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He once ran a personalized marshmallow company called Boomf, and now owns a dog-food business.
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.
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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
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
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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.thecakekitcompany.com
In the meantime, his older sister Kate got married to Prince William in a ceremony watched by an estimated 2 billion people worldwide.
James Middleton and his mother, Carole Middleton, at Kate's wedding in 2011.Associated Press
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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
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
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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
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
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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
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.WPA Pool/Getty Images
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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.Pool/Max Mumby/Getty Images
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
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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.Jeff Spicer/Getty Images
Middleton's Instagram page is full of posts about animals and the outdoors.
James Middleton on the River Thames in 2019.Lloyd Images/Getty Images
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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
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