Never Rewrite

In this episode, Jeffrey Sherman and Isaac Askew explore how AI can monitor release processes by analyzing error logs, detecting anomalies, and improving deployment confidence. They discuss practical tools, strategies, and the potential for automation in system monitoring.

Jeffrey Sherman shares his experience using AI to accelerate a 10-year API rewrite, highlighting practical strategies, challenges, and insights into modern development practices.Co-host: Isaac AskewGuests: Dustin Rea

Today we're joined by Ravi Ram, a kindred refactoring spirit. Ravi joins us today to discuss his approach to refactoring and how he leverages AI effectively to dramatically reduce the time it takes to implement refactors and fixes for his clients.Ravi Ram  |  [email protected]://www.linkedin.com/in/dhali/-------------------------------------Dhali30211 Avenida de las Bandera, STE 200Rancho Santa Margarita, CA 92688References:Practical RefactoringWoody Zuill | Llewellyn Falcohttps://www.youtube.com/watch?v=aWiwDdx_rdoSandi Metz' Rules For Developershttps://thoughtbot.com/blog/sandi-metz-rules-for-developers(Book) Tidy First: A Personal Exercise in Empirical Software DesignKent Beck

Jeffrey Sherman discusses using AI to complete a decade-long API rewrite, focusing on strategies for parity, documentation, testing, and migration. This episode offers insights into managing legacy systems and leveraging AI for efficient software development.

This episode explores the evolving practices of code review in the age of AI, focusing on the size of pull requests, the role of human oversight, and how AI tools like Claude are transforming development workflows.Features Jeffrey Sherman, Isaac Askew, and Dustin Rea.

In this episode, Jeffrey Sherman shares insights on how AI can optimize legacy code testing, improve build times, and address the challenges of organic codebases. Discover practical strategies and the importance of conventions in maintaining reliable tests.

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 app, and the implications of AI-driven, ephemeral solutions.

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 an AI-driven world.

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 effectively while avoiding common pitfalls like feature bloat and misaligned objectives.

In this episode, Jeffrey Sherman and Isaac Askew explore the nuances of rewriting, rebuilding, and iteratively shipping software. They clarify common terminology, share practical insights, and emphasize the importance of safe, incremental delivery.

In this episode, Isaac and Jeffrey explore how reputation is becoming the new barrier to entry in a world flooded with AI-generated content, apps, and information. They discuss the importance of genuine trust, the pitfalls of vibe coding, and how real reputation emerges through solving real problems.

In this episode, Jeffrey Sherman and Isaac Askew explore how to extend the philosophy of shipping solutions beyond the tech stack, focusing on real-world stories of identifying friction and automating processes to improve outcomes across organizations.

Isaac Askew, Jeffrey Sherman, and Dustin Rea explore the impact of vibe coding on software development, maintenance, and industry practices. The conversation covers real-world experiences, risks, and the future of AI-assisted coding.

Jeffrey Sherman and Isaac Askew explore the pitfalls of token-based billing models, comparing them to hourly billing and value-based billing. They discuss how these models create adversarial relationships, obscure true costs, and impact incentives for vendors and users alike.

Today we're exploring the story of John Henry as a metaphor for the modern struggle between human labor and automation. The conversation delves into the dignity of work, the impact of AI on jobs, and how to adapt to technological change.

Jeffrey Sherman and Isaac Askew discuss the realities of AI in software modernization, emphasizing that AI accelerates but does not eliminate manual testing and manual work in legacy code projects.

Isaac Askew, Jeffrey Sherman, and Dustin Rea how agentic AI development is transforming developer roles, emphasizing empathy, tight iteration, and legacy code management.

Jeffrey Sherman and Isaac Askew discuss the pitfalls of aiming for feature parity during software rewrites, emphasizing the importance of communication, boundaries, and incremental improvements over blind feature replication.

Isaac and Jeffrey explore the pitfalls of rewrites in software development, including the trap of delayed risk, sunk cost fallacy, and human psychology. Learn strategies to avoid costly rewrites and focus on incremental delivery and early feedback.

Isaac Askew and Jeffrey Sherman explore how the metaphor of moving houses relates to software rewrites, and how AI can revolutionize the process of packing, unpacking, and deciding what to keep in tech projects.

Jeffrey Sherman and Isaac Askew explore the importance of celebrating small wins in iterative projects, how to track progress effectively, and ways to keep team morale high through accountability and customer feedback.

In this episode, Isaac Askew and Jeffrey Sherman explore the evolving landscape of software development, focusing on the relevance of rewrites in the age of AI. They discuss how AI tools like Claude are transforming engineering workflows, reducing the need for full rewrites, and shifting bottlenecks towards product management.

Isaac Askew shares his journey of building a hyperlocal event aggregator using AI, exploring the technical challenges, tools, and lessons learned along the way. Discover how modern AI workflows can rapidly prototype and deploy complex projects without traditional coding.

Exploring the intersection of creativity, taste, and technical skill in software engineering, inspired by Rick Rubin's quote. Discussing how AI and human intuition shape the future of product design and development.

Sophia Rosa, a transformational expert, shares insights on managing organizational change, especially in technology implementations like ERP systems. Topics include assessing readiness, building trust, effective communication, and the role of mindfulness in change management.

Isaac Askew and Dustin Rea discuss how AI is transforming careers, workflows, and organizational practices.

Isaac Askew, Dustin Rea, and Jeffrey Sherman discuss the past challenges of browser compatibility. They reflect on the significant time spent in the past ensuring websites functioned uniformly across different browsers, a task that has become less prominent in modern development.

Isaac Askew, Dustin Rea, and Jeffrey Sherman discuss the outdated programming technique of bit masking, exploring its historical context, current relevance, and the cognitive load it imposes on developers. They emphasize that while bit masking may still have niche applications in high-frequency trading, the general trend in software development has shifted towards prioritizing engineering time and maintainability over micro-optimizations. The discussion highlights the importance of understanding when efficiency is truly necessary and when it can be sacrificed for better clarity and ease of development.

Isaac Askew and Jeffrey Sherman discuss tactics used in project management to obscure the true state of projects, especially when they are not going well. They explore the shift from deliverables to phases, the focus on work instead of outcomes, and strategies to bring clarity and accountability back into project management through naming conventions and demos.

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

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

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.

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.

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.

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.

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.

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.

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.

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.

Happy Thanksgiving everybody!

Isaac Askew and Jeffrey Sherman engage with Mark Mandau, a principal consultant, to explore the complexities surrounding software rewrites. They discuss the dual perspectives of engineering and business, highlighting case studies like Facebook and Sonos to illustrate the risks and challenges associated with rewrites. The conversation delves into the pitfalls of code freezes, the doom loop effect, and the importance of customer feedback. Mark introduces the 'peak fix' approach as a structured alternative to rewrites, emphasizing the need for early engagement with consultants to navigate these challenges effectively.

SummaryIn this episode of Never Rewrite, hosts Isaac Askew, Dustin Rea, and Jeffrey Sherman discuss the real-life implications of leaky abstractions in software development. They share personal anecdotes about the challenges faced when dealing with time zone discrepancies, database case sensitivity, and the importance of user experience. The conversation highlights the need for continuous investment in software and the lessons learned from past mistakes, emphasizing the balance between perfectionism and business viability.

Isaac Askew, Jeffrey Sherman, and Dustin Rea discuss the critical role of credit in management and teamwork, sharing personal experiences of idea ownership and the challenges faced in consulting environments. They emphasize the importance of recognizing contributions to foster a collaborative culture and the impact of social dynamics on idea sharing. The discussion also highlights the necessity of documenting ideas to ensure proper attribution and the broader implications of credit on team morale and organizational efficiency.

Isaac Askew and Jeffrey Sherman reflect on a past experience with a software company that made a strategic decision to extend the Objective-C compiler, ultimately leading to its downfall. They discuss the implications of this decision, the challenges faced in software development, and the lessons learned from the experience. The conversation explores the importance of making informed technology decisions, the consequences of poor project management, and the potential alternatives to rewriting software.

Isaac Askew, Dustin Rea, and Jeffrey Sherman discuss the complexities and challenges associated with abstractions in software development, particularly focusing on time zones and currency. They explore the engineering and product perspectives on these issues, emphasizing the importance of standardization to avoid costly bugs and inefficiencies. The discussion also touches on the social dynamics within teams, the exponential nature of complexity, and the need for clear documentation and communication across the organization to address these challenges effectively.

Isaac Askew and Jeffrey Sherman explore the complexities of iterative development versus complete rewrites in software engineering. They discuss the challenges of legacy frameworks, the importance of intentionality in adopting new technologies, and the necessity of communication among teams. The discussion also highlights the Strangler Fig pattern as a viable strategy for transitioning to new frameworks while maintaining existing systems. Ultimately, they conclude that iterative development does not prevent the adoption of new frameworks and can lead to better outcomes than a Big Bang rewrite.

Isaac Askew and Jeffrey Sherman discuss the complexities of working with clients who have risky software setups. They explore the importance of documentation, the risks associated with development environments, and the necessity of clear communication between consultants and clients. The discussion also highlights the need for compliance and risk management strategies, particularly in financial contexts, and emphasizes the importance of establishing a staging environment to mitigate risks.

We're joined by guest Austen Tucker to explore the concept of communication gaps in tech environments. The discussion emphasizes the importance of setting clear expectations and using pedagogical techniques to enhance collaboration.Show notes:https://www.thearcades.me/https://www.linkedin.com/newsletters/7312541452108972032/

In this conversation, Isaac Askew and Jeffrey Sherman explore the analogy of changing jobs to rewriting code, discussing the intentionality behind job changes, the impact of company culture on career growth, and the importance of aligning personal values with professional roles. They reflect on their own experiences with job transitions, the feelings of stagnation and underappreciation, and the challenges of resetting perceptions in a new role. The discussion also touches on the costs of employee turnover and the need for companies to recognize and retain valuable talent.