Never Rewrite

Episode 153: The Rewrite Trap & Sunk Cost Fallacy

Isaac Askew and Jeffrey Sherman — Fri, 24 Apr 2026 13:00:00 GMT

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.

Episode 152: The Moving House Metaphor for Software Rewrites: How AI Changes the Game

Isaac Askew and Jeffrey Sherman — Fri, 17 Apr 2026 13:00:00 GMT

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.

Episode 151: Celebrating Wins During Constant Iteration

Isaac Askew and Jeffrey Sherman — Fri, 10 Apr 2026 13:00:00 GMT

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.

Episode 150: The AI Rewrite Trap

Isaac Askew and Jeffrey Sherman — Fri, 03 Apr 2026 13:00:00 GMT

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.

Episode 149: Isaac Does a Rewrite?

Isaac Askew and Jeffrey Sherman — Fri, 27 Mar 2026 04:25:01 GMT

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.

Episode 148: How Human Taste Shapes the Future of AI and Coding

Isaac Askew and Jeffrey Sherman — Fri, 20 Mar 2026 15:47:41 GMT

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.

Episode 147: Managing Organizational Change ft. Sophia Rosa

Isaac Askew and Jeffrey Sherman — Fri, 13 Mar 2026 13:00:00 GMT

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.

Episode 146: How AI is Reshaping Careers and Workflows

Isaac Askew and Jeffrey Sherman — Fri, 06 Mar 2026 20:00:00 GMT

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

Episode 145: Outdated Programming Techniques: Browser Compatibility

Isaac Askew and Jeffrey Sherman — Fri, 27 Feb 2026 14:00:00 GMT

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.

Episode 144: Outdated Programming Techniques: Bit Masking

Isaac Askew and Jeffrey Sherman — Fri, 20 Feb 2026 14:00:00 GMT

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.

Episode 143: Tactics to Obscure (Parody)

Isaac Askew and Jeffrey Sherman — Fri, 13 Feb 2026 14:00:00 GMT

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.

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

Isaac Askew and Jeffrey Sherman — Fri, 06 Feb 2026 14:00:00 GMT

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/JeffreySherman
https://intro.co/IsaacAskew

Episode 141: How Rewrites Create Accountability Black Holes

Isaac Askew and Jeffrey Sherman — Fri, 30 Jan 2026 14:00:00 GMT

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/JeffreySherman
intro.co/IsaacAskew

Episode 140: Evolving Past Boomer AI

Isaac Askew and Jeffrey Sherman — Fri, 23 Jan 2026 15:00:00 GMT

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.

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

Isaac Askew and Jeffrey Sherman — Fri, 16 Jan 2026 14:00:00 GMT

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.

Episode 98: DOGE's Social Security Rewrite - Killing Americans to Save Money

Isaac Askew and Jeffrey Sherman — Fri, 04 Apr 2025 13:00:00 GMT

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/

Episode 59: The Myth of the Boy Scout Rule

Isaac Askew and Jeffrey Sherman — Fri, 28 Jun 2024 13:00:00 GMT

Isaac and Jeffrey discuss the myth of the Boy Scout rule, which is the idea of leaving code better than you found it. Isaac shares his experience of encountering problems when trying to follow this rule in a codebase with no test coverage. He explains how fixing one issue led to unintended consequences and a cascade of errors. They emphasize the importance of being cautious when making changes in old and tightly coupled code and the need for thorough testing. They conclude that while refactoring is important, it should be done intentionally and not mixed with other changes.

Episode 34: (F*ck-Up Friday Series) Don’t Fix What Ain’t Broken

Isaac Askew and Jeffrey Sherman — Fri, 29 Dec 2023 14:00:00 GMT

Continuing our F*ck-Up Friday series, Jeffrey has another humorous story where he went out of his way to fix functionality to match the name of its function...with expensive results.

Episode Six - How Company Culture Makes Or Breaks Your Team

Isaac Askew and Jeffrey Sherman — Thu, 27 Apr 2023 15:57:20 GMT

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 55: Writing Your Job Out Of Existence

Isaac Askew and Jeffrey Sherman — Fri, 24 May 2024 13:00:00 GMT

Isaac and Jeffrey discuss the mindset of writing your job out of existence. They explore the idea that being irreplaceable can be a trap and that making your current role disappear in a positive way is the key to career growth. They share examples of individuals who get stuck in repetitive tasks and fail to see the opportunity to transform their work. The conversation highlights the importance of reframing problems as opportunities for improvement and the need to overcome the fear of change. They also touch on the issue of intentionally not fixing problems to protect one's job.

Episode 123: Is Switching Jobs a Career 'Rewrite'?

Isaac Askew and Jeffrey Sherman — Fri, 26 Sep 2025 13:00:00 GMT

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.

Episode 120: Bad Testing & Release Practices Are Cultural Problems, Not Technical Problems

Isaac Askew and Jeffrey Sherman — Fri, 05 Sep 2025 13:00:00 GMT

Today we discuss the cultural implications of testing and release practices in software development, emphasizing that these issues are often rooted in organizational culture rather than technical challenges. We explore the transition from startup mentality to a more structured approach as businesses grow, the fragility of early successes, and the importance of quality over speed in releases. The discussion also highlights the role of leadership in fostering a culture of accountability and continuous improvement, as well as the need for developers to take ownership of their code.

Episode 51: How Company Culture Impacts Code Delivery

Isaac Askew and Jeffrey Sherman — Fri, 26 Apr 2024 13:00:00 GMT

Company culture can have a significant impact on the style of code delivery. A rigid and bottlenecked code review process can slow down code delivery and create frustration. On the other hand, a collaborative and open culture can lead to faster and more efficient code delivery. It is important to strike a balance between code quality and speed of delivery. Perfect code that doesn't solve the problem is not useful, while imperfect code that is easy to change and improve can be valuable. When considering a job, it is important to ask about the company's code delivery style and whether there is a culture of collaboration and openness.

Episode 75: Rewriting is Gambling - A Lesson in Risk

Isaac Askew and Jeffrey Sherman — Fri, 25 Oct 2024 13:00:00 GMT

Jeffrey and Isaac discuss the inherent risks associated with software rewrites, emphasizing how rewrites push risk to the end of the development cycle. The discussion highlights the need for iterative development and the significance of delivering independent components to ensure project success, particularly within the SaaS model, which thrives on continuous improvement and customer satisfaction.

Episode 73: The Politics of Delivering Trivial Changes

Isaac Askew and Jeffrey Sherman — Fri, 11 Oct 2024 13:00:00 GMT

Isaac and Jeffrey discuss the philosophy of continuous iteration in software development, emphasizing the importance of making small, incremental changes rather than large, risky updates. They explore the challenges of communicating the value of these trivial changes to non-technical stakeholders and the benefits of refactoring code for future development. The discussion also highlights the significance of storytelling in conveying the purpose and impact of these changes to a broader audience.

Episode 52: The Two-Clock Problem

Isaac Askew and Jeffrey Sherman — Fri, 03 May 2024 13:00:00 GMT

Isaac and Jeffrey discuss the 'two clock problem' as a metaphor for software rewrites. They explain that adding a new system doesn't improve understanding if you don't know how the current system is wrong. They also emphasize that rewriting a system without understanding the current system is costly and may not be worth it. Instead, they suggest spending more time understanding and documenting the current system to mitigate the need for a rewrite.

Episode Five - Perverse Incentives

Isaac Askew and Jeffrey Sherman — Wed, 19 Apr 2023 18:15:21 GMT

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

Isaac Askew and Jeffrey Sherman — Fri, 12 Dec 2025 14:00:00 GMT

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.

Episode 131: Rewrites from a Product Perspective ft. Mark Mandau

Isaac Askew and Jeffrey Sherman — Fri, 21 Nov 2025 14:00:00 GMT

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.

Episode 94: What Did You Think You Were Saying Yes To?

Isaac Askew and Jeffrey Sherman — Fri, 07 Mar 2025 14:00:00 GMT

Jeffrey and Isaac explore the motivations and expectations surrounding software rewrites from various stakeholders, including developers, IT leadership, product groups, marketing, finance, support, and customers. They discuss the perceived benefits and the reality of rewrites, emphasizing that while many believe rewrites will lead to improved reliability and a better work environment, the truth is that rewrites often fail to deliver on these promises.

Episode 125: Navigating Risky Software Setups

Isaac Askew and Jeffrey Sherman — Fri, 10 Oct 2025 13:00:00 GMT

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.

Episode 29: (F*ck-Up Friday Series) The Saleswoman Who Faked Cancer

Isaac Askew and Jeffrey Sherman — Fri, 24 Nov 2023 14:00:00 GMT

A non technical story of deception, good deeds with terrible consequences, and weak HR.

Episode 91: Pushing Pain to Users

Isaac Askew and Jeffrey Sherman — Fri, 14 Feb 2025 14:00:00 GMT

Isaac Askew and Jeffrey Sherman discuss the implications of externalizing costs in software development, particularly the consequences of pushing pain to users. They explore the differences between internal and external software, the importance of customer experience, and the cost of support when users face difficulties. The discussion highlights the ethical considerations of prioritizing features over user satisfaction and the long-term impact on both customers and developers.

Episode 107: Rebuilding vs. Rewriting vs. Refactoring?

Isaac Askew and Jeffrey Sherman — Fri, 06 Jun 2025 13:00:00 GMT

Jeffrey and Isaac dive into a comment made by Allen Holub to 'rebuild' instead of 'rewriting' legacy software and dive into the terminology.

Show Notes:‪

Allen Holub's thread mentioned: https://bsky.app/profile/allenholub.bsky.social/post/3lmcyvi3kag2f

Episode Four - Nozomi

Isaac Askew and Jeffrey Sherman — Thu, 13 Apr 2023 03:53:36 GMT

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 128: Revisiting An Old Story With Our Current Experience

Isaac Askew and Jeffrey Sherman — Fri, 31 Oct 2025 13:00:00 GMT

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.

Episode 93: How to Put Work Down When Priorities Change

Isaac Askew and Jeffrey Sherman — Fri, 28 Feb 2025 14:00:00 GMT

Isaac and Jeffrey discuss the complexities of managing work priorities in a constantly changing environment. They explore the challenges of putting work down when priorities shift, emphasizing the importance of iterative development and smaller work increments to minimize risk and maintain productivity. The discussion also touches on the balance between delivering features and building trust with users, particularly in the context of product releases that may impact customer satisfaction.

Episode 92: A Framework for Prioritizing Tech Debt ft. Dustin Rea

Isaac Askew and Jeffrey Sherman — Fri, 21 Feb 2025 14:00:00 GMT

We're joined today by Dustin Rea to discuss frameworks for prioritizing technical debt in software development. We explore the 'Jobs to Be Done' framework, emphasizing the importance of aligning engineering and product teams on customer needs. The conversation covers strategies for managing tech debt effectively, the significance of team dynamics, and the role of technical leadership in guiding prioritization efforts.

Episode 82: Can You Like Tests And Also Believe You're Faster Without Them?

Isaac Askew and Jeffrey Sherman — Fri, 13 Dec 2024 15:57:13 GMT

Isaac and Jeffrey discuss the balance between unit testing and the need for speed in software development. The discussion delves into the contexts in which testing is most valuable, the challenges of rapid development, and real-world examples of testing practices. Ultimately, they emphasize the importance of adapting testing strategies based on the specific project and team dynamics.

Episode 136: Key Questions to Ask When Navigating Your Career

Isaac Askew and Jeffrey Sherman — Fri, 26 Dec 2025 14:00:00 GMT

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.

Episode 96: Inverting the Testing Pyramid - Testing Infrastructure Changes ft. Rob Gonnella

Isaac Askew and Jeffrey Sherman — Fri, 21 Mar 2025 13:00:00 GMT

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.

Episode 70: Resource Engineering

Isaac Askew and Jeffrey Sherman — Fri, 20 Sep 2024 13:00:00 GMT

Isaac and Jeffrey delve into the concept of resource engineering, emphasizing the importance of understanding cost implications in engineering decisions. They discuss how engineers often overlook financial aspects while focusing on technical solutions, leading to potential inefficiencies. The dialogue highlights the need for engineers to have greater visibility into costs, particularly in cloud services like AWS, and how this awareness can drive better decision-making. They also explore the balance between optimizing costs and developing new features, advocating for a more business-oriented mindset among engineers to enhance overall effectiveness.

Episode 116: Inverting the Testing Pyramid Pt. 2

Isaac Askew and Jeffrey Sherman — Fri, 08 Aug 2025 13:00:00 GMT

Isaac Askew and Jeffrey Sherman discuss the ongoing debate between end-to-end tests and unit tests in software development. The discussion delves into the implications of the testing pyramid, the potential future of testing with AI, and the evolving role of product teams in the testing process. They emphasize the need for a balanced approach to testing, cautioning against over-reliance on end-to-end tests while recognizing their value in certain scenarios.

Episode 111: The Social Aspects of a Failed Rewrite

Isaac Askew and Jeffrey Sherman — Fri, 04 Jul 2025 13:00:00 GMT

Isaac Askew and Jeffrey Sherman discuss the social and emotional ramifications of failed rewrites in project management. They explore the loss of patience from leadership, the burnout experienced by teams, and the importance of taking responsibility for project outcomes. The discussion emphasizes the need for teams to salvage lessons from failures and to approach leadership with solutions rather than just problems. The conversation concludes with strategies for ensuring future success and maintaining trust within teams.

Chapters

00:00 The Impact of Failed Rewrites

03:03 Team Dynamics and Leadership Pressure

06:01 Salvaging Lessons from Failure

09:00 Taking Responsibility for Project Outcomes

12:02 Strategies for Future Success

Episode 21 - Impostor Syndrome

Isaac Askew and Jeffrey Sherman — Fri, 08 Sep 2023 01:52:48 GMT

In this episode Isaac defines impostor syndrome and ways to combat the feelings that you aren't qualified for your job.

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

Isaac Askew and Jeffrey Sherman — Fri, 19 Dec 2025 14:00:00 GMT

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.

Episode Eighteen - Strategies for Upgrading Software

Isaac Askew and Jeffrey Sherman — Sat, 12 Aug 2023 19:28:34 GMT

Isaac discusses strategies he's used to help companies upgrade their software, and Jeffrey helps distill them into a series of steps.

Episode 22: Running an Iterative Refactoring Workshop

Isaac Askew and Jeffrey Sherman — Thu, 14 Sep 2023 16:14:51 GMT

Jeffrey has been running an iterative refactoring workshop to improve his colleague’s development skills. This episode dives into how the workshop is run, what the developers get out of it, and how it directly improves the company’s codebase. If you’ve ever wanted to help your fellow developers but didn’t know how to start, this show is for you!

Episode Fourteen - How do you define ‘Minimum Viable Product’?

Isaac Askew and Jeffrey Sherman — Thu, 29 Jun 2023 15:47:28 GMT

In this episode Isaac and Jeffrey discuss the concept of a product MVP and misconceptions around what a 'minimum viable product' has to be.

Episode Twelve - Company Culture Pt. 2 with Thomas Morris

Isaac Askew and Jeffrey Sherman — Wed, 07 Jun 2023 13:00:00 GMT

In this episode we re-visit the talks about company culture, this time with guest speaker Thomas Morris.

Episode Ten - The Rewrite Cycle

Isaac Askew and Jeffrey Sherman — Wed, 24 May 2023 16:43:38 GMT

In this episode Jeffrey and Isaac discuss the common phases of a rewrite cycle, and how iteration eliminates complexity.

Episode Sixteen - Tricks to Facilitate Conversation

Isaac Askew and Jeffrey Sherman — Fri, 21 Jul 2023 21:27:03 GMT

Jeffrey suggests using a straw man to help facilitate difficult conversations about how to proceed; Isaac adds further examples and methods by which teams can generate productive conversations.

Episode Seven - Risk

Isaac Askew and Jeffrey Sherman — Wed, 03 May 2023 18:16:29 GMT

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 24: When AI Writes Your Documentation

Isaac Askew and Jeffrey Sherman — Fri, 20 Oct 2023 16:35:18 GMT

AI tools can now write your incident retrospectives. Do developers lose by not formalizing their thoughts by writing? In this episode Isaac and Jeffrey weigh the pros and cons of having AI write incident retrospectives and documentation.

Episode 35: The Subtle Art of Refusing Meetings

Isaac Askew and Jeffrey Sherman — Fri, 05 Jan 2024 14:00:00 GMT

Jeffrey & Isaac discuss methods to clear out your recurring meetings and protect your time as new meetings get added to your calendar.

Episode 87: 2025 Update - State of AI Programming

Isaac Askew and Jeffrey Sherman — Fri, 17 Jan 2025 14:00:00 GMT

In this conversation, Isaac and Jeffrey discuss the advancements of AI in coding, reflecting on its potential to replace junior developers and the evolving role of developers in the tech industry. They explore the implications of AI tools on productivity, the necessity for developers to adapt their skills, and the future landscape of software development as AI continues to improve.

Episode 115: [CI/CD] Beautiful Feedback Loops with guest Spriha Tucker

Isaac Askew and Jeffrey Sherman — Fri, 01 Aug 2025 13:00:00 GMT

In this episode of Never Rewrite, hosts Isaac Askew and Jeffrey Sherman engage with Spriha Tucker, the Field CTO at BuildKite, to explore the intricacies of Continuous Integration and Continuous Deployment (CI/CD). They discuss the importance of deployment in CI/CD practices, the significance of feedback loops in iterative development, and the necessity of understanding customer context for effective solutions. Spriha shares insights on the role of a Field CTO, the value of communication in development teams, and strategies for rapid prototyping. The conversation emphasizes building trust with customers and the importance of de-risking in the development process, ultimately highlighting that CI/CD is about more than just tools—it's about creating value for customers through effective collaboration and feedback.

Episode 113: Do You Want a Better Version of What You Have?

Isaac Askew and Jeffrey Sherman — Fri, 18 Jul 2025 13:00:00 GMT

In this episode of Never Rewrite, Isaac Askew and Jeffrey Sherman emphasize the importance of understanding customer needs and the risks associated with maintaining old features while developing new ones. The conversation highlights the value of iterative delivery and the significance of API versioning in ensuring a smooth transition for users. Ultimately, they advocate for a pivoting approach rather than a complete rewrite, allowing for a more adaptive and responsive development process.

(Isaac used the wrong microphone for recording and Jeffrey said nothing...)

Episode 108: Consolidating Tech Stacks - Is It Worth It?

Isaac Askew and Jeffrey Sherman — Fri, 13 Jun 2025 13:00:00 GMT

We debate the merits of consolidating technology stacks versus diversifying them. Today we explore the implications of each approach on business value, engineering efficiency, and organizational dynamics. Key points include the importance of evaluating the business value of consolidation, the impact on developer fungibility, and the balance between engineering optimization and business leverage.

Episode 37: Interview Insights - Changing the Game for Interviewers and Candidates

Isaac Askew and Jeffrey Sherman — Fri, 19 Jan 2024 14:00:00 GMT

Isaac and Jeffrey dissect the flaws in the interviewing process and offer valuable insights for both interviewers and interviewees. They discuss the broken aspects of traditional interviews, highlight the importance of resume tailoring, and share anecdotes about handling past job experiences during interviews. The episode serves as a guide for interviewers to improve the hiring process and for candidates to enhance their chances by navigating the pitfalls and maximizing opportunities.

Episode 57: White Label CRM Updates with Dustin Rea

Isaac Askew and Jeffrey Sherman — Fri, 07 Jun 2024 15:41:07 GMT

We check in with Dustin Rea, head of Red Hook Agency, to discuss where White Label CRM is with their 'turnaround story' - how they're handling 'bug hell', scaling issues, and what their trajectory is now.

Episode Eight - Transforming your Internal Software into a SaaS with Brian Begy

Isaac Askew and Jeffrey Sherman — Thu, 11 May 2023 20:13:05 GMT

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 89: How Sonos Lost $500 Million Attempting a Rewrite

Isaac Askew and Jeffrey Sherman — Fri, 31 Jan 2025 14:00:00 GMT

Isaac Askew and Jeffrey Sherman discuss the disastrous app rewrite by Sonos, exploring the technical debt, decision-making processes, and the consequences of the rewrite. They emphasize the importance of incremental updates over big bang releases and reflect on the lessons learned from this case.

Show notes:

https://www.wsj.com/tech/sonos-speakers-app-ceo-24250f2c

https://www.linkedin.com/pulse/what-happened-sonos-app-technical-analysis-andy-pennell-wigwc/

Episode 109: Conway's Law and Software Quality

Isaac Askew and Jeffrey Sherman — Fri, 20 Jun 2025 13:00:00 GMT

Today we discuss the relationship between Conway's Law and software quality, exploring how a company's structure and culture can impact code quality. We delve into the signs of a toxic culture, the consequences of a 'yes culture', and strategies for identifying and changing company culture. The conversation emphasizes the importance of communication patterns and the long-term nature of cultural transformation in organizations.

Episode 90: The Hero and the Lifeguard

Isaac Askew and Jeffrey Sherman — Fri, 07 Feb 2025 14:00:00 GMT

Isaac Askew and Jeffrey Sherman explore the dynamics between two types of developers: the 'hero' who swoops in to solve problems and the 'lifeguard' who encourages self-sufficiency. They discuss the tension that arises from these differing approaches and how to navigate conflicts between them. The conversation emphasizes the importance of balance in mentoring and the need for developers to understand when to guide and when to let others learn through experience.

Episode 105: A Core Engine Rewrite with Nick Gerace

Isaac Askew and Jeffrey Sherman — Fri, 23 May 2025 13:00:00 GMT

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/

Episode 80: What is "De-Risking"?

Isaac Askew and Jeffrey Sherman — Fri, 29 Nov 2024 14:00:00 GMT

Isaac and Jeffrey delve into the concept of de-risking in project management. They discuss the importance of iterative delivery over big bang releases, using gambling analogies to illustrate risk management strategies. The conversation emphasizes the value of decoupling projects to reduce risk and the significance of obtaining feedback early in the development process. The hosts highlight how these strategies not only mitigate risks but also provide opportunities for value delivery and informed decision-making throughout the project lifecycle.

Episode 88: Creating a Culture of Continuous Improvement with Guest Erik Enge

Isaac Askew and Jeffrey Sherman — Fri, 24 Jan 2025 14:00:00 GMT

Erik Enge, COO of Ghost, discusses the principles of creating a culture of continuous improvement within organizations. He emphasizes the importance of applying the scientific method in business, setting measurable goals, and maintaining a learning loop to reflect on outcomes. The discussion also covers the significance of collaboration within teams, the risks associated with rewriting code, and the necessity of keeping context in software development. Real-world examples illustrate how these principles can lead to better decision-making and improved outcomes.

https://www.linkedin.com/in/erikenge/

https://ghost.org/

Episode 133: The Consequences of Having Multiple Sources of Truth

Isaac Askew and Jeffrey Sherman — Fri, 05 Dec 2025 14:00:00 GMT

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.

Episode Nine (F*ck-Up Friday Series) - How Our Customers Got Raided by the FBI

Isaac Askew and Jeffrey Sherman — Fri, 19 May 2023 13:00:00 GMT

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 45 - Year In Review

Isaac Askew and Jeffrey Sherman — Fri, 15 Mar 2024 13:00:00 GMT

Isaac and Jeffrey celebrate the one-year anniversary of the podcast. They discuss the challenges of maintaining a consistent schedule and reflect on the evolution of topics covered in the past year. They also talk about running out of failure stories and the importance of finding interesting guests. The hosts discuss the concept of forcing functions for successful rewrites and the risks associated with rewrites. They also explore the idea of the Ship of Theseus and how it relates to software development. Lastly, they discuss how rewrites can discourage learning about the current system. In this episode, the hosts discuss various themes related to software development and the process of rewriting code. They emphasize the importance of the investigation process and how it can be used to improve code quality. They also discuss the benefits of tidying up code and the value of iterative workshops. The hosts highlight the importance of understanding the business side of software development and the need for developers to develop human skills in the age of AI. They also reflect on past interviews with industry experts and invite listeners to participate in future guest episodes.

Episode 68: The Fallacy of Rewriting Software to Save Money

Isaac Askew and Jeffrey Sherman — Fri, 06 Sep 2024 16:22:00 GMT

Jeffrey and Isaac discuss the fallacy of rewriting software to save money. They highlight that organizations end up running multiple systems simultaneously, resulting in increased costs. The conversation also touches on the challenges of maintaining multiple versions of a software system and the importance of continuous delivery and iteration. It concludes by emphasizing the need to prove the ability to migrate existing pages before starting a rewrite.

Episode 53: Cloud Infrastructure "Rewrites"

Isaac Askew and Jeffrey Sherman — Fri, 10 May 2024 13:00:00 GMT

Isaac and Jeffrey discuss the topic of doing full rewrites when it comes to architecture. They explore a case where a client needed to move from a single EC2 instance to a more stable system with load-balanced instances. They discuss the parallels between rewriting code and rewriting architecture, and the challenges and risks involved.

Episode 46: Workshopping Live with Dustin Rea

Isaac Askew and Jeffrey Sherman — Fri, 22 Mar 2024 13:00:00 GMT

In this conversation, Dustin Rea discusses the challenges faced by one of his clients who has a CRM. The CRM is built on a legacy codebase with issues in quality, scalability, and deliverability. The team has been working on improving the system, but there are still problems with emails, SMS, payments, and automations. The company is mission-driven and relies on the CRM to run their business, so rebuilding customer trust is crucial. They have made some improvements in infrastructure and email deliverability, but there is still work to be done. The conversation covered several topics related to database architecture and system design. The main themes include database optimization, handling heavy reads and writes, improving error handling and incident response, and enhancing observability. The speakers discussed the need for a purpose-driven database, implementing caching with Redis, tracking heavy queries, and addressing inconsistencies in the email service. They also mentioned the importance of logging and monitoring tools like Sentry and Grafana. Overall, the conversation highlighted the challenges and potential solutions for improving the performance and reliability of the system.

Episode 32: Getting Started with Brownfield Testing (Part 2)

Isaac Askew and Jeffrey Sherman — Fri, 15 Dec 2023 14:00:00 GMT

Isaac and Jeffrey continue discussions around testing brownfield code, delving deeper into next steps and refactoring.Our ‘FlowSheet’ guide to help you with your testing and refactoring decisions: https://images.squarespace-cdn.com/content/v1/64127dab7e53173c1e7c39a1/9d699636-4625-4fc3-862c-a66907fd47dc/Getting+Started+With+Brownfield+Code.png?format=2500w

Episode 60: Anybody Could Have Done It...But I Actually Did

Isaac Askew and Jeffrey Sherman — Fri, 05 Jul 2024 13:00:00 GMT

Isaac and Jeffrey discuss the feeling of anyone being able to make small, simple changes in code and question the value of their own contributions. They share anecdotes of fixing issues that others could have easily addressed but didn't, highlighting the importance of being the one to take action. They emphasize the value of iterative changes and the knowledge work involved in understanding the system. They also encourage developers to listen to complaints and pain points in order to identify opportunities for impactful improvements.

Episode 106: How to Stop a Rewrite in Progress

Isaac Askew and Jeffrey Sherman — Fri, 30 May 2025 13:00:00 GMT

Isaac and Jeffrey explore how to halt a rewrite, the importance of learning from the process, and how to effectively communicate changes in direction to a team. The conversation emphasizes the value of reframing discussions around rewrites to focus on new insights and solutions rather than perceived failures.

Episode 95: We're Writing a Book!

Isaac Askew and Jeffrey Sherman — Fri, 14 Mar 2025 11:00:00 GMT

Never Rewrite is going analog! Out of 2000 minutes over the last two years we think we've got plenty of content to coalesce it into a book. If you have a rewrite story to share, now's your chance to get forever immortalized in the podcast hosted by two randos.

Episode Seventeen (F*ck-Up Friday Series) - Losing $1 billion for 4 hours

Isaac Askew and Jeffrey Sherman — Fri, 28 Jul 2023 16:33:37 GMT

In this episode Jeffrey discusses a f*ck-up of his own for this special 'F*ck-Up Friday' series - how a develop lost $1 billion (just for a little while).

Episode 58: When You Can’t Iterate

Isaac Askew and Jeffrey Sherman — Fri, 14 Jun 2024 17:00:22 GMT

Isaac and Jeffrey discuss situations where software development teams are pushed to have fewer, larger releases. They highlight the challenges of big release-driven development and the need for careful planning and more QA before each release. They also explore strategies to make the problem less severe, such as minimizing the final push, using an API-first strategy, and feature flagging.

Episode 122: Providing Constructive Feedback

Isaac Askew and Jeffrey Sherman — Fri, 19 Sep 2025 13:00:00 GMT

In this episode of 'Never Rewrite', Isaac Askew and Jeffrey Sherman delve into the nuances of providing constructive feedback in software development. They discuss the importance of framing feedback in a way that encourages open communication and psychological safety, particularly when dealing with legacy code and the developers who created it. The conversation emphasizes empathy for past developers, the significance of understanding context, and the need to separate the code from the individual who wrote it. They also explore how to give feedback on UX design, highlighting the importance of assuming positive intent and understanding the constraints that may have influenced design decisions.

Episode 65: Exploring Different Perspectives on Risk with Dustin Rea

Isaac Askew and Jeffrey Sherman — Fri, 09 Aug 2024 13:00:00 GMT

Isaac, Dustin, and Jeffrey discuss different profiles for de-risking releases. They explore the perspectives of software engineers, project managers, product owners, and executives in managing risk. They debate the benefits of incremental releases versus giant functionality releases and the importance of user feedback in de-risking product changes. They also discuss the trade-offs between time, size, and change in managing risk. The conversation touches on the challenges of balancing risk and reward, the importance of lean strategies in startups, and the need to be prepared for success as well as failure.

Episode 118: Recovering Value From Failed Projects

Isaac Askew and Jeffrey Sherman — Fri, 22 Aug 2025 13:00:00 GMT

Isaac and Jeffrey discuss the challenges faced in recovering value from failed projects, particularly focusing on a specific project that was halted due to legal concerns. They explore the importance of A-B testing, the role of legal feedback, and the lessons learned from the experience. The discussion emphasizes the need for quick iterations, optimizing processes for future projects, and maintaining a positive team attitude in the face of setbacks.

Episode 79: The Toxicity of "Certainty"

Isaac Askew and Jeffrey Sherman — Fri, 22 Nov 2024 14:00:00 GMT

Isaac and Jeffrey explore the concept of certainty in software development and its potential toxicity. They discuss how certainty can lead to poor decision-making, the importance of experimentation, and the human behaviors that contribute to toxic environments. The dialogue emphasizes the need for a balance between certainty and uncertainty, particularly in leadership roles, and highlights the dangers of strong opinions that masquerade as certainty.

Episode 44 - Do More With Less

Isaac Askew and Jeffrey Sherman — Fri, 08 Mar 2024 14:00:00 GMT

Jeffrey and Isaac discuss the concept of ‘doing more with less.’ They explore the initial visceral reaction to this idea and highlight the importance of doing less of things that don't matter. The impact of layoffs and the need to work smarter, not harder, are also discussed. The hosts emphasize the value of having honest discussions and creating a culture of transparency. They caution against burnout and advocate for trimming the fat responsibly. The episode concludes with a reminder to acknowledge mistakes and continuously learn.

Episode 110: MVPs, YAGNI, and the Goldilocks Problem

Isaac Askew and Jeffrey Sherman — Fri, 27 Jun 2025 13:00:00 GMT

Isaac Askew, Dustin Rea, and Jeffrey Sherman delve into the complexities of developing Minimum Viable Products (MVPs) and the challenges of balancing simplicity with the need for future scalability. They discuss the Goldilocks problem in software development, emphasizing the importance of finding the right balance between over-engineering and under-engineering. The discussion highlights the distinction between maintainability and optionality, the significance of timing in product development, and the lessons learned from past experiences. The trio also explores the concept of gaming out scenarios to prepare for potential challenges and the importance of aligning teams to ensure a cohesive approach to development.

Episode 78: Is Frontend Modernization a Valid Reason for Rewriting?

Isaac Askew and Jeffrey Sherman — Fri, 15 Nov 2024 14:00:00 GMT

Isaac and Jeffrey discuss the validity of rewriting front-end systems for modernization. They argue against the notion that a dated front end necessitates a complete rewrite, emphasizing the importance of iterative updates and customer experience. The conversation explores the risks of big bang rewrites, the benefits of gradual improvements, and the need for design consistency while still delivering value to customers. Ultimately, they advocate for a more thoughtful approach to modernization that prioritizes user experience over aesthetic uniformity.

Episode 28: Making Non-Compatible Changes During Long-Running Upgrades

Isaac Askew and Jeffrey Sherman — Thu, 16 Nov 2023 05:35:34 GMT

Sometimes an upgrade to a new version of a framework takes weeks or even months. What do you do when you need to make changes to areas that are being affected by the upgrade?

Episode 41: Rewrites from a Manager's Perspective with Ryan Cowan

Isaac Askew and Jeffrey Sherman — Fri, 16 Feb 2024 14:00:00 GMT

In this episode, Isaac Askew interviews Ryan Cowan, a software engineering manager, about the perspective of managers on rewrites. They discuss the challenges of placating individual engineers who want to rewrite code, the role of managers in supporting engineers' ideas, and the frequency and success of large rewrites. Ryan shares a case study of data engineers rewriting a data pipeline and highlights the importance of understanding the root cause of concerns before deciding on a rewrite. They also discuss the difference between refactoring and rewriting and the expectations engineers have from their managers.

Episode 50: Fulfilling Friday - Saving Customers Millions

Isaac Askew and Jeffrey Sherman — Fri, 19 Apr 2024 13:00:00 GMT

In our new series 'fulfilling Fridays', Jeffrey shares a fulfilling software project he worked on at Guaranteed Rate, a mortgage broker company.

Episode 40: Convincing Emotionally-Committed Colleagues It's Not Worth It

Isaac Askew and Jeffrey Sherman — Fri, 09 Feb 2024 14:00:00 GMT

Isaac and Jeffrey provide strategies for working with colleagues who are emotionally committed to rewriting old and flawed code at their companies.

Episode 99: DOGE Pt. 2: Government Rewrites with Guest Dan Hon

Isaac Askew and Jeffrey Sherman — Fri, 11 Apr 2025 13:00:00 GMT

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.html

Original Wired.com article: https://www.wired.com/story/doge-rebuild-social-security-administration-cobol-benefits/

Episode 27: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 2

Isaac Askew and Jeffrey Sherman — Thu, 09 Nov 2023 15:37:30 GMT

Special Guest Aadil Farid joins us again to continue his discussion on the harsh realities he confronted when he led a team that computerized ticketing on India’s Railways in the 1980s.

Episode Fifteen - Red Flag Development Ideas

Isaac Askew and Jeffrey Sherman — Fri, 07 Jul 2023 07:14:12 GMT

In this episode Jeffrey brings up red flag development ideas that should make you second guess whether or not you're making the right decision for your product.

Episode 121: A Helpful Analogy For Understanding Legacy Code & Tech Debt

Isaac Askew and Jeffrey Sherman — Fri, 12 Sep 2025 13:00:00 GMT

Isaac Askew and Jeffrey Sherman explore the complexities of legacy code and tech debt through the analogy of construction in old houses. They discuss how unexpected issues can arise when making changes, the importance of communication between engineers and product managers, and the need for thorough investigation before committing to projects. The discussion emphasizes the significance of understanding costs and efforts involved in engineering tasks, and how to effectively convey this information to stakeholders.

Episode Eleven - You Can’t Build to Spec

Isaac Askew and Jeffrey Sherman — Thu, 01 Jun 2023 02:41:34 GMT

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 Two - Iteratively Replace

Isaac Askew and Jeffrey Sherman — Wed, 22 Mar 2023 22:26:46 GMT

In this episode we provide an alternative to rewriting a codebase from scratch: iteratively replacing bits of functionality over time.

Episode 119: Iterating, Adapting, & Pivoting ft. Day Martin

Isaac Askew and Jeffrey Sherman — Fri, 29 Aug 2025 13:00:00 GMT

In this episode, Day Martin, founder of Swayday, shares her journey from creating a standing desk company to developing motion gaming experiences aimed at improving educational outcomes for children with ADHD. The conversation explores the iterative process of game development and the importance of feedback. Day notably reuses instead of rewrites the gaming code of her pilot gaming project to pivot towards an idea with better traction.

Show Notes

Swayday: https://swayday.com/Times Tables: AR Space Game: https://apps.apple.com/az/app/times-tables-ar-space-game/id6743813232

Episode 101: Relief vs. Cure

Isaac Askew and Jeffrey Sherman — Fri, 25 Apr 2025 17:43:39 GMT

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.

Episode 126: Does Iterative Replacement Trap You In Legacy Frameworks?

Isaac Askew and Jeffrey Sherman — Fri, 17 Oct 2025 13:00:00 GMT

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.

Episode 76: Aligning Your Company Standards to its Lifecycle Phase

Isaac Askew and Jeffrey Sherman — Fri, 01 Nov 2024 13:00:00 GMT

Guest Dustin Rea joins us to discuss the importance of aligning a company's standards and processes with its lifecycle stages. The discussion covers five key phases: the MVP phase, where the foundation is built; the Product User Fit phase, focusing on understanding customer needs; the Product Market Fit phase, solidifying the offering; the Scaling Up phase, managing growth; and finally, the Multi-Product Platform phase, where companies expand their offerings. Each phase presents unique challenges and requires different approaches to maintain quality and efficiency.

Episode 25: A Rewrite Success Story with Brian Genisio from Khan Academy

Isaac Askew and Jeffrey Sherman — Thu, 26 Oct 2023 21:54:14 GMT

Special guest Brian Genisio from Khan Academy joins us to talk about their 3.5 year rewrite that successfully wrapped up this year. Learn how Brian’s team was able to achieve the nearly impossible act of successfully completing a rewrite using many of the techniques we’ve talked about in the past, plus some brand new ones! If you want to learn about what it takes to do a rewrite, buckle up!

Episode 100: Detecting B.S. as a Non-Technical Founder

Isaac Askew and Jeffrey Sherman — Fri, 18 Apr 2025 13:31:00 GMT

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.

Episode 49: Falsehoods Programmers Believe About Projects Part 2

Isaac Askew and Jeffrey Sherman — Fri, 12 Apr 2024 13:00:00 GMT

Isaac and Jeffrey discuss falsehoods that programmers believe about projects. They explore the misconception that the project will solve the stated problem, highlighting instances where the delivered software did not actually solve the problem. They also discuss the importance of understanding how the user will use the software and the need for clear communication and feedback loops to ensure that the project is on track. They emphasize that the success of a project is not solely determined by the software, but also by factors such as the alignment of project goals and the availability of resources. Overall, they highlight the need for critical thinking and continuous communication to avoid common pitfalls in project development.

Episode 61: Challenges of Multi-Product Platforms ft. Dustin Rea

Isaac Askew and Jeffrey Sherman — Fri, 12 Jul 2024 13:00:00 GMT

Dustin Rea, CEO of Red Hook Agency, discusses the challenges and considerations of bringing new products into an existing platform and splitting products within the same platform. The conversation covers topics such as authentication and authorization, merging different products onto a platform, reorganizing teams, and converting internal tools to SaaS. The speakers also touch on the importance of onboarding experiences for new and existing customers.

Episode 62: The Peculiar Failure of Correctly Predicting Problems

Isaac Askew and Jeffrey Sherman — Fri, 19 Jul 2024 13:00:00 GMT

Isaac and Jeffrey discuss the peculiar failure of correctly predicting problems. Jeffrey shares his experience of being able to accurately predict problems in projects but failing to gain traction and prevent them. They explore the importance of buy-in from leadership and the need for a collaborative engagement structure. They also discuss the role of consultants and the difference between being diagnostic and being collaborative. The conversation highlights the challenges of convincing leadership and the potential consequences of not being able to prevent problems.

Episode 63: Fulfilling Friday: SMS Spamming Saved

Isaac Askew and Jeffrey Sherman — Fri, 26 Jul 2024 13:00:00 GMT

Isaac shares a story about a project where a quick MVP was built to send text messages to users. As the project gained more partners and volume, it became clear that the system couldn't handle mass texting at scale. A small change in the architecture caused some batches of text messages to be reprocessed multiple times, resulting in some users seemingly receiving an excessive number of texts. However, through many strokes of luck, each area where duplicate texts could have been sent was saved by a downstream setting. The issue was resolved, and the team learned the importance of implementing proper safeguards and architecture.

Episode 66: Squashing the Right Bugs

Isaac Askew and Jeffrey Sherman — Fri, 23 Aug 2024 13:00:00 GMT

Isaac and Jeffrey discuss the importance of effective bug bashing and how to prioritize bug fixes. They highlight the need for categorizing bugs, understanding customer impact, and installing analytics to make informed decisions. They also emphasize the importance of writing tests and having a team member close to the customer to provide context. They recommend starting with backlog grooming and prioritization before diving into bug fixing. Overall, the conversation provides valuable insights for managers and developers dealing with bug backlogs.

Episode 36: Becoming an Expert in your Company's Business

Isaac Askew and Jeffrey Sherman — Fri, 12 Jan 2024 14:00:00 GMT

Jeffrey & Isaac discuss why understanding how your company makes money can help you build products that solve the right problems.

Episode 97: Fulfilling Friday - A Tattoo Scam?

Isaac Askew and Jeffrey Sherman — Fri, 28 Mar 2025 13:06:00 GMT

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...

Episode 23: Live Workshop with Rob Gonnella

Isaac Askew and Jeffrey Sherman — Fri, 22 Sep 2023 16:01:15 GMT

Senior DevOps Engineer Rob Gonnella joins us in this special episode to live workshop an example of a rewrite case he believes is valid.

Episode 83: The Impact of AI on Recruiting

Isaac Askew and Jeffrey Sherman — Fri, 20 Dec 2024 14:00:00 GMT

Special guest Paul Giron discusses the transformative impact of AI on recruiting and interviewing processes. He highlights the challenges faced by recruiters in adapting to AI tools, emphasizing that while AI can streamline resume sorting, it does not necessarily improve the quality of hires. The discussion also touches on the importance of understanding high performers within organizations and how structured interviewing can enhance recruitment outcomes. Ultimately, the conversation reflects on the need for organizations to invest in training recruiters to leverage AI effectively and improve hiring practices. Paul's contact information: https://www.linkedin.com/in/paulpgiron/ paul@g-techrecruitment.com

Episode 33: How to be a Terrible Teammate

Isaac Askew and Jeffrey Sherman — Fri, 22 Dec 2023 20:29:55 GMT

In this humorous holiday episode, Isaac and Jeffrey discuss ways to be the worst possible teammate in ways that won’t get you immediately terminated by HR. If you didn’t make the naughty list this year and want to lock it in next time, this episode is for you!

Episode Nineteen - The Beachhead Strategy

Isaac Askew and Jeffrey Sherman — Fri, 25 Aug 2023 01:59:38 GMT

Jeffrey identifies a strategy we employed in a previous project that helped us dramatically improve the experience of 90% of our customers without requiring a complete rewrite of an email sending engine.

Episode 30: Investing in Yourself Beyond Education

Isaac Askew and Jeffrey Sherman — Fri, 01 Dec 2023 14:00:00 GMT

Isaac and Jeffrey discuss ways to improve yourself outside of traditional means like college, courses, or reading.

Episode 130: The Pains Caused by Differing Abstractions Pt. 2 - Real World Examples

Isaac Askew and Jeffrey Sherman — Fri, 14 Nov 2025 14:00:00 GMT

Summary

In 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.

Episode 129: Credit Where Credit Is Due

Isaac Askew and Jeffrey Sherman — Fri, 07 Nov 2025 14:00:00 GMT

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.

Episode 84: The Impact of AI on Interviewing

Isaac Askew and Jeffrey Sherman — Fri, 27 Dec 2024 14:00:00 GMT

Special guest Paul Giron discusses the transformative impact of AI on the interview experience, highlighting changes in candidate assessment, the shift towards remote interviews, and the evolving expectations of candidates. The discussion delves into the implications of AI in recruitment, including potential biases and the need for organizations to adapt their interview processes to attract top talent. Paul's contact information: https://www.linkedin.com/in/paulpgiron/ paul@g-techrecruitment.com

Episode 104: An Infrastructure Rewrite Story with Guest Paul Stack

Isaac Askew and Jeffrey Sherman — Fri, 16 May 2025 13:00:00 GMT

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

Episode 42: Iteration as a Defense From Micromanagement

Isaac Askew and Jeffrey Sherman — Fri, 23 Feb 2024 14:00:00 GMT

Jeffrey and Isaac discuss how iteration can be a defense against micromanagement. They explore the reasons behind micromanagement, such as a lack of progress and fear, and how iteration provides observability and reassurance to managers. They emphasize the importance of breaking down nebulous projects into smaller deliverables and providing checkpoints to show progress.

Episode 81: The Pause

Isaac Askew and Jeffrey Sherman — Fri, 06 Dec 2024 14:00:00 GMT

'The Pause'—a critical juncture where development on the old system is halted in favor of completing a new system. Isaac and Jeffrey discuss the inherent risks of this approach, the implications for customer value, and the often misguided desire for dramatic reveals in software releases. The conversation emphasizes the importance of maintaining continuous value delivery and offers strategies to avoid the pitfalls associated with pausing development.

Episode 137: 2025 Year in Review

Isaac Askew and Jeffrey Sherman — Fri, 02 Jan 2026 14:00:00 GMT

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.

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

Isaac Askew and Jeffrey Sherman — Fri, 09 Jan 2026 14:00:00 GMT

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.

Episode 74: Musketeering

Isaac Askew and Jeffrey Sherman — Fri, 18 Oct 2024 13:00:00 GMT

Jeffrey and Isaac explore the concept of 'musketeering' in software development, emphasizing the importance of collaboration in solving complex problems. They discuss the challenges of legacy code, the necessity of testing, and the strategy of 'divide and conquer' to tackle intertwined issues effectively.

Episode 72: Perfectionism in Programming

Isaac Askew and Jeffrey Sherman — Fri, 04 Oct 2024 13:00:00 GMT

Isaac and Dustin Rea discuss the impact of perfectionism in programming, particularly how it can hinder project success. They explore the importance of launching minimum viable products (MVPs) to validate ideas in the market, the challenges of managing change in production software, and the balance between perfectionism and practicality. The discussion also highlights the significance of team dynamics and customer empathy in software development, as well as lessons learned from scaling and responding to customer demands.

Episode Three - Why You Hate Testing

Isaac Askew and Jeffrey Sherman — Sat, 08 Apr 2023 06:45:43 GMT

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 26: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 1

Isaac Askew and Jeffrey Sherman — Fri, 03 Nov 2023 19:14:00 GMT

Special Guest Aadil Farid joins us to discuss the harsh realities he confronted when he led a team that computerized ticketing on India’s Railways in the 1980s.

Episode 31: Getting Started with Brownfield Testing (Part 1)

Isaac Askew and Jeffrey Sherman — Fri, 08 Dec 2023 14:00:00 GMT

Brownfield code is existing code (rather than new code) that you might need to add tests for. Join us for a two-part episode on how to get started testing and refactoring existing applications.

Episode 20 - Shrink Mode

Isaac Askew and Jeffrey Sherman — Thu, 31 Aug 2023 22:13:48 GMT

Sometimes companies shrink instead of grow, and that impacts your work, your team, and your career. In this episode we discuss what to expect from a shrinking company.

Episode 71: Are Ignorable Errors Still "Errors"?

Isaac Askew and Jeffrey Sherman — Fri, 27 Sep 2024 13:00:00 GMT

Isaac and Jeffrey explore the complexities of error management in software development, particularly focusing on the significance of logs, the philosophical implications of ignoring errors, and the importance of proactive log management. They discuss how to differentiate between true errors and warnings, the role of telemetry in alerting, and the necessity of maintaining clean logs to enhance system understanding and customer experience.

Episode 43: Rewriting in the Age of AI

Isaac Askew and Jeffrey Sherman — Fri, 01 Mar 2024 14:00:00 GMT

Jeffrey and Isaac discuss their stance on 'never rewriting' given the possibility of AI making rewriting faster, cheaper, and less risky. They explore the limitations of current AI capabilities and the potential benefits of AI-assisted refactoring. The conversation delves into the idea of using AI to write tests and improve code quality. They also discuss the challenges and opportunities of AI in language switching and high-performance code optimization. Overall, the episode highlights the evolving role of AI in the rewriting process and the potential impact it may have on software development in the future.

Episode 117: How to Make Incremental Changes Visible

Isaac Askew and Jeffrey Sherman — Fri, 15 Aug 2025 13:00:00 GMT

Isaac Askew and Jeffrey Sherman discuss the significance of making incremental changes visible in software development. They emphasize the importance of metrics in measuring performance, system reliability, and user behavior. The discussion covers A-B testing, decision-making based on data, and real-world applications of metrics in projects, highlighting how these practices can lead to better outcomes and improved communication within teams.

Episode 69: Anxiety When Fixing a System You Didn't Create

Isaac Askew and Jeffrey Sherman — Fri, 13 Sep 2024 13:00:00 GMT

Isaac and Jeffrey delve into the anxiety developers face when dealing with legacy systems they did not create. They explore the reasons behind the fear of fixing such systems, the challenges of refactoring, and the skills required to navigate these situations. The discussion emphasizes the importance of understanding legacy code, learning from it, and developing strategies to reduce anxiety when approaching refactoring tasks. Practical tips are provided for developers to build confidence and make meaningful contributions to legacy systems.

Episode 103: Recognizing When a Rewrite is Failing

Isaac Askew and Jeffrey Sherman — Fri, 09 May 2025 13:00:00 GMT

Isaac and Jeffrey discuss the challenges and signs of failing rewrites in software development.

Episode 48: Falsehoods Programmers Believe About Projects

Isaac Askew and Jeffrey Sherman — Fri, 05 Apr 2024 13:00:00 GMT

In this episode, Isaac and Jeffrey discuss falsehoods that programmers believe about projects. They explore assumptions such as projects having defined beginnings and endings, the role of priorities in project work, and the importance of clear communication and feedback. They also touch on the challenges of working on successful projects that transition into ongoing maintenance and the consequences of failed projects that continue to exist. The conversation highlights the need for programmers to question these assumptions and adapt their approach to project management.

Episode 102: Rewrite Stories with Guest Nick Stinemates

Isaac Askew and Jeffrey Sherman — Fri, 02 May 2025 13:00:00 GMT

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

Episode 64: Aligning Yourself With the Company's Risk Profile

Isaac Askew and Jeffrey Sherman — Fri, 02 Aug 2024 17:24:11 GMT

Isaac and Jeffrey discuss the importance of aligning oneself with a company's risk profile. They explore the concept of risk tolerance and how it varies depending on the company's stage of development and industry. They highlight the need for a balance between security and other business priorities, as well as the importance of having conversations about risk tolerance with managers and teams. They also touch on the potential misalignment between managers and companies, and the implicit cultural risk tolerance that can lead to security vulnerabilities. Overall, they emphasize the need for understanding and navigating risk in the context of software development.

Episode 86: Annual Reminder - Prune Your Meetings

Isaac Askew and Jeffrey Sherman — Fri, 10 Jan 2025 14:00:00 GMT

Isaac and Jeffrey discuss the importance of reassessing the necessity of meetings, especially at the beginning of the year. They emphasize the need to cancel unnecessary meetings, optimize meeting structures, and empower team members to decline meetings that do not require their input. The conversation highlights the significance of effective communication and time management in the workplace.

Episode One

Isaac Askew and Jeffrey Sherman — Thu, 16 Mar 2023 04:15:00 GMT

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.

Episode 39 - Project Risk with Jonathan Stark

Isaac Askew and Jeffrey Sherman — Fri, 02 Feb 2024 14:00:00 GMT

Jonathan Stark joins as a guest to discuss the risks of hourly billing and the parallels between risk in a rewrite and in hourly billing.

Episode 132: A Thankful Thanksgiving Episode

Isaac Askew and Jeffrey Sherman — Fri, 28 Nov 2025 14:00:00 GMT

Happy Thanksgiving everybody!

Episode Thirteen - Transitioning from Microservices to Monolith with Josh Beckman

Isaac Askew and Jeffrey Sherman — Wed, 14 Jun 2023 22:16:01 GMT

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 38 - Maintenance Work as a Flight to Safety

Isaac Askew and Jeffrey Sherman — Fri, 26 Jan 2024 15:50:35 GMT

Isaac and Jeffrey explore the significance of maintenance work for developers, stressing its strategic value during uncertain periods like layoffs. They share personal experiences, highlighting how tackling these tasks can lead to trust, new opportunities, and a more impactful role within a team.

Episode 56: AI-Driven Testing

Isaac Askew and Jeffrey Sherman — Fri, 31 May 2024 13:00:00 GMT

Isaac and Jeffrey discuss the potential of AI-driven testing and code generation. They reference an article by Codium AI, which explores the use of AI to generate tests and increase code coverage. While the generated tests may not be perfect, they can serve as scaffolding for legacy code and help identify areas for improvement. The conversation also touches on the idea of using AI to provide business context and legal compliance guidance during code refactoring. Overall, the discussion highlights the potential benefits of AI in improving code quality and reducing risk.

Episode 77: Who Gets To Define 'Shit' Code?

Isaac Askew and Jeffrey Sherman — Fri, 08 Nov 2024 14:00:00 GMT

Isaac and Jeffrey explore the subjective nature of coding standards and what constitutes 'shit code.' They discuss the lack of industry-wide standards, the importance of intention in coding, and the balance between flexibility and adaptability in code quality. The conversation also touches on the fluidity of language and how it parallels coding practices, emphasizing that coding standards should evolve with the context and needs of the project.

Episode 127: The Pains Caused by Differing Abstractions

Isaac Askew and Jeffrey Sherman — Fri, 24 Oct 2025 13:00:00 GMT

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.

Episode 124: Treating Communication Gaps Like Tech Debt ft. Austen Tucker

Isaac Askew and Jeffrey Sherman — Fri, 03 Oct 2025 13:00:00 GMT

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/

Episode 114: Old Projects Never Die, They Just Fade Away

Isaac Askew and Jeffrey Sherman — Fri, 25 Jul 2025 13:00:00 GMT

Isaac and Jeffrey discuss why abandoned projects or failed rewrites have code that always seems to just linger - is it worth fixing?

Episode 112: The Impact & Cost of Hidden Business Rules

Isaac Askew and Jeffrey Sherman — Fri, 11 Jul 2025 13:00:00 GMT

Today we highlight he significant impact and costs associated with hidden business rules in software development. We explore the challenges of implementation, the importance of documenting business rules effectively, and how AI can assist in managing these rules. Our discussion emphasizes the need for an internal product book to consolidate knowledge and improve communication among teams, ultimately leading to more efficient development processes.

Episode 85: 2024 Year In Review

Isaac Askew and Jeffrey Sherman — Fri, 03 Jan 2025 14:00:00 GMT

Isaac and Jeffrey reflect on their podcast journey throughout 2024, discussing their goals, achievements, and notable episodes. They share insights on their recording process, the impact of AI on their discussions, and the concept of 'musketeering' in problem-solving. The hosts also highlight their listener engagement and growth, expressing gratitude for their audience's support and outlining plans for the future.

Episode 67: Revisiting "The Joel Test: 12 Steps to Better Code"

Isaac Askew and Jeffrey Sherman — Fri, 30 Aug 2024 13:00:00 GMT

Jeffrey revisits The Joel Test, a 12-question test to determine if a software development team is set up for success. Jeffrey and Isaac discuss the relevance of each question in today's context and how the industry has evolved over the years. The topics covered include source control, building and deployment processes, bug tracking, bug fixing, project scheduling, specifications, working conditions, and tools.

Episode 54: Shadow Your Colleagues

Isaac Askew and Jeffrey Sherman — Fri, 17 May 2024 16:08:47 GMT

Jeffrey and Isaac discuss how to get started with shadowing people and solving their problems. They share their experiences and strategies for shadowing, including reaching out to the people you want to shadow, observing their tasks, and identifying areas for improvement. They emphasize the importance of shadowing during the onboarding process and the value of asking questions and challenging existing processes. They also highlight the benefits of building relationships and earning credibility by solving problems for others.

Episode 47 - Maintenance Work as a Flight to Safety - A Manager's Perspective

Isaac Askew and Jeffrey Sherman — Fri, 29 Mar 2024 13:00:00 GMT

Isaac and Jeffrey discuss the flight to maintenance work as a safety option from the manager's perspective. They explore different perspectives on maintenance work and the value of taking on such work. They emphasize the importance of understanding the reality of the system and approaching maintenance work as an opportunity to solve real problems. They also discuss the role of accountability and changing the culture around maintenance work. The episode concludes with a discussion on the impact of not addressing maintenance work and the benefits of going slow to go fast.