JOHN COLLISON, the president of Stripe, had a very Silicon Valley problem.
The fintech company he had cofounded with his brother Patrick in 2010 was a juggernaut—a huge player in payment processing and financial software, and at one point the most valuable startup in America.
By the fall of 2022, however, Stripe was in a bind. Its sales had been rocketing upward at a 60% annual rate during the pandemic, leading Stripe to boost its spending—only to see its growth slow drastically as inflation rose. What’s more, many of the startup’s early employees would see their ownership shares in the company start to expire beginning in 2024. The founders wanted to make those employees whole, but buying their shares would cost a fortune: The tax bill alone would reportedly reach $3.5 billion.
Stripe needed to raise a lot of money, quickly. And with tech stocks plummeting as interest rates climbed, the timing couldn’t be worse: It was certain to be a dreaded “down round.” Stripe had raised money in 2021 at a $95 billion valuation; this time around, they’d be lucky to hit half that, and some investors would not want to re-up.
By September 2022, when John Collison went to The Weekend, an annual tech conference in Aspen, he could hear an ominously ticking clock in his head. But while there, he ran into a friendly face: Joshua Kushner, the founder of New York City–based boutique firm Thrive Capital. Thrive had invested in Stripe’s 2014 Series C round, and Collison found himself explaining his conundrum to Kushner, who listened with what turned out to be a lot more than polite interest.
Kushner, who’s now 38, had spent the previous decade building Thrive’s business. The firm did only a few large deals a year, and Kushner had built a reputation for supporting founders at splashy startups including Slack, Instagram, Instacart, and GitHub—staying loyal and lavishing them with attention even when they hit rocky stretches. “Josh is very much dancing to his own tune,” Collison says. “And venture is an industry where that is the opposite.”
Now he was considering going all in on Stripe. Back in New York, he and Thrive’s nine-person investment team kicked around the pros and cons, recalls Kareem Zaki, who leads the team alongside Kushner. Kushner saw the deal as a chance to boost his stake in the best of the new breed of retail payment “acquirers”—at a huge discount.
“We were very conscientious of the fact that it was a difficult moment,” Kushner tells Fortune. “But difficult moments are when you want to show up.”
On a Sunday evening early in 2023, Collison was in the car when he got a call from Kushner: Thrive was in for $1 billion. What followed was a two-week blur, as Kushner and his team worked the phones—and their frequent-flier miles—to round up financing.
Because of the size of the deal, Kushner needed to raise a “special purpose vehicle” (SPV), a one-deal-only fund that could include investors other than Thrive’s LPs. His team flew repeatedly from New York to San Francisco for breakfast meetings with Collison and potential investors. Kushner went to India—for one day—to raise money from Mukesh Ambani, India’s wealthiest man.
In all, Kushner’s team called on more than 100 different investors. When the funding round came together this March, Thrive invested $1.8 billion, $1 billion more than any other firm—and the largest check that Thrive had ever written—to assume a stake of about 7%.
Not long ago, Kushner would have seemed an unlikely person to be at the center of such a massive deal. Thrive, compared to famous industry names like Sequoia and Andreessen Horowitz, was relatively small and based on
