Video: Jack Dorsey Shakes Down Arrington, Calacanis, And Google In Seconds

Today at the TechCrunch Disrupt conference in New York, Square co-founder Jack Dorsey took the stage to show a demo of Square running on the iPhone. To do the demo, Dorsey had a good idea: take money from Michael Arrington.

Dorsey took $100 from Mike with the swipe of a credit card. Mike was concerned about Dorsey’s intentions for the money, but it will actually go towards Charity Water as a donation, Dorsey assured. He then sat down to talk a bit with Mike and Erick Schonfeld about Square, and his experience raising funding.

At the end of the interview, Mike asked the audience if anyone would be willing to use Square to donate $1,000 to Charity Water. Mahalo CEO Jason Calacanis graciously volunteered. Then, after being humorously called out, so did Google (thanks to developer evangelist Don Dodge).

Funny stuff for a good cause. Watch it all in the video below.

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Join 10k+ tech and VC leaders for growth and connections at Disrupt 2025

Netflix, Box, a16z, ElevenLabs, Wayve, Hugging Face, Elad Gil, Vinod Khosla — just some of the 250+ heavy hitters leading 200+ sessions designed to deliver the insights that fuel startup growth and sharpen your edge. Don’t miss a chance to learn from the top voices in tech. Grab your ticket before doors open to save up to $444.

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