He once ran a personalized marshmallow company called Boomf, and now owns a dog-food business.
He announced on Instagram that he is expecting his first child with wife Alizee Thevenet.
By now, royal fans are well acquainted with Kate Middleton, and probably know her younger sister, Pippa, too. But the Princess of Wales has another sibling: James.
Beyond his royal connections, the youngest Middleton is perhaps best known for heading a personalized marshmallow company called Boomf, which he founded in 2013 and sold last year. He also founded a freeze-dried dog-food business, Ella & Co, in 2020.
On Wednesday, he announced he's expecting his first child with his wife, Alizee Thevenet.
Take a closer look at James Middleton's life, both before and after Kate became a member of the royal family.
James, 36, is the youngest Middleton sibling. He grew up with Kate and Pippa in Bucklebury, a village in West Berkshire, England.
James Middleton in 2011.
Getty/Ian Gavan
When news outlets were first reporting Kate and Prince William's budding romance, James Middleton took extreme measures to minimize rumors and chatter.
"I used to be first up in the morning to make sure I could get to the papers and rip out any stories about my sister, so nobody would see them and there would be no conversations about them," he told the Daily Mail in 2016.
He dropped out of the University of Edinburgh after one year because he knew college wasn't for him.
James Middleton in 2012.
Getty/Clive Rose
"I knew that that mouthful of academic prescription was not going to do it for me," he told British GQ, according to a 2012 article. "My dream, which came to me when I was flying back up to Edinburgh after a weekend home, was to build a cake empire."
In 2007, he launched the Cake Kit Company, which provided customers with DIY kits for festive party cakes.
A web archive screenshot of the now-defunct Cake Kit Company website.
Following Kate's wedding, her siblings began to get a lot of media attention.
James and Pippa Middleton celebrate Queen Elizabeth II's Diamond Jubilee in 2012.
Chris Jackson/Getty Images
Around this time, Pippa and James Middleton were frequently photographed together in public. At the time, the two shared an apartment, according to British GQ.
In 2013, Middleton was first spotted with British media personality and actor Donna Air.
James Middleton and Donna Air at a party in June 2013.
Jon Furniss/Invision/AP
Donna Air has a 19-year-old daughter named Freya from a previous relationship. In 2016, Middleton told the Daily Mail, "I love Donna very much and Freya is very much part of Donna. I love them both equally."
Middleton went through a major style evolution in 2014: He grew a beard.
Pippa and James participate in the Race Across America in June 2014.
Larry French/Getty Images
"My mother looks at it and says, 'When are you going to get rid of it?'" he told the Daily Mail. "But then that's because she wants me to be her little boy."
That same year, he appeared on "Good Morning America" to promote a new venture, Boomf.
James Middleton during an appearance on "Good Morning America" in 2014.
RW/MediaPunch/IPX
Boomf launched as a service that allowed customers to print graphics and personal photos on marshmallows.
Speaking about his company to The Cut in 2014, Middleton said, "When you see yourself on a marshmallow, or your loved one or your pet, you have a little moment with that little marshmallow. There aren't many products in the world like that."
He told digital magazine TYD in 2015 that while he has a famous sister, he's not coasting on her success as an entrepreneur.
"I work incredibly hard — just like every other person in business," he said. "Aside from the fact that yes, I am the brother of someone very important, I am, at the end of the day, just James."
In early 2018, Air confirmed that she and Middleton had split.
James Middleton and Donna Air at a red carpet event in 2015.
Getty/Tim P. Whitby
In February 2018, she told the Daily Mail: "James and I are no longer an item. We parted ways in December but remain the very best of friends and always will be."
Middleton started working as a tour guide at Pippa's father-in-law's hotel in 2018.
James Matthews and Pippa Middleton on their wedding day in May 2017.
The hotel is owned by David Matthews, the father of Pippa's husband, James Matthews, who works as a hedge fund manager. Pippa and her husband wed in 2017 and have three children.
"The countryside is where I'm at my happiest and I'll be taking my four dogs to Glen Affric with me," James Middleton told The Telegraph in 2018.
The youngest Middleton sibling married French financial analyst Alizee Thevenet in 2021.
Alizee Thevenet and James Middleton at Lady Gabriella Windsor and Thomas Kingston's wedding in 2019.
Jean-Gabriel told the Daily Mail that his daughter is "deliriously happy" and that the couple is "very much in love."
According to an unnamed family friend, Middleton and Alizee Thevenet met in a bar when he "offered her a drink."
Thevenet has an undergraduate degree in accounting and finance, as well as a master's degree in investment and finance, the Daily Mail reported.
He often spends time with Kate's children.
Prince William, Kate Middleton, Prince George, Princess Charlotte, Pippa Middleton, and James Middleton attend Church on Christmas Day in December 2016.
Samir Hussein/Samir Hussein/WireImage
"I just want to be the best uncle possible," he once told "Good Morning America." "Like any uncle wants to be, I want to be the cool uncle. The fun uncle. That's what sort of I'll always try and be."
When he's not working, he pursues an interesting set of hobbies: He keeps bees, restores old tractors and Land Rovers, and breeds dogs.
James Middleton at GQ's Men of the Year Awards in 2019.
Although it's not clear whether the Boomf founder had just made his profile public, or if it was just discovered, it appears Middleton had been posting under the username, jmidy, from as early as July 2013.
Judging by his Instagram, he is particularly fond of animals. The youngest Middleton sibling often posts photos of numerous dogs, lambs, chickens, and more.
In 2020, Middleton launched Ella & Co, a freeze-dried raw dog-food company named after his dog Ella.
James Middleton with his dogs Inka, Luna, Ella, and Mabel.
Kirsty O'Connor/PA Images via Getty Images
"A few years back, my dogs helped pull me out of a really difficult battle with depression," Middleton wrote on Ella & Co's website. "When I reached the other side, I set out on a mission to make their lives just as happy and as healthy as they've made mine, starting with the food they eat."
In July, Middleton announced on Instagram that he and Thevenet are expecting their first child.
James Middleton and Alizee Thevenet in 2022.
David M. Benett/Dave Benett/Getty Images for Bulgari
"We couldn't be more excited … well Mable might be," Middleton captioned a photo of Thevenet holding her baby bump with their dog Mable. "It was a very difficult start to the year after losing my beloved Ella however we will end the year with the most precious little addition to our growing family."
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