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Latest Interviews

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  1. Sequoia Capital37 min

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

    Jack Dorsey, Brian Grassadonia, Alyssa Henry, Rolof Boerta

    Founded in 2009 by Jack Dorsey and Jim McKelvey, Block Inc. disrupted the payment industry by offering free hardware and standardized fees to small businesses, a strategy that included a controversial exclusive deal with Starbucks which initially caused significant financial losses. The company pivoted its Cash App division from a money-transfer tool into a comprehensive financial ecosystem serving the unbanked population, eventually driving half of the company's total revenue after implementing fee-generating features under a strict 2016 profitability deadline. Demonstrating its culture of long-term strategic bets, Block acquired Australian buy-now-pay-later provider Afterpay for $29 billion in 2021 to integrate its merchant and consumer networks into a unified financial platform.

  2. Goldman Sachs22 min

    The State of Small Business in America

    Warren Buffett, Lloyd Blankfein, Michael Bloomberg, Jack Dorsey, Savannah Guthrie

    Goldman Sachs, Square, and various business leaders convened to address the systemic financial and regulatory hurdles facing established small businesses, noting that traditional banking approves only 10% of capital requests while regulatory costs consume significant operational time. The program highlighted Square's success in approving over 98% of loan applicants through automated repayment models and emphasized a hiring philosophy prioritizing resilience and passion over elite credentials. Strategic insights from Jack Dorsey, Mayor Bloomberg, and Warren Buffett focused on reducing bureaucratic burdens, fostering open organizational cultures, and aiming to delight customers to drive sustainable growth.

  3. Y Combinator29 min

    Jack Dorsey at Startup School 2013

    Jack Dorsey

    The session explores the convergence of Robert Henry's philosophy on intrinsic creativity and Bill Walsh's disciplined approach to organizational excellence, emphasizing that true mastery requires a personal "standard of performance" rather than external validation. Speakers detail how leaders must actively combat the "success disease" by establishing specific "Do and Don't" lists that enforce accountability, prevent complacency, and drive innovation through shared purpose rather than comfortable routines. Ultimately, the dialogue urges creators and executives to embrace solitude, reject conventional shortcuts, and build products that resonate deeply by remaining fiercely committed to their own vision.