

Never Rewrite
Isaac Askew and Jeffrey Sherman
‘Never Rewrite’ is a mantra of ours in the programming realm. Often times when software developers encounter nightmare codebases, the thought crosses their mind to work towards a rewrite, a port to a new language, or despair that their code is unfixable.
It’s not unfixable, and we explore how to get started along with an array of other software topics in our eponymous podcast.
It’s not unfixable, and we explore how to get started along with an array of other software topics in our eponymous podcast.
Episodes
Mentioned books

Apr 10, 2026 • 12min
Episode 151: Celebrating Wins During Constant Iteration
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.

Apr 3, 2026 • 32min
Episode 150: The AI Rewrite Trap
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.

Mar 27, 2026 • 49min
Episode 149: Isaac Does a Rewrite?
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.

Mar 20, 2026 • 35min
Episode 148: How Human Taste Shapes the Future of AI and 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.

Mar 13, 2026 • 38min
Episode 147: Managing Organizational Change ft. Sophia Rosa
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.

Mar 6, 2026 • 28min
Episode 146: How AI is Reshaping Careers and Workflows
Isaac Askew and Dustin Rea discuss how AI is transforming careers, workflows, and organizational practices.

Feb 27, 2026 • 7min
Episode 145: Outdated Programming Techniques: Browser Compatibility
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.

Feb 20, 2026 • 7min
Episode 144: Outdated Programming Techniques: Bit Masking
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.

Feb 13, 2026 • 11min
Episode 143: Tactics to Obscure (Parody)
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.

Feb 6, 2026 • 24min
Episode 142: Are You Ready to Scale? A Local Case Study
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 existing systems, evaluating technology choices, and balancing short-term fixes with long-term strategies. The conversation emphasizes a consultative approach that prioritizes the client's needs and the practicalities of their business environment.Book a call with us today:https://intro.co/JeffreyShermanhttps://intro.co/IsaacAskew


