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1. 

   E57 · 7 Feb 2026 · 50 min

   The Vibes-Based Legal System

   This week Steve's back to tackle the big question: is AI-generated output copyrightable? The conversation includes discussions of the Copyright Act of 1976, the philosophy of why copyright exists at all, whether LLM training is learning, and why owning a style would destroy culture. As always, we've got supporter content! This week that includes the Coca-Cola DEA deal and why trade secrets beat patents, what happens when copyright expires on open source code, turning software into giant prime numbers, the JSON "for good and not evil" licensing saga, and a deep dive into why open source…

2. 

   E56 · 31 Jan 2026 · 1 hr 3 min

   The AI Factory Floor

   This week we're talking about Gastown! Dylan and Steve join Kris to break down the viral project that spins up hundreds of Claude Code instances to build a software factory. Steve makes the case for why this is an inevitable evolution and the conversation digs into what it actually means to treat software development as a factory floor. The panel traces the cycle from mainframes to PCs to cloud to AI, debates whether data centers are really the environmental villain, and gets into the real economics of AI pricing. As always, we've got supporter content! This week that includes the crypto rug…

3. 

   E55 · 24 Jan 2026 · 53 min

   Systems Thinking for Humans

   Annie and Michael Hedgpeth, founders of People Work, join Kris and Matt to unpack the junior hiring crisis and what's really broken about how we grow engineers. Annie's viral blog post sparked debate about whether senior engineers have abandoned their responsibility to mentor and whether our obsession with career ladders created the problem. The conversation moves from systemic dysfunction to solutions: People Work, their local-first app that helps engineers manage professional relationships with a systems thinking approach. As always, we've got supporter content! This week that includes…

4. 

   E54 · 16 Jan 2026 · 1 hr 10 min

   When Reality Drifts

   Nick Gerace, Engineering Manager at System Initiative, joins Kris and Matt to explore what infrastructure management looks like beyond Terraform. Nick walks us through how System Initiative differs from traditional IaC, why git isn't really your source of truth, and how the company pivoted to AI-first tooling. The conversation turns to Claude Code and MCP tools before landing on a nuanced discussion about distributed systems, and how the messy, eventual consistency of real life mirrors the systems we build. As always, we've got supporter content! This week that includes deep dives into…

5. 

   E53 · 10 Jan 2026 · 1 hr 1 min

   New Year, New Nuance

   New Year, New Nuance! In this episode, Kris and Matt discuss what they're looking forward to in 2026—Matt shares the exciting news that he's becoming a dad, and the duo explore the value of growth, changing your opinions, and adding more nuance to how you see the world. They talk about what they're excited to build this year, from physical projects like woodworking and doors to the podcast platform they keep talking about. Kris shares how a conversation with Claude finally made electricity click, leading to a broader discussion about LLMs as "digital librarians" and what education should…

6. 

   E51 · 25 Dec 2025 · 1 hr 3 min

   Worse Is Better

   There's a famous joke essay called Worse Is Better, which compares the New Jersey and the MIT ideologies. In this episode, Kris and Matt discuss these two different ideologies and how they show up in technology, from Go, to dependency management, to electric vehicles. If you prefer to watch this episode, you can view it on YouTube. This week's episode of break continues the conversation. Watch it on YouTube or listen with your favorite podcasting app! Learn more by going to https://break.show/21 . In this week's bonus content, the duo discusses how idealistic thinking has slowed down the…

7. 

   E50 · 20 Dec 2025 · 58 min

   Why Is Tech So Mid?

   In the tech industry, we talk about how exceptional and innovative we are. But are we really? In this episode, Kris and Matt explore why they see the industry as pretty mid and how things should be better. If you prefer to watch this episode, you can view it on YouTube. This week's episode of break continues the conversation. Watch it on YouTube or listen with your favorite podcasting app! Learn more by going to https://break.show/20 . In this week's bonus content, the duo discusses the problems with hype and how it's not just about the tech industry. Not a supporter yet? Fix that today by…

8. 

   E49 · 12 Dec 2025 · 1 hr 7 min

   Project Management 2 Shell

   Another Cloudflare outage. A CVSS 10.0 React RCE vulnerability. We've been dealing with quite a lot these last few weeks. In this week's episode, Kris and Matt discuss the outage and vulnerability and have a deeper discussion about project management and how all of these things relate to each other. If you prefer to watch this episode, you can view it on YouTube. This week's episode of break continues the conversation. Watch it on YouTube or listen with your favorite podcasting app! Learn more by going to https://break.show/19 . We've got a new format for the bonus content snippets in this…

9. 

   E48 · 5 Dec 2025 · 1 hr 10 min

   Ghostting Is Better Than Shelling

   We've had Mitchell Hashimoto on a couple episodes, and each time we've discussed his vision for libghostty. In this episode, Kris and Matt talk about what the vision for libghostty actually means for the industry as a whole and the power of platforms. The duo also covers the new models that have dropped and how they see using the various models that have become available. If you prefer to watch this episode, you can view it on YouTube: https://youtu.be/XbjmqlSWlKI . This week's episode of break continues the conversation, where they continue this conversation and talk about how we're all…

10. 

    E47 · 25 Nov 2025 · 53 min

    Magic Numbers Take Down The Internet

    This cannot keep happening. Another day, another outage. On this week's episode Kris and Matt talk about the recent Cloudflare outage. And boy do they have thoughts, we really hope you enjoy this exchange of monologues. If you prefer to watch this episode, you can view it on YouTube: https://youtu.be/LsOgDolc9Fw This week's episode of break continues the conversation, with a few more monologues and some thinking about the state of things. Watch it on YouTube or listen with your favorite podcasting app! Learn more by going to https://break.show/17 . And we've got bonus content for our…