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(Preorder) The Rewrite Trap Why Software Rewrites Fail and What To Do Instead
A practical guide for startup engineers and leaders who want to fix software, not rebuild it from scratch.
What you'll learn:
- How to identify when a rewrite is risky
- How to incrementally modernize systems
- Case studies from real companies
- The "TheeSeeShip" approach
Preorder today and get:
- Early draft chapters
- Exclusive Q&A session with the authors
- Your name in the acknowledgements
$25.00$39.00
Preorder the book‘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 complete rewrite.
Don’t do that.
We explore what to do instead along with an array of other software topics in our eponymous podcast.
Listen & subscribe
Latest episodes
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34:21
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.
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19:45
Using AI to Complete a Half-Finished Rewrite (Ep. 169)
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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21:37
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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25:28
AI & WIP Fundamentals (Ep. 167)
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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17:55
Solutioning in the Age of AI (Ep. 166)
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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18:30
AI & The Age of Transient Apps (Ep. 165)
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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21:40
AI Horror Stories (Ep. 164)
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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20:12
Can AI Tell You What Your Goals Are? (Ep. 163)
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.
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12:17
Terminology: Rewrite, Refactor, Rebuild, Redo? (Ep. 162)
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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22:54
You Can't Vibe Code Reputation (Ep. 161)
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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20:51
TheseusShipping Outside of the Tech Stack (Ep. 160)
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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18:49
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.
About the podcast
Never Rewrite is a weekly software engineering podcast for developers and engineering leaders. Jeffrey Sherman and Isaac Askew dig into the real decisions behind shipping and maintaining software — when to modernize instead of rewrite, how AI and agentic coding tools are changing the craft, scaling, team standards, and engineering careers. Browse every episode on the episodes page.
- What is the Never Rewrite podcast about?
- Never Rewrite is a software engineering podcast hosted by Jeffrey Sherman and Isaac Askew. Each episode is a candid conversation about why complete software rewrites fail, how to modernize legacy code instead, and how AI and agentic coding tools are changing the day-to-day work of building software.
- Is Never Rewrite a coding podcast?
- Yes. It's a coding and software engineering podcast for working developers and engineering leaders. Topics range from legacy systems and incremental modernization to AI-assisted development, scaling, team standards, and engineering careers.
- Who should listen?
- Software developers, engineering managers, CTOs, and startup founders who would rather fix and evolve their software than rebuild it from scratch.
- How often do new episodes come out?
- New episodes are released weekly, with more than 150 episodes already in the archive.
- Where can I listen to Never Rewrite?
- Never Rewrite is available on Apple Podcasts, Spotify, Amazon Music, and YouTube. You can also browse every episode on neverrewrite.com.