed at, with Pippa once again accused of trading on her royal connections and of stating the obvious.
In 2014, she launched a celebrity cookery book, titled Heartfelt, to raise money for the British Heart Foundation.
By 2016, it was reported Pippa had been ‘quietly and diplomatically reined in’ by Prince William, who was understood to have been advising her on her future role. Calculated changes brought Pippa’s life as a media personality to a close
However, by 2016, it was reported Pippa had been ‘quietly and diplomatically reined in’ by Prince William, who was understood to have been advising her on her future role.
The now Prince of Wales was said to be aware that commercial ventures associated with the Royal Family, including Pippa’s projects, might bring difficulties of their own.
A friend of Pippa said at the time: ‘It was felt by William in particular that she needed some guidance and support. It was felt something needed to be done. So Pippa has been quietly and diplomatically reined in.’
Calculated changes brought Pippa’s life as a media personality to a close, steadily replacing it with one based on charity fundraising.
She wed high-flying James Matthews in 2017, and the pair later later hired PR mastermind Jo Milloy, who worked closely on Brand Beckham.
However, the royal couple now tend to live a more low key life with their three children: Arthur, seven, Grace, five, and Rose, three, and remain close to the Prince and Princess of Wales.
