Two years ago, just after Stripe’s valuation had rocketed to $95 billion, Collison bought a stake in a forlorn airport outside of Dublin, a facility mostly used for pilot training that he hopes will become a hub for short-hop electric planes over the next decade. Collison, a veteran pilot, has also purchased his own twin-engine airplanes, which he has used to ferry Stripe executives around the country. Recently, he flew himself to Los Angeles from the San Francisco Bay Area to interview 99-year-old investing icon Charlie Munger. Stripe’s own publishing arm plans to release a collection of Munger’s business yarns called "Poor Charlie’s Almanack" this November.

Both Collison brothers help underwrite a private summit of techno-optimists in remote Sea Ranch, Calif., called "frontier camp." Every summer the conversations focuses on futurist topics like supersonic aviation, nuclear energy, charter cities and boosting birth rates, according to three people who have been invited. Attendees at this month's camp include "Snow Crash" author Neal Stephenson, former Tesla and OpenAI executive Andrej Karpathy, and Nobel Prize–winning economist Paul Romer, according to one invitee.

John Collison has been able to finance some of these endeavors by cashing in small parts of his 12% ownership stake in Stripe over the years. (His older brother has a roughly similar stake.) The privately held company has allowed regular sales of shares for employees and outside investors, which the founders could also utilize, people familiar with the matter said. Collison’s stake in the company now sits at about $6 billion at the firm’s most recent $50 billion valuation. That sets him up for decades of discovering new passions. "Everything I’ve seen him do has had a very long-term focus to it," said Kinsella, who runs a computer science program at University of Limerick that Collison helps fund and organize. "He’s not a creature of a passing whim."

The Abbey Leix estate in County Laois, Ireland, which John Collison bought for more than $15 million in 2021.

This year, Collison’s most prized and lucrative investment—the internet payments company he helped build when he was still a teenager—has required more urgent attention. In early February, he took over temporarily as Stripe’s chief financial officer just as the company faced pressing questions over its need for cash. It was an unusual move for the heady, technical founder—and an especially challenging one coming amid a sinking valuation and a downturn in profits, all while employee stock grants faced expiration. Stripe’s internal problems spilled into public view with the layoffs of 14% of employees in November, a rare, humbling moment for the Collisons, who had reached almost mythical status in Silicon Valley and near-cultlike popularity inside Stripe.

As expressed in interviews with more than two dozen friends, current and former employees, and investors, John Collison’s new responsibilities atop Stripe will etch his legacy—for better or worse—as a business leader. He has been leading Stripe’s marketing and sales for more than a decade but remains several years junior to other millennial tech titans, like OpenAI’s Sam Altman, Airbnb’s Brian Chesky and Coinbase’s Brian Armstrong. "He’s still so young," said one Stripe investor who is close to Collison. "This is the first time he’s really diving in deep." (Through their representatives at Stripe, both Collison brothers declined interview requests for this story.)

Collison has been able to notch some big wins in his expanded role. He largely succeeded as Stripe’s chief pitchman, raising $7 billion from investors across seven weeks in January, February and March, the largest single haul of cash ever for a U.S. private company. In interviews, three current Stripe investors were upbeat about the company’s progress so far in turning profitable again. They attribute much of that success to Collison himself, who also led a cost-management effort requiring his sign-off on significant hiring increases. The role could mark an evolution of sorts for Collison—from a young executive who struggled to give direct feedback and could be too hands off, as former colleagues remember, to one who’s now comfortable delivering "brutal feedback," closely scrutinizing internal productivity measures and procurement contracts, and even comparing product teams to Navy SEALs.

Still, the new environment has dampened internal spirits compared to Stripe’s headier days. The rate of revenue growth in the first quarter this year was roughly flat, according to two people familiar with the company’s performance. Stripe recently lowered the salary ranges it offers some employees and has required staff to gain special permission to work remotely, according to a recently departed employee.

Collison, by most accounts, has recently trained nearly all of his focus on Stripe, although he still carves out time to pursue his outside interests. Last month he attended the Paris Air Show, one of the aviation industry’s biggest trade shows, days before he and Patrick visited Stripe’s London office for important internal meetings. Days later, the company laid off a few dozen staff in its recruiting office as it reoriented hiring plans.

John Collison said in May at a San Francisco conference hosted by news organization Axios that he wasn’t spending all that much time at the Irish country manor he bought. "I’m mostly here these days," said Collison in his lightly lilting Irish accent. "Somehow Patrick and I are [suckers] for work."

Stripe co-founders Patrick and John Collison in 2018. Photo: David Paul Morris/Getty Images

In the early months of 2022, Collison spoke live on a video screen from Stripe’s Dublin office during the company’s well-attended weekly "fireside chats." He often mixed talk of company progress with outside intellectual interests, like drone-delivery logistics and California housing policy. At the time, his updates bristled with confidence: Stripe’s key net revenue metric had grown 57% from the year prior, to $2.6 billion. The company was awash in cash. Three out of five tech firms that had gone public the year before used Stripe’s software to process payments—meaning each of their transactions transferred a tiny chunk of revenue back to the company.

Still, some employees worried about the broader state of the global economy and their job security. Interest rates were rising, triggering talk of a possible recession. One week, the Collisons presented research that suggested a more uncertain picture about the economy, according to two people present. But the Stripe founders’ actions until the middle of 2022 indicated they were confident about the good times enduring. Headcount had doubled between 2021 and 2022, from roughly 4,000 to 8,000 workers. The company had grown revenue about 33 times over between 2015 and 2022, expanded onto almost every continent and launched a cavalcade of new software products.

But by the middle of last year, Stripe’s internal systems were buckling under the strain. Managers harped on the company’s "watermelon problem," the Information previously reported. This was Stripe shorthand for processes that looked on track (green) to outside observers, but were clearly heading off the rails (red) from the perspective of insiders. The company was struggling to finish some new projects because employees had failed to report bad news up the chain.

The company had been dealing with another situation, an ironic one for one of the world’s most lauded financial technology companies: Its finance department was struggling with its own systems. John Collison had recruited the company’s finance chief, Dhivya Suryadevara, to join Stripe a couple years earlier. She came from a corporate behemoth—General Motors—fanning speculation that she was hired to help take Stripe public. But Suryadevara had a thornier, more fundamental job than that—getting the company’s internal systems ready for regular financial reporting.

The finance team’s track record was mixed under her tenure, according to several former employees and investors. The company improved its ability to close its books in a timely fashion. But employees in the division complained that accurately forecasting the nonpayments business and measuring the profit margins of different product lines remained difficult. Meanwhile, Stripe was missing some of its financial goals. Last January, it announced that Suryadevara was leaving the company for family reasons.

Investors also were grumbling about how much Stripe was spending on employees as it grew, sending it into the red while bets on new business lines pulled in relatively little revenue. The high spending put Stripe in a poor light compared to competitors, like Dutch payments company Adyen, which kept a leaner workforce for what was essentially the same payments business model. One Stripe investor passed around an internal presentation that showed how the payments company was spending 5 or 6 times more per employee than Adyen. Another Stripe investor complained the company hadn’t yet found a hit product outside its core payments business. Stripe’s revenue from everything other than payments—including a suite of software products that helped other companies bill their customers and set up recurring payments—was just about 9% of the total, according to a presentation later made to investors.

John Collison had seemed aware of this potential problem as early as 2020. "What’s probably painful for a lot of technology founders is their eyes are bigger than their bellies," he said on the "Invest Like the Best" podcast in June of that year. "There’s a huge number of enticing investment areas, and more than they have resources to actually be able to go after."

But even that foreboding couldn’t stop the Collisons from falling victim to an overabundance of optimism—one shared by many tech leaders during the past decade of zero interest rates. Last November, the company finally bowed to new realities, laying off more than 1,000 employees, with John and Patrick appearing on the fateful Zoom call together. Decent severance packages—14 weeks of pay—helped soften the blow for fired workers. But some employees winced when they learned that John Collison had been staying at a five-star hotel in Singapore just before the layoffs occurred, a former employee said. (He pays for his own travel, a Stripe spokesperson said.)

Stripe’s year of missteps echoed similar mistakes made by other revered tech companies during and after the pandemic. "Everyone thought Covid trends would keep going up and to the right," said James Dyett, a former Stripe sales executive who occasionally went on long runs around San Francisco with Collison. "It was a moment that if John and Patrick had been contrarian, they would’ve cemented themselves as the best founding team ever," said Dyett, who left the company for OpenAI in February. "But they took the same approach as all their peers around here."

As the company faltered last year, grumbles about the Collisons’ decision-making and management style began to spread inside the company.

One complaint was that they struggled at times to fold new executives into the company’s unique, Collison-driven culture. For years, the company had seen a revolving door of marketing, sales and now finance leaders. One Stripe investor compared the phenomenon to "organ rejection" by the brothers. As founders, the two men are the company’s unquestioned leaders, with other longtime executives like product head Will Gaybrick and former chief operating officer Claire Hughes Johnson holding significant sway. The Collisons, however, are the only executives on the company’s board, which includes outside tech executives, investors and a former governor of the Bank of England.

John Collison’s move into the top finance seat was an extension of his existing roles. For years, investors spoke of the Collisons as an inseparable unit. Both had a coding background, including developing early iPhone apps back when they were teenagers living in the "middle of nowhere, Ireland," as John put it. (Their father was an electric engineer who ran a remote lakeside hotel near Limerick.) The two brothers wrote the first lines of code for Stripe in the fall of 2009, when both were in college in the U.S.—John at Harvard University, Patrick at the Massachusetts Institute of Technology.

When they dropped out and moved to San Francisco in 2010 to start Stripe, their different duties took shape. Patrick concentrated on software development and other technical areas; John focused more on sales, marketing and public relations, even running Stripe’s Twitter account for a time. Investors and employees saw the brothers’ strengths as synergistic. In the company’s earliest days, Silicon Valley’s top financiers—Sequoia Capital, Peter Thiel, Elon Musk, Andreessen Horowitz—poured in money.

Inside Stripe, other differences between the two brothers became more apparent. One former employee, who at one point had a desk near Patrick Collison’s in the open floor plan of the Stripe office, said the older Collison’s face often wore a "a tick of intensity that I’ve not seen from anyone else I ever worked for ever." John, on the other hand, "has always seemed more at ease, more comfortable, sociable, vastly easier for him to strike a conversation with a random person."

Unlike a lot of other tech founders, John was funny and steeped in pop culture. On a 2020 podcast, he once compared Stripe’s board members to "different Pokémon with different strengths and weaknesses." The younger Collison took on priorities that required a more collaborative touch, especially enterprise sales, which required him to hobnob with executives at other firms. He took over the company’s overseas expansion, frequently traveling to London, Dublin, the Middle East and Asia. He started penning the company’s annual letter, in the style of Warren Buffett’s annual Berkshire Hathaway shareholder treatise. "Fundamentally, John is the voice of Stripe to the market," said Dyett, the former Stripe sales employee. "It’s John’s voice."

John Collison also effused interest in different aspects of investing. One former employee remembered seeing Collison with stacks of other companies’ corporate finance documents printed out on his desk in Stripe’s former South of Market office in San Francisco. He planned to read them over the holidays. "It’s Christmas!" Collison said. He occasionally tweets recommendations for books about corporate accounting shenanigans and investing strategies.

"You have to imagine a 21-year-old…who was extremely fascinated by Larry Ellison," said longtime friend Aaron Levie, CEO of software firm Box and an early investor in Stripe. "Not normal 21-year-old interests."

As Stripe moved into a crucial 2023, Collison would need to orchestrate a real-life turnaround, presumably using strategies he’d picked up in his corporate studies.

First came an exercise that Stripe, an investor darling, had never really had to do—pitch itself, hard, to outside investors from around the world. The company needed several billion dollars to cover tax withholding payments so it could allow nearly 10,000 current and former employees to sell their privately held stock grants, without forcing the firm to go public. For the first time, global investors rummaged through the financial information in Stripe’s private data rooms and Excel files, debating what they saw: Would the Collisons’ company really turn out to be a resounding, long-term success? Or would Stripe eventually fade?

John Collison played the lead pitchman. In a meeting in January with Stripe’s fundraising team, along with bankers from Goldman Sachs, Collison made light of the company’s plight. "It’s the perfect time to do this," he said jokingly of the fundraise. "We have no Ebitda in a market that only cares about Ebitda."

Over dozens of meetings in New York and San Francisco Bay Area conference rooms, Collison walked prominent investors through financial models that argued the firm’s struggles were a blip—forecasting that growth would accelerate again and profit margins would expand. The promises seemed too optimistic to one investor, who saw the fundraising deck and didn’t do the deal. But he ticked off the reasons it tempted him. For one, the company could grow its profit margins fairly easily in the coming years. Plus, he said, there was the "halo of the Collison brothers."

Stripe had already assured some level of success in the funding round, with influential existing investor Thrive Capital committing nearly $2 billion. Goldman Sachs, whose investment bankers ran the fundraising process, also invested its own capital. But some of the company’s prospective new investors balked at a valuation of $55 billion. Collison made the call over a weekend in February to offer them a lower price. Though the move nearly halved the firm’s value from two years earlier, it nonetheless clinched the largest private funding round in U.S. startup history. Stripe ended up with $7 billion, at a $50 billion valuation, with the fresh capital used to buy employee stock and front the taxes associated with the sales. ("Just in time for St. Patrick’s Day," Collison tweeted in March.)

The process won Collison some new fans inside the company and rewarded the faith of old ones. In May, employees were able to cash out as much of their stakes as they wanted, albeit at a much lower price than they had previously thought those stakes were worth. Others held on to most of their shares, hoping the value would rise in the coming year. "Moment-in-time prices are just that," the Collisons wrote to former employees after the fundraising. "The better test will be what we’re worth in 2030 (and 2040), and, on that front, we’ve never felt better."

The fundraising success kept a door open for Stripe to stay private for years to come, helping the Collisons continue tinkering with their company away from the sometimes unflattering gaze of the public markets. John Collison had gone out of his way to declare that an initial public offering wasn’t a foregone conclusion. An Irish journalist asked him in 2021 whether it was inevitable the company would go public. "No," he replied bluntly. The stance befitted what friends and colleagues say is the Collisons’ preferred mode—to maintain "optionality."

But in meetings with investors this year, Collison privately made a commitment that he is reluctant to issue publicly: He said Stripe would someday go public, according to a person in the meetings. It would likely be through a direct listing, Stripe and its bankers told investors, meaning the company wouldn’t sell new shares in an offering, instead allowing existing shareholders to sell immediately. They didn’t put a date on a potential listing. Still, the point is a contentious one: A Stripe spokesperson disputed that Collison ever made such a statement.

In the meantime, Collison will have to help Stripe polish its finances. One investor said his firm gained confidence that the company would improve its bottom line because Collison himself would be personally approving any significant staff additions. In models shared with investors, Stripe also forecasted it would kick-start revenue growth above 40% in 2024, compared to growth that stood at 23% last year. Meanwhile, it planned to grow its number of employees by 12% at most through 2024, meaning it would likely add fewer than 1,000 people.

Investors seem bullish about the results so far. The company is now regularly reporting financial updates to a wide range of investors for the first time, with John Collison presenting to the board of directors about progress. And they’re mostly upbeat about what they are once again seeing—profits. The company told investors earlier this year it expected to generate about $100 million in Ebitda (earnings before interest, taxes, depreciation and amortization) this year, pushing the company back into the black, at least by that metric.

"Seeing him operate as an interim CFO and doing what he has done to make the business profitable almost immediately, that is just unbelievable," said Josh Kushner, founder of Thrive Capital, an early Stripe investor.

John Collison’s track record has put him in unusual company—a prominent Silicon Valley leader who has avoided "becoming a pantomime villain," as one Irish journalist wrote last year. The national press also picked up an almost comically heartwarming story about Collison earlier this year: He had adopted more than 40 abandoned horses to live on the grounds of his estate.

Irish manors and jet strips aside, Collison comes off as a "quite a regular guy," said Tom Lyons, chief executive of The Currency, an Irish business publication, who has met Collison twice. Lyons has talked to Dublin locals who have spotted Collison at pubs and pizzerias. "He’s not somebody known for being on the party circuit or out in nightclubs," he said. "You wouldn’t see people come up and say hello to him like if you see Bono."

Collison posing with U2 frontman Bono during the Dalkey Book Festival in 2022. Photo: Instagram

He’s also part of a quiet Silicon Valley power center. He recently proposed to his longtime girlfriend, Laura Behrens Wu, who founded and built her own highly valued startup, Shippo, which makes software enabling e-commerce businesses to reduce shipping costs. The two share a cat in their home in San Francisco. (Patrick Collison is an investor in Shippo, according to a company press release. Bessemer Venture Partners and other investors valued Shippo at about $1 billion in 2021.) Some of their closest tech friends, including GitHub founder Nat Friedman and former Y Combinator partner Daniel Gross, are on the front lines of artificial intelligence startup investing.

More broadly, John Collison's interests are expansive. "I’ll just call it ‘human progress,’" said his friend Blake Scholl, founder and CEO of aviation startup Boom Technology, which is making supersonic jets and counts Collison as an investor. Publicly, Collison and his brother have funded nonprofits focused on studying an emerging intellectual field on how to reignite human progress. "He looks at fields outside of tech and sees we’re not moving at the same pace," Scholl said.

Another close friend said Collison’s heart is still in Ireland. He has spent more time there in recent years than Patrick, who has taken more to California. Kinsella, the Irish economist, said he and Collison have spent hours talking philosophy, Dublin housing policy and the future of Ireland’s music scene. He thinks that, at least relatively speaking, Collison has remained humble in his pursuits. "The thought experiment I’d put is: Faced with great wealth, you have to make choices about allocation," Kinsella said. "It seems to me that, roughly speaking, he’s gotten it right."