Do we like them?Do we like Jack Dorsey?
Our score: 6 out of 10. No harmful words or acts of his own turned up and there is real giving, but big layoffs and his company's regulator troubles keep it from higher.
Dorsey is the Twitter co-founder who went on to build Square, now Block, the parent of Cash App. These days he is a Bitcoin evangelist and a backer of open, decentralised tech. He is not a celebrity in the red-carpet sense, so the question here is mostly about how he runs things, not what he says on a podcast.
The big recent story is the layoffs. In a shareholder letter, Dorsey said “Intelligence tools have changed what it means to build and run a company” as Block announced it would cut more than 4,000 jobs. Investors loved it and the share price jumped, but that is cold comfort if you were one of the people shown the door. Block was upfront that AI was part of the reason, which some will call honest and others will call brutal.
On regulators, Block agreed in April 2025 to a US$40 million penalty with New York's financial regulator over alleged anti-money-laundering gaps at Cash App, plus an independent monitor for a year. Block did not admit the findings. That is a company matter, not a personal one, but he is the boss and it happened on his watch.
Back in 2023 the short seller Hindenburg Research alleged that Block overstated its genuine user numbers and let fraud run through its platform. The report was an allegation, not a finding, and it came from someone betting against the stock. We haven't found a court ruling against Dorsey personally.
On the harm check, we found no campaigning against LGBTQ+ or trans people, no anti-vax or climate-denial push and no run of work with people who do those things. That is an absence of evidence in what we read, not a glowing reference, and he has had a messy relationship with content moderation over the years. Faith, politics and tech-libertarian instincts aren't a fail here; harm is, and we didn't find it.
The real good stuff is real. In April 2020 he pledged US$1 billion of his Square equity to a fund for global COVID-19 relief, and in 2025 he put US$10 million cash through his StartSmall foundation behind an open-source collective, “and Other Stuff”. Giving that much, early, counts for plenty.