Episodes

  • Episode 150: The AI Rewrite Trap
    Apr 3 2026

    In this episode, Isaac Askew and Jeffrey Sherman explore the evolving landscape of software development, focusing on the relevance of rewrites in the age of AI. They discuss how AI tools like Claude are transforming engineering workflows, reducing the need for full rewrites, and shifting bottlenecks towards product management.

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    32 mins
  • Episode 149: Isaac Does a Rewrite?
    Mar 27 2026

    Isaac Askew shares his journey of building a hyperlocal event aggregator using AI, exploring the technical challenges, tools, and lessons learned along the way. Discover how modern AI workflows can rapidly prototype and deploy complex projects without traditional coding.

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    49 mins
  • Episode 148: How Human Taste Shapes the Future of AI and Coding
    Mar 20 2026

    Exploring the intersection of creativity, taste, and technical skill in software engineering, inspired by Rick Rubin's quote. Discussing how AI and human intuition shape the future of product design and development.

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    35 mins
  • Episode 147: Managing Organizational Change ft. Sophia Rosa
    Mar 13 2026

    Sophia Rosa, a transformational expert, shares insights on managing organizational change, especially in technology implementations like ERP systems. Topics include assessing readiness, building trust, effective communication, and the role of mindfulness in change management.

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    38 mins
  • Episode 146: How AI is Reshaping Careers and Workflows
    Mar 6 2026

    Isaac Askew and Dustin Rea discuss how AI is transforming careers, workflows, and organizational practices.

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    28 mins
  • Episode 145: Outdated Programming Techniques: Browser Compatibility
    Feb 27 2026

    Isaac Askew, Dustin Rea, and Jeffrey Sherman discuss the past challenges of browser compatibility. They reflect on the significant time spent in the past ensuring websites functioned uniformly across different browsers, a task that has become less prominent in modern development.

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    7 mins
  • Episode 144: Outdated Programming Techniques: Bit Masking
    Feb 20 2026

    Isaac Askew, Dustin Rea, and Jeffrey Sherman discuss the outdated programming technique of bit masking, exploring its historical context, current relevance, and the cognitive load it imposes on developers. They emphasize that while bit masking may still have niche applications in high-frequency trading, the general trend in software development has shifted towards prioritizing engineering time and maintainability over micro-optimizations. The discussion highlights the importance of understanding when efficiency is truly necessary and when it can be sacrificed for better clarity and ease of development.

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    7 mins
  • Episode 143: Tactics to Obscure (Parody)
    Feb 13 2026

    Isaac Askew and Jeffrey Sherman discuss tactics used in project management to obscure the true state of projects, especially when they are not going well. They explore the shift from deliverables to phases, the focus on work instead of outcomes, and strategies to bring clarity and accountability back into project management through naming conventions and demos.

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    11 mins