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Jeffrey Sherman

@jeffreysherman.bsky.social

120 followers 38 following 122 posts

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Jeffrey Sherman @jeffreysherman.bsky.social · 08/10/2026

AI-Monitored Release Processes: A Log Anomaly Checker (Never Rewrite Ep. 172) In an ideal world your system will have wonderful observability, monitoring, and alerting. For most of us, our systems are observable, and generally unobserved. www.youtube.com/watch?v=OsBI...

AI-Monitored Release Processes: A Log Anomaly Checker (Ep. 172)

YouTube video by Never Rewrite

Jeffrey Sherman @jeffreysherman.bsky.social · 11/09/2026

Using AI to Complete a Half-Finished Rewrite, Part 2 (Ep. 171) Jeffrey brought a 10-year old api rewrite to completion in 2 weeks using AI. It turns out development fundamentals still matter! If you want to finish stalled projects, this is the episode for you! www.youtube.com/watch?v=zE9c...

Using AI to Complete a Half-Finished Rewrite, Part 2 (Ep. 171)

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 02/09/2026

Refactoring: What Changes (And Doesn't) in the Age of AI (Ep. 170) Ravi Ram built his consultancy on refactoring and rescuing ancient ASP systems. If you do legacy system rescue and are worried about AI's impact on your business model, this is the episode for you! www.youtube.com/watch?v=ktV9...

Refactoring: What Changes (And Doesn't) in the Age of AI ft. Ravi Ram (Ep. 170)

YouTube video by Never Rewrite

Reposted by Jeffrey Sherman

Pavel @spavel.bsky.social · 28/03/2025

Haters tell me "but that's not the technology's fault, you can also use it to enhance your own writing rather than outsource everything to the machine" And this is a great lesson in User Experience Design: you CAN but you WON'T, because of how the software is designed. Let's talk about friction.

Jeffrey Sherman @jeffreysherman.bsky.social · 27/08/2026

Using AI to Complete a Half-Finished Rewrite (Never Rewrite Ep. 169) Can AI finish off a decade-long API rewrite in 2 weeks? Jeffrey said, challenge accepted! If you want to learn how we plan to do audacious things, this is the episode for you! www.youtube.com/watch?v=xHb6...

Using AI to Complete a Half-Finished Rewrite (Ep. 169)

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 24/08/2026

Are AI-Driven Pull Requests Too Large? (Ep. 168) In this age of agentic coding, where the reviewer might only glance at the code, does size still matter? If you've been struggling to revise your workflows in the age of AI, this is the episode for you! www.youtube.com/watch?v=NlWs...

Are AI-Driven Pull Requests Too Large? (Ep. 168)

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 12/08/2026

AI & WIP Fundamentals (Never Rewrite Ep. 167) When AI can fix your mess with 1 giant merge, or 100 small ones, which should you choose? If you are struggling with agents creating giant merges, this is the episode for you! www.youtube.com/watch?v=bSr1...

AI & WIP Fundamentals (Ep. 167)

YouTube video by Never Rewrite

Jeffrey Sherman @jeffreysherman.bsky.social · 06/08/2026

Solutioning in the Age of AI (Never Rewrite Ep. 166) Solutioning is when a developer is told exactly how to solve a problem instead of being told the problem and given freedom to determine the best course of action. So what happens when an engineer solutions AI? www.youtube.com/watch?v=mVwR...

Solutioning in the Age of AI (Ep. 166)

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 31/07/2026

AI Horror Stories (Never Rewrite Ep. 164) Data leaks! Runaway billing! Accidently deleting production! AI agents didn't create any of these risks, they just make them more common. www.youtube.com/watch?v=uiOR...

AI Horror Stories (Ep. 164)

YouTube video by Never Rewrite

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Reposted by Jeffrey Sherman

Allen Holub @allenholub.bsky.social · 27/07/2026

If a big story provides value, a smaller version will provide (a smaller amount of) value, but it still does something useful for (a smaller subset of) users (working in a narrower context). I approach the larger value incrementally, by implementing many smaller stories. 2/6

Jeffrey Sherman @jeffreysherman.bsky.social · 20/07/2026

Can AI Tell You What Your Goals Are? (Never Rewrite Ep. 163) AI can write your code, but can AI tell you what code to write? If you add every commonly recommended feature, will you have a great product or a bloated one? www.youtube.com/watch?v=vQDF...

Can AI Tell You What Your Goals Are? (Ep. 163)

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 18/07/2026

Terminology: Rewrite, Refactor, Rebuild, Redo? (Ep. 162) With rewriting, rebuilding, and iteratively shipping software you start in the same place, and hope to end up at the same destination. So what's the difference? Only every aspect of the journey! www.youtube.com/watch?v=xKf3...

Terminology: Rewrite, Refactor, Rebuild, Redo? (Ep. 162)

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 01/07/2026

You Can't Vibe Code Reputation You can vibe code an email server, but Google won't deliver it's emails because it has no reputation. If you're wondering about the practical difference between writing software and running it, this is the episode for you! www.youtube.com/watch?v=c17I...

You Can't Vibe Code Reputation (Ep. 161)

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 23/06/2026

TheseusShipping Outside of the Tech Stack What happens when you try and apply incremental improvements outside of the tech stack?Can you really change processes incrementally? If you're ready to start making other people's lives better, this is the episode for you! www.youtube.com/watch?v=XEwN...

TheseusShipping Outside of the Tech Stack (Ep. 160)

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 14/06/2026

Never Rewrite: Vibe Coding Vibe coding is the new "I had my genius nephew make me an MVP." If you're a software consultant wondering how those introductory business meetings have changed, this is the episode for you! www.youtube.com/watch?v=4FX7...

Vibe Coding (Ep. 159)

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 07/06/2026

Never Rewrite: Token-Based Billing Is Nuts "Hourly Billing Is Nuts", by Jonathan Stark, explores how hourly billing creates an adversarial relationship between software consultants and their customers. Are tokens the new hours? www.youtube.com/watch?v=rtjQ...

Episode 158: Token-Based Billing Is Nuts

YouTube video by Never Rewrite

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Reposted by Jeffrey Sherman

Allen Holub @allenholub.bsky.social · 04/06/2026

The attached post 👇 is absolutely true for those companies that approached AI in a mindless way. The fact is that pretty much everybody is using AI. The "you'll be left behind if you don't adopt AI" thing is stale. Everybody's adopted AI. 1/10

Jeffrey Sherman @jeffreysherman.bsky.social · 03/06/2026

Never Rewrite: Is AI Making You The New John Henry? John Henry challanged a steam drill and died with his hammer in his hands; are developers headed to the same fate? If you've been wondering how to adapt, this is the episode for you! www.youtube.com/watch?v=p4Bz...

Episode 157: Is AI Making You The New John Henry?

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 19/05/2026

Never Rewrite: Feature Parity Pitfalls Do you need feature parity, or are you avoiding talking with your users? If you've ever been pitched "feature parity" and suspected something was off, this is the episode for you! www.youtube.com/watch?v=tcg1...

Episode 154: Feature Parity Pitfalls

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 15/05/2026

Never Rewrite: The Sunk Cost Fallacy Past investment doesn't matter. What matters is how much value you'll get out of future investment. If you've ever wanted to keep going on a project because of how much time you've invested, this is the episode for you! www.youtube.com/watch?v=4Td_...

Episode 153: The Rewrite Trap & Sunk Cost Fallacy

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 02/05/2026

Never Rewrite: The Moving House Metaphor for Software Rewrites: How AI Changes the Game A rewrite is a lot like moving homes with all the packing and making things work in a new environment. What changes when AI can do your metaphorical packing and unpacking? www.youtube.com/watch?v=Bmrv...

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

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 16/04/2026

Never Rewrite: Celebrating Wins During Constant Iteration @isaacaskew.com and I preach iteration on small changes to get lots of small wins. Small wins are small, unremarkable, and forgettable. So, how do you create meaningful celebrations from small wins? www.youtube.com/watch?v=5iuu...

Episode 151: Celebrating Wins During Constant Iteration

YouTube video by Never Rewrite

Jeffrey Sherman @jeffreysherman.bsky.social · 13/04/2026

Never Rewrite: The AI Rewrite Trap AI can rewrite your code. It is unlikely that this will solve any of your actual problems. If your system is broken and you think an AI rewrite will solve your problems, this is the episode for you! www.youtube.com/watch?v=r6GB...

Episode 150: The AI Rewrite Trap

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 01/04/2026

Never Rewrite: How Human Taste Shapes the Future of AI and Coding Famous music producer Rick Rubin said "My job is not to have any technical skill whatsoever, my job is to know what I like." Is the same true about software in the age of AI? www.youtube.com/watch?v=OeJh...

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

YouTube video by Never Rewrite

Jeffrey Sherman @jeffreysherman.bsky.social · 15/03/2026

Never Rewrite: Managing Organizational Change Transformation expert Sophia Rosa delivers a master class on the human factors behind changing organization. If you've ever tried to drive change by changing technology, and failed, this is the episode for you! www.youtube.com/watch?v=lG5k...

Episode 147: Managing Organizational Change ft. Sophia Rosa

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 10/03/2026

Never Rewrite: How AI is Reshaping Careers and Workflows Can the hourly billing model survive Agentic coding? If you've been wondering how AI is impacting the developer's dream of going freelance, this is the episode for you! www.youtube.com/watch?v=YWqM...

Episode 146: How AI is Reshaping Careers and Workflows

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 04/03/2026

Never Rewrite: Outdated Programming Techniques: Browser Compatibility Once upon a time web browsers worked differently. If you want to hear about the "old days" of 10 years ago, this is the episode for you! www.youtube.com/watch?v=9tcV...

Episode 145: Outdated Programming Techniques: Browser Compatibility

YouTube video by Never Rewrite

Jeffrey Sherman @jeffreysherman.bsky.social · 25/02/2026

Never Rewrite: Outdated Programming Techniques: Bit Masking If you've ever wondered about software optimizations that aren't worth doing anymore, this is the episode for you! www.youtube.com/watch?v=ORVM...

Episode 144: Outdated Programming Techniques: Bit Masking

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 08/02/2026

Never Rewrite: Are You Ready to Scale? A Local Case Study Are you ready to hire a developer to scale your business? Are you sure? In today's episode @isaacaskew.com walks us through how he attempts to convince perspective customers not to hire him! www.youtube.com/watch?v=h_Mh...

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

YouTube video by Never Rewrite

Jeffrey Sherman @jeffreysherman.bsky.social · 30/01/2026

Never Rewrite: How Rewrites Create Accountability Black Holes What happens to new bugs in a system being rewritten? Do they get fixed in both systems, just the new system, or neither systems? www.youtube.com/watch?v=XZ12...

Episode 141: How Rewrites Create Accountability Black Holes

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 20/01/2026

The Roadmap to Hell Is Written In Features The road to hell is paved with good intentions; the roadmap is written in features. shermanonsoftware.com/2026/01/19/t...

Author: Jeffrey Sherman
Title: The Roadmap to Hell Is Written In Features

Hook:
The road to hell is paved with good intentions; the roadmap is written in features.

Link To Post:
https://shermanonsoftware.com/2026/01/19/the-roadmap-to-hell-is-written-in-features/

Call To Action:
Improve Your NDR By Improving Your Software

Join my mailing list and get these articles directly to your inbox!
https://shermanonsoftware.com/subscribe/

Jeffrey Sherman @jeffreysherman.bsky.social · 14/01/2026

How I Will Talk You Out Of A Rewrite If you come to me saying “we need a rewrite”, I will try to talk you out of it. Here’s how. shermanonsoftware.com/2026/01/14/h...

Author: Jeffrey Sherman
Title: How I Will Talk You Out Of A Rewrite

Hook:
If you come to me saying “we need a rewrite”, I will try to talk you out of it. Here’s how.

Link To Post:
https://shermanonsoftware.com/2026/01/14/how-i-will-talk-you-out-of-a-rewrite/

Call To Action:
Improve Your NDR By Improving Your Software

Join my mailing list and get these articles directly to your inbox!
https://shermanonsoftware.com/subscribe/

Jeffrey Sherman @jeffreysherman.bsky.social · 12/01/2026

What does this button do? Lessons in web design courtesy of a minivan car door. shermanonsoftware.com/2026/01/12/w...

Author: Jeffrey Sherman
Title: What Does This Button Do?

Hook:
Lessons in web design courtesy of a minivan car door.

Link To Post:
https://shermanonsoftware.com/2026/01/12/what-does-this-button-do/

Call To Action:
Improve Your NDR By Improving Your Software

Join my mailing list and get these articles directly to your inbox!
https://shermanonsoftware.com/subscribe/

Jeffrey Sherman @jeffreysherman.bsky.social · 09/01/2026

Never Rewrite: The MVP Worked. Do We Rewrite It To Scale? You've made an MVP and it can't handle its own success. Do you rewrite it? If you've ever had code crushed by success, this is the episode for you! www.youtube.com/watch?v=6O7Y...

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

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 03/01/2026

This whole thread is a masterpiece on why big releases are terrible

Reposted by Jeffrey Sherman

Allen Holub @allenholub.bsky.social · 03/01/2026

Think of the money they could have saved by deciding it wasn't worth building based on early feedback. Big releases are really a sign of corporate we-know-what-the-customers-want-better-than-the-customers arrogance. 6/13

Jeffrey Sherman @jeffreysherman.bsky.social · 07/12/2025

Never Rewrite: The Consequences of Having Multiple Sources of Truth It is called the source of truth because it is the single, verifiable, source of truth. But what if you had 2, independent, sources of truth? Would that be twice as truthy? www.youtube.com/watch?v=4qcS...

Episode 133: The Consequences of Having Multiple Sources of Truth

YouTube video by Never Rewrite

Jeffrey Sherman @jeffreysherman.bsky.social · 24/11/2025

Never Rewrite Episode 131: Rewrites from a Product Perspective ft. Mark Mandau If you have been nodding along with us about rewrites, but wondering how non-developers feel, this is the episode for you! www.youtube.com/watch?v=WKEB...

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

YouTube video by Never Rewrite

Jeffrey Sherman @jeffreysherman.bsky.social · 15/11/2025

Never Rewrite: The Pains Caused by Differing Abstractions Pt. 2 - Real World Examples If you've ever wondered why timezones are hard and how much trouble they can cause, this is the episode for you! www.youtube.com/watch?v=WMJM...

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

YouTube video by Never Rewrite

Jeffrey Sherman @jeffreysherman.bsky.social · 12/11/2025

Incremental ETL Patterns For SaaS Developers Lessons from a world driven by the fear of being woken up at 3am to fix a process that must finish before 8am. shermanonsoftware.com/2025/11/12/i...

Author: Jeffrey Sherman
Title: Incremental ETL Patterns For SaaS Developers

Hook:
Lessons from a world driven by the fear of being woken up at 3am to fix a process that must finish before 8am.

Link To Post:
https://shermanonsoftware.com/2025/11/12/incremental-etl-patterns-for-saas-developers/

Call To Action:
Improve Your NDR By Improving Your Software

Join my mailing list and get these articles directly to your inbox!
https://shermanonsoftware.com/subscribe/

Jeffrey Sherman @jeffreysherman.bsky.social · 07/11/2025

Never Rewrite: Credit Where Credit Is Due Who gets credit for what is a recurring problem. If you've ever had someone else take credit for your ideas, this is the episode for you! www.youtube.com/watch?v=svAn...

Episode 129: Credit Where Credit Is Due

YouTube video by Never Rewrite

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Reposted by Jeffrey Sherman

Allen Holub @allenholub.bsky.social · 02/11/2025

One piece of common wisdom that I've come to disagree with is "do the most complicated thing first." In a waterfall world, that's a risk-reduction strategy, but in an incremental development context, it's actually the opposite. 1/7

Jeffrey Sherman @jeffreysherman.bsky.social · 01/11/2025

Amazing thread on the tension between art and ux!

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Jeffrey Sherman @jeffreysherman.bsky.social · 24/10/2025

Episode 127: The Pains Caused by Differing Abstractions What is time? What is money? If you've ever wondered how expensive these questions can be to answer this is the episode for you! www.youtube.com/watch?v=1g7l...

Episode 127: The Pains Caused by Differing Abstractions

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 17/10/2025

NeverRewrite: Does Iterative Replacement Trap You In Legacy Frameworks? @isaacaskew.com and I argue that Rewrites aren't an alternative because they almost never succeed. But if you follow our advice on Iterative Replacement, will you be trapped in legacy frameworks? www.youtube.com/watch?v=s89b...

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

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 13/10/2025

Pumping A Leaky Balloon - The Reality of SaaS Business Models The SaaS Business Model is like pumping air into a balloon with a leak. Without a steady stream of new customers, the balloon deflates and the SaaS will go out of business. shermanonsoftware.com/2025/10/13/p...

Author: Jeffrey Sherman
Title: Pumping A Leaky Balloon - The Reality of SaaS Business Models

Hook:
The SaaS Business Model is like pumping air into a balloon with a leak. Without a steady stream of new customers, the balloon deflates and the SaaS will go out of business.

Link To Post:
https://shermanonsoftware.com/2025/10/13/pumping-a-leaky-balloon-the-reality-of-saas-business-model/

Call To Action:
Improve Your NDR By Improving Your Software

Join my mailing list and get these articles directly to your inbox!
https://shermanonsoftware.com/subscribe/

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Jeffrey Sherman @jeffreysherman.bsky.social · 10/10/2025

Never Rewrite: Navigating Risky Software Setups As a consultant, how do you handle a potential client's risky software setup? If you've ever wondered if you can, or should, help a client with a risky setup, this is the episode for you! www.youtube.com/watch?v=bXqJ...

Episode 125: Navigating Risky Software Setups

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 06/10/2025

The Software Engineer And The Mechanical Engineer: A Parable Once upon a time a Software Engineer and a Mechanical Engineer needed to lift the leg of a table and slide a carpet underneath. shermanonsoftware.com/2025/10/06/t...

Author: Jeffrey Sherman
Title: The Software Engineer And The Mechanical Engineer: A Parable

Hook:
Once upon a time a Software Engineer and a Mechanical Engineer needed to lift the leg of a table and slide a carpet underneath.

Link To Post:
https://shermanonsoftware.com/2025/10/06/the-software-engineer-and-the-mechanical-engineer-a-parable/

Call To Action:
Improve Your NDR By Improving Your Software

Join my mailing list and get these articles directly to your inbox!
https://shermanonsoftware.com/subscribe/

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Jeffrey Sherman @jeffreysherman.bsky.social · 03/10/2025

Never Rewrite: Treating Communication Gaps Like Tech Debt ft. Austen Tucker Are communication gaps tech debt? Do they cause tech debt? Can they be worse than tech debt? Austen Tucker joins us this week to ponder communication's role in building software. www.youtube.com/watch?v=Q40g...

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

YouTube video by Never Rewrite

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Jeffrey Sherman @jeffreysherman.bsky.social · 26/09/2025

Never Rewrite: Is Switching Jobs a Career 'Rewrite'? Can changing jobs be a rewrite on your career? In this episode @isaacaskew.com and I work through the similarities and differences of career rewrites. www.youtube.com/watch?v=5qWa...

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

YouTube video by Never Rewrite