She seemed to have the world at her feet, with a £400,000 advance for her party planning book, lucrative contracts with glossy magazines and even a budding career as a television presenter.
However the Duchess of Cambridge‘s younger sister has struggled to step out of her the royal’s shadow, with her party-planning book, Celebrate, flopping in 2012, while a burgeoning US TV career never materialised.
Despite her career woes, Pippa is unlikely to ever worry about finances having married billionaire James Matthews, 36, in 2017, and since then they have welcomed two children, Arthur, two, and one-month-old Grace.
Here, FEMAIL revisits Pippa’s bumpy ride to the top of the social circuit…
Pippa Middleton won a global fan base after her star turn as a bridesmaid at the Royal Wedding – but has struggled to make her mark
However the Duchess of Cambridge’s younger sister has struggled to step out of her the royal’s shadow, with her party-planning book, Celebrate, flopping (left) while a burgeoning US TV career never materialised (right, pictured in 2014 dancing with cowboys during a visit to the States)
Despite her career woes, Pippa is unlikely to ever worry about finances having married billionaire James Matthews, 36, in 2017
Pippa famously stole the spotlight during the Royal Wedding in 2011 when she donned a curve-hugging white bridesmaid’s gown for the ceremony.
A website devoted to her bottom, made famous by her contour-hugging bridesmaid’s dress at the royal wedding, had more than one million hits.
Speaking in 2018, she said she hadn’t expected the reaction, revealing: ‘I was surprised and still don’t understand it.’
‘I have had a few years of being in the public eye and I have developed something of a thick skin.
‘But managing it all on my own has been quite hard. I have quite a lot thrown at me, such as being followed by people hiding behind cars and jumping out with cameras. It can be unnerving.’
Pippa famously stole the spotlight during the Royal Wedding in 2011 when she donned a curve-hugging white bridesmaid’s gown for the ceremony
PARTY BOOK FLOP
In 2012, it was announced Pippa had landed a book deal from Penguin worth £400,000 for a party planning tome.
In the foreword to her party planning guide Celebrate Pippa wrote: ‘It’s a bit startling to achieve global recognition before the age of 30 on account of your sister, your brother-in-law and your bottom. One day I might be able to make sense of this.
‘I certainly have opportunities many can only dream of. But in most ways I’m a typical girl in her twenties trying to forge a career and represent herself in what can sometimes seem rather strange circumstances.’
However, reaction to her party planning book, Celebrate, was grim. There was a critical panning and and sales were poor.
In 2012, it was announced Pippa had landed a book deal from Penguin worth £400,000 for a party planning tome
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’ .
As a children’s Halloween game, Miss Middleton suggested the ‘doughnut tree’, stringing the treats from tree branches for youngsters to try and bite without using their hands, but she adds: ‘If you play indoors, line the floor with plenty of newspapers.’
Pippa’s outdoor game of choice for a bonfire night party was conkers, with the English Literature graduate writing: ‘Each player has a conker threaded onto a piece of knotted string… and pairs of players take it in turns to hit each others conker.’
The book was widely slated by critics and readers, with Pippa’s tips including advice on making ice and having a bonfire on bonfire night (pictured)
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.
Meanwhile Pippatips, a spoof Twitter account mocking the ‘banal’ party hints contained in Celebrate, quickly gained 20,000 followers.
In a 2016 interview, she said credibility was her issue. She felt ‘she hadn’t earned the right’ to author such a book, ridiculed for being a list of blindingly obvious tips.
She said: ‘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.’
Friends have since said she would not seek to write another volume on party organising.
ATTEMPT AT MEDIA CAREER INCLUDING GIG IN THE US
Pippa became a regular columnist for several publications in 2012, and contributed several articles to The Spectator magazine.
The same year, it was reported that NBC would offer Pippa $600,000 to be a royal correspondent but this was denied by the network.
She started having a food column in the supermarket magazine Waitrose Kitchen beginning in spring 2013.
At the time, it was said that ‘Pippa’s Friday Night Feasts’ would advise on the best meals to start the weekend off with friends.
Pippa became a regular columnist for several publications in 2012, and contributed several articles to The Spectator magazine and Vanity Fair – but it has now been years she has written anything (pictured, in 2012)
Editor William Sitwell said the signing would be ‘an excellent contributor…bringing with her a wealth of experience of entertaining’.
He added: ‘Readers will love her relaxed and easy entertaining ideas which will help with the preparation for all sorts of occasions.’
However the decision for her to replace Delia Smith was met with uproar among many of its customers, who had relied on the chefs cooking know-how for decades.
In June 2013 she was named a contributing editor of Vanity Fair and wrote a series of columns for the magazine.
Meanwhile in 2014, according to the Daily News, the freelance columnist hoped for a deal ‘upward of $500,000’ to report on lifestyle and health issues for NBC, after doing her first ever TV interview with Matt Lauer (pictured)
Pippa also began started writing a fortnightly sports and social column for The Sunday Telegraph that September.
And in 2014, according to the Daily News, the freelance columnist hoped for a deal ‘upward of $500,000’ to report on lifestyle and health issues for NBC.
Pippa was in talks with the ‘peacock network’ 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.
That same year, excited locals in Jackson Hole posted pictures of Pippa dancing to local bluegrass group all over social media.
However the deal never materialised and, within months, Pippa also parted ways with The Telegraph.
That same year, excited locals in Jackson Hole posted pictures of Pippa dancing to local bluegrass group all over social media as she reportedly tried to begin a media career in the US
Meanwhile her last columns for the Spectator and Vanity Fair magazines were published in 2015.
She continued to try to win new work and turned to the leading strategist Andrew Williams who also works for the upmarket Mayfair wealth management company LJ Partnership in 2015.
He advised on the task of forming ‘Team Pippa’, along with various media and sports experts. But they kept hitting stumbling blocks.
‘Pippa was great to deal with,’ said a source at the time. ‘She was friendly, professional and really wanted to get the ball rolling. The brief was sports and there wasn’t really a boundary.
‘We were looking at personal training. There was talk at one point about a nutrition range. There were a number of endorsements on the table, all sorts.
‘The problem was that when it got down to signing off on any of the deals and doing any business, a line was drawn. Pippa would always say no.
‘She was the one driving it all and then it got to a point where she backed out and nothing would happen. Some of us assumed it was the Palace and I think at times it was quite frustrating for Pippa, because there was never any progression when she wanted things to move forward.’
Pippa was also initially the ‘face’ of her parents’ company Party Pieces, an online party supplies company, and wrote a monthly online blog with tips and tricks for readers.
However in 2016, traces of Pippa were removed from the site and she stopped writing the blog, which is now produced by another employee simply known as ‘Rebecca’.
REINED IN BY WILLIAM
In 2016, it was reported Pippa had been ‘quietly and diplomatically reined in’ by the Duke of Cambridge, who was understood to have been helping advise her on her future role.
Prince William was said to be sharply aware that commercial ventures associated with the Royal Family, including Pippa’s projects, might bring criticism or damage the family reputation.
A friend of Pippa said at the time: ‘It was felt by William in particular that she needed some guidance and support.
In 2016, it was reported Pippa had been ‘quietly and diplomatically reined in’ by the Duke of Cambridge, who was understood to have been helping advise her on her future role (pictured, Pippa attending a British Heart Foundation event in 2019)
‘Among some courtiers, there were also echoes of Sarah Ferguson, the Duchess of York, after her break-up with Prince Andrew and how she sold herself out with various corporate deals.
‘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.
It is understood that William and Kate spoke privately to Pippa and then-boyfriend James Matthews to suggest what could be done to assist her in a suitable career.
She is now an ambassador for The British Heart Foundation, Disability Snowsport UK and The Mary Hare school for deaf children.
MARRIED A BILLIONAIRE
But despite her struggles to make a mark on the media or sports landscapes, Pippa is unlikely to be tightening her purse strings any time soon.
After she started dating 41-year-old financier James Matthews in 2016, the two tied the knot in May 2017.
Racing driver-turned city trader James, who was privately educated at Uppingham School proposed with a 3.5 carat £200,000 diamond ring.
James is set to inherit the Scottish courtesy title of ‘Laird of Glen Affric’ which came with the 10,000-acre estate of the same name near Inverness that his father bought in 2008. James is listed as managing director of Beaufort Glen Affric.
Racing driver-turned city trader James Matthews, who was privately educated at Uppingham School, proposed with a 3.5 carat £200,000 diamond ring in 2016 before the pair married in 2017
James (pictured with Pippa’s parents Mike and Carole and brother James) owns a £3m private jet and bought a six-bedroomed, £17m house in 2014, which boasts a car-stacking garage in the basement, along with an underground home cinema and a lift
One of James’ smaller companies, Beaufort Glen Affric Ltd, based in Inverness, was in the red to the tune of £9.95m, according to the latest published accounts in 2019.
Having launched his own hedge fund company, Eden Rock Capital Management Group – named after his father David’s exclusive £1,000-a-night hotel in St Barths – in 2017, James was estimated to be ‘close to’ to being a billionaire by founder of the Wealth Quotient website, David Friedman. More recent estimates of his wealth have put it at up to £2bn.
He owns a £3m private jet and bought a six-bedroomed, £17m house in 2014, which boasts a car-stacking garage in the basement, along with an underground home cinema and a lift.
James and Pippa have since welcomed two children, who are cousins of Princes George and Louis and Princess Charlotte – two-year-old Arthur and one-month-old Grace (pictured, last month on a walk)
In 2018, Pippa welcomed baby Arthur in the Lindo Wing of St. Mary’s Hospital, the same place where sister Kate gave birth to all three of her children.
She continued her Waitrose column while pregnant with her son, but doesn’t appear to have continued the venture since becoming a mother.
Last month, the couple welcomed their second child – a daughter named Grace Elizabeth.