All Episodes
Never Rewrite — 172 episodes
AI-Monitored Release Processes: A Log Anomaly Checker (Ep. 172)
Using AI to Complete a Half-Finished Rewrite, Part 2 (Ep. 171)
Refactoring: What Changes (And Doesn't) in the Age of AI ft. Ravi Ram (Ep. 170)
Using AI to Complete a Half-Finished Rewrite (Ep. 169)
Are AI-Driven Pull Requests Too Large? (Ep. 168)
AI & WIP Fundamentals (Ep. 167)
Solutioning in the Age of AI (Ep. 166)
AI & The Age of Transient Apps (Ep. 165)
AI Horror Stories (Ep. 164)
Can AI Tell You What Your Goals Are? (Ep. 163)
Terminology: Rewrite, Refactor, Rebuild, Redo? (Ep. 162)
You Can't Vibe Code Reputation (Ep. 161)
TheseusShipping Outside of the Tech Stack (Ep. 160)
Vibe Coding (Ep. 159)
Token-Based Billing Is Nuts (Ep. 158)
Episode 157: Is AI Making You The New John Henry?
Episode 156: Modernization: Where AI Doesn't Save You Any Steps
Episode 155: Agentic Development Is Turning Engineers Into Product Owners
Episode 154: Feature Parity Pitfalls
Episode 153: The Rewrite Trap & Sunk Cost Fallacy
Episode 152: The Moving House Metaphor for Software Rewrites: How AI Changes the Game
Episode 151: Celebrating Wins During Constant Iteration
Episode 150: The AI Rewrite Trap
Episode 149: Isaac Does a Rewrite?
Episode 148: How Human Taste Shapes the Future of AI and Coding
Episode 147: Managing Organizational Change ft. Sophia Rosa
Episode 146: How AI is Reshaping Careers and Workflows
Episode 145: Outdated Programming Techniques: Browser Compatibility
Episode 144: Outdated Programming Techniques: Bit Masking
Episode 143: Tactics to Obscure (Parody)
Episode 142: Are You Ready to Scale? A Local Case Study
Episode 141: How Rewrites Create Accountability Black Holes
Episode 140: Evolving Past Boomer AI
Episode 139: Rewrites - A Failure of the Imagination ft. Mark Mandau
Episode 138: The MVP Worked. Do We Rewrite It To Scale?
Episode 137: 2025 Year in Review
Episode 136: Key Questions to Ask When Navigating Your Career
Episode 135: Is Changing an ERP System a Rewrite? ft. Sophia Rosa
Episode 134: A Stream of Consciousness Chat on AI, Tech, & Layoffs
Episode 133: The Consequences of Having Multiple Sources of Truth
Episode 132: A Thankful Thanksgiving Episode
Episode 131: Rewrites from a Product Perspective ft. Mark Mandau
Episode 130: The Pains Caused by Differing Abstractions Pt. 2 - Real World Examples
Episode 129: Credit Where Credit Is Due
Episode 128: Revisiting An Old Story With Our Current Experience
Episode 127: The Pains Caused by Differing Abstractions
Episode 126: Does Iterative Replacement Trap You In Legacy Frameworks?
Episode 125: Navigating Risky Software Setups
Episode 124: Treating Communication Gaps Like Tech Debt ft. Austen Tucker
Episode 123: Is Switching Jobs a Career 'Rewrite'?
Episode 122: Providing Constructive Feedback
Episode 121: A Helpful Analogy For Understanding Legacy Code & Tech Debt
Episode 120: Bad Testing & Release Practices Are Cultural Problems, Not Technical Problems
Episode 119: Iterating, Adapting, & Pivoting ft. Day Martin
Episode 118: Recovering Value From Failed Projects
Episode 117: How to Make Incremental Changes Visible
Episode 116: Inverting the Testing Pyramid Pt. 2
Episode 115: [CI/CD] Beautiful Feedback Loops with guest Spriha Tucker
Episode 114: Old Projects Never Die, They Just Fade Away
Episode 113: Do You Want a Better Version of What You Have?
Episode 112: The Impact & Cost of Hidden Business Rules
Episode 111: The Social Aspects of a Failed Rewrite
Episode 110: MVPs, YAGNI, and the Goldilocks Problem
Episode 109: Conway's Law and Software Quality
Episode 108: Consolidating Tech Stacks - Is It Worth It?
Episode 107: Rebuilding vs. Rewriting vs. Refactoring?
Episode 106: How to Stop a Rewrite in Progress
Episode 105: A Core Engine Rewrite with Nick Gerace
Episode 104: An Infrastructure Rewrite Story with Guest Paul Stack
Episode 103: Recognizing When a Rewrite is Failing
Episode 102: Rewrite Stories with Guest Nick Stinemates
Episode 101: Relief vs. Cure
Episode 100: Detecting B.S. as a Non-Technical Founder
Episode 99: DOGE Pt. 2: Government Rewrites with Guest Dan Hon
Episode 98: DOGE's Social Security Rewrite - Killing Americans to Save Money
Episode 97: Fulfilling Friday - A Tattoo Scam?
Episode 96: Inverting the Testing Pyramid - Testing Infrastructure Changes ft. Rob Gonnella
Episode 95: We're Writing a Book!
Episode 94: What Did You Think You Were Saying Yes To?
Episode 93: How to Put Work Down When Priorities Change
Episode 92: A Framework for Prioritizing Tech Debt ft. Dustin Rea
Episode 91: Pushing Pain to Users
Episode 90: The Hero and the Lifeguard
Episode 89: How Sonos Lost $500 Million Attempting a Rewrite
Episode 88: Creating a Culture of Continuous Improvement with Guest Erik Enge
Episode 87: 2025 Update - State of AI Programming
Episode 86: Annual Reminder - Prune Your Meetings
Episode 85: 2024 Year In Review
Episode 84: The Impact of AI on Interviewing
Episode 83: The Impact of AI on Recruiting
Episode 82: Can You Like Tests And Also Believe You're Faster Without Them?
Episode 81: The Pause
Episode 80: What is "De-Risking"?
Episode 79: The Toxicity of "Certainty"
Episode 78: Is Frontend Modernization a Valid Reason for Rewriting?
Episode 77: Who Gets To Define 'Shit' Code?
Episode 76: Aligning Your Company Standards to its Lifecycle Phase
Episode 75: Rewriting is Gambling - A Lesson in Risk
Episode 74: Musketeering
Episode 73: The Politics of Delivering Trivial Changes
Episode 72: Perfectionism in Programming
Episode 71: Are Ignorable Errors Still "Errors"?
Episode 70: Resource Engineering
Episode 69: Anxiety When Fixing a System You Didn't Create
Episode 68: The Fallacy of Rewriting Software to Save Money
Episode 67: Revisiting "The Joel Test: 12 Steps to Better Code"
Episode 66: Squashing the Right Bugs
Episode 65: Exploring Different Perspectives on Risk with Dustin Rea
Episode 64: Aligning Yourself With the Company's Risk Profile
Episode 63: Fulfilling Friday: SMS Spamming Saved
Episode 62: The Peculiar Failure of Correctly Predicting Problems
Episode 61: Challenges of Multi-Product Platforms ft. Dustin Rea
Episode 60: Anybody Could Have Done It...But I Actually Did
Episode 59: The Myth of the Boy Scout Rule
Episode 58: When You Can’t Iterate
Episode 57: White Label CRM Updates with Dustin Rea
Episode 56: AI-Driven Testing
Episode 55: Writing Your Job Out Of Existence
Episode 54: Shadow Your Colleagues
Episode 53: Cloud Infrastructure "Rewrites"
Episode 52: The Two-Clock Problem
Episode 51: How Company Culture Impacts Code Delivery
Episode 50: Fulfilling Friday - Saving Customers Millions
Episode 49: Falsehoods Programmers Believe About Projects Part 2
Episode 48: Falsehoods Programmers Believe About Projects
Episode 47 - Maintenance Work as a Flight to Safety - A Manager's Perspective
Episode 46: Workshopping Live with Dustin Rea
Episode 45 - Year In Review
Episode 44 - Do More With Less
Episode 43: Rewriting in the Age of AI
Episode 42: Iteration as a Defense From Micromanagement
Episode 41: Rewrites from a Manager's Perspective with Ryan Cowan
Episode 40: Convincing Emotionally-Committed Colleagues It's Not Worth It
Episode 39 - Project Risk with Jonathan Stark
Episode 38 - Maintenance Work as a Flight to Safety
Episode 37: Interview Insights - Changing the Game for Interviewers and Candidates
Episode 36: Becoming an Expert in your Company's Business
Episode 35: The Subtle Art of Refusing Meetings
Episode 34: (F*ck-Up Friday Series) Don’t Fix What Ain’t Broken
Episode 33: How to be a Terrible Teammate
Episode 32: Getting Started with Brownfield Testing (Part 2)
Episode 31: Getting Started with Brownfield Testing (Part 1)
Episode 30: Investing in Yourself Beyond Education
Episode 29: (F*ck-Up Friday Series) The Saleswoman Who Faked Cancer
Episode 28: Making Non-Compatible Changes During Long-Running Upgrades
Episode 27: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 2
Episode 26: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 1
Episode 25: A Rewrite Success Story with Brian Genisio from Khan Academy
Episode 24: When AI Writes Your Documentation
Episode 23: Live Workshop with Rob Gonnella
Episode 22: Running an Iterative Refactoring Workshop
Episode 21 - Impostor Syndrome
Episode 20 - Shrink Mode
Episode Nineteen - The Beachhead Strategy
Episode Eighteen - Strategies for Upgrading Software
Episode Seventeen (F*ck-Up Friday Series) - Losing $1 billion for 4 hours
Episode Sixteen - Tricks to Facilitate Conversation
Episode Fifteen - Red Flag Development Ideas
Episode Fourteen - How do you define ‘Minimum Viable Product’?
Episode Thirteen - Transitioning from Microservices to Monolith with Josh Beckman
Episode Twelve - Company Culture Pt. 2 with Thomas Morris
Episode Eleven - You Can’t Build to Spec
Episode Ten - The Rewrite Cycle
Episode Nine (F*ck-Up Friday Series) - How Our Customers Got Raided by the FBI
Episode Eight - Transforming your Internal Software into a SaaS with Brian Begy
Episode Seven - Risk
Episode Six - How Company Culture Makes Or Breaks Your Team
Episode Five - Perverse Incentives
Episode Four - Nozomi
Episode Three - Why You Hate Testing
Episode Two - Iteratively Replace
Episode One