Never Rewrite

Never Rewrite

Isaac Askew and Jeffrey Sherman

Episodes 158
Avg. Duration 21m
Activity Highly Active
Apple Rating 5.0 (6)
Since Mar 2023
Latest Episode Jun 2026

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Publishing Details

Schedule
Weekly
Format
Episodic
Consistency
81%
Hosting
api.riverside.fm

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About This Podcast

‘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.

Podcasting 2.0 Features

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Recent Episodes

S1E158 Episode 158: Token-Based Billing Is Nuts

Jun 05, 2026 26m Transcript

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…

S1E157 Episode 157: Is AI Making You The New John Henry?

May 29, 2026 23m Transcript

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…

S1E156 Episode 156: Modernization: Where AI Doesn't Save You Any Steps

May 22, 2026 9m Transcript

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.

S1E155 Episode 155: Agentic Development Is Turning Engineers Into Product Owners

May 15, 2026 21m Transcript

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

S1E154 Episode 154: Feature Parity Pitfalls

May 10, 2026 12m Transcript

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…

S1E153 Episode 153: The Rewrite Trap & Sunk Cost Fallacy

Apr 24, 2026 19m Transcript

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…

S1E152 Episode 152: The Moving House Metaphor for Software Rewrites: How AI Changes the Game

Apr 17, 2026 16m Transcript

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…

S1E151 Episode 151: Celebrating Wins During Constant Iteration

Apr 10, 2026 11m Transcript

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…

S1E150 Episode 150: The AI Rewrite Trap

Apr 03, 2026 31m Transcript

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…

S1E149 Episode 149: Isaac Does a Rewrite?

Mar 27, 2026 49m Transcript

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…

S1E148 Episode 148: How Human Taste Shapes the Future of AI and Coding

Mar 20, 2026 35m Transcript

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…

S1E147 Episode 147: Managing Organizational Change ft. Sophia Rosa

Mar 13, 2026 38m

Sophia Rosa, a transformational expert, shares insights on managing organizational change, especially in technology implementations like ERP systems. Topics include assessing readiness, building…

S1E146 Episode 146: How AI is Reshaping Careers and Workflows

Mar 06, 2026 27m

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

S1E145 Episode 145: Outdated Programming Techniques: Browser Compatibility

Feb 27, 2026 6m

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…

S1E144 Episode 144: Outdated Programming Techniques: Bit Masking

Feb 20, 2026 6m

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…

S1E143 Episode 143: Tactics to Obscure (Parody)

Feb 13, 2026 10m

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…

S1E142 Episode 142: Are You Ready to Scale? A Local Case Study

Feb 06, 2026 23m

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…

S1E141 Episode 141: How Rewrites Create Accountability Black Holes

Jan 30, 2026 14m

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…

S1E140 Episode 140: Evolving Past Boomer AI

Jan 23, 2026 35m

SummaryIn 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…

S1E139 Episode 139: Rewrites - A Failure of the Imagination ft. Mark Mandau

Jan 16, 2026 34m

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…

Frequently Asked Questions

How many episodes does Never Rewrite have?

Never Rewrite has published 158 episodes since March 2023, covering topics in Technology.

Is Never Rewrite still active?

Never Rewrite is currently highly active with new episodes weekly. Average episode length is 21m.

How do I contact Never Rewrite for sponsorship or guest appearances?

Sign up on Grep.FM to access contact details for Never Rewrite, including email and social media links.

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