Illustrations: Deb Lee

The Giving Apps: How Venmo and Cash App Upended a Century-Old Charity Model

In 2020, Venmoing total strangers in need became a radical act of support — and trust

Caitlin Dewey
Published in
16 min readDec 2, 2020


RRaised in a six-bedroom mansion in Philadelphia’s outer exurbs — the kind with a grand circular driveway, tucked 100 yards from the street — 25-year-old Jake learned from an early age that wealthy families like his had a moral obligation to give back through charity.

Jake, who asked OneZero to protect his last name, shares his surname with a major college that renamed itself in honor of his late grandmother. His grandfather, the millionaire founder of a family-run tax software firm, cut $2,500 checks each Christmas to the charities each grandchild selected. Growing up, Jake watched his parents primp for charity galas and endow scholarships. They would casually pick up the tuition of kids they met on their international vacations. For a period in his childhood, Jake’s parents even operated their own children’s health nonprofit.

Despite that white-gloved lineage, Jake — who voted for Bernie Sanders in the Democratic primary, and still struggles to explain the wealth he inherited — does not exude Carnegie or Rockefeller vibes. In conversation, the freelance film technician is boisterous and self-deprecating and very, very earnest, prone to incidental overshares and meandering asides. On Twitter, he posts about movies, indie rock, social justice, and the guilt of growing up in a family rich enough to rent the occasional private plane.

As the Covid-19 pandemic deepened this spring, so too did Jake’s shame. “Being unwoke and rich seems great, but I’m rich and aware of other humans so I wanna die,” he tweeted.

Over the course of several days, Jake sent more than $5,400 in direct payments.

So in early spring, Jake embarked on a charity spree of his own. He sent a few laid-off buddies money to help cover their rent. He donated to a series of small bail funds. Then — scrolling through Twitter one afternoon in May, inundated by racial wealth gap statistics and “high out of his mind” on Xanax — Jake hatched another, more unusual idea: He promised to Venmo or Cash App funds directly to anyone…



Caitlin Dewey

Enterprise reporter @thebuffalonews, formerly @washingtonpost.