Never Rewrite

Isaac Askew and Jeffrey Sherman

5.0 (6)
TECHNOLOGY
UPDATED WEEKLY

‘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.

5H AGO

Episode 142: Are You Ready to Scale? A Local Case Study

In this conversation, Isaac Askew and Jeffrey Sherman discuss the challenges faced by a small business looking to scale its operations. Isaac shares insights from a recent consultation where he aimed to help a client understand their inefficiencies and explore potential solutions without immediately resorting to hiring a full-time employee. The discussion covers the importance of understanding existing systems, evaluating technology choices, and balancing short-term fixes with long-term strategies. The conversation emphasizes a consultative approach that prioritizes the client's needs and the practicalities of their business environment. Book a call with us today: https://intro.co/JeffreyShermanhttps://intro.co/IsaacAskew

24 min
JAN 30

Episode 141: How Rewrites Create Accountability Black Holes

In this episode, Isaac Askew and Jeffrey Sherman discuss the phenomenon of accountability black holes created by software rewrites. They explore how the decision to rewrite can lead to neglecting existing bugs, the challenges of prioritization in development, and the implications of resource allocation. The conversation emphasizes the importance of weighing the impact of bugs against the resources available for fixing them, ultimately concluding that the decision to address bugs often depends on various factors. Book a call with us today: https://intro.co/JeffreyShermanintro.co/IsaacAskew

14 min
JAN 23

Episode 140: Evolving Past Boomer AI

Summary In this episode, Isaac Askew and Dustin Rea discuss the evolving landscape of AI in software development, focusing on the transition from traditional coding methods to more advanced, AI-driven workflows. They explore the implications of these changes on legacy systems, team dynamics, and the essential human element in technology. The conversation highlights the need for developers to adapt to new tools and processes while maintaining a focus on understanding user needs and business goals.

35 min
JAN 16

Episode 139: Rewrites - A Failure of the Imagination ft. Mark Mandau

In this episode, Isaac Askew and Jeffrey Sherman are joined by Mark Mandau to explore the complex topic of software rewrites. They discuss the reasons behind the decision to rewrite software, the implications of neglecting maintenance, and the risks associated with such a drastic move. The conversation emphasizes the importance of understanding legacy systems, the role of leadership in decision-making, and the necessity of customer feedback in product development. Mark shares insights on how to approach the topic of rewrites with stakeholders and offers advice on maintaining existing systems to avoid the pitfalls of starting anew.

34 min
JAN 9

Episode 138: The MVP Worked. Do We Rewrite It To Scale?

Isaac Askew and Jeffrey Sherman explore the complexities of rewriting a Minimum Viable Product (MVP) and whether such actions can be classified as a 'rewrite.' The conversation emphasizes the value of rewriting code that has proven to be effective and the need for new terminology in the software development community.

21 min
JAN 2

Episode 137: 2025 Year in Review

Isaac Askew and Jeffrey Sherman reflect on their podcast's achievements in 2025, discussing their goal of producing 52 episodes and analyzing listener engagement through various metrics. They explore the most popular episodes, insights from analytics, and strategies for improving content engagement. The conversation also touches on future plans for 2026, emphasizing the importance of listener interaction and feedback.

23 min
12/26/2025

Episode 136: Key Questions to Ask When Navigating Your Career

Jeffrey Sherman and Dustin Rea discuss how to navigate career development, emphasizing the importance of understanding one's career stage, exploring various career paths, and being intentional about career choices. They highlight the significance of networking, shadowing others, and maintaining a dynamic career to avoid stagnation. The conversation encourages listeners to reflect on their goals and aspirations to shape their professional journeys effectively.

14 min
12/19/2025

Episode 135: Is Changing an ERP System a Rewrite? ft. Sophia Rosa

In this episode, Sophia Rosa, a project and organizational change manager, discusses the complexities of changing an ERP system. The conversation explores the definition of ERP, the challenges of customization, the importance of change management, and the need for user adoption and training. Sophia emphasizes the significance of communication from project sponsors and the role of mindfulness in managing change. The discussion also highlights the necessity of mock cutovers and the potential resistance to change from users, concluding with insights on how to navigate these challenges effectively.

50 min

5

out of 5

6 Ratings

‘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.

Creator

Isaac Askew and Jeffrey Sherman
Years Active

2023 - 2026
Episodes

142
Rating

Clean
Copyright

© 2026 Isaac Askew and Jeffrey Sherman
Show Website

Never Rewrite