Breaking the Build

Should you say "please" and "thank you" to your AI? Tim does. James absolutely does not. In this episode of Breaking the Build, Tim and James debate AI politeness, token optimization, caveman speak prompts, and whether being rude to your LLM shapes the agent you're building over time. Plus: the Gemini calendar incident, AI as therapist, and James's plan to outsource his...

A bicycle fell on Tim's iPhone. The repair took three hours. In suburban Columbus, Ohio — a place entirely built around having a phone — this was a minor crisis. In episode eight of Breaking the Build, Tim and James explore what it actually means to disconnect from technology, why intentional unplugging feels nothing like forced unplugging, and whether raw-dogging a flight is a spiritual exper...

If you've been sneaking in AI prompts from the couch while your family watches TV, this episode is for you. Tim and James get honest about how much time they're actually spending with AI coding tools, what they've built, and whether any of us really know what we're doing — or just watching a very convincing cardboard town. Topics covered: AI coding tools, Claude Code, vibe coding,...

From 40-inch curved monitors to tiny foldable phones — does the size of your device actually affect how well you get work done? In episode nine of Breaking the Build, Tim and James debate the perfect screen setup, the case for and against foldable phones, and the very specific rules Tim has developed about which device is allowed to do what. Topics covered: monitor sizes, foldable phones, device p...

A PhD professor once claimed he could predict future programmers from a 25-question quiz. That paper has since been retracted. But the question it raised — are some people wired for technology, or does technology rewire how you think? — is exactly what Tim and James dig into in episode ten of Breaking the Build. Topics covered: software development aptitude, learning to code, AI and programming, d...

Vinyl is outselling CDs. Physical books are making a comeback. Retro gaming is driving demand for CRT televisions. And server-side rendering is being rediscovered by a generation of developers who learned on React. In episode three of Breaking the Build, Tim and James ask: Is this nostalgia, or is something else going on? Topics covered: vinyl records vs streaming, physical books vs e-books, film...

Is Google actually getting worse — or is there just too much internet? In episode two of Breaking the Build, Tim and James get into why search results have become a minefield of SEO spam, why everyone secretly adds "Reddit" to their Google searches, and what a React security vulnerability has to do with JavaScript running where it was never supposed to. Topics covered: Google search qual...

JavaScript turned 30 this year — which officially makes it a millennial. In this first episode of Breaking the Build, Tim and James dig into three decades of web development history: browser wars, the rise of TypeScript, and why nobody would get in a JavaScript space shuttle (except maybe Tim). Topics covered: JavaScript history, TypeScript vs JavaScript, AI in software development, vibe coding, f...