John Collison and I spent far too long looking at books.
Charles Dickens, Tom Wolfe, and Charlie Munger line the shelves in "The Library," a nook in Stripe’s San Francisco offices. Collison shares my love for Wolfe (he agrees that his best work transcends The Electric Kool-Aid Acid Test). We pick up books, thumb through them, talking like two obsessive readers who are making just a bit of a book stack-mess.
Stripe’s president and cofounder, Collison sits down with an 82-year-old Dickens compilation. I grasp an iridescent Stripe Press copy of M. Mitchell Waldrop’s The Dream Machine, a once-elusive volume about mid-century computer visionary J.C.R. Licklider. (Stripe Press is the company’s unexpected publishing arm.) As I raise the topic of my visit—Stripe Billing—I tell him I have a confession: I have a friend who’s a Stripe Billing user, and she’s given me a review to pass on to him. I take a beat to see how he reacts.
Collison pops back up, both (I think) as a small act of physical comedy and mild genuine nerves. He begins returning the books to their rightful spots, chuckling: "Just putting everything back on the shelf!" He visibly exhales when I tell him that she loves the product.
And my friend’s not alone. Lots of people have been using Stripe Billing, a product that grew out of customer requests and years of development at Stripe, a $70 billion financial infrastructure giant that’s become known for payments—but wants to be seen as more.
Stripe Billing, which came out in 2018, has been steadily growing for years. Now, for the first time, we’re starting to get some sense of just how big that part of Stripe’s business is: Stripe Billing has propelled the company’s Revenue and Finance Automation suite to the point where, at the end of January, the division surpassed $500 million in annual revenue run rate, the company told Fortune.
The AI boom especially sent Stripe Billing into superdrive, as companies like OpenAI, Anthropic, Perplexity, and others (all Billing customers) have needed the most nuanced pricing capabilities possible, said Collison.
"Look at the AI world, how fast-growing it is, how it monetizes, that it’s also incredibly competitive," he told Fortune. "If your pricing is wrong, you’re going to rapidly lose market share to someone who is pricing right."
It’s not just AI startups that need to be able to adapt, and large companies are also in the crosshairs, said Collison. And just because a company was once a pioneer, doesn’t mean it will always be. Collison believes in "the tyranny of being first"—that being an early adopter can morph into a long-term disadvantage, creating layers, mazes, and frictions that compound over time, creating terrible customer experiences—think: DMV, taxes, and, well, billing. Many companies that were early movers in software, he says, today find themselves stuck with the installed software of yore.
"It’s striking, where a startup will be working with Google Drive and Docs, whereas the very large, established companies have giant Excel docs," Collison told Fortune. "It’s a funny thing, where we think that large companies have all these advantages…But sometimes there can be an inverted curve, especially in matters of software."
I walked away from meeting Collison thinking about the relationship between the past and the future, and what it actually means to have a good idea that accounts for existing systems and those to come. At one point, Collison and I looked at the 1943 Dickens compilation and The Dream Machine, considering the two books side-by-side. He’s not entirely satisfied with Stripe Press’s The Dream Machine.
"We spend a lot of time at Stripe Press thinking about whether fonts are too big, or if the paper is kind of plasticky,” said Collison. "I’ve been thinking about Penguin paperbacks. If it’s old, it slightly yellows because bacteria actually eats the paper. So, maybe we should engineer changes to the character of the paper very slightly. I'm happy with the cover, but not fully happy with the paper, not yet."
Collison looks at books (and billing) with a new eye on something old—realistic about what no longer works, but with a discerning reverence for the best of the past.
In case you missed it…My colleagues Jessica Mathews and Sharon Goldman broke the news that AI safety researcher and philanthropist Holden Karnofksy has joined Anthropic. Karnofksy is married to the AI juggernaut’s cofounder and president, Daniela Amodei. Read more here.
See you Monday,
Allie Garfinkle
X: @agarfinks
Email: alexandra.garfinkle@fortune.com
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