Never Rewrite: Software Engineering & AI Coding

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.

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.

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.

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.

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.

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.

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.

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.

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

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.

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...

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.

In this conversation, Isaac Askew and Jeffrey Sherman discuss the challenges faced by a small business looking to scale its operations. Isaac shares insights from a recent consultation where he aimed to help a client understand their inefficiencies and explore potential solutions without immediately resorting to hiring a full-time employee. The discussion covers the importance of understanding exi...

In this episode, Isaac Askew and Jeffrey Sherman discuss the phenomenon of accountability black holes created by software rewrites. They explore how the decision to rewrite can lead to neglecting existing bugs, the challenges of prioritization in development, and the implications of resource allocation. The conversation emphasizes the importance of weighing the impact of bugs against the resources...

Summary In this episode, Isaac Askew and Dustin Rea discuss the evolving landscape of AI in software development, focusing on the transition from traditional coding methods to more advanced, AI-driven workflows. They explore the implications of these changes on legacy systems, team dynamics, and the essential human element in technology. The conversation highlights the need for developers to adapt...

In this episode, Isaac Askew and Jeffrey Sherman are joined by Mark Mandau to explore the complex topic of software rewrites. They discuss the reasons behind the decision to rewrite software, the implications of neglecting maintenance, and the risks associated with such a drastic move. The conversation emphasizes the importance of understanding legacy systems, the role of leadership in decision-ma...