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Artwork for Never Rewrite: Software Engineering & AI Coding

Never Rewrite: Software Engineering & AI Coding

Isaac Askew and Jeffrey Sherman
Software Development
Artificial Intelligence
Project Management
Rewrites
Software Engineering
Logging
Sonos
Error Handling
Customer Value
Iterative Development
Metrics
Spotify
Legacy Systems
Refactoring
Apis
Time Zones
Testing
Customer Experience
Frontend Modernization
Unit Testing

‘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.

PublishesWeeklyEpisodes166Founded3 years ago
Number of ListenersCategory
Technology

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Artwork for Never Rewrite: Software Engineering & AI Coding

Latest Episodes

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.

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... more

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... more

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 effecti... more

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Recent Guests

Sophia Rosa
Transformational expert, change practitioner, mindfulness facilitator
Episode: Episode 147: Managing Organizational Change ft. Sophia Rosa
Dustin Rea
Guest discussing AI and development workflows
Episode: Episode 140: Evolving Past Boomer AI
Mark Mandau
Special guest from Mandau Executives
Mandau Executives
Episode: Episode 139: Rewrites - A Failure of the Imagination ft. Mark Mandau
Thomas Morris
Episode: Episode 134: A Stream of Consciousness Chat on AI, Tech, & Layoffs
Austen Tucker
Guest facilitator focusing on communication gaps in tech teams
ActiveCampaign (mentioned)
Episode: Episode 124: Treating Communication Gaps Like Tech Debt ft. Austen Tucker
Day Martin
Founder of Swayday
Swayday
Episode: Episode 119: Iterating, Adapting, & Pivoting ft. Day Martin
Spriha Tucker
Field CTO at BuildKite
BuildKite
Episode: Episode 115: [CI/CD] Beautiful Feedback Loops with guest Spriha Tucker
Dan Hon
CEO of Very Little Gravitas, a government consultancy specializing in digital modernization.
Very Little Gravitas
Episode: Episode 99: DOGE Pt. 2: Government Rewrites with Guest Dan Hon
Rob Gonnella
Software engineer with experience in testing infrastructure changes
Episode: Episode 96: Inverting the Testing Pyramid - Testing Infrastructure Changes ft. Rob Gonnella

Hosts

Isaac Askew
Host of the show; frequent contributor with deep involvement in software architecture, AI experimentation, and modernization discussions.
Jeffrey Sherman
Co-host with a focus on pragmatism in engineering, product-technical interfaces, and team dynamics.
Dustin Rea
Host/Co-host contributing to discussions on modernization, rewrite strategies, and AI-assisted workflows.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#147
Philippines/Technology

Talking Points

Recent interactions between the hosts and their guests.

Episode 124: Treating Communication Gaps Like Tech Debt ft. Austen Tucker
Q: What is the role of a facilitator in closing these gaps without triggering a rewrite frenzy?
Act as relief rather than authority, surface the gap through collaborative exercises, and use techniques like prototyping and cognitive-load-aware workflows to align on a shared model before any major changes.
Episode 124: Treating Communication Gaps Like Tech Debt ft. Austen Tucker
Q: How do you identify a communication gap in a codebase or project team?
Listen for phrases that indicate unspoken expectations or disconnects, such as 'I didn't know that' or 'we can do that,' and look for friction in the team; these are signs of past unmet expectations that will reoccur if not addressed.
Episode 119: Iterating, Adapting, & Pivoting ft. Day Martin
Q: For the original idea, what led you to build the initial version and pursue iteration instead of a full rewrite?
I believed in the idea and listened to feedback from others who saw potential in it for someone else; meanwhile, I kept the MVP lean and used iterations to test market fit, which eventually led to pivoting toward a child-focused, educational direction.
Episode 115: [CI/CD] Beautiful Feedback Loops with guest Spriha Tucker
Q: Can you share a story where you determined a customer wasn't the right fit for BuildKite, and what did you do about it?
A senior exec was considering a complex, architectural rewrite using cattle-style deployment strategies; after probing, it became clear the company didn't need that level of change yet, so BuildKite stayed in touch and revisited later when it aligned with the customer's priorities, ultimately delivering value when the time was right.
Episode 115: [CI/CD] Beautiful Feedback Loops with guest Spriha Tucker
Q: What is the biggest blocker you run into in day-to-day feedback loops?
The biggest blocker is scaling the field engineering effort—the right mix of technical and customer-facing skills is hard to staff, and without enough bridges between teams, feedback moves too slowly through the organization.

Audience Metrics

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Frequently Asked Questions About This Podcast

What is This Podcast about and what kind of topics does it cover?

A tech-focused conversation series centered on practical software engineering, architecture, and organizational questions around rewriting, modernization, and AI-assisted development. Across episodes, hosts dissect where rewrites make sense, how AI tools reshape coding practices and collaboration, and the social dynamics that influence delivery, testing, and product ownership. The banter is hardware-leaning but grounded in real-world anecdotes, with recurring themes around avoiding all-or-nothing rewrites, incremental value delivery, and balancing speed with reliability. Noteworthy traits include a strong stance against magical AI shortcuts, a willingness to critique legacy code without abandoning the goal of progressive improvement, and th... more

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this podcast launched 3 years ago and published 166 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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Recent guests on this podcast include:

1. Sophia Rosa
2. Dustin Rea
3. Mark Mandau
4. Thomas Morris
5. Austen Tucker
6. Day Martin
7. Spriha Tucker
8. Dan Hon

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