All Episodes
Every episode of the Never Rewrite podcast — a long-running conversation between Jeffrey Sherman and Isaac Askew about why complete software rewrites fail and what engineering teams should do instead. Click any thumbnail to play here, or visit the channel.
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Episode 156: Modernization: Where AI Doesn't Save You Any Steps
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Episode 155: Agentic Development Is Turning Engineers Into Product Owners
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Episode 154: Feature Parity Pitfalls
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Episode 153: The Rewrite Trap & Sunk Cost Fallacy
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Episode 152: The Moving House Metaphor for Software Rewrites: How AI Changes the Game
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Episode 151: Celebrating Wins During Constant Iteration
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Episode 150: The AI Rewrite Trap
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Episode 149: Isaac Does a Rewrite?
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Episode 148: How Human Taste Shapes the Future of AI and Coding
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Episode 147: Managing Organizational Change ft. Sophia Rosa
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Episode 146: How AI is Reshaping Careers and Workflows
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Episode 145: Outdated Programming Techniques: Browser Compatibility
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Episode 144: Outdated Programming Techniques: Bit Masking
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Episode 143: Tactics to Obscure (Parody)
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Episode 142: Are You Ready to Scale? A Local Case Study
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Episode 141: How Rewrites Create Accountability Black Holes
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Episode 140: Evolving Past Boomer AI
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Episode 139: Rewrites - A Failure of the Imagination ft. Mark Mandau
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Episode 138: The MVP Worked. Do We Rewrite It To Scale?
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Episode 137: 2025 Year in Review
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Episode 136: Key Questions to Ask When Navigating Your Career
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Episode 135: Is Changing an ERP System a Rewrite? ft. Sophia Rosa
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Episode 134: A Stream of Consciousness Chat on AI, Tech, & Layoffs
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Episode 133: The Consequences of Having Multiple Sources of Truth
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Episode 132: A Thankful Thanksgiving Episode
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Episode 131: Rewrites from a Product Perspective ft. Mark Mandau
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Episode 130: The Pains Caused by Differing Abstractions Pt. 2 - Real World Examples
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Episode 129: Credit Where Credit Is Due
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Episode 128: Revisiting An Old Story With Our Current Experience
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Episode 127: The Pains Caused by Differing Abstractions
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Episode 126: Does Iterative Replacement Trap You In Legacy Frameworks?
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Episode 125: Navigating Risky Software Setups
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Episode 124: Treating Communication Gaps Like Tech Debt ft. Austen Tucker
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Episode 123: Is Switching Jobs a Career 'Rewrite'?
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Episode 122: Providing Constructive Feedback
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Episode 121: A Helpful Analogy For Understanding Legacy Code & Tech Debt
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Episode 120: Bad Testing & Release Practices Are Cultural Problems, Not Technical Problems
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Episode 119: Iterating, Adapting, & Pivoting ft. Day Martin
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Episode 118: Recovering Value From Failed Projects
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Episode 117: How to Make Incremental Changes Visible
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Episode 116: Inverting the Testing Pyramid Pt. 2
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Episode 115: [CI/CD] Beautiful Feedback Loops with guest Spriha Tucker
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Episode 114: Old Projects Never Die, They Just Fade Away
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Episode 113: Do You Want a Better Version of What You Have?
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Episode 112: The Impact & Cost of Hidden Business Rules
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Episode 111: The Social Aspects of a Failed Rewrite
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Episode 110: MVPs, YAGNI, and the Goldilocks Problem
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Episode 109: Conway's Law and Software Quality
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Episode 108: Consolidating Tech Stacks - Is It Worth It?
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Episode 107: Rebuilding vs. Rewriting vs. Refactoring?
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Episode 106: How to Stop a Rewrite in Progress
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Episode 105: A Core Engine Rewrite with Nick Gerace
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Episode 104: An Infrastructure Rewrite Story with Guest Paul Stack
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Episode 103: Recognizing When a Rewrite is Failing
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Episode 102: Rewrite Stories with Guest Nick Stinemates
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Episode 101: Relief vs. Cure
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Episode 100: Detecting B.S. as a Non-Technical Founder
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Episode 99: DOGE Pt. 2: Government Rewrites with Guest Dan Hon
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Episode 98: DOGE's Social Security Rewrite - Killing Americans to Save Money
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Episode 97: Fulfilling Friday - A Tattoo Scam?
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Episode 96: Inverting the Testing Pyramid - Testing Infrastructure Changes ft. Rob Gonnella
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Episode 95: We're Writing a Book!
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Episode 94: What Did You Think You Were Saying Yes To?
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Episode 93: How to Put Work Down When Priorities Change
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Episode 92: A Framework for Prioritizing Tech Debt ft. Dustin Rea
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Episode 91: Pushing Pain to Users
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Episode 90: The Hero and the Lifeguard
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Episode 89: How Sonos Lost $500 Million Attempting a Rewrite
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Episode 88: Creating a Culture of Continuous Improvement with Guest Erik Enge
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Episode 87: 2025 Update - State of AI Programming
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Episode 86: Annual Reminder - Prune Your Meetings
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Episode 85: 2024 Year In Review
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Episode 84: The Impact of AI on Interviewing
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Episode 83: The Impact of AI on Recruiting
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Episode 82: Can You Like Tests And Also Believe You're Faster Without Them?
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Episode 81: The Pause
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Episode 80: What is "De-Risking"?
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Episode 79: The Toxicity of "Certainty"
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Episode 78: Is Frontend Modernization a Valid Reason for Rewriting?
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Episode 77: Who Gets To Define 'Shit' Code?
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Episode 76: Aligning Your Company Standards to its Lifecycle Phase
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Episode 75: Rewriting is Gambling - A Lesson in Risk
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Episode 74: Musketeering
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Episode 73: The Politics of Delivering Trivial Changes
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Episode 72: Perfectionism in Programming
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Episode 71: Are Ignorable Errors Still "Errors"?
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Episode 70: Resource Engineering
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Episode 69: Anxiety When Fixing a System You Didn't Create
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Episode 68: The Fallacy of Rewriting Software to Save Money
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Episode 67: Revisiting "The Joel Test: 12 Steps to Better Code"
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Episode 66: Squashing the Right Bugs
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Episode 65: Exploring Different Perspectives on Risk with Dustin Rea
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Episode 64: Aligning Yourself With the Company's Risk Profile
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Episode 63: Fulfilling Friday: SMS Spamming Saved
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Episode 62: The Peculiar Failure of Correctly Predicting Problems
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Episode 62: The Peculiar Failure of Correctly Predicting Problems
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Episode 61: Challenges of Multi-Product Platforms ft. Dustin Rea
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Episode 60: Anybody Could Have Done It...But I Actually Did
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Episode 59: The Myth of the Boy Scout Rule
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Episode 58: When You Can’t Iterate
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Episode 57: White Label CRM Updates with Dustin Rea
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Episode 56: AI-Driven Testing
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Episode 55: Writing Your Job Out Of Existence
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Episode 54: Shadow Your Colleagues
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Episode 53: Cloud Infrastructure "Rewrites"
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Episode 52: The Two-Clock Problem
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Episode 51: How Company Culture Impacts Code Delivery
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Episode 50: Fulfilling Friday - Saving Customers Millions
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Episode 49: Falsehoods Programmers Believe About Projects Part 2
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Episode 48: Falsehoods Programmers Believe About Projects
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Episode 47 - Maintenance Work as a Flight to Safety - A Manager's Perspective
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Episode 46: Workshopping Live with Dustin Rea
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Episode 45 - Year In Review
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Episode 44 - Do More With Less
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Episode 43: Rewriting in the Age of AI
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Episode 42: Iteration as a Defense From Micromanagement
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Episode 41: Rewrites from a Manager's Perspective with Ryan Cowan
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Episode 40: Convincing Emotionally-Committed Colleagues It's Not Worth It
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Episode 39 - Project Risk with Jonathan Stark
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Episode 38 - Maintenance Work as a Flight to Safety
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Episode 37: Interview Insights - Changing the Game for Interviewers and Candidates
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Episode 36: Becoming an Expert in your Company's Business
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Episode 35: The Subtle Art of Refusing Meetings
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Episode 34: (F*ck-Up Friday Series) Don’t Fix What Ain’t Broken
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Episode 33: How to be a Terrible Teammate
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Episode 32: Getting Started with Brownfield Testing (Part 2)
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Episode 31: Getting Started with Brownfield Testing (Part 1)
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Episode 30: Investing in Yourself Beyond Education
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Episode 29: (F*ck-Up Friday Series) The Saleswoman Who Faked Cancer
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Episode 28: Making Non-Compatible Changes During Long-Running Upgrades
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Episode 27: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 2
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Episode 26: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 1
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Episode 25: A Rewrite Success Story with Brian Genisio from Khan Academy
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Episode 24: When AI Writes Your Documentation
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Episode 23: Live Workshop with Rob Gonnella
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Episode 22: Running an Iterative Refactoring Workshop
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Episode 21 - Impostor Syndrome
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Episode 21: Impostor Syndrome
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Episode 20 - Shrink Mode
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Episode 19 - The Beachhead Strategy
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Episode Nineteen - The Beachhead Strategy
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Episode Eighteen - Strategies for Upgrading Software
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Episode Seventeen (F*ck-Up Friday Series) - Losing $1 billion for 4 hours
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Episode 17 (F*ck-Up Friday Series) - Losing $1 billion for 4 hours
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Episode 16 - Tricks to Facilitate Conversation
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Episode Sixteen - Tricks to Facilitate Conversation
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Episode Fifteen - Red Flag Development Ideas
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Episode 14 - How do you define ‘Minimum Viable Product’?
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Episode Fourteen - How do you define ‘Minimum Viable Product’?
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Episode 13 - Transitioning from Microservices to Monolith with Josh Beckman
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Episode Thirteen - Transitioning from Microservices to Monolith with Josh Beckman
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Episode Twelve - Company Culture Pt. 2 with Thomas Morris
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Episode 12 - Company Culture Pt. 2 with Thomas Morris
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Episode Eleven - You Can’t Build to Spec
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Episode 11 - You Can't Build to Spec
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Episode Ten - The Rewrite Cycle
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Episode 10 - The Rewrite Cycle
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Episode 9 (F*ck-Up Friday Series) - How Our Customers Got Raided by the FBI
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Episode Nine (F*ck-Up Friday Series) - How Our Customers Got Raided by the FBI
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Episode Eight - Transforming your Internal Software into a SaaS with Brian Begy
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Episode 8 - Transforming Your Internal Software into a SaaS with Brian Begy (Full Version)
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Episode Seven - Risk
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Episode Six - How Company Culture Makes Or Breaks Your Team
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Episode Five - Perverse Incentives
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Episode 4 - Nozomi (Full Version - Video)
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Episode Four - Nozomi
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Episode Three - Why You Hate Testing
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Episode Two - Iteratively Replace
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Episode One
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