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But the ambitious new venture comes with an inherent tension. To protect Page, Osborne has long remained hidden, the man behind the megabillionaire’s curtain. But unlike Koop, Way2B1 is a for-profit business that needs to attract clients and make money. “Wayne advertises for Way2B1 by talking about it with everyone he talks to in the course of his work with Koop,” a former employee says. “They’re highly overlapping jobs.” As Osborne has taken on the role of salesman, venturing into the world to promote his enterprise, he has confronted an uncomfortable dilemma: How do you safeguard the privacy of one of the world’s richest men while hawking the secrets to his success?
To run their family offices, most tech titans rely on former wealth managers and business-school alumni. Sergey Brin, who cofounded Google with Page, employs George Pavlov, a former venture capitalist. Mark Zuckerberg leans on Iconiq Capital, a financial-services firm. Jeff Bezos looks to Melinda Lewison, a Harvard Business School grad and former financial analyst.
Osborne started his career not in finance but in faith. Born in Mississippi, he graduated from Princeton Theological Seminary with a master’s degree in divinity. But Osborne, who identified as gay, soon found himself ostracized by his own church. In 1997, three years after he was ordained as a Presbyterian elder, the church tightened its rules blocking gays and lesbians from serving as elders, ministers, and deacons. When two church members objected to Osborne serving on the governing body of his Connecticut church, the case went to an ecclesiastical court. After a high-profile battle, Osborne won.
His victory reverberated through Presbyterian congregations — and his refusal to answer questions from church leaders about his sexual activity with his partner garnered national headlines. “That is not an appropriate question,” he explained to reporters, adding that it was something “even my best friends don’t ask me.”
The experience gave Osborne a taste of what it feels like to have your private affairs thrust into the national spotlight. And his industry peers say the ministry, with its emphasis on service to others, is not unlike the role of a family officer. “You could say it’s almost an ideal background,” says Natasha Pearl, the CEO of Aston Pearl, a consulting firm that works with family offices.
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In keeping with their mission, most of Koop’s staffers are vague about their work histories on their résumés and LinkedIn pages. Before joining the family office, they’re required to sign nondisclosure agreements, and background checks can be repeated annually. One person Osborne has leaned on for protecting Koop’s security, according to two people familiar with the process, is Michael Floyd, a former CIA officer and an author of “Spy the Lie,” a training manual for spotting deception. Floyd, says someone who knows him, is Osborne’s “human lie detector,” using his expertise in espionage to identify anything that could threaten the privacy and sanctity of PageWorld. Sometimes, as Osborne explained on the Minerva podcast, “your weakest link is from within.”
Befitting its billionaire tech-founder boss, Koop has an impressive fleet of engineers working on the Page family’s enterprises, assets, and philanthropic interests. Under Osborne’s supervision, Koop collaborated with Composite Energy Technologies to build an electro-foiling catamaran, a 37-foot vessel designed to glide over the water at impressive speeds with little human control and, in time, zero emissions. (A person familiar with the project says the catamaran belongs to Page.) Koop also formed an LLC for Oceankind, the marine-conservation charity run by Page’s wife, Lucy Southworth, making it difficult to track the millions of dollars flowing through it.
Within the insular world of family offices, Koop has a reputation as a well-run enterprise that’s not allergic to a little fun. According to one person who attended a particularly memorable Mardi Gras-themed party for Koop employees and trusted industry friends held at Nola, a Creole restaurant in Palo Alto, a live alligator hung out on the bar. (A representative for Osborne denied this happened.) Osborne himself is seen as charismatic, friendly, and a sharp dresser. “Always good shoes, good jeans, good jackets,” someone who has worked with him says. “He takes care of himself really well, too.”
Osborne can also be oddly finicky, those who know him say, insisting on things being just the way he wants them. One person who dined out with Osborne recalls watching him recoil when his dish arrived. Apparently displeased with the chef’s architectural plating concept, he sent the dish back and ordered that the food be laid out flat on his plate.
Page did not respond to a request for comment for this story, and Osborne issued a short statement. “It is clear that Business Insider’s goal is to create a sensationalized, misleading article that falls short of responsible journalism,” it reads. “Anyone familiar with the individuals mentioned in your article will recognize how inaccurate your story is.”
As befitting his role at Koop, Osborne’s public profile is limited — one of the few public photos of him is the headshot on Way2B1’s website. But he reveals bits of himself on his personal Tumblr. One tab contains a humorous “presidential platform in progress,” with ideas ranging from the sweet (“The elderly will be interviewed, their thoughts and wisdom recorded for posterity”) to the silly (“Every citizen will receive a free margarita (frozen or on the rocks) after more than 8 hours of work”) to the impossible (“All days will have 12 hours of sunshine”). In another list, called “My 55 Ways to be Satisfied,” Osborne starts with “have good morning workouts” before proceeding through “write poetry, draw objects, paint canvas, and read a good book” (No. 10), “have a good bedtime tea every night” (No. 19), and “vote in every election” (No. 51).
“Everyone wants to connect with Wayne because he’s connected to Larry.”
The idea for Way2B1 is rooted in the tech-forward approach Osborne brought to his role at Koop. When he took over Page’s family office, he was bothered by the fact that there was no tech platform designed to manage the increasingly complex lives of wealthy families. So he told his employers — presumably Page and Southworth, though he avoids mentioning them — about a concept he had raised with Mortimer Zuckerman: “What if, with one username and password, you could access your whole world?”
In 2015, Osborne proposed developing the tech on his own. “I’d like to set up a company. I don’t want you investing,” he told the family. “What you’ll get out of this is you’ll get the most advanced family office in the world.” His employers told him to go for it. They were, he said, “very supportive.”
As Osborne tells it, he had been developing the Way2B1 software for about a year when his employers suggested it was time to talk. “I got a little nervous, to be honest,” he told the Minerva podcast. But in fact, the family was thrilled. “It’s changed our life,” they told him. “It’s given us peace of mind. Will you let us invest?”
The central insight behind Way2B1 is that the secrecy inherent in family offices and the insularity of their small teams have actually put the wealthy at a disadvantage. “Every family is reinventing the wheel for themselves,” Osborne says. “A lot of families are making really big mistakes because they’re building this thing from scratch.” By downloading the industry’s best practices into a single platform, Osborne is following Big Tech’s playbook: Start by testing your idea in beta, then roll it out to a wider audience.
Way2B1, which Osborne calls “the new paradigm,” is essentially a fancy task-management system, designed to ensure investments are vetted, LLCs are set up, nannies are paid, and property repairs are done on time. The idea is that the family principals and family-office coordinators can see everything in one place, making it easier to approve purchases, green light investments, and ensure background checks are completed, all protected with what Way2B1 likes to boast is the same encryption services used by the US government. In some ways, Osborne sees Way2B1 as a means of helping other family offices build themselves in Koop’s image: “We think it’s important that families have privacy, that they keep their teams small.”
Though Koop and Way2B1 have seemingly been intertwined from the outset, Osborne has erected some internal walls. For starters, not everyone who works at Way2B1 knows that their CEO also runs one of the world’s most lucrative family offices. “Just being there isn’t enough to grant you access to those circles,” a former employee says. When Koop is mentioned at Way2B1, it’s referred to by its code name: Taurus.
Still, the connections between the two firms run deep. Osborne has hired former Koop employees for his side hustle, and he sometimes solicits feedback from Koop employees on Way2B1 products.
Despite its ties to — and investment from — one of the world’s richest men, Way2B1 remains lean, with fewer than 100 employees. And even though it’s been around for less than a decade, insiders say it’s already been through at least one round of layoffs.
Some Way2B1 employees resent what they see as Osborne’s unquestioning fealty to Page. “He thinks Larry has his money by divine right,” one says. They worry that for Osborne, Page will always come first, and Way2B1 a distant second. “Any chance he’d get,” another former employee recalls, “he’d brag about how much his Pixel phone was better than the iPhone.”
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Such tensions have forced Osborne to perform a delicate juggling act. Way2B1 isn’t the only game in town, and it’s competing with a host of other software systems being shopped around the world of family offices. Forbes keeps a running list of some of the best, and industry insiders mentioned Nines and Summitas as two favorites. That means Osborne needs to find a way to spread the word about his product, and how it builds on the expertise he has honed in Page’s service, without subjecting his boss to unwanted scrutiny.
But in public, the separation between Way2B1 and Page’s family fund has proved difficult to navigate. In June, Way2B1’s chief operating officer, Hal Bailey, a former director at Google, spoke at a conference touting Way2B1’s technology. To demonstrate its effectiveness, he pointed to how the software had helped one client navigate the complex web of global bureaucracy and donate supplies to a cluster of islands at the height of the COVID pandemic. To anyone paying attention, it appeared to be a reference to donations Page made in July 2021, soon after his purchase of a Fijian island.
It was a strange thing for Way2B1 to brag about, given the controversy sparked by Page’s donation. After Fijian broadcasters revealed that Page was behind the supplies, Fijian health authorities ordered them to take down the story. The censorship, first reported by Business Insider, unleashed a wave of bad press for Fiji, which had allowed billionaires like Page to slip past its closed borders on superyachts and private jets. A month later, the government of New Zealand was forced to admit that Page’s 12-year-old son had been evacuated from Fiji and brought to New Zealand for medical treatment even as its own citizens were barred from returning home.
For Way2B1 to let slip a story about Page’s generosity wasn’t necessarily the worst thing in the world. And it’s possible the anecdote was shared with Page’s blessing. But whether Page likes it or not, Osborne’s new venture is bringing fresh attention to his personal affairs. Through his investment in Way2B1, Page is seeking to make money by monetizing the techniques he uses to make money. And that, inevitably, is going to thrust him into the limelight he has spent so dearly to avoid.
Hugh Langley is a senior correspondent at Business Insider.