Still an Apex Donor? What's Changing, and Staying the Same, About Jack Dorsey's Giving

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In 2021, Jack Dorsey seemed poised to become a philanthropic power player. Having taken away President Donald Trump’s most potent megaphone with a Twitter ban following the January 6 insurrection, Dorsey was also busy fire-hosing nonprofits with COVID relief and racial justice funding through his giving vehicle Start Small. Like many billionaires at the time, the Twitter and Square (now Block) founder also enjoyed a precipitously rising net worth, which soared to over $14 billion in 2021.

Even though Dorsey’s wealth and charitable giving have never rivaled that of the biggest American mega-philanthropists, his power moves at the time were enough to earn him mention in the same breath as MacKenzie Scott as one of a handful of emerging apex donors engaged in a new brand of rapid, no-strings-attached mega-giving. 

But roughly two years later, does that still hold? Or has the heady nature of Dorsey’s initial giving relaxed into something more modest, even conventional? 

Well, outside the world of philanthropy, it’s safe to say Dorsey’s star has faded somewhat. He severed ties with Twitter as it was taken over by the far richer (but less philanthropically inclined) Elon Musk, who is currently busy taking a wrecking ball to the platform that put Dorsey on the tech billionaire map.

Meanwhile, Dorsey remains a vocal crypto booster even as that field struggles to navigate choppy waters. And most recently, he’s come under fire for his enthusiastic endorsement of conspiracy theorist Robert F. Kennedy Jr., whose dark-horse Democratic candidacy in the 2024 presidential campaign has proved attractive to the tech-bro set but remains deeply unappealing to most liberal voters. 

Back in the philanthrosphere, there’s also reason to believe Dorsey’s not living up to the hype of 2020 and 2021. For one thing, he’s not as rich. As has long been the case, the majority of Dorsey’s current $4.8 billion net worth comes from his stake in Block, Inc. (formerly Square, Inc.), which he cofounded in 2009 and is best known for its Square mobile payments platform. The assets in Start Small came from a $1 billion transfer of shares in what was then Square to the Start Small LLC. That means Start Small’s overall resources fluctuate with Square’s stock price, just like Dorsey’s own wealth, although I should note that a portion of those shares has since been transferred to DAFs. The numbers below reflect both the Start Small LLC and associated DAFs, and are drawn from Start Small’s publicly available Google Sheet. 

Back when Start Small debuted, Dorsey said, “One of the awesome things about this [Start Small] model is, as Square grows in value in terms of its stock price, the fund has more to access.” Well, the reverse also applies. After reaching a high point of around $4 billion in 2021, Start Small’s overall grantmaking assets have slipped back to about $1.2 billion as Square’s stock price deflated — in Dorsey’s defense, still higher (before inflation) than when he started.

Also in his defense, Dorsey hasn’t let a falling net worth exert much of a chilling effect on his giving. Year after year, money is steadily moving out from Start Small despite the vast fluctuations in its overall assets. 

In 2023 so far, approximately $83.4 million has gone out the door. That’s already nearly as much as Start Small gave last year (about $87 million) and approaches the total from 2021 (about $98 million). The only outlier in terms of yearly giving totals was 2020, when Start Small’s initial COVID relief prerogative spurred Dorsey to give away around $330 million. Large additional gifts also went to racial justice causes that year. It’s possible Dorsey considered ramping things up as his wealth skyrocketed in 2021 and then backtracked, but that isn’t really reflected in giving totals.

When he founded Start Small, Dorsey gave it an explicit direction to take after the pandemic ended: girls’ health and education, and universal basic income. Looking through the list of gifts from 2022 and 2023, the former is still definitely a priority. The majority of gifts this year have gone to girls’ health and education work, both in the U.S. and abroad. Some of these larger recent gifts include $1 million apiece for the Women’s Refugee Commission, Right to Play, Yamba Malawi and Teach for All. However, most of Dorsey’s recent donations for girls’ health and education plateau at about $1 million, with many organizations getting sums in the low to mid six figures. 

Some of Dorsey’s largest gifts tend to flow to a smaller group of charities Start Small has supported year after year, often associated with big-name celebrities. Rihanna’s Clara Lionel Foundation, which engages in global education, climate and emergency response work, has received over $53 million since 2020, including a gift of $12.5 million earlier this year. 

Meanwhile, REFORM Alliance, the star-studded criminal justice reform outfit, has received a total of $14 million. And the Shawn Carter Scholarship Fund and the Shawn Carter Foundation, associated with recording artist Jay-Z, have received $6.5 million. Another major recipient to note is Resolve to Save Lives, the global health organization founded by former CDC Director Tom Frieden — it’s landed $88 million since 2020. Organizations in the tech and crypto space have also gotten significant recent backing, including the Open Sats Initiative ($10 million earlier this year), Graphene OS and the Tor Project.

What hasn’t benefited from much support recently is universal basic income, supposedly one of Start Small’s twin post-pandemic pillars. Dorsey’s philanthropic backing for the antipoverty policy, a favorite of the tech mogul set, reached its peak around the end of 2020 when he kicked in $15 million apiece to expand Mayors for a Guaranteed Income (MGI) and the Open Research Lab’s Basic Income Project. 

Dorsey’s support was a major boost for MGI and arguably contributed to a range of local basic income pilots getting off the ground across the country. But as COVID-era federal relief programs come to an end, it’s unclear whether those local experiments will have much of an effect on wider national policy. And since that time, Dorsey hasn’t done much through Start Small to further push basic income. 

An even bigger question going forward is to what extent Dorsey’s giving will remain identifiably progressive at all. He certainly started out that way, pairing copious COVID support with donations to the Movement for Black Lives, Boston University's Center for Antiracist Research, Color of Change, the National Domestic Workers’ Alliance and a bunch of other left-leaning groups. Dorsey followed up on that with support for groups fighting anti-Asian hate in 2021 as well as progressive civic engagement organizations and LGBTQ nonprofits. 

Support for progressive groups continued through the beginning of last year in the form of a group of often sizable gifts given “in partnership with the Clara Lionel Foundation” to places like the Black Feminist Fund ($5 million) and the Center for Popular Democracy ($2.5 million). Since then, though, far less money has flowed to big-name progressive groups in the U.S., and considering Dorsey’s RFK Jr. endorsement, it’s worth asking whether his political inclinations have shifted somewhat.

Still, it’s too early to say whether Dorsey’s giving is truly moving away from its progressive roots toward something more moderate (or fringe). Much of his giving this year remains progressive-adjacent, including the girls’ health and education support, a philanthropic focus for which he doesn’t get enough credit. But there has been a noticeable shift away from overt movement building and toward more conventional aid and direct service work. In that respect, Dorsey’s hardly alone among liberal megadonors as the tumult of 2020 fades from view.