PayPal — What I Think
PayPal won the war it was fighting and lost the one it wasn’t paying attention to.
The original insight was perfect, and people forget how radical it was. Email is an address, and an address is all you need to move money. In 1999, the idea that you could pay a stranger by typing their email, no shared bank, no account numbers, no waiting, was as strange as airdropping a file across a room. PayPal turned the identifier you already had into a payment rail. That’s the whole trick. Every Venmo, every UPI handle, every wallet-to-wallet flow since is a child of that one move: collapse the payment credential into the identity.
Then eBay needed trust between strangers, PayPal supplied it, and PayPal became the settlement layer for the first real marketplace economy. That’s not luck. Same instinct that made it work in the first place. Find the place where two strangers need to transact and there’s no trusted middleman, and become the middleman.
What they got wrong: they stopped being early. PayPal had the wallet, the graph, the two-sided trust, the brand. Every primitive you’d need to own the consumer financial super-app, a decade before “super-app” was a word. WeChat built it. Nubank built a version. PayPal had the parts laid out on the table and assembled a checkout button. The button is excellent. But you can feel the company that optimized the conversion funnel instead of imagining what a billion people with a money-identity could actually do.
The deeper miss is structural. PayPal’s whole nature is to be a friendly skin over the existing banking system, a nice layer over ACH and cards. That made it safe and made it work. It also means PayPal never owned settlement. It rents. When stablecoins arrived it moved, and PYUSD is a correct instinct, but it moved as a follower into a space it should have defined. The company that taught the world money could travel by identifier should have been the company that made money travel without banks at all.
It saw the door. It built a turnstile next to it.
Favorite & worst CEO
Favorite: Dan Schulman. He inherited a spun-off payments processor and reframed it around a real thesis, democratizing access to financial services, then actually expanded the surface area to chase it, P2P, Venmo, credit, crypto. Not every bet paid. But he led with a direction, and he made PayPal stand for more than a checkout button.
Least connected to: I’ll keep this about era, not the person. The years where PayPal optimized itself into the “branded checkout button” identity, where the ambition shrank to winning the click instead of reimagining the wallet. Tactically sharp, strategically small.
Part of “What I Think About the Top 50 Fintech Companies of All Time.” I’m Prajjwal Chittori. prajjwalchittori.com.