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Between Two Founders

Between Two Founders

Written by: Digits
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An enlightening series of fireside chats, hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups. Gain rare insights from their journeys, and first hand experience.Digits Economics Leadership Management & Leadership
Episodes
  • Zapier, AI Workflows, and the Future of Integration | Wade Foster
    Dec 1 2025

    Episode 009 of Between Two Founders: Jeff sits down with Wade Foster, Co-founder and CEO of Zapier, to uncover how a “weird,” fully remote team built one of tech’s most influential platforms, now behind 81+ billion automations.


    Wade also shares Zapier’s origins, from a Startup Weekend in Columbia to a second shot at YC, and reveals how Zapier is weaving AI into its workflow engine to make automation both reliably structured and intelligently adaptive.


    Stay till the end to hear Wade answer: What’s the CEO of Zapier’s favorite use of his own product?


    00:00 Trailer

    01:09 Introduction

    02:45 Wade Foster's Journey: From Missouri to Zapier

    08:14 Building Zapier: Challenges and Successes

    22:40 Navigating Unconventional Business Strategies

    25:48 Innovative Practices for Remote Teams

    31:56 AI Integration and Future Prospects

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    46 mins
  • Building AI That Multiplies CFOs: Runway
    Nov 11 2025

    Episode 008 of Between Two Founders: Join Jeff as he sits down with Siqi Chen, CEO and co-founder of Runway, to explore a journey that spans gaming, virtual reality, and B2B SaaS, culminating in a mission to make finance teams 10x more efficient through AI and design.


    Siqi shares why the most powerful products amplify human intelligence rather than replace it, how design principles from consumer tech can simplify even the most complex systems, and how he is building what he calls an “Ironman suit for finance teams.”


    Tune in now to hear why Siqi Chen believes, "For every intellectual task, for sure, the AI will do a better job of it."


    00:00 Trailer

    01:20 Introduction to Siqi Chen and His Journey

    02:36 Early Career and NASA Experience

    07:38 First Venture and Facebook Platform Success

    29:23 Building Accounting Software from Scratch

    31:23 The Role of Excel in Financial Planning

    37:17 The Future of AI in Finance

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    58 mins
  • Between Two Founders (Episode 007) - Jean-Denis Greze
    Jul 30 2025

    Join Jeff as he engages with Jean-Denis Greze, Co-Founder of Town and former CTO of Plaid, for an insightful dialogue about revolutionizing industries and pushing boundaries.

    Jean-Denis shares his remarkable experiences from scaling Plaid into a fintech powerhouse, detailing how they bridged the gap between consumers' bank accounts and their favorite apps.

    Now at Town, Jean-Denis is leveraging AI to redefine tax assistance for small businesses, ensuring they receive the high-quality advantages typically reserved for large corporations. Hear firsthand how he navigated the transition from being an operator at Plaid to launching his own venture with an $18 million seed round.

    Tune in to discover the challenges and triumphs of scaling a startup, the intricacies of leadership, and the exciting future of financial technology. Don’t miss this episode packed with insights and inspiration from two transformative thought leaders in the fintech world.

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    1 hr and 27 mins
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