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Chronicles

The story behind the story

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A look at Jack Dorsey's Square, whose success in recent quarters and steadily rising stock price means it could soon pass Twitter in value

Twitter may be President Trump's favorite platform, but Square, a payments company also run by Jack Dorsey, has had more success in recent quarters. Tweets: @katiebaynes , @puiwingtam , and @mdudas Tweets: Katie / @katiebaynes : The comparison to Twitter is click-bait, but the meat of this story reveals a lot more about Square than “payments” https://www.nytimes.com/... Pui-Wing Tam / @puiwingtam : .@jack is known for Twitter. But his other co, Square, is about to pass Twitter in value, reports @nathanielpopper http://www.nytimes.com/... Mike Dudas / @mdudas : Square is an incredible company http://www.nytimes.com/...

New York Times Nathaniel Popper

Context & Ripple Effects

Square's approach to this crossover point has been building since its 2015 listing: the company filed for its NYSE debut disclosing a $560.6M first-half revenue against a $77.6M loss, then closed its first day up 45% at $13.07 per share — an early signal that public investors saw more than a payments terminal. The through-line since has been Dorsey's push to use transaction data to minimize lending risk and widen margins, turning Square from a hardware vendor into a financial-services business.

The market-value comparison with Twitter is the headline hook, but the deeper story is that both companies answer to the same CEO — and the coverage of how Dorsey evolved as a leader at Square before returning to save Twitter makes the divergence a referendum on where his attention and methods pay off.

First-order effects

  • Public-market investors are repricing Square as a data-driven financial services company rather than a card-reader maker, validating the margin strategy Dorsey laid out in 2015.
  • Twitter, running on the same dual-CEO structure, faces renewed investor scrutiny over why the company Dorsey built second is overtaking the one he returned to lead.

Second-order effects

  • A Square valuation above Twitter's would sharpen pressure on Twitter's board and shareholders to justify the platform's standalone economics, with activist interest a plausible next step.
  • Competing payments and small-business lenders must now compete against a rival whose underwriting data advantage compounds with every transaction, pushing them toward their own lending-and-software bundles.

Third-order effects

  • If the pattern holds, it marks a structural inversion of the 2010s hierarchy: infrastructure businesses monetizing payment flows outvaluing advertising-dependent social platforms, even when the platform carries the political and cultural prominence.
  • The divergence also tests the dual-CEO model itself — later reporting that Dorsey delegates or delays major decisions at both companies suggests the structure survives only while the weaker asset stays cheap enough to ignore.

The trend: Payment-infrastructure companies built on transaction data are steadily outgrowing the consumer social platforms they once played sidekick to, and Square passing Twitter would be the clearest marker yet.