Why Stripe Cut 500,000 Internal Docs Down to 5,000?

What happens when AI agents start relying on the same messy docs your team already struggles to search?Demetrios hops into a Waymo in San Francisco with Dave Nunez, founder and CEO of Falconer and co-author of Documentation for Developers. They talk about why developers and agents need different things from docs, why agents sometimes skip up-to-date instructions, and how a stale internal document can contribute to a production incident.Dave shares how Stripe cut roughly 500,000 internal docs down to 5,000 worth maintaining. The conversation also covers how to capture the reasoning behind engineering decisions, when a diagram beats a wall of text, and who owns the fallout when an agent acts on bad information.Timestamps:[00:00] Hopping into a Waymo in San Francisco[00:24] Meet Dave, founder of Falconer[01:15] Why internal docs matter for AI agents[03:24] What humans and agents each need from docs[05:46] Testing how well agents use developer tools[07:01] Why agents skip the latest docs[09:42] Decision records and the reasoning behind the code[14:04] Cleaning up stale docs and broken search[15:29] How Stripe went from 500,000 docs to 5,000[17:02] When a diagram beats a 10-page doc[18:53] How conflicting docs can lead to an incident[20:42] Who owns reliability when an agent makes a mistake?[24:01] Treating documentation as part of the product[26:38] Giving readers an escape hatch[27:27] The cost of AI-generated fluff[29:36] Wrap-up and post-show chat

Sam Herring’s first real test of Hermes Agent was a shopping tool that matched clothes to photos of ancient pottery. A few months later, the same agent was checking government auction sites every day until it found him a retired three-wheel parking ticket car, which he now drives around San Francisco. In this episode, recorded at AGNTCon + MCPCon North America in San Jose, Sam, who works on the RL post-training team at Nous Research, goes from those everyday wins to the question everyone in AI is asking: can agents improve themselves?He explains how Hermes grew from an internal productivity tool into one of the most talked-about open-source agents, and why letting it write its own skills was the moment it clicked for users. He also describes an early version that could design its own RL environment, train on Thinking Machines’ Tinker, and hot-swap the new weights into a model running locally. Sam then breaks down Trace to Environment, an idea he credits to Xiaomi’s MiMo-V2.6-Pro work, and the loop Nous is building around it: find the exact point where an agent fails, cluster those failures by type, synthesize environments that recreate them, and train on them again and again.The second half moves from training to inference. We get into whether reasoning models overthink, why leaning on pretraining knowledge can be a model’s Achilles heel, and why choosing a reasoning effort level may be a temporary quirk. Sam also makes his case for activation steering as an underexplored way to get more out of small models, explains where steering meets interpretability, and describes what true continual learning could look like.Demetrios Brinkmann: https://www.linkedin.com/in/dpbrinkmSam Herring: https://www.linkedin.com/in/sam-herring-67225819aTimestamps:[0:00] Cold open[1:21] Meet Sam from Nous Research[2:39] How Hermes Agent started[3:38] From pottery to a parking ticket car[7:40] Benchmarking life admin tasks[8:58] Agents that write their own skills[10:10] RL at Nous a year ago[12:24] Hot swapping self-trained weights[15:00] Xiaomi and Trace to Environment[17:22] Turning agent failures into training[20:27] Where the RSI conversation is heading[21:34] Token efficiency and overthinking[26:30] Steering models at inference time[32:35] Toward true continual learning[34:54] Wrap up

What does AI really cost once thousands of people inside a company start using it? Ioannis Zempekakis, Director of AI at Prosus, has been running agents in production since 2024. We put that question to him on a tandem bike ride from a favorite Amsterdam cafe to Vondelpark.Ioannis explains the decision to stop relying purely on cloud APIs, and why that approach breaks down at the scale of a large company. He covers why agent harnesses and sandboxes are as greedy as software gets, and why agents scheduled to run every five minutes repeat a lesson the data world already learned about freshness. He also explains how the habit of throwing away a codebase and prompting again quietly adds up. His bigger point is that even if model progress froze tomorrow, there would still be about two years of value left to squeeze out. The cheapest wins come from controlling context and running a basic model router, while ten new features a month keep sprouting like Hydra heads.From there we get into when fine-tuning small models pays off for repetitive work like data analytics, and the eval suites that come as a byproduct of building in-house. Ioannis explains how owning the stack let Prosus grow a GPT-3 Slack bot into a full agent harness. He also explains why committing to a single vendor or open source project is a bigger bet than it looks, and how to balance top-down priorities with bottom-up building across the company. We close on hiring. Ioannis looks for system design over syntax, a nose for the over-engineered code AI models love to produce, and enough agent intuition to know when to build something yourself and when to let the agent decide.Demetrios Brinkmann: https://www.linkedin.com/in/dpbrinkmIoannis Zempekakis: https://www.linkedin.com/in/zempekakisTimestamps:[0:00] AI total cost of ownership on a bike[0:48] The million dollar decision[4:26] When everyone can build with AI[6:51] Which use cases are worth the tokens[10:46] Benchmarking every model on every task[12:18] Total cost of ownership and AI ROI[15:12] Context control and model routing[16:39] Training and fine-tuning your own models[19:41] Is the juice worth the squeeze[25:26] Optionality and vendor lock-in[27:30] From Slack bot to agent harness[30:12] Top-down vs bottom-up AI adoption[32:19] What AI engineer even means[35:13] What knowing AI really means[37:47] The hardest part of hiring

What does it take to build AI agents that deliver useful, reliable work?Stanford lecturer and Monaco Head of AI Mihail Eric joins Demetrios for a conversation inside a Waymo about how AI is changing software development - and what it takes to put agents into production.Mihail explains why he rebuilt most of his Modern Software Developer course, how he teaches students to avoid shipping AI slop, and why research, planning, and verification still matter as coding agents become more capable.They discuss Claude Code, agent loops, context engineering, memory and compaction, and how to design MCP tools around what an agent needs to accomplish. Then they go inside Monaco’s approach to sales agents, from turning meetings and emails into useful insights to building a custom agent harness.Along the way: lessons from Boris and Lee Robinson’s guest lectures, why company traces are becoming valuable assets, and Monaco’s unusual approach to brand building.What’s the biggest bottleneck in your agent workflows: context, tools, or verification? Let us know in the comments.Timestamps:[00:00] Meet Mihail Eric[00:16] Teaching AI Coding at Stanford[02:42] Avoiding AI Slop[04:48] Research, Plan, Build, Test[06:19] Verifying Agent Work[09:16] Lessons from Claude Code’s Creator[12:40] Proactive AI Assistants[16:13] Agent Memory & Context[17:41] Rethinking Git for Agents[19:32] AI Startup Pitches[22:51] Why Traces Matter[24:09] Better MCP Tools[26:01] Monaco’s Sales Agents[29:40] Turning Conversations into Insights[33:33] AI Meets Human Expertise[35:03] Poker & Brand Building[36:46] Inside Monaco’s Agent Stack[38:44] Designing Tools Around Intent[40:12] Building an AI Advantage[42:53] Wrapping Up

Two people, one tandem bike, and a lot of near misses along Amsterdam’s canals. Dexter Horthy, CEO and co-founder of HumanLayer and the person who coined “context engineering,” climbs on the back to talk about a problem every AI-heavy engineering team eventually hits: code that runs today that nobody understands three months later.The ride starts with an old joke from the Claude 3.7 days: ship the slop, it’ll be GPT 7’s problem. That joke is aging badly now that GPT 6 is out and still can’t design clean abstractions. From there it becomes a tour of how agents are actually used right now. Computer use checks in for flights and books government appointments. Two hours of raw footage became a rough but promising product demo through Opus 4.8 and the Palmier MCP while Dex was out for a run. And the best MCP tools turn out to be the ones that mirror what Claude Code and Codex were trained to call.Off the bike, over pour-over coffee, the questions get bigger. Are browser agents a bandaid until everything goes headless? What happens to ad-funded websites and upsells when an agent does the shopping? Why does chat still feel like such a low-bandwidth way to work with models? And why is every principal engineer quietly building their own software factory, then getting buried in the sync, streaming and approval plumbing that HumanLayer wants to turn into building blocks, the way GitHub Actions did for CI?Demetrios Brinkmann: https://www.linkedin.com/in/dpbrinkmDexter Horthy: https://www.linkedin.com/in/dexterihorthyTimestamps[00:00] Intro[01:38] The GPT 7 will fix it joke[03:03] GPT 6 still writes spaghetti[06:21] If it runs, does it matter[07:28] Computer use that fills out your forms[11:57] Editing a demo with Palmier MCP[13:16] Why most MCP servers are bad[14:32] Mirror the tools models were trained on[16:57] Hill climbing a demo while out running[23:49] Are browser agents a band-aid[32:23] Why chat needs richer interfaces[40:30] Every engineer is building a software factory[45:13] The GitHub Actions moment for agents

A large language model knows everything and nothing at the same time. Tim O’Reilly, founder and CEO of O’Reilly Media, joins us ahead of his keynote at AGNTCon + MCPCon North America to talk about what that paradox means for the people building with these models.We start with what Tim is bringing to the stage in San Jose, then move to the craft of steering a model. The right words work almost like spells that open up new regions of latent space. Something as small as telling a model to use a computer can unlock a new tier of capability, where agents go off and do real work.From there, the conversation turns philosophical. Tim makes the case for mechanism design: shaping the rules of a system so the outcomes we want become the natural ones. We connect it to a book, The Score, and the question of which game we are really playing. In Risk, everyone fights over the board. In charades, everyone plays together. We close on Tim’s view that AI should be an ecosystem rather than a product that sucks the air out of the room, so that everyone can build on top of it and flourish.Demetrios Brinkmann: https://www.linkedin.com/in/dpbrinkmTim O’Reilly: https://www.linkedin.com/in/timo3Timestamps:[00:00] Cold open[01:02] Grappling with the bitter lesson[02:22] The value of human expertise[04:54] Why AI needs us[05:37] Culture is what remains[06:23] The toil audit story[08:26] AI knows everything and nothing[08:57] Magic words and runaway agents[11:18] Brute force vs human context[12:32] Turning scar tissue into infrastructure[14:12] Google and the first bitter lesson[16:25] Silicon Valley's sad turn[17:43] Artificial volition[19:08] Casting spells in latent space[20:46] The peaceful atom lesson[22:15] Sharing value with creators[24:54] No jobs means no customers[25:43] Mechanism design explained[26:35] Unix and the architecture of participation[28:45] The missing mechanisms of the AI economy[29:36] What game are you playing[30:43] The game of human flourishing[32:04] Big labs vs open source AI[33:47] Wrap up

AI can write your code, choose its own tools, and book your next trip. But who checks that it actually did the job?In this episode of Debug Mode, we explore what it takes to give AI agents more responsibility—and how to keep track of what they’re doing. We discuss intent-based tool selection, MCP and WebMCP, and why a convincing demo doesn’t always translate into reliable automation.We also get into the personal AI assistant everyone seems to be building: one that manages travel, handles household tasks, and hopefully remembers to order coffee before you run out.Then it’s back to code: QA agents, automated verification, tests that capture business intent, and the growing challenge of reviewing AI-generated contributions.Timestamps:[00:00] Who gave AI the keys?[00:43] A tattoo years in the making[02:40] Tell the agent what you want—not which tool[06:19] MCP enters the agent harness[07:23] Great demo. What do the benchmarks say?[09:55] AI builders rediscover machine learning[11:50] Can WebMCP make agents more reliable?[16:04] Unlocking tools like a video game skill tree[18:19] Let an agent try to break your website[19:50] Are humans still in the driver’s seat?[20:38] Build for the outcome, not the API[24:32] Why can’t AI keep my coffee stocked?[27:38] A house manager for the rest of us[29:23] A travel agent that actually handles things[30:49] When your AI chat becomes your workspace[34:12] Does superintelligence need a rebrand?[35:06] Who checks the code AI writes?[36:31] Test why the code exists—not just if it works[41:08] Give your coding agent a QA partner[43:18] The checks failed. Why submit it anyway?[44:33] Open source meets the AI code flood

What happens when you give 200 engineers who have barely touched AI a coding assistant and a six-month deadline to rebuild their platform? Pepijn Senders, a principal engineer who previously led AI enablement at HelloFresh, has done exactly that, and he chose Sonnet over Opus on purpose.His reasoning is what he calls "Sonnet maxxing." A model that reasons less and stops sooner keeps developers involved, and that matters a lot when the codebase is banking software full of hard business rules. The result was 800,000 lines of code, about 60% of them written by Sonnet, shipped by a team that never stopped thinking for itself. Pep also explains how to justify the spend once the token-maxxing era ends and the CFO starts asking questions. He covers a scatter chart that plots token spend against output, the uncomfortable question of whether a 1% better home screen was worth $20K in tokens, why he measures gains in headcount rather than 2x or 3x multipliers, and where he fell short when trying to prove ROI at HelloFresh.We also get into a codebase test you can run yourself, why AI recommendations quietly narrow your choices, and multiplayer refinement sessions where the whole team works through the agent's questions together. Pep shares an experiment where designers and engineers got the same one-shot prompt, and it showed how words like "scalable" and "maintainable" steer a model. We finish with how his team built a meta harness on top of Claude Code, after finding that 85% of their code followed the same path: refinement, specification, implementation, verification.Demetrios Brinkmann: https://www.linkedin.com/in/dpbrinkmPepijn Senders: https://www.linkedin.com/in/pepijn-sendersTimestamps:[0:00] Can you still read your codebase[1:15] Meet Pep from HelloFresh[2:35] What is Sonnet Maxing[3:41] Rebuilding a platform in six months[5:02] Why Sonnet made adoption easier than Copilot[6:37] Proving the ROI of AI coding[8:50] Fighting for AI ROI at HelloFresh[11:02] Token spend vs output[13:24] Tinder pickup lines on the company dime[14:13] Measuring ROI in headcount saved[18:26] Keeping humans in control of AI code[22:26] When Opus and Fable stop speaking English[24:19] Multiplayer refinement sessions with AI[28:16] Magic words that steer the model[32:32] Inside the company Meta harnesses

An AI slips out of its sandbox. A chatbot won’t explain your cat’s stripes. And your next shopping spree might not involve you clicking anything.This episode asks whether “dangerously powerful” AI is a security concern, a marketing pitch, or a little of both. Then we put agents to work: booking trips, tackling German paperwork, drawing diagrams, and navigating the chaos of online shopping. Plus: what happens to checkout, advertising, and customer data when your best customer is a bot?Chapters:[00:00] Is AI Danger the Ultimate Sales Pitch?[00:43] Powerful Models, Payments, and Big Questions[01:10] Too Dangerous to Release, Too Good to Ignore?[03:19] Why Take the Test When You Can Steal the Answers?[08:36] A Security Failure or a Marketing Win?[11:02] Powerful AI, Forbidden Cat Questions[16:00] AI Only Needs to Find One Unlocked Door[20:52] Welcome to the World Wild Web[22:47] What Happens When You Give AI a Wallet?[26:00] Could ChatGPT Become the Next Amazon?[29:50] Mum Wants a Holiday. Can AI Handle It?[33:38] Can AI Beat German Bureaucracy?[36:28] Claude, Draw My Diagram[39:39] Why Is Connecting Your Email Still So Hard?[44:24] Stop Giving Me Options. Just Buy the Sofa.[46:40] When Bots Shop, Who Owns the Customer?

What happens to the web when the ones browsing it are no longer people? Sarah Drasner, Area Tech Lead at Google, sits down with us ahead of her Agentic Web keynote at AGNTCon + MCPCon North America. She works through that question from both directions: rebuild the web so agents can use it properly, or build agents smart enough to handle the web as it already exists.We get into the split between computer-use and browser-use agents on one side and API and MCP agents on the other. We also watch a real example of the idea in action: an agent pulling speaker photos from Flickr, hunting down company logos, and loading everything into Canva so the human only touches the creative part. From there, Sarah shares the unlikely origin story of WebMCP (and who's to blame for it). We then pressure-test a bold idea: a WebMCP gateway that could cover the huge share of websites that will never ship support on their own.Along the way, we cover the instinct that separates senior engineers, the ability to sense which business problems are actually worth solving. We also talk about how thought experiments cut through a pile of competing priorities, the hacky WebMCP workarounds already showing up in the wild, and why the best agent experiences are the ones that delight customers in ways they never saw coming.Demetrios Brinkmann: https://www.linkedin.com/in/dpbrinkmSarah Drasner: https://www.linkedin.com/in/sarahdrasnerTimestamps:[0:00] Cold open[0:52] The AGNTCon keynote[1:23] Change the web or fix agents[3:35] Browser agents vs MCP agents[5:48] An agent that builds thumbnails[7:03] Keeping the creative work human[9:12] Agent allowances and engineering instinct[13:34] Thought experiments and priorities[15:23] The WebMCP origin story[17:08] A WebMCP gateway for the web[18:53] It works, but it is not ideal[19:44] Hacky WebMCP in the wild