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.