Standing on the elevated stage at the New York Stock Exchange, dressed in a pink button-down and three-piece suit, the flamboyant and media centric investor Chamath Palihapitiya smiled brightly as he rang the bell. It was 2017 and the first day of trading for Social Capital Hedosophia, the blank check company Palihapitiya launched with a little known British financier named Ian Osborne.
Far to Palihapitiya's right, hardly standing out against the American flag situated behind him, the tall, blonde Osborne clapped, his cherub cheeks flushing slightly as he scanned the crowd below. Later Osborne would be inexplicably cropped out of the photo sent out on Twitter.
An elusive power broker, Osborne does not like to be in the spotlight, though he's frequently at the center of the action. Social Capital Hedosophia (SCH) dazzled Wall Street with its first reverse merger with Virgin Galactic in 2019, igniting the current SPAC craze. This week, Osborne's half of SCH, Hedosophia, announced plans to go solo with a technology-focused SPAC of its own in Amsterdam.
Part connector, part fixer-for-hire, the 38-year-old Osborne is an unlikely lord of high finance and tech. His career didn't begin as a banking hotshot or a computing whiz, but as a teenage theater producer in London's West End.
Through means that aren't entirely clear to even some close acquaintances, he has finagled his way into the circuits and pocketbooks of the world's most rich and famous, earning favor by doing favors, and parlaying his impressive black book into a lucrative, and sometimes mysterious, career.
That career includes a variety of businesses from strategic communications to venture capital, and clients like Li Ka-Shing and Ronald Perelman. Extending from Silicon Valley to Downing Street, Osborne's network has allowed him to bring together billionaires like Alibaba's Jack Ma and Snap's Evan Spiegel, and to connect CEOs with politicians — all the while accumulating stakes in some of the hottest startups. His SPAC shares are now worth as much as $300 million, according to the Financial Times.
"How he got to the level he did, I don't know but it's an art," one longtime friend and business associate told Insider.
Insider spoke to more than 30 associates of Osborne from over the years to learn more about the enigmatic cofounder of the firm at the forefront of the "blank check" investment frenzy. Many declined to be named out of fear of compromising their business relationships.
Osborne declined to be interviewed for this story.
"As you will likely know from speaking to plenty of folks about me, I prefer to leave it to others to speak publicly," Osborne said in an email.
Rupert called to say "he was enjoying this"
True to his roots in the world of theater, Osborne knows the value of suspense and mystique.
He is often on the move between Hong Kong and London, and former colleagues said they never knew which country he would be in from one day to the next.
He's known for hosting dinners and parties around the world, including the 2013 "philanthropy nightcap"with laser-eyed taxidermy art at Davos alongside Sean Parker and Marc Benioff. He was the organizer of Uber's infamous Manhattan dinner party in 2014, where an executive suggested the embattled ride-share startup leak damaging personal information about critical journalists.
Osborne associates from over the years recall hearing stories about his time spent with rockstars, or flying between continents on so-and-so's private jet. While Osborne keeps a low profile in the public eye, his image has consistently benefitted from a halo of money and power that's occasionally perplexed observers.
Osborne was frequently described in the media as a Tory advisor when David Cameron was Britain's Prime Minister a decade ago. Yet two former Cameron aides insist that Osborne never had an official role in the administration and didn't work with Cameron directly. Cameron's office did not return a request for comment.
A startup founder that Insider spoke to recalled making room for Osborne in a round of financing, only for Osborne to never wire a check despite repeatedly saying it was on the way. One PR industry insider who has interacted with Osborne describes him less charitably as a "Talented Mr Ripley" in reference to the Matt Damon movie about a charming impostor.
His connection to media-billionaire-turned-mayor Michael Bloomberg is a prime example. One person Insider spoke to heard that Osborne got Bloomberg face time with the British royal family, and convinced his friends to drive Range Rovers to the meeting to give the impression that he was part of a large envoy. Someone else heard that Osborne dated one of Bloomberg's daughters.
Kevin Sheekey, a longtime Bloomberg LP executive and campaign manager, told the Financial Times a simpler story: Osborne first got involved with the billionaire after co-hosting a dinner in London.
Whatever the backstory, Osborne's connection to Bloomberg was instrumental when, soon after graduating college in the early aughts, Osborne moved to New York and launched a marketing firm. He became an outside consultant for Bloomberg, a source with direct knowledge of the matter told Insider, and was frequently around Bloomberg LP's office in New York, coordinating strategic meetings on Bloomberg's behalf and carrying out other tasks.
Thanks to relationships with in-the-know media industry types like journalist Michael Wolff and Andrew Ross Sorkin, Osborne added to his allure by passing along intelligence and gossip about other billionaires as it crossed his path.
"What you might not know — and what Michael Wolff told me yesterday to pass onto you," Osborne wrote at the beginning of a 2008 email to Kevin Sheekey, Bloomberg's right-hand man.
The email, which Insider obtained through the NYC Municipal Archives, explained that Rupert Murdoch had personally leaked an incendiary rumor to Newsweek that Bloomberg was considering buying the New York Times, and that Murdoch, then CEO of News Corp, was going to encourage his own publication to report it as well.
"Yesterday, Rupert called Michael [Wolff] to say he was enjoying this," Osborne wrote. "The fun & games continue!"
A career anchored by proximity to power and defining relationships
Osborne works for himself across three different firms: Osborne & Partners for strategic communications, Connaught for financial advisory, and Hedosophia for investments. Together, the companies "have acted for eight of the fifteen most valuable private companies in the technology sector," according to a 2017 public filing from SCH.
The son of a lawyer, Osborne was raised in an upper-middle class family near London, where he attended the exclusive St. Paul's School. He continued on to King's College, then the London School of Economics, where he now sponsors £180,000 in scholarships.
By all accounts, his wealth is self-made. One person close to his businesses estimated Osborne's personal net worth was, at minimum, in the tens of millions prior to SCH.
Sometimes his businesses work together: For each company that Osborne and Palihapitiya take public through a SPAC deal for example, Osborne's financial advisory firm Connaught also gets paid to work on the deal. Connaught stands to make more than $31 million once all of the blank check transactions have closed, financial disclosures show.
Osborne is an active investor, on behalf of himself and Hedosophia, with investments that include Alibaba's Ant Financial, British fintech company Transferwise, and the German fintech company N26, of which he reportedly owns 15%.
Though he runs his own businesses, his career has been anchored by defining relationships with Bloomberg, DST Global's Yuri Milner, Horizons Ventures' Li Ka-Shing, and Germany media mogul Hubert Burda, people close to him said.
A spokesperson for Burda said that while the pair have known each other for a while, they do not have a business relationship.
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His success has often come from making himself useful to important people.
"Your assistance and enthusiasm were invaluable," Boris Johnson, at the time the Mayor of London, wrote Osborne in 2009 following a visit to New York according to an email obtained by Insider through a public records request. The visit included a star-studded party at Michael Bloomberg's Upper East Side home, a former Johnson official told Insider.
A spokesperson for Johnson did not return a request for comment.
The favor appears to have paid off for Osborne, who could now count the future British prime minister as part of his global network. In 2014, emails show, Johnson accepted another invitation from Osborne to attend a networking dinner at Restaurant Gentinta in Davos, Switzerland during the World Economic Forum.
Proximity to the rich and powerful — or the mere suggestion of it — is a central theme that runs through Osborne's activities. At 19, as a college student, he broke into London's theater scene as a producer for "Jesus Hopped the 'A' Train." The play garnered global press coverage thanks to another one of its producers, Madonna.
He went on to produce multiple stage adaptations of works by British media personality Toby Young, including a salacious satire about Boris Johnson called "Who's the Daddy?"
"As a producer, Ian was a writer's dream: put up the money, never gave me a single note on the script and didn't try and cheat me out of any of the profits," Young told Insider in an email. "I wouldn't be surprised if he ends up buying a movie studio."
Yuri's best man
Osborne's entry into tech came through the Russian tycoon Yuri Milner, who started working with Osborne around the time that Milner invested in Facebook in 2009, a long-time business associate told Insider.
Milner, through his fund DST Global, took significant stakes in Facebook and Twitter, investing billions of dollars into US companies in just a couple of years. The Russian oligarch, himself a fish out of water in California, was impressed with what Osborne could do for his tech companies, so he made more introductions, the associate said.
Some techies were suspicious about Milner's money — and their suspicions were validated in 2017 when the Paradise Papers revealed that DST had surreptitiously invested hundreds of millions of dollars from Russian state-controlled financial institutions into tech companies — but if Osborne had any misgivings he didn't show it publicly. He received a partnership interest in its second fund in 2011, according to a DST spokesperson, and was even best man when Milner married his wife Julia at the couple's $100 million Los Altos Hills mansion, one person told Insider.
Milner's image improved around that time. Writing for Wired in 2011, the journalist Michael Wolff flew to Moscow to meet with Milner for a tour of his family home. The final piece was a definitive profile casting the Russian tycoon as an intellectually curious iconoclast disrupting "the tight-knit club of Valley venture capitalists."
Wolff, who describes himself as "close friends" with Osborne for more than 15 years, said the pair has worked together on "several media-related" projects, and that Osborne's company handled some aspects of public relations for Milner, including coordinating the logistics for his trip to Russia.
A spokesperson for DST Global said less than 3% of the $12.5 billion it's invested since 2009 came from Russian institutions (or less than $375 million) and that all Russian money was returned by 2013. Osborne said while he was aware of the Russian LPs, he did not deal with them.
Osborne's role at DST put him in the center of a tech scene that was heating up — he was often seen hanging out with CEOs in DST's portfolio like Spotify's Daniel Ek, Foursquare's Dennis Crowley and Twitter's Jack Dorsey, associates said.
But in 2012, Osborne stopped working with DST to form his own investment firm Hedosophia, taking many of his founder relationships with him.
A valuable person to know
As a tech columnist at the New York Times during those years, Nick Bilton had crossed paths with Osborne in California and at Davos, where Osborne hosted fancy chateau parties and paraded around with a rotating cast of young tech celebrities.
Bilton's relationship with Osborne became more complicated while he was working on a book called "Hatching Twitter" that was about the drama and feuding between the company's founders during its early days. A number of different parties took pains to try to discredit Bilton's reporting or get ahead of the book, Bilton recalled. Osborne, he said, was one of them.
"They were dispatched by Jack to try to stop the book," another person, who heard about the operation directly from Osborne's camp, told Insider, referring to Twitter cofounder Jack Dorsey.
Osborne even managed to get his hands on the book proposal, according to Bilton, who recalled a period of stress for himself and his publisher.
Osborne told Insider he did not seek out or obtain the book proposal or try stop the book, but instead forwarded along publicly available documents.
In the end, "Hatching Twitter" was published as planned in 2014.
Twitter declined to comment.
On other occasions, Osborne would make things happen that few people in the industry could pull off, further solidifying his reputation as the ultimate fixer.
One of those things was an introduction between Snapchat CEO Evan Spiegel and Alibaba CEO Jack Ma that might have never otherwise happened, according to a source familiar with the meeting, who said that Osborne convinced Ma to take a meeting with Spiegel at a time when Snapchat was known primarily as a sexting app.
Soon after, in 2015, Alibaba invested $200 million into Snapchat, valuing the company at $15 billion.
To Osborne's camp, this was a networking success story, though Snap credits its former executive Imran Khan, who worked as a banker on the Alibaba IPO, with winning that funding.
It's not clear whether Osborne did much for Snapchat in the years after that introduction, aside from coordinating meetings for some executives in Europe. Yet Osborne was rewarded handsomely for his work.
When Snapchat went public in 2017, Osborne's financial advisory firm Connaught was listed as an underwriter alongside more traditional IPO banks like Morgan Stanley and Goldman Sachs. Connaught was allocated 307,692 shares, worth about $5.2 million at the IPO price of $17.
The SPAC boom's odd couple
About six months after Snapchat's IPO, Osborne and Chamath Palihapitiya made their big stock market debut.
Palihapitiya and Osborne first crossed paths a decade earlier, around the time that DST invested in Facebook, where Palihapitiya worked as an executive. They hung out socially, attending the White House Correspondents Dinner together in 2012 at the invitation of Michael Bloomberg, and grew closer when Osborne worked as a fixer for Li Ka-Shing's firm Horizons Ventures, an early limited partner in Social Capital.
People close to SCH describe it as a synergistic partnership. Palihapitiya is the carnival barker, driving retail investors to SCH through frequent TV appearances, and a bold Twitter presence which frequently promotes his portfolio, and occasionally courts controversy, like when he prematurely announced that he would run for governor of California. (He won't.)
Osborne avoids the spotlight, but lends the project credibility among institutional investors and Wall Street types.
The SPAC frenzy has also exposed him to new liabilities. Osborne and Palihapitiya are named as defendants in several shareholder lawsuits against Clover Health, following revelations that the company, which went public through a merger with SPH in January, was under investigation by the US Department of Justice over allegations of sales fraud.
The Securities and Exchange Commission also recently indicated it would increase scrutiny on blank-check companies, a regulatory move that could slow down SCH's push to get its remaining SPACs out the door and potentially even bring an end to the blank-check bonanza.
Osborne's next endeavor with Hedosophia, to raise a $558 million SPAC and take a European tech unicorn public, will test whether his reputation alone can keep investors buzzing.
Even if the SPAC music stops, Osborne can fall back to familiar territory.
His latest on-stage hit is "Everybody's Talking about Jamie," a musical about a 16-year-old boy who dreams of becoming a drag queen, and fights for his right to attend prom in a dress. By the end, Jamie wins admission to the event and befriends the school bully. The show closes with a heartwarming musical number called "Out of the darkness."
Out of the darkness
Into the spotlight
There is a new star
Shining so bright
The movie version is set to come out this year.
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