

Never Rewrite
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.
It’s not unfixable, and we explore how to get started along with an array of other software topics in our eponymous podcast.
Episodes
Mentioned books

May 23, 2025 • 42min
Episode 105: A Core Engine Rewrite with Nick Gerace
Guest Nick Gerace discusses the rewrite of the core engine at System Initiatives, detailing the challenges faced, the technical decisions made, and the importance of aligning development with business goals. The conversation covers the transition from the old engine to the new, the role of user feedback, and the iterative process that led to a more efficient and user-friendly product.Show Notes:Domain-Driven Design book: https://www.oreilly.com/library/view/domain-driven-design-tackling/0321125215/Nick's LinkedIn: https://www.linkedin.com/in/nickgerace/

May 16, 2025 • 34min
Episode 104: An Infrastructure Rewrite Story with Guest Paul Stack
Guest Paul Stack shares his experiences in transforming a massive logging infrastructure from a monolithic architecture to a microservices-based system. He discusses the challenges faced during the transition, the implementation of Kafka for log management, and the importance of data retention and cost management. The conversation highlights the evolution of logging practices and the empowerment of teams through decentralization, ultimately leading to a more efficient and effective infrastructure.Show Notes:Paul's LinkedIn: https://www.linkedin.com/in/stack72/Paul's Github: https://github.com/stack72

May 9, 2025 • 21min
Episode 103: Recognizing When a Rewrite is Failing
Isaac and Jeffrey discuss the challenges and signs of failing rewrites in software development.

May 2, 2025 • 26min
Episode 102: Rewrite Stories with Guest Nick Stinemates
Nick Stinemates from System Initiative joins us to explore the complexities and challenges of software rewrites. We discuss the nuances between rewrites and refactors, the pitfalls of full rewrites, and the importance of incremental changes. The conversation delves into team dynamics during rewrites, the existential reasons that can drive a rewrite, and the parallels between software rewrites and software adoption.Show Notes:Nick's X account: https://x.com/nickstinemates

Apr 25, 2025 • 16min
Episode 101: Relief vs. Cure
Jeffrey and Isaac explore the complex trade-off between providing immediate relief for software issues versus investing time and resources into finding a permanent cure. They discuss the implications of these choices on customer satisfaction, business budgets, and the overall health of software systems. Through real-world examples, they illustrate how sometimes quick fixes can be more practical than ideal solutions, emphasizing the importance of understanding the context and priorities of a business.

Apr 18, 2025 • 30min
Episode 100: Detecting B.S. as a Non-Technical Founder
Isaac, Dustin, and Jeffrey discuss the challenges faced by non-technical founders when working with developers. They explore issues of trust, communication, and the importance of iterative development. The discussion emphasizes the need for clear frameworks in product development, the significance of addressing technical debt and security concerns, and how to identify red flags in developer behavior. The conversation concludes with advice on balancing survival and enhancement in development and the importance of having technical expertise in-house.

Apr 11, 2025 • 37min
Episode 99: DOGE Pt. 2: Government Rewrites with Guest Dan Hon
Guest Dan Hon discusses the complexities and risks associated with rewriting government software, particularly in the context of social security systems. He emphasizes the importance of understanding legacy systems, the role of ideology in software development, and the need for transparency and user-centered design. The discussion also touches on lessons learned from the private sector and the challenges of modernization in government services.Show Notes:Dan's LinkedIn: https://www.linkedin.com/in/danhon/Dan's Newsletter: newsletter.danhon.com/ Reference to Jamie Zawinski: https://www.jwz.org/gruntle/nomo.htmlOriginal Wired.com article: https://www.wired.com/story/doge-rebuild-social-security-administration-cobol-benefits/

Apr 4, 2025 • 33min
Episode 98: DOGE's Social Security Rewrite - Killing Americans to Save Money
Isaac Askew and Jeffrey Sherman discuss DOGE's proposed rewrite of the Social Security system, focusing on the implications of transitioning from COBOL to a modern programming language like Java. They explore the motivations behind the rewrite, the challenges of legacy code, the potential role of AI, and the human cost of possible failures. The conversation culminates in predictions about the outcome of the rewrite and the impact on millions of Americans relying on Social Security.Show Notes:Wired Magazine article referenced: https://www.wired.com/story/doge-rebuild-social-security-administration-cobol-benefits/

Mar 28, 2025 • 18min
Episode 97: Fulfilling Friday - A Tattoo Scam?
Isaac tells a 'fulfilling Friday' story about how he gained the attention of a famous tattoo artist. He just needed to act quickly and send money to secure the appointment...

Mar 21, 2025 • 17min
Episode 96: Inverting the Testing Pyramid - Testing Infrastructure Changes ft. Rob Gonnella
Isaac Askew and Jeffrey Sherman discuss the complexities of testing infrastructure changes with guest Rob Gonnella. They explore the importance of building a robust testing infrastructure, the role of different types of tests, and the challenges faced when transitioning to new systems. Rob shares his experiences in developing local testing environments, engaging developers, and identifying bugs through end-to-end tests. The conversation emphasizes the need for a balanced approach to testing, particularly when making significant infrastructure changes.