Never Rewrite

Isaac Askew and Jeffrey Sherman
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Jan 30, 2026 • 14min

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
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Jan 23, 2026 • 35min

Episode 140: Evolving Past Boomer AI

SummaryIn 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.
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Jan 16, 2026 • 34min

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.
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Jan 9, 2026 • 21min

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.
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Jan 2, 2026 • 23min

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.
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Dec 26, 2025 • 14min

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.
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Dec 19, 2025 • 50min

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.
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Dec 12, 2025 • 24min

Episode 134: A Stream of Consciousness Chat on AI, Tech, & Layoffs

Jeffrey is out today, so we're joined by guest Thomas Morris to have a fun stream-of-consciousness style chat on what's on his mind these days.
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Dec 5, 2025 • 15min

Episode 133: The Consequences of Having Multiple Sources of Truth

Isaac Askew and Jeffrey Sherman discuss a humorous yet insightful story about the challenges of managing market data in financial systems, particularly focusing on the consequences of having multiple sources of truth. They explore the technical aspects of market data protocols, the issues arising from unsequenced messages, and the eventual solutions implemented to address these problems. The conversation highlights the importance of data integrity and the lessons learned from software bugs in trading systems.
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Nov 28, 2025 • 7min

Episode 132: A Thankful Thanksgiving Episode

Happy Thanksgiving everybody!

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