Episodios

  • AI Horror Stories (Ep. 164)
    Jul 17 2026

    In this episode, Isaac Askew and Dustin Rea share real-world AI security stories, highlighting the importance of security best practices when deploying autonomous agents. From data leakage to infrastructure risks, learn how to protect your systems in an AI-driven world.

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    22 m
  • Can AI Tell You What Your Goals Are? (Ep. 163)
    Jul 10 2026

    In this episode, Isaac Askew, Jeffrey Sherman and Dustin Rea explore the challenges and opportunities of using AI in software development, focusing on goal clarity, requirements, feature coherence, and security. They discuss how to harness AI effectively while avoiding common pitfalls like feature bloat and misaligned objectives.

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    20 m
  • Terminology: Rewrite, Refactor, Rebuild, Redo? (Ep. 162)
    Jul 3 2026

    In this episode, Jeffrey Sherman and Isaac Askew explore the nuances of rewriting, rebuilding, and iteratively shipping software. They clarify common terminology, share practical insights, and emphasize the importance of safe, incremental delivery.

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    12 m
  • You Can't Vibe Code Reputation (Ep. 161)
    Jun 26 2026

    In this episode, Isaac and Jeffrey explore how reputation is becoming the new barrier to entry in a world flooded with AI-generated content, apps, and information. They discuss the importance of genuine trust, the pitfalls of vibe coding, and how real reputation emerges through solving real problems.

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    23 m
  • TheseusShipping Outside of the Tech Stack (Ep. 160)
    Jun 19 2026

    In this episode, Jeffrey Sherman and Isaac Askew explore how to extend the philosophy of shipping solutions beyond the tech stack, focusing on real-world stories of identifying friction and automating processes to improve outcomes across organizations.

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    21 m
  • Vibe Coding (Ep. 159)
    Jun 12 2026

    Isaac Askew, Jeffrey Sherman, and Dustin Rea explore the impact of vibe coding on software development, maintenance, and industry practices. The conversation covers real-world experiences, risks, and the future of AI-assisted coding.

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    19 m
  • Token-Based Billing Is Nuts (Ep. 158)
    Jun 5 2026

    Jeffrey Sherman and Isaac Askew explore the pitfalls of token-based billing models, comparing them to hourly billing and value-based billing. They discuss how these models create adversarial relationships, obscure true costs, and impact incentives for vendors and users alike.

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    27 m
  • Episode 157: Is AI Making You The New John Henry?
    May 29 2026

    Today we're exploring the story of John Henry as a metaphor for the modern struggle between human labor and automation. The conversation delves into the dignity of work, the impact of AI on jobs, and how to adapt to technological change.

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    23 m