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.

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S1 · E175
Friday · 16 min
Revisiting 'The Goal: A Process of Ongoing Improvement' (Ep. 175)
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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S1 · E174
September 25 · 27 min
The Rise of Personal AI Assistants (Ep. 174)
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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S1 · E173
September 18 · 23 min
How My Workflow Is Impacted by AI (Ep. 173)
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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S1 · E172
September 11 · 10 min
AI-Monitored Release Processes: A Log Anomaly Checker (Ep. 172)
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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S1 · E171
September 4 · 29 min
Using AI to Complete a Half-Finished Rewrite, Part 2 (Ep. 171)
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 Askew Guests: Dustin Rea
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S1 · E170
August 28 · 34 min
Refactoring: What Changes (And Doesn't) in the Age of AI ft. Ravi Ram (Ep. 170)
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.com https://www.linkedin.com/in/dhali/ ------------------------------------- Dhali 30211 Avenida de las Bandera, STE 200 Rancho Santa Margarita, CA 92688 References: Practical Refactoring Woody Zuill | Llewellyn Falco https://www.youtube.com/watch?v=aWiwDdx_rdo Sandi Metz' Rules For Developers https://thoughtbot.com/blog/sandi-metz-rules-for-developers (Book) Tidy First: A Personal Exercise in Empirical Software Design Kent Beck
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S1 · E169
August 21 · 19 min
Using AI to Complete a Half-Finished Rewrite (Ep. 169)
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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S1 · E168
August 14 · 21 min
Are AI-Driven Pull Requests Too Large? (Ep. 168)
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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S1 · E167
August 7 · 25 min
AI & WIP Fundamentals (Ep. 167)
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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S1 · E166
July 31 · 17 min
Solutioning in the Age of AI (Ep. 166)
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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S1 · E165
July 24 · 18 min
AI & The Age of Transient Apps (Ep. 165)
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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S1 · E164
July 17 · 21 min
AI Horror Stories (Ep. 164)
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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S1 · E163
July 10 · 20 min
Can AI Tell You What Your Goals Are? (Ep. 163)
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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S1 · E162
July 3 · 12 min
Terminology: Rewrite, Refactor, Rebuild, Redo? (Ep. 162)
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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S1 · E161
June 26 · 22 min
You Can't Vibe Code Reputation (Ep. 161)
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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S1 · E160
June 19 · 20 min
TheseusShipping Outside of the Tech Stack (Ep. 160)
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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S1 · E159
June 12 · 18 min
Vibe Coding (Ep. 159)
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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S1 · E158
June 5 · 26 min
Token-Based Billing Is Nuts (Ep. 158)
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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S1 · E157
May 29 · 23 min
Episode 157: Is AI Making You The New John Henry?
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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S1 · E156
May 22 · 9 min
Episode 156: Modernization: Where AI Doesn't Save You Any Steps
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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