Ken Howery is a quiet, unassuming tech investor who prioritizes discretion. And yet, he has ended up in the middle of two of the noisiest story lines of the incoming Trump administration.
One is the expanding ambition of Elon Musk, Mr. Howery’s close friend and fellow party-scene fixture since the two helped run PayPal 25 years ago.
The other is the expansionist ambition of Mr. Musk’s boss, President-elect Donald J. Trump, who has set his sights on buying Greenland, the world’s largest island.
As Mr. Trump’s pick for ambassador to Denmark, Mr. Howery is expected to be central to what Mr. Trump hopes will be a real-estate deal of epic proportions. The only hitch is that Denmark, which counts Greenland as its autonomous territory, says the island is not for sale.
Whether he likes it or not, Mr. Howery, a globe-trotter known for his taste for adventure and elaborate party planning, is likely to find himself in the middle of a geopolitical tempest.
Mr. Trump has been explicit about his expectations for his new ambassador filling a once-sleepy post. When he announced Mr. Howery for the role, which requires Senate confirmation, he reiterated his designs on Greenland for the first time since winning the presidency.
“For purposes of National Security and Freedom throughout the World, the United States of America feels that the ownership and control of Greenland is an absolute necessity,” Mr. Trump wrote on Truth Social late last year. “Ken will do a wonderful job in representing the interests of the United States.”
Thanking Mr. Trump on X, Mr. Howery mentioned not just the U.S. Embassy in Copenhagen but also the U.S. Consulate in Nuuk, Greenland, saying he was eager to “deepen the bonds between our countries.”
On cue, Mr. Musk chimed in: “Congrats! Help America gain Greenland.”
Mr. Howery’s mission is an example of what awaits the crop of Silicon Valley donors who swarmed to Mr. Trump during the campaign and now intend to follow him into public office. While many are seasoned deal-makers, their private sector experience may only go so far in serving the unpredictable Mr. Trump.
Mr. Howery did not respond to requests for comment. In private conversations, friends say he holds traditional conservative views and is hardly a Trump die-hard. He is drawn to diplomatic roles not out of ideology but for the overseas experience, they said. He is expected to be in Washington this week, hosting a rooftop cocktail reception opening the inauguration weekend on Friday, according to a copy of the invitation.
Mr. Howery is, in fact, signing up for a second tour for Mr. Trump. He served as ambassador to Sweden for 16 months during Mr. Trump’s first term; a delayed Senate confirmation shortened his tenure.
Still, he received some practice in the art of explaining Mr. Trump to skeptics overseas. As Mr. Trump denigrated NATO, which Sweden was moving toward joining, Mr. Howery defended Mr. Trump as “unconventional” and he visited the Arctic, an important outpost for NATO’s defenses.
Persuading Denmark to part with Greenland may require Arctic diplomacy of a whole other level. Leaders in both Denmark and Greenland have repeatedly said they are not interested in a sale, and chortled at Mr. Trump’s approach to deal-making on social media.
“I think Ken Howery was an effective ambassador to Sweden several years back. I absolutely believe in the private-sector experience,” said Rufus Gifford, who served as President Barack Obama’s ambassador to Denmark and was a top fund-raising official on Vice President Kamala Harris’s presidential campaign.
“But I’d say this: If you’re entering into the political firestorm that would be Donald Trump’s stated desire to purchase Greenland, I don’t believe there’s very much on your résumé that can help you navigate that,” he said.
Mr. Howery’s résumé begins at Stanford University in the 1990s, where he showed an early interest in politics as an undergraduate editor in chief at the conservative Stanford Review. When he graduated in 1998, he connected quickly with Peter Thiel, The Stanford Review’s rabble-rousing founder, to execute the investor’s orders.
Mr. Howery and Mr. Thiel soon started PayPal, the online payment service, where they were later joined by Mr. Musk. The three became charter members of the “PayPal Mafia” that has grown to dominate Silicon Valley. Mr. Howery and Mr. Thiel, who are still very close, went on to start Founders Fund, one of the industry’s leading venture capital firms.
With blond hair and a youthful face, the 49-year-old Mr. Howery, who is known as Kenny by friends, has little of the abrasive swagger or edge of Mr. Thiel and Mr. Musk. Some close to him described him as more of a people-pleaser than a cutthroat corporate operator. Nearly all of Mr. Howery’s associates interviewed for this article spoke on the condition of anonymity so as not to damage their relationship with Mr. Howery, who typically shuns the spotlight.
That does not mean Mr. Howery is a wallflower. He is known in part for his elaborate parties and lifestyle: In November 2020, he threw himself a birthday party at a castle near Stockholm. (Mr. Musk later said he contracted Covid on that trip.)
For a Halloween celebration in 2022, he invited plenty of billionaires, including Mr. Thiel, to a castle in Transylvania, Romania, for a “Transylmania” party, according to a social-media post from one of the planners, who said it required seven months of effort. (Although he no longer had his diplomatic job, Mr. Howery included an insignia of his ambassadorship on the thank-you letters to the planners.)
Mr. Howery, who is unmarried, has a daredevil streak, according to friends, some of whom have watched his global exploits with alarm. Calling himself an “explorer” who has been to 99 countries, he travels widely to surf and kite-board or chase tornadoes and thunderstorms. In 2008, he raced a Tesla Roadster in the Gumball 3000, a 3,000-mile road race with varying global routes. He has recently taken an interest in yacht racing, competing in competitions around the world in his Gunboat 68 Tosca. He has learned free diving in Fiji and trained to be a chef for three months in Paris, according to social media posts that are now private.
Yet, Mr. Howery’s public persona has largely been defined by his tight relationship to the world’s richest man. People who want to get notes or even packages to Mr. Musk have been told to send them to Mr. Howery first, Mr. Howery has told associates. Job-seekers have sent their résumés to Mr. Howery for delivery to Mr. Musk.
And Mr. Musk has often slept at Mr. Howery’s home in Austin in recent years, although Mr. Howery has told others that he does so less than he used to.
Mr. Howery has been there as Mr. Musk’s wealth and interests grew. He advised Mr. Musk on the purchase of Twitter, and invested personally in Mr. Musk’s other new businesses, including Neuralink and xAI.
But unlike some other friends of Mr. Musk, he does not flaunt his relationship: “I’m friends with Elon. I really don’t like to comment on my personal friendships in a public forum,” he told a Swedish interviewer in 2019. “But obviously an amazing person. Very inspirational.”
He has joined Mr. Musk in growing more and more political during the Trump era; he attended the Republican National Convention as part of a contingent of tech leaders who party-hopped at times with Donald Trump Jr. Mr. Howery is a member of the Rockbridge Network, an ascendant group of Republican donors, many with Silicon Valley ties.
This September, he co-hosted JD Vance, Mr. Trump’s vice-presidential pick, for a fund-raising dinner in Austin.
When Mr. Musk decided to start a super PAC last spring, he asked other donors to pitch in first to help him to hide his involvement for as long as possible. In June 2024, Mr. Howery made some of the very first contributions, making four separate $250,000 contributions to cover the super PAC’s initial costs.
“He went out of his way to donate and be helpful when I was helping to raise money for President Trump at the start of Elon’s America PAC,” recalled Joe Lonsdale, a friend and fellow Republican donor.
After Mr. Trump’s victory, both Mr. Musk and Mr. Howery have reaped rewards. Mr. Howery has been a reliable presence at Mar-a-Lago since election night, and he accompanied Mr. Trump and Mr. Musk to the recent SpaceX launch in Boca Chica, Texas.
After his abbreviated tenure in Sweden, Mr. Howery began to strategize with friends about angling for a European encore. He bandied about several countries and ended up on one with half the population as his last Scandinavian one.
But he told friends that he was specifically enticed by Denmark in part because of the possible Greenland acquisition. The challenge of working on one of the most complicated real-estate transactions on behalf of a real-estate mogul is one that could bring Mr. Howery the sort of attention he prefers.
After all, even as Mr. Howery keeps a low profile, he has, in private conversations over the years, mused about running for office some day, possibly in his home state of Texas.