20+ people, many who worked with Jack Dorsey at Square or Twitter, recall how he avoids decision-making, is a slower thinker, and sometime responds in riddles
“Jack is thinking about things at a different pace from the rest of us,” says Greg Kidd, who has known Jack Dorsey, now 42, since Dorsey was 19. Tweets: @bendwalsh , @_harshilshah , @hlplost , @dariasolo , @mylesudland , and @alexeheath Tweets: Ben Walsh / @bendwalsh : “He speaks in riddles... it was like listening to a fortune-cookie talk.” https://finance.yahoo.com/... Harshil Shah / @_harshilshah : “Jack's at a slower pace where he's noticing things that the rest of us don't notice,” he explains. “That's extremely valuable to society. It's like a Forrest Gump thing.” Incredible stuff https://twitter.com/... H.L.Plost / @hlplost : Dorsey: “So somebody puts something out there, somebody follows it,people follow the follower, and it just builds up. So that feedback loop, which is what's [now] happening at Twitter, was really an insight that he was already seeing with swarms of ants.” https://finance.yahoo.com/... @dariasolo : In which Jack Dorsey's “friends” speak in riddles about how @jack likes to speak in riddles. But it's not a bad thing #bigtech https://finance.yahoo.com/... Myles Udland / @mylesudland : Longtime Jack Dorsey friend tells Yahoo Finance that he thinks at the pace of ... *checks notes* ... Forrest Gump. https://finance.yahoo.com/... Alex Heath / @alexeheath : In this story, Jack Dorsey described as: - being like Forrest Gump by an early Twitter investor - “oracular” - “sphinx-like” - “like listening to a fortune-cookie talk” https://finance.yahoo.com/...
Context & Ripple Effects
This portrait lands mid-arc. Four years earlier, investor Chris Sacca was publicly campaigning for Dorsey to take Twitter's top job again (urging the board in a tweetstorm), and Re/code framed his Square tenure as the leadership training that would 'save' Twitter. The intervening years produced the 18-hour-days dual-CEO grind at Twitter and Square (documented by the Wall Street Journal).
What this Yahoo Finance reporting adds is the texture behind that schedule: more than 20 colleagues describing a leader who speaks in riddles and thinks at 'a different pace.' A year later, the same two companies' employees told the WSJ that this style had hardened into something structural — delegation and delay taken to extremes — which turns what reads here as temperament into an operating model.
First-order effects
- Twitter and Square staff absorb the direct cost: decisions that could be made by a conventional CEO are instead deferred, delegated, or left ambiguous, forcing lieutenants to interpret riddles into roadmaps.
- Dorsey himself faces the reputational bill — the piece reframes traits once marketed as visionary (the Forrest Gump framing from Greg Kidd and Harshil Shah) as a governance liability.
Second-order effects
- Investors like Sacca, who spent 2015 lobbying for Dorsey's return, are forced to reconcile that endorsement with a leadership record now described as avoidance — raising the bar of proof any future founder-return campaign must clear.
- Boards at founder-led companies get a cautionary data point: when the CEO's cadence becomes the company's cadence, succession planning stops being theoretical and becomes a live board agenda item.
Third-order effects
- If the pattern holds, it feeds the broader reassessment of founder-idolatry in tech governance — the idea that a singular founder vision compensates for weak operational decision-making, a premise Silicon Valley's dual-class structures quietly depend on.
The trend: Tech boards are moving from treating idiosyncratic founder behavior as visionary moat to auditing it as an operational risk, with Dorsey's dual-CEO decade as the case study.