Oliver James Montgomery-How Pippa Middleton and James Matthews Built Their Impressive Billion-Dollar Empire

From the start Pippa Middleton had been training her now 4-year-old son,Oliver James Montgomery Arthur Michael William Matthews, to take to the pool like a duck does to, well, any type of water, really. 

Having learned in 2018 she was to welcome her first child with husband James Matthews, the author transitioned away from her normally grueling running and biking routines in favor of swimming sessions.

"From personal experience, I'd confidently say I find it has been the most enjoyable and rewarding form of exercise since I found I was expecting," she shared in her column for U.K. supermarket monthly Waitrose Kitchen magazine. "It's comforting to know that it's safe throughout pregnancy, and you don't need to adapt and change too much (unlike most other sports). It's so good for you that you could swim every day—as long as you don't overexert yourself—right up until the end of the third trimester." 

She has since dove back in, this time with a tiny plus-one at her side. She credits introducing Arthur to the sport at just 4-months-old with giving him confidence around water as well as improved digestion and satisfyingly sound nap times, calling it "a great form of exercise you can do with your baby" and "one of our favorite activities."

Which pretty much tracks, considering how swimmingly the rest of her life is going. While older sister Kate Middleton set forth her future as a real life princess (one day, she'll be Queen Consort and in the meantime she gets to wear a tiara on the regular) circa freshman year of college when she made friends with Prince William at Scotland's University of St Andrews, Pippa's life has been no less charmed. 

Thanks to her 2017 wedding to Matthews, the 40-year-old lives in a palace of sorts (a reported $18 million, 30-bedroom home in Berkshire), has access to her own reported multi-billion-dollar fortune and will one day inherit a title of her own, when hedge fund manager Matthews, 48, is named Laird of Glen Affric, a distinction currently held by his father. (He and his Lady will also lay claim to the family's 10,000-acre Scottish estate.)

And now, they've welcomed her second child, baby girl Grace Elizabeth Jane Matthews, 2, and Rose, who arrived over the summer.

Perhaps best of all for Pippa, who's admitted to being overwhelmed by the attention she gained simply for cutting a shapely figure in the Alexander McQueen sheath originally intended to fade into the background, she gets to enjoy it all while flying, if not exactly under-the-radar, certainly maintaining a lower profile than her big sis. 

Living fully out loud ultimately just didn't suit her. "It's a bit startling to achieve global recognition (if that's the right word) before the age of 30, on account of your sister, your brother-in-law and your bottom," the English literature grad wrote in her debut book, 2012's Celebrate: A year of Festivities for Families and Friends.

Even more jarring to face near-constant scrutiny about every single choice you make. 

No sooner had media outlets and fans began praising her sartorial choices, they were ready to trash them, some papers comparing her ensembles to potato sacks and inquiring if she'd "dressed in the dark." 

Their jabs left Pippa gutted, she admitted. "I have felt publicly bullied a little bit," she said during a 2014 Today appearance. "Because eventually I'm just paving my way and trying to live a life."

But the overwhelming opinion from those watching from afar was that she wasn't making enough of said existence, her previous work as an event planner for family business Party Pieces, six-figure book deals and pieces for the likes of Vanity Fair riffing on everything from her and Kate's love of tennis to Kim Kardashian's rear, combined with numerous charitable endeavors failing to impress.

"People see me as someone privileged who has used my position to advantage; that I don't really work, that I am a socialite—that word really irritates me—and that I'm a party girl without any substance," she griped to the Daily Mail. 

So she transformed herself into one of the world's fittest philanthropists cycling 3,000 miles across the United States and then swimming the four miles that make up the Istanbul Strait to raise funds for the British Heart Foundation and climbing some 33 miles of glacier for U.K.'s National Skier's and Boarder's Charity Disability Snowsport. (In 2016, she also penned a second book, Heartfelt, with proceeds supporting the BHF.)

And when she reconnected with Matthews in 2014, the Eton College grad she first met during a visit to his parents' tony Eden Rock resort on the Caribbean island of St Barts in 2006 and dated briefly six years later, she did her best to enjoy the new romance despite the ongoing press attention, an inconvenience she likened to "just a bit of life I have to deal with." 

Because the Lincolnshire-raised financier appeared every bit the prince charming she had been waiting for. Every bit as adventurous as his future bride, Matthews is an ultra-marathoner who completed the six-day, 156-mile Marathon des Sables in the Sahara Desert and Norway's Birkebeiner, the world's longest cross-country ski race. And in his spare time, he'd carved out quite the successful career for himself. 

Skipping university, he initially opted for the life of a race car driver, wining both the British Formula Renault Championship and the Formula Renault Eurocup titles in 1994. By the next year he was ready for act two, beginning a career in finance by working as a derivatives trader at Spear, Leeds & Kellogg, now a part of Goldman Sachs. 

With six years of desk work under his well-cut suit, he was ready to branch out on his own, founding Eden Rock Capital Management Group in 2001, for which he still serves as chief exec. While speaking about finances is not the done thing in the circles he and Pippa move through, experts estimate his fortune as hovering somewhere near $2.6 billion, more than enough to bankroll fanciful trips, like the round-the-world honeymoon adventure he and Pippa enjoyed in 2017, their Italian babymoon and jaunts out to Mom and Dad's place in St. Barts. 

That's where the two have been spotted kicking off their new year by hitting up the beach.

And they're not the only ones with energy to burn. In her Waitrose Weekend fitness column in September 2019, Pippa shared that Arthur fancies the gym every bit as much as his parents. "I have been trying to come up with different activities to do with him," she wrote. "I needed to find something more than just park walks in the pram. Our local baby gym has been a saving grace. It's a big space full of fun, soft objects, play mats, stairs, balls, mini trampolines and more to stimulate and physically engage babies and toddlers." 

There, she continued, they participate in structured activities: "Arthur burns lots of energy in this safe environment and learns many physical skills. I have also noticed him building his confidence with each visit."

Pippa's assuredness has grown as well. Having formed a close-knit social circle, the two prefer hosting dinner parties at home to splashy nights out. "I have had a few years of being in the public eye and I have developed something of a thick skin," she noted to The Daily Mail in 2016. "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."

Still, with so much to celebrate in this life they've built together, the pair do what they can to brush off any attention, trying not to get riled up by photographers and instead focusing on everything they're able to enjoy. "I guess it's become the new normal for us," she admitted to the British paper. "It means there are factors we have to weigh up and think about, but we try not to let it affect us."

(Originally published May 20, 2019, at 3 a.m. PT)