
Episode #179
AI & Eternal Software Projects (Ep. 179)
Today Isaac and Jeffrey discuss how AI changes software projects that before never seemed to end. Isaac: Yes, I wasn't selecting my Shure SM7B as the correct microphone. Sad.


technology
Hosted by Isaac Askew and Jeffrey Sherman · technology · EN
‘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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Signup to Generate a Pitch‘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.
Never Rewrite: Software Engineering & AI Coding is hosted by Isaac Askew and Jeffrey Sherman. The show has published 178 episodes to date.
Recent episodes include "AI & Eternal Software Projects (Ep. 179)" (30 October 2026, 18 minutes), "Cancel All Your Meetings, AI Edition (Ep. 178)" (23 October 2026, 19 minutes), and "The SaaSpocalypse Is Here (Ep. 177)" (16 October 2026, 30 minutes).
Never Rewrite: Software Engineering & AI Coding publishes roughly weekly, with episodes averaging 21 minutes across 178 episodes.
Booking probability for Never Rewrite: Software Engineering & AI Coding is 36%, and the host is rated Selective on guests. Never Rewrite: Software Engineering & AI Coding requires a Pod Score of 80 or higher. Never Rewrite: Software Engineering & AI Coding's contact route on record: verified email.
The strongest fits for Never Rewrite: Software Engineering & AI Coding are IT Services & Software Development. Never Rewrite: Software Engineering & AI Coding has a technology audience.
Isaac Askew and Jeffrey Sherman hosts Never Rewrite: Software Engineering & AI Coding, a technology podcast with 178 episodes published.
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

Episode #179
Today Isaac and Jeffrey discuss how AI changes software projects that before never seemed to end. Isaac: Yes, I wasn't selecting my Shure SM7B as the correct microphone. Sad.

Episode #178
In this episode, Jeffrey Sherman and Isaac Askew explore how AI-generated transcripts are transforming meeting culture, power dynamics, and organizational honesty. They discuss whether transcripts encourage longer...

Episode #177
In this episode, Isaac Askew and Jeffrey Sherman explore the future of SaaS development, reverse engineering software, and the implications of open source AI tools for software creation and business models.

Episode #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...

Episode #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...

Episode #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...

Episode #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...

Episode #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

Episode #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...

Episode #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...

Episode #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.

Episode #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...

Episode #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...

Episode #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...

Episode #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...

Episode #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...

Episode #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...

Episode #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...

Episode #157
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...

Episode #156
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.
Recent guests on Never Rewrite: Software Engineering & AI Coding. Study who booked and why before you pitch.
pricing expert, author of Hourly Billing Is Nuts, host of Ditching Hourly, and co-host of The Business of Authority, Jonathan Stark Consulting
System Initiatives
Ghost
Red Hook Agency
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