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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VENTURE DEALS
- Tines, a Dublin-based AI-powered workflow platform, raised $125 million in Series C funding, valuing the company at $1.125 billion. Growth Equity at Goldman Sachs Alternatives led the round and was joined by SoftBank Vision Fund 2 and Activant and existing investors Accel, Felicis, CrowdStrike Falcon Fund, and Addition.
- EnCharge AI, a Santa Clara, Calif.-based AI chip developer, raised $100 million in Series B funding. Tiger Global led the round and was joined by Maverick Capital, Samsung Ventures, IQT, and others.
- Newleos Therapeutics, a Boston-based neuropsychiatric therapies developer, raised $93.5 million in Series A funding. Goldman Sachs Alternatives led the round and was joined by Novo Holdings A/S, Longwood Fund, DCVC Bio, and Arkin Bio Capital.
- Antithesis, a Vienna, Va.-based autonomous software testing platform, raised $30 million in funding. Amplify Partners led the round and was joined by Spark Capital.
- Koala, a San Francisco-based tool for sales reps, raised $15 million in Series A funding. CRV led the round and was joined by HubSpot Ventures, Recall Capital, and Afore.
- Suger, a San Francisco-based cloud marketplace tools provider, raised $15 million in Series A funding. Threshold Ventures led the round and was joined by existing investors Craft Ventures, Intel Capital, and Y Combinator.
- Tofu, a San Francisco-based AI-powered B2B marketing platform, raised $12 million in Series A funding. SignalFire led the round and was joined by HubSpot Ventures, Tau Ventures, Correlation Ventures, existing investors Index Ventures, Stage 2 Capital, Liquid 2 Ventures, and others.
- CarbonZero.Eco, a Los Altos, Calif.-based biochar production technology developer, raised $3.5 million in seed funding from Rich Miner, Linda Tong, Sana Fathima, and others.
- Bluebook, a Stockholm-based accounting AI agents developer, raised $3 million in funding. EQT Ventures led the $2.5 million pre-seed round and was joined by angel investors. Y Combinator invested $500,000.
- Teneo Protocol, a Vienna-based social media data access provider, raised $3 million in seed funding. RockawayX and Borderless led the round and was joined by Generative Ventures and others.
PRIVATE EQUITY
- PSG invested $150 million in Uscreen, a North Bethesda, Md.-based video content monetization platform for creators.
- BGF acquired a minority stake in Paperchase Accountancy, a London-based hospitality financial management platform. Financial terms were not disclosed.
- Harlan Capital Partners acquired and recapitalized Immersive Gamebox, a London-based group game experiences provider. Financial terms were not disclosed.
- PT Solutions, a portfolio company of General Atlantic, acquired the physical and occupational therapy division of OrthoCarolina, a Charlotte-based orthopedic care provider. Financial terms were not disclosed.
- RF Investment Partners acquired S&K Building Services, an Indianapolis-based commercial building and window cleaning services provider. Financial terms were not disclosed.
OTHER
- HiBob acquired Mosaic, a San Diego-based financial planning and analysis platform. Financial terms were not disclosed.
- Holonym Foundation acquired Gitcoin Passport, which will relaunch as Human Passport, from Gitcoin, a Boulder-based decentralized autonomous organization, for $10 million in tokens and cash.
- LaunchDarkly acquired Houseware, a San Francisco-based warehouse product analytics solutions provider. Financial terms were not disclosed.
- Pittco Management acquired a minority stake in RepScrubs, a Sanford, Fla.-based healthcare vendor compliance solutions provider. Financial terms were not disclosed.
IPOS
- SailPoint, an Austin-based identity security solutions provider for enterprises, raised $1.4 billion in an offering of 60 million shares (4% secondary) priced at $23 on the Nasdaq. The company posted $824 million in revenue for the year ending Oct. 31, 2024. Thoma Bravo backs the company.
- Karman Holdings, a Huntington Beach, Calif.-based defense and space systems developer, raised $506 million in an offering of 23 million shares (63% secondary) priced at $22 on the NYSE. The company posted $331 million in revenue for the year ending Sept. 30, 2024. Trive Capital and Norman Carl Christensen back the company.
- Aardvark Therapeutics, a San Diego-based metabolic diseases therapies developer, raised $94 million in an offering of 5.9 million shares priced at $16 on the Nasdaq. Decheng Capital and Vickers Venture Partners, and Jane Wu Lee back the company.
PEOPLE
- Bessemer Venture Partners, a San Francisco-based venture capital firm, promoted Lance Co Ting Keh to venture partner.
- Lux Capital, a New York City-based venture capital firm, added Brett McGurk as a venture partner. Previously, he was deputy assistant to former President Joe Biden for national security affairs.
