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PODCAST

Never Rewrite: Software Engineering & AI Coding

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.

technology

All Episodes

00:16:31

Revisiting 'The Goal: A Process of Ongoing...

Never Rewrite: Software Engineering & AI Coding ·

2026/10/02

Jeffrey Sherman and Isaac Askew explore the timeless principles of the book 'The Goal' by Eliyahu Goldratt, focusing on the theory of constraints and its relevance to modern software development and AI workflows. They discuss how identifying and optimizing bottlenecks can dramatically improve system efficiency and adapt to changing constraints.Show notes:The Goal: https://en.wikipedia.org/wiki/The_Goal_(novel)The Phoenix Project: https://itrevolution.com/product/the-phoenix-project/

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00:27:57

The Rise of Personal AI Assistants (Ep. 174)

Never Rewrite: Software Engineering & AI Coding ·

2026/09/25

In this episode, Isaac Askew and Jeffrey Sherman explore the rapid rise of personal assistant AI like Muse, its implications for privacy, security, and the future of online shopping and productivity. They discuss how AI is transforming trust, automation, and the way companies must adapt to stay relevant.

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00:23:33

How My Workflow Is Impacted by AI (Ep. 173)

Never Rewrite: Software Engineering & AI Coding ·

2026/09/18

In this episode, Isaac Askew and Jeffrey Sherman explore how AI impacts productivity, workflow, and creativity in software development. They discuss real-world experiences with AI tools, challenges faced, and the evolving nature of AI-human collaboration.

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00:10:06

AI-Monitored Release Processes: A Log Anomaly Checker...

Never Rewrite: Software Engineering & AI Coding ·

2026/09/11

In this episode, Jeffrey Sherman and Isaac Askew explore how AI can monitor release processes by analyzing error logs, detecting anomalies, and improving deployment confidence. They discuss practical tools, strategies, and the potential for automation in system monitoring.

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00:29:24

Using AI to Complete a Half-Finished Rewrite, Part 2...

Never Rewrite: Software Engineering & AI Coding ·

2026/09/04

Jeffrey Sherman shares his experience using AI to accelerate a 10-year API rewrite, highlighting practical strategies, challenges, and insights into modern development practices.Co-host: Isaac AskewGuests: Dustin Rea

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00:34:20

Refactoring: What Changes (And Doesn't) in the Age of...

Never Rewrite: Software Engineering & AI Coding ·

2026/08/28

Today we're joined by Ravi Ram, a kindred refactoring spirit. Ravi joins us today to discuss his approach to refactoring and how he leverages AI effectively to dramatically reduce the time it takes to implement refactors and fixes for his clients.Ravi Ram | ravi@dhali.comhttps://www.linkedin.com/in/dhali/-------------------------------------Dhali30211 Avenida de las Bandera, STE 200Rancho Santa Margarita, CA 92688References:Practical RefactoringWoody Zuill | Llewellyn

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00:19:44

Using AI to Complete a Half-Finished Rewrite (Ep. 169)

Never Rewrite: Software Engineering & AI Coding ·

2026/08/21

Jeffrey Sherman discusses using AI to complete a decade-long API rewrite, focusing on strategies for parity, documentation, testing, and migration. This episode offers insights into managing legacy systems and leveraging AI for efficient software development.

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00:21:37

Are AI-Driven Pull Requests Too Large? (Ep. 168)

Never Rewrite: Software Engineering & AI Coding ·

2026/08/14

This episode explores the evolving practices of code review in the age of AI, focusing on the size of pull requests, the role of human oversight, and how AI tools like Claude are transforming development workflows.Features Jeffrey Sherman, Isaac Askew, and Dustin Rea.

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00:25:27

AI & WIP Fundamentals (Ep. 167)

Never Rewrite: Software Engineering & AI Coding ·

2026/08/07

In this episode, Jeffrey Sherman shares insights on how AI can optimize legacy code testing, improve build times, and address the challenges of organic codebases. Discover practical strategies and the importance of conventions in maintaining reliable tests.

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00:17:54

Solutioning in the Age of AI (Ep. 166)

Never Rewrite: Software Engineering & AI Coding ·

2026/07/31

Isaac & Jeffrey discuss how delivering incredibly literal acceptance criteria ('solutioning') changes when the engineering work pivots to the AI agent rather than a human engineer.

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00:18:29

AI & The Age of Transient Apps (Ep. 165)

Never Rewrite: Software Engineering & AI Coding ·

2026/07/24

Isaac and Jeffrey explore the concept of transient software, sharing insights on building personalized tools with AI, cost-effective infrastructure, and the future of software development. They discuss real-world examples, including a band management app, and the implications of AI-driven, ephemeral solutions.

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00:21:40

AI Horror Stories (Ep. 164)

Never Rewrite: Software Engineering & AI Coding ·

2026/07/17

In this episode, Isaac Askew and Dustin Rea share real-world AI security stories, highlighting the importance of security best practices when deploying autonomous agents. From data leakage to infrastructure risks, learn how to protect your systems in an AI-driven world.

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00:20:12

Can AI Tell You What Your Goals Are? (Ep. 163)

Never Rewrite: Software Engineering & AI Coding ·

2026/07/10

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.

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00:12:17

Terminology: Rewrite, Refactor, Rebuild, Redo? (Ep. 162)

Never Rewrite: Software Engineering & AI Coding ·

2026/07/03

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.

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00:22:54

You Can't Vibe Code Reputation (Ep. 161)

Never Rewrite: Software Engineering & AI Coding ·

2026/06/26

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.

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00:20:51

TheseusShipping Outside of the Tech Stack (Ep. 160)

Never Rewrite: Software Engineering & AI Coding ·

2026/06/19

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.

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00:18:49

Vibe Coding (Ep. 159)

Never Rewrite: Software Engineering & AI Coding ·

2026/06/12

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.

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00:26:42

Episode 158: Token-Based Billing Is Nuts

Never Rewrite: Software Engineering & AI Coding ·

2026/06/05

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.

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00:23:13

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

Never Rewrite: Software Engineering & AI Coding ·

2026/05/29

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.

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00:09:43

Episode 156: Modernization: Where AI Doesn't Save You...

Never Rewrite: Software Engineering & AI Coding ·

2026/05/22

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.

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