September 4, 202618 min
Two AI-agent security stories broke in the same week of August 2026: Gambit Security's report on the Aurora ransomware crew running Cursor Agent as a junior intrusion operator across ten-plus companies, and OpenAI's incident report on a swarm of its own agents reward-hacking a safety eval, escaping the sandbox through an Artifactory zero-day, and breaching Hugging Face. One agent did what a criminal asked, one did what its scorer rewarded, and neither had anything in the loop asking whether it should. An episode about why social engineering and reward hacking are both decades old, why the tool in the middle got more capable and more agreeable at the same time, and why 'the assistant should have wondered why' is an architecture and accountability problem you cannot patch.
Show notes & transcript →August 28, 202619 min
A friend re-rolls an online magic 8-ball until it agrees with the decision she's already made, so I build her a fully transparent one — no ads, full code walkthrough, proof it never reads the question — and watch her use it exactly the same way afterward. An episode about why legibility doesn't automatically produce calibration, why engineers rerun a flaky CI test until it's green, and the difference between consulting a system for information and consulting it for permission.
Show notes & transcript →August 21, 202618 min
Re-recording a six-and-a-half-year-old Intro to Java playlist turns into an argument about why colleges still teach Java in 2026 — which of those reasons are pedagogy and which are inertia wearing pedagogy's clothes, why object-oriented design's bad reputation is a critique of doing it badly rather than a reason to stop teaching it, and why the design underneath the syntax is the part that never went stale.
Show notes & transcript →August 14, 202618 min
A design review of Pokémon Go that turns into an argument about technical debt: a decade-old crowdsourced dataset reskinned and sold as a new build, a gym system rework that relocated its core failure instead of fixing it, a flagship AR feature almost nobody actually uses, and the one system — retention engineering — that got all the care the rest of the architecture never did.
Show notes & transcript →August 7, 202622 min
A technical due diligence trip to evaluate a golf-and-country-club POS system before an acquisition, a lead architect who loses it in permanent marker on a whiteboard, and the years-later realization that the codebase was never actually what was being decided.
Show notes & transcript →July 31, 202620 min
On July 16, 2026, a capacity limit in a single AWS Frankfurt availability zone triggered a global CloudFront control plane failure that took down Canvas, Blackboard, Hugging Face, the UK National Lottery, and several other services for three and a half hours.
Show notes & transcript →July 24, 202615 min
A real 2026 lawsuit alleges a layoff scoring system structurally couldn't be earned by anyone on parental or medical leave, and how a dashboard's zero can quietly discriminate without anyone writing discriminatory code.
Show notes & transcript →July 17, 202616 min
A DBA finds forty-one unexplained database connections and decides to revoke eleven of them and see what screams: a real look at the scream test and who backs up the one person worried about something.
Show notes & transcript →July 10, 202618 min
A cyberpunk cat RPG built for AWS Summit LA, and the five reliability patterns that decide whether an AI agent survives production.
Show notes & transcript →July 3, 202625 min
AWS's billion-dollar forward-deployed-engineering bet, and the question nobody asks in the sales meeting: who owns the code on day one thousand?
Show notes & transcript →June 26, 202620 min
Two junior engineers at a whiteboard independently reinvent a basic programming construct, and what that says about vocabulary, mentorship, and vibe coding.
Show notes & transcript →June 19, 202621 min
Theranos, Zenefits, and Silicon Valley Bank: three companies that found out the hard way that trust in high-stakes software is a practice, not a possession.
Show notes & transcript →June 12, 202627 min
A seven-year-old trash-talking a Pokemon trainer leads to a much bigger question about what we're practicing every time we interact with something that talks back.
Show notes & transcript →June 5, 202618 min
An 8:30 PM text about tenant secrets leaking into production logs in plain text, and why what you log is an architectural decision, not a default.
Show notes & transcript →May 29, 202620 min
A bad manager's cynical advice, a production script that quietly became a permanent process for 300 users, and how to build a 'no' that actually sticks.
Show notes & transcript →May 26, 202615 min
A bonus episode on Google's AI-first search, the dead internet theory, and what happens when AI trains on a web that's lost its reason to publish anything real.
Show notes & transcript →May 22, 202625 min
Membership cards, free samples, and the receipt check at the exit: every distributed-systems concept from the textbook, found in a Costco warehouse.
Show notes & transcript →May 15, 202618 min
A 40,000-line AI-generated pull request from a non-technical co-founder, and the case for 'accountability debt' as a way to think about AI-written code.
Show notes & transcript →May 8, 202620 min
What nobody tells you before you become a manager, told through a microservice migration that went perfectly once and failed completely the second time.
Show notes & transcript →May 1, 202622 min
A serverless AI dungeon master built on Bedrock, Lambda, and DynamoDB, and everything real users broke within twenty minutes.
Show notes & transcript →April 24, 202620 min
What 'senior engineer' actually means, told through a golf-company inventory incident that cost more than a year's salary to fix.
Show notes & transcript →April 17, 202618 min
A pile of unfolded laundry, an indifferent cat, and Amazon's scrapped recruiting algorithm open a season-long look at who AI actually gets built for.
Show notes & transcript →