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Stripe's $3.2B Cash Machine — and Why Sam Thinks It Screwed Up by Staying Private

From #159 — Did OpenAI Stage Its Own Cyber Incident? | Stripe Buying Paypal, Frontier Model Economics, Peptides · July 24, 2026 · 7:31 min · Jessica Lessin, Dave Morin, Brit Morin, Sam Lessin

Clip from the full recording, 41:13–48:44 · download mp4 · watch at this point on YouTube

Stripe's free cash flow surges 52% to $3.2 billion and it's teaming with Advent to chase PayPal, but Sam argues the company fumbled its shot at being a multi-trillion-dollar power player by never going public and building a currency to buy the pieces around it.

Jess brings the numbers: Stripe’s revenue was up 30% last year, with free cash flow surging 52% to $3.2 billion, and the company — still very much planning to stay private, per Dave’s read of its messaging — is now teaming with private-equity firm Advent on a takeover approach for PayPal, though nothing is close to done and other bidders will likely emerge. The group’s early theory for the growth: it’s simply riding the entire internet economy (and the AI-driven surge in spend flowing through cards), with Sam noting Stripe is effectively “the ultimate index bet on the whole internet” and that products like OpenRouter route payments through Stripe by default because it’s so easy to integrate.

Sam then pivots into his real argument, sourced from someone else’s take he found compelling: Stripe screwed up by never going public. Had it done so years ago like a normal company, it could have used a public currency to acquire aggressively — the way Meta bought WhatsApp — and become a genuinely trillion-dollar, generational financial powerhouse. Instead, at roughly $150 billion (a number the group visibly struggles to pin down, guessing anywhere from “a hundred and fifty” to comparing it to “ten percent of ChatGPT”), Stripe is stuck: a great, profitable company that’s been “sideways” at a hundred-billion-dollar-ish valuation for years while payments’ inherently low margins get compressed further at scale. Jess and Dave push back gently — maybe founders Patrick and John Collison simply don’t want to run a public company, and Stripe’s version of founder control (unlike Elon’s “max crazy”) is comparatively tame and defensible. Sam ultimately agrees that’s logical, but still sees an opening for Stripe to re-enter the growth story in a big way if it chooses to.

Key points

• Stripe: revenue up 30%, free cash flow up 52% to $3.2 billion; teaming with PE firm Advent on a still-uncertain takeover approach for PayPal.
• Dave: Stripe's own messaging suggests its plan is to never go public — though Jess doubts investors will accept that forever.
• Sam's core thesis: Stripe "screwed up" by not going public years ago, missing the chance to use a public currency to acquire aggressively (à la Meta/WhatsApp) and become a multi-trillion-dollar power.
• Group estimates Stripe's value around $150 billion — Brit notes that's roughly 10% of ChatGPT's valuation, and far below Visa's $665 billion (which has grown 40% in five years).
• Sam frames the issue as margin compression: payments is inherently low-margin, and Stripe's growth story hasn't "paced" with what it could have been.
• Jess/Dave counter that founders Patrick and John Collison may simply prefer total, low-drama control over a public company's spotlight — a legitimate, logical choice.
• Sam concedes the founders' choice is defensible but still sees a real opening for Stripe to re-enter the growth narrative aggressively.

Where they landed

Quotes

“They could have been a truly important, generational company because they could have used the currency to buy everyone — kind of like Meta's strategy buying WhatsApp with a public currency. Instead, because they didn't go public, they're far more hemmed in.”— Sam

“Visa is the biggest, and Visa's at 665 billion, and they've actually grown 40% in the last five years.”— Brit

“Stripe's version of 'I have total control' is like min-crazy, unlike Elon's max-crazy version. And that's completely fine for them — they're multi-billionaires, they do whatever they want.”— Sam

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