There was no shortage of scene-stealers at the old Four Seasons restaurant in New York City on a recent fall night. The Kering Foundation, the philanthropic arm of the owner of Gucci and Bottega Veneta, had corralled an A-list posse that included Oprah Winfrey, Leonardo DiCaprio, and Nicole Kidman for its second annual Caring for Women dinner. But for all the star wattage at the Pool, it was hard to miss the man in the 10-gallon cowboy hat and matching belt buckle.

Kimbal Musk, the brother of Tesla and SpaceX billionaire Elon, the richest man in the world, is a successful entrepreneur and philanthropist in his own right (with a net worth of $700 million and counting), and on this solemn occasion he was preening in a glimmering black suit that recalled the country singer Dwight Yoakam. Was there about to be a gunfight on the charity circuit, or did the younger Musk crave the spotlight for himself just this once?

kering foundation caring for woman dinner
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Salma Hayek Pinault, Kimbal Musk and Christiana Musk at the Kering Foundation Caring for Women dinner on September 12, 2023 in New York City.

The cowboy drag, it turns out, is not his only calling card. Kimbal also has the manners of a Southern gent. It didn’t go unnoticed that on the way to his table (where he and his second wife, Christiana, were seated alongside gala co-chair Salma Hayek Pinault, the actress and spouse of Kering boss François-Henri Pinault, whose dad François is the 47th-richest man in the world), Musk frère made small talk with Kim Kardashian and Lauren Sánchez, the girlfriend of Jeff Bezos, the third-richest man on the planet. More than one inquiring mind wondered about the affable fellow in the Stetson. Is he the aw-shucks optimist he appears to be on the international do-gooder scene, or the gregarious face of the controversial Musk clan, all hat and no cattle?

If the attendees had been following Kimbal’s exploits on social media, they would have known that away from the hammer and glamour of the auction scene, the 51-year-old tech and food tycoon is indeed as homespun as a Dolly Parton lyric.

On Insta­gram, where he has 205,000 followers (he has 359,000 on X, where his brother boasts 161 million acolytes), his posts cover his three children; his mother, the model and entrepreneur Maye Musk; and his hats, as well as his philanthropic endeavors.

“Kimbal has an almost endearing online presence,” says Taylor Lorenz, who covers the tech industry as a reporter for the Washington Post and author of the new book Extremely Online: The Untold Story of Fame, Influence, and Power on the Internet. “It’s definitely him doing all his own posts—he’s not trying to growth-hack. He is this likable, happy-go-lucky younger brother of a maniacal billionaire whom everyone has come to hate.”

If Kimbal scans as more comfortable in his own skin and has the more positive personal brand of the Musk men (Lorenz describes them as “the Logan and Jake Paul of the tech and business worlds”), it’s not that impressive an achievement. Elon, among his encyclopedia of missteps, recently took his toddler son, X, to meet repressive Turkish president Recep Tayyip Erdogan. And the Musk paterfamilias, Errol, got his stepdaughter pregnant. Twice. Errol is a piece of work, serving up reality TV–worthy cringe about his disarmed sons, telling one Australian radio show last year that Kimbal is his “pride and joy” and that Elon needs to go on a diet.

Though Kimbal’s success is forever dwarfed by his brother’s, it would be a mistake to see him as a Zeppo to Elon’s Groucho. The picture that emerges in interviews and in Walter Isaacson’s recent blockbuster biography of Elon is of an inveterate charmer with the gumption to challenge his brother’s outsize intelligence.

elon and kimbal musk in 1988
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Elon and Kimbal in 1988. They moved with Maye to Canada after their parents’ divorce and sold their first startup, Zip2, in 1999.

Isaacson recounts a fearless young Kimbal cold-calling potential mentors that Elon had read about in the newspaper. “If we were able to get through on the phone, they usually would have lunch with us,” Kimbal told Isaac­son. Yet it’s in their ambitions that there’s daylight between the siblings.

Unlike Elon’s lofty wish to conquer new frontiers, Kimbal has more grounded aspirations: to reimagine farming and reengineer the American stomach. Elon’s views “are stratospheric, while mine are more in the ground” is a go-to refrain. A trained chef who studied at the French Culinary Institute in New York, Kimbal owns and runs the Kitchen Restaurant Group, which has locations in Boulder, Denver, and Chicago. He also runs the nonprofit Big Green, which teaches and gives grants and gardens to schools and motivates communities to embrace their inner farmers.

elon musk and kimbal musk in 1974
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The Musk brothers in 1974. Born a year apart to Errol and Maye Musk, Elon and Kimbal grew up in Pretoria, South Africa.

Perhaps it’s best to view the siblings’ respective evolutions as a Sliding Doors moment. The tech bros were born a year apart and grew up in Pretoria, South Africa (they have a younger sister, Tosca, 49, who runs a bodice-ripper streaming service), and later attended the same college in their mother’s native Canada. The pair founded the digital platform Zip2 in 1995, sleeping in their offices in their salad days before selling to Compaq four years later for $307 million. Kimbal put that windfall into investments in tech companies, including Elon’s X.com, a precursor to PayPal that was ultimately sold to eBay for $1.5 billion. He was also an early investor in Elon’s spacecraft manufacturer, SpaceX, and today is a shareholder and member of Tesla’s board of directors.

Elon chose world domination, or so the narrative goes, and Kimbal ran roughshod over expectations and followed his gut. But for all his yeehaw swagger and modern cosmopolitanism (his wife, the daughter of former Texas billionaire Sam Wyly, was previously married to Deborah Anne Dyer, better known as Skin, the lead singer of the British rock band Skunk Anansie), Kimbal may not be that different from his brother.

There were plenty of fisticuffs along the way, Isaacson writes, including one fight at Zip2 when Kimbal bit Elon’s arm, leading to stitches and a tetanus shot. But Kimbal goes to great lengths to not question his brother’s genius. There’s also that pesky 2022 matter with the Securities and Exchange Commission over whether the brothers violated insider trading laws in the wake of an iffy tweet from Elon asking if he should sell 10 percent of the shares in Tesla. Kimbal had sold $108 million worth of company shares the day before the tweet. (The SEC has not commented on its probe.)

kimbal and elon musk 2020
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Tech bros in life and business: Kimbal is today a major shareholder in Elon’s Tesla.

Kimbal has also learned to keep the press at bay (twice he ignored T&C’s entreaties to chat), choosing instead to communicate directly with his social media fans. Meanwhile, during Covid, some employees at his Next Door chain of restaurants were frozen out of a rainy-day fund that they had contributed to from their paychecks. For good measure, Square Roots, the feel-good tech farming startup he founded in 2016, proved to be a bad seed; workers were informed last July that it was closing most of its operations and eliminating jobs across the board.

With business this hard, no wonder Kimbal Musk is cozying up to the bon ton. If you climb into the saddle, be ready for the ride. A budding spiritualist, Kimbal seems to be leaning into outlaw Elon territory lately, sharing this koan from the grounds of this year’s Burning Man: “If you die before you die, you won’t die when you die.” Easy, cowboy.

This story appears in the December 2023/January 2024 issue of Town & Country, with the headline "O Brother, Who Art Thou?" SUBSCRIBE NOW