Breaking the Build

The average person has around 255 passwords, and logging in has never been harder. Somehow nothing has ever felt less secure, either. In episode eleven of Breaking the Build, Tim and James take on computer security: why passwords fail, why passkeys can’t agree on where they live, and how AI is making both attacks and defenses better at the same time.

Topics covered: password security, password managers, passkeys, two-factor authentication (2FA), social engineering, phishing, AI deepfakes and voice cloning, AI in cybersecurity, data breaches, smart home and IoT security, encrypted messaging and Signal, privacy vs usability.

This casual tech podcast looks at why security is lopsided: defenders have to be perfect and attackers need one mistake. It also asks why most people will trade privacy for convenience every time. Along the way: why the old-people password book is more secure than it looks, AI as a $25-a-month protection racket, how Independence Day beat the aliens with malware, which smart appliance you’d want on your side in an AI war, and a would-you-rather that falls apart over whether good bagels should be toasted.

Perfect for: tech professionals, developers, IT and security folks, anyone who has helped a parent reset a password, and anyone who has typed a one-time code just to order a pizza.

74% of shoppers have used an AI agent, but only 14% trust one to actually place the order. In episode ten of Breaking the Build, Tim and James dig into agentic shopping: whether anyone will really let an AI spend their money, why Amazon Dash buttons and Alexa ordering never took off, and who's on the hook when your agent buys something you never wanted.

Topics covered: agentic commerce, AI shopping assistants, AI agents, ecommerce fraud and chargebacks, AI product recommendations, AEO (answer engine optimization), paid placements in AI answers, Instacart and grocery delivery, voice shopping and smart speakers, AI adoption by generation.

This casual tech podcast splits shopping into the predictable stuff you'd happily hand off and the fun stuff you wouldn't, then asks what banks, insurers, and retailers will have to change before an agent can check out for you. Also: a closet full of Costco chips, ten jars of peanut butter, "agent jail," a vending-machine AI that went full Gilded Age tycoon, and the official rule that agents may only shop for you once you can hurt their feelings.

Perfect for: ecommerce professionals, retailers and marketers, developers building with AI agents, tech enthusiasts, anyone who has ever closed the Rufus pop-up on Amazon.

Tech's favorite gospel is "launch fast, iterate, see what sticks" — but Tim and James want to know who's actually running the beta test. (It's you. You're the beta test. You're also paying for it.)

This episode wanders from the death of the "viable" in MVP through the Google and Microsoft product graveyards, the tragic murder of shuffle-less music apps, and the Zune's doomed quest to be cool. Along the way: why Netflix's eight-episodes-and-cancel model may have killed the sitcom entirely, how streamers accidentally reinvented weekly television and called it innovation, and the slow horror of realizing you don't actually own your thermostat, your smartwatch, or your recipes. Plus the crab theory of software evolution, a genuine pitch to bring back Clippy, and three would-you-rathers about corporate abandonment that spiral exactly as far off-topic as you'd hope.

The theme, as always: at the end of the day, the customer suffers.

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 mean prompting to a dedicated executioner bot.

Topics covered: AI politeness, token usage, prompt engineering, LLM behavior, caveman speak, anthropomorphizing AI, AI addiction, Claude Code, ChatGPT, Google Gemini, AI tools for developers.

Perfect for: developers and tech professionals who use AI tools daily, anyone curious about how prompt style affects AI output, and people who have ever felt vaguely guilty about being rude to a chatbot.

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 experience or just suffering with good posture.

Topics covered: digital detox, smartphone dependency, tech and mental health, work-life balance in tech, phantom notifications, screen time, location sharing, and disconnecting from technology.

This fun technology podcast takes an honest look at what modern life with a phone actually feels like — and what happens when it's suddenly gone. Includes: phantom buzzes on a Garmin watch, a detailed Survivor strategy, and Tim's long-term plan to return from a year off the grid and crash a finale ceremony.

Perfect for: tech professionals, anyone interested in digital wellness, people who've thought about doing a phone detox but haven't, and remote workers.

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, AI addiction, software development productivity, building with AI, AI limitations, prompt engineering, and using AI for non-developers.

This casual tech podcast covers the real day-to-day experience of building with AI: the wins, the database deletions, and the weird slot machine psychology that keeps you coming back. Featuring the truss plate theory of AI-assisted development, a goof plate that Google couldn't find but Claude could, and Tim's plan to run the entire development process from school drop-off.

Perfect for: developers using AI tools, tech enthusiasts, anyone curious about AI in software development, and people wondering if AI will replace programmers.

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 productivity, remote work setup, tablet vs laptop, responsive web design, mobile vs desktop, retro gaming phones, work from home tech.

This casual tech podcast explores the surprisingly personal relationship people have with their devices — and what it says about you when you pull out a tri-fold phone in a business meeting. Also: why Tim sits on his phone, the physics limit of foldable screens, a Windows 98 website that someone built in 2024 on purpose, and Tim's prediction that humans will eventually need blue light to survive.

Perfect for: tech enthusiasts, remote workers, developers, and anyone who has ever argued about monitor setups or phone sizes.

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, developer mindset, how technology changes thinking, coding bootcamps vs traditional education, structured thinking in tech, and digital literacy.

This fun technology podcast traces the personality traits that seem to cluster around developers — curiosity, fearlessness, a preference for structure — and asks whether those traits lead people to tech or whether tech creates them. Includes: Tim's nonprofit for teaching kids to code, his brother's first experience debugging CSS, two separate hardware fires, and a formal prediction that by 2027, we will be making sacrifices to appease AI.

Perfect for: software developers, people learning to code, tech enthusiasts, anyone curious about how a developer's brain works, and career changers considering a tech career.

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 photography vs digital, retro gaming and CRT monitors, server-side rendering, HTMX and Astro.js, streaming copyright and digital ownership, and the future of physical media.

This fun technology podcast covers the retro tech revival from both the consumer and developer sides — and lands on a theory about why some formats come back while others (DVDs, we're looking at you) just quietly die. Also: a t-shirt cannon that shoots 1,500 feet, a shirt press that nearly sent someone to the hospital, and the case for cargo shorts.

Perfect for: tech enthusiasts, developers, retro tech fans, vinyl collectors, and anyone worried about content disappearing from streaming platforms.

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 quality, SEO and content farms, Next.js and React security vulnerabilities, JavaScript on the server, Node.js, abstraction in modern web development, paid vs free search engines.

This casual tech podcast covers both the big-picture frustrations of using the internet in 2025 and the very specific developer pain of maintaining code built on too many layers of abstraction. Plus: a Pi-hole that accidentally broke household shopping, and a working theory that the internet just needs a hard reboot.

Perfect for: web developers, software engineers, tech enthusiasts, and anyone who has ever added "Reddit" to a Google search.