Block ft. Jack Dorsey - A controversial hack week project becomes the #1 financial services app

CEO Jack Dorsey’s ultimate vision for Block was always about economic empowerment for all. Initially called Square, the company’s first product—the white dongle that let small businesses turn an iPhone into a credit card reader—was just a first step. So when a hack week project called Cash App that let anyone send money for free started gaining traction, Dorsey wanted to support it. It was easier said than done. It seemed like a strategic departure and it was costing lots of time and money. “Everyone wanted to kill it,” Dorsey says. Today, Cash App accounts for half the company’s revenue. In this episode, Dorsey explains how the company navigated this strategic shift, and how companies can succeed by weaving successive products and experiences around a singular, core vision. Jack Dorsey Jack Dorsey is the head of, chairman, and cofounder of Block (formerly Square). Prior to Block, Jack Dorsey founded Twitter and served as the company’s CEO. Brian Grassadonia Brian Grassadonia is the executive VP & general manager of Block’s Cash App. Alyssa Henry Alyssa Henry is the CEO of the Square business at Block. Outside of Block, Alyssa sits on the board of directors of Confluent.

Eventbrite ft. Julia Hartz - A company that took 14 years to build nearly disappeared in 14 days
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Eventbrite ft. Julia Hartz - A company that took 14 years to build nearly disappeared in 14 days

Building the Generative Web with AI ft Vercel CEO Guillermo Rauch
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Building the Generative Web with AI ft Vercel CEO Guillermo Rauch

Jack Dorsey | Making Square Hip (5/25/11)
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Jack Dorsey | Making Square Hip (5/25/11)

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UK Chancellor Pledges Fiscal Buffer In City Pitch | The Opening Trade 7/23/2026

Nvidia ft. Jensen Huang - An overnight success story 30 years in the making
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Nvidia ft. Jensen Huang - An overnight success story 30 years in the making

Snowflake CEO Sridhar Ramaswamy on Using Data to Create Simple, Reliable AI for Businesses
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Snowflake CEO Sridhar Ramaswamy on Using Data to Create Simple, Reliable AI for Businesses

UiPath ft. Daniel Dines - From Bootstrapping in Bucharest to One of Software’s Biggest IPOs
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UiPath ft. Daniel Dines - From Bootstrapping in Bucharest to One of Software’s Biggest IPOs

Inside Marc Andreessen & Ben Horowitz’s Multi-Family Office
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Inside Marc Andreessen & Ben Horowitz’s Multi-Family Office

Main Stage | Fireside Chat with Jack Dorsey & Adam Stacoviak
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Main Stage | Fireside Chat with Jack Dorsey & Adam Stacoviak

Rory Sutherland: Why Cost Reduction Isn't A Strategy
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Rory Sutherland: Why Cost Reduction Isn't A Strategy

Aamir Zargham (Lightspeed): Rebuilding long-range planning in 60 days
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Aamir Zargham (Lightspeed): Rebuilding long-range planning in 60 days

Square's Dorsey on Earnings, New Growth, Outlook
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Square's Dorsey on Earnings, New Growth, Outlook

AI integration for enterprise ft. CJ Desai of ServiceNow
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AI integration for enterprise ft. CJ Desai of ServiceNow

DMZ Fireside Chats | Jack Dorsey, Co-Founder and CEO of Square & Twitter
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DMZ Fireside Chats | Jack Dorsey, Co-Founder and CEO of Square & Twitter

Digital Asset Treasuries Under Pressure, IMF Warns of Tokenization Risks | Bloomberg Crypto 4/7/2026
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Digital Asset Treasuries Under Pressure, IMF Warns of Tokenization Risks | Bloomberg Crypto 4/7/2026

Ideas for Tomorrow | Jack Dorsey, Twitter, Inc. & Square, Inc.
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Ideas for Tomorrow | Jack Dorsey, Twitter, Inc. & Square, Inc.

How Brands Stay Visible When AI Decides | Profound CEO James Cadwallader
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How Brands Stay Visible When AI Decides | Profound CEO James Cadwallader

1. Introduction for 15.S12 Blockchain and Money, Fall 2018
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1. Introduction for 15.S12 Blockchain and Money, Fall 2018

Turning Academic Open Source into Startup Success ft Databricks Founder Ion Stoica
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Turning Academic Open Source into Startup Success ft Databricks Founder Ion Stoica

The Power of Curiosity and Inspiration
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The Power of Curiosity and Inspiration