Never Rewrite: Software Engineering & AI Coding

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.

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.

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.

Jeffrey Sherman and Isaac Askew discuss the realities of AI in software modernization, emphasizing that AI accelerates but does not eliminate manual testing and manual work in legacy code projects.

Isaac Askew, Jeffrey Sherman, and Dustin Rea how agentic AI development is transforming developer roles, emphasizing empathy, tight iteration, and legacy code management.

Jeffrey Sherman and Isaac Askew discuss the pitfalls of aiming for feature parity during software rewrites, emphasizing the importance of communication, boundaries, and incremental improvements over blind feature replication.

Isaac and Jeffrey explore the pitfalls of rewrites in software development, including the trap of delayed risk, sunk cost fallacy, and human psychology. Learn strategies to avoid costly rewrites and focus on incremental delivery and early feedback.

Isaac Askew and Jeffrey Sherman explore how the metaphor of moving houses relates to software rewrites, and how AI can revolutionize the process of packing, unpacking, and deciding what to keep in tech projects.

Jeffrey Sherman and Isaac Askew explore the importance of celebrating small wins in iterative projects, how to track progress effectively, and ways to keep team morale high through accountability and customer feedback.

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.