Isaac Askew and Jeffrey Sherman
Never Rewrite: Software Engineering & AI Coding
‘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.
Author
Isaac Askew and Jeffrey Sherman
Category
Podcast website
Latest episode
Jul 10, 2026
Where to listen?
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Episodes
Episode Thirteen - Transitioning from Microservices to Monolith with Josh Beckman 14.06.2023 44:14
Josh Beckman is our guest in this episode where we talk about his experience in successfully transitioning multiple micro services back into a monolith - and why it was the right decision.
Episode Twelve - Company Culture Pt. 2 with Thomas Morris 07.06.2023 41:00
In this episode we re-visit the talks about company culture, this time with guest speaker Thomas Morris.
Episode Eleven - You Can’t Build to Spec 01.06.2023 25:18
In this episode Jeffrey talks about an old manager who never seemed to be content with his deliverables, even if he met the acceptance criteria exactly. Isaac adds more to the conversation around managers that are too strict versus managers that are too aloof.
Episode Ten - The Rewrite Cycle 24.05.2023 26:07
In this episode Jeffrey and Isaac discuss the common phases of a rewrite cycle, and how iteration eliminates complexity.
Episode Nine (F*ck-Up Friday Series) - How Our Customers Got Raided by the FBI 19.05.2023 26:47
In Episode 9 we start our first of many 'F*ck-up Fridays', where we talk about an interesting or crazy thing that has happened to a company we've worked at. Today Isaac talks about an early startup he worked for that ultimately failed after its customers were raided by the FBI.
Episode Eight - Transforming your Internal Software into a SaaS with Brian Begy 11.05.2023 31:34
Brian Begy is a guest in this week's episode. Brian shares his experience with companies that have attempted to transform software built for internal processes to using and selling it as a service.
Episode Seven - Risk 03.05.2023 20:32
Jeffrey brings up the concept of risk in this episode, tying it back to our previous conversation with guests Nathan Keyes and Colleen Grafton in Episode 4 where we discussed their project 'Nozomi'.
Episode Six - How Company Culture Makes Or Breaks Your Team 27.04.2023 51:16
In this episode Isaac and Jeffrey discuss patterns they've seen in both highly performant and poorly-performing teams - how team culture is shaped, how overall company culture helps shape it, and why trust is one of the most important drivers of great teams.
Episode Five - Perverse Incentives 19.04.2023 19:05
Jeffrey introduces the concept of 'perverse incentives' for rewriting - reasons for rewriting that are pushed not for a better product or for the customer, but for the benefit of the engineer or the manager responsible for the project.
Episode Four - Nozomi 13.04.2023 44:53
In this episode Isaac and Jeffrey invite Colleen Grafton and Nathan Keyes to talk about a shared experience of a rewrite gone wrong - and what to learn from it.
Episode Three - Why You Hate Testing 08.04.2023 29:55
In this episode Isaac talks about his early experience understanding the importance of testing, and reflects on three distinct reasons why testing seems to be hated by developers.
Episode Two - Iteratively Replace 22.03.2023 16:19
In this episode we provide an alternative to rewriting a codebase from scratch: iteratively replacing bits of functionality over time.
Episode One 16.03.2023 24:14
In our pilot episode of “Never Rewrite”, we discuss what we mean when we tell developers to never rewrite code. Isaac reflects on what drives engineers to rewrite, and Jeffrey adds some real-world analogies involving baseball and New York stadiums.
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