Rick Watson and Jessica Lesesky work through the reported talks, and Rick lands firmly on the skeptical side. Stripe grows around 34% a year by the hosts' count, throws off billions in cash flow, and has spent years buying up pieces of the stack, including Indie Hackers, Payable, Index, and Lemon Squeezy. It runs in stablecoins, crypto, and AI routing. The one thing missing is a consumer relationship, which is what PayPal and especially Venmo are supposed to supply. Jessica's counterpoint is that the PayPal button already lost that fight to Apple Pay and Google Pay, partly because she forgets her login half the time. Rick's objection is harder. PayPal has not grown since 2021, so this is a volume purchase rather than a growth one.

The Shopify piece is where merchants have something at stake. Shopify has put over $350 million into Stripe and accounts for roughly 13% of Stripe's volume, and it built Shop Pay while PayPal watched, which Rick calls one of the most criminal things to happen in payments in twenty five years and intends as a compliment. Shopify still routes partner payouts to app developers and integrators through PayPal. PayPal's European coverage reaches markets Stripe's does not. Every one of these companies is renting something from a competitor.

Jessica's read for merchants is the payments version of the argument she makes about sales channels. You take Shop Pay because at this point it is universal, and then you go looking for diversification everywhere else. What she leaves unanswered is how a brand holds onto a customer when the checkout, the wallet, and the payout rails all belong to somebody upstream.

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